Fare Guide
Estimated lowest fares found within 7 days
Cheapest Airline
The cheapest airline(s) flying from Chicago to Orlando is Frontier Airlines.
Cheapest Month
May
Travel Period: May 2024 - April 2025
The cheapest month(s) to fly from Chicago to Orlando is May.
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May 2024
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Jun 2024
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Jul 2024
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Aug 2024
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Sep 2024
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Oct 2024
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Nov 2024
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Dec 2024
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Jan 2025
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Feb 2025
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Mar 2025
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Apr 2025
Cheapest Day of the Week
Saturday
The cheapest day(s) of the week to fly from Chicago to Orlando is Saturday.
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Sun Sunday
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Mon Monday
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Tue Tuesday
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Wed Wednesday
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Thu Thursday
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Fri Friday
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Sat Saturday
Cheapest Time
8pm
The cheapest time of the day to fly from Chicago to Orlando is in the evening.
Early Morning 12:01am - 06:00am
Morning 6:01am - 12:00pm
Afternoon 12:01pm - 6:00pm
Evening 6:01pm to 12:00am
12am
6am
12pm
6pm
Flight Schedules
Last Updated: Tue, 2 Apr, 2024
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Depart
Earliest
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Filter by Airline
All
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Total Duration
- Shortest
- Longest
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All
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Availability
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19:47 - 23:23RFD - SFB
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19:47 (RFD)Chicago Rockford Airport
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23:23 (SFB)Orlando Sanford International Airport
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Allegiant Air LLC (G4 2886)Airbus - 2h 36m
- Direct
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- -
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- Airbus
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19:47 - 23:23RFD - SFB
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19:47 (RFD)Chicago Rockford Airport
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23:23 (SFB)Orlando Sanford International Airport
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Allegiant Air LLC (G4 2886)Airbus - 2h 36m
- Direct
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- M
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- Airbus
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20:55 - 00:30+ 1MDW - MCO
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20:55 (MDW)Chicago Midway Airport
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00:30 (MCO)Orlando International Airport + 1
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(WN 2970)Boeing 737 800 - 2h 35m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 800
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05:40 - 09:10MDW - MCO
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05:40 (MDW)Chicago Midway Airport
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09:10 (MCO)Orlando International Airport
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(WN 332)Boeing 737 800 - 2h 30m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 800
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06:00 - 09:30MDW - MCO
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06:00 (MDW)Chicago Midway Airport
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09:30 (MCO)Orlando International Airport
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(WN 332)Boeing 737 700 - 2h 30m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
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06:15 - 09:45MDW - MCO
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06:15 (MDW)Chicago Midway Airport
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09:45 (MCO)Orlando International Airport
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(WN 332)Boeing 737 700 - 2h 30m
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
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06:30 - 10:10ORD - MCO
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06:30 (ORD)Chicago O'Hare International Airport
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10:10 (MCO)Orlando International Airport
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(WN 2985)Boeing 737 700 - 2h 40m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
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06:35 - 10:05MDW - MCO
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06:35 (MDW)Chicago Midway Airport
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10:05 (MCO)Orlando International Airport
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(WN 332)Boeing 737 800 - 2h 30m
- Direct
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- M
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- -
- T
- F
- -
- -
- Boeing 737 800
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07:20 - 11:02ORD - MCO
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07:20 (ORD)Chicago O'Hare International Airport
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11:02 (MCO)Orlando International Airport
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United Airlines (UA 1768)Boeing 737 800 - 2h 42m
- Direct
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- M
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- S
- S
- Boeing 737 800
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07:25 - 22:20MDW - MCO
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07:25 (MDW)Chicago Midway Airport
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22:20 (MCO)Orlando International Airport
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(WN 3307)Boeing 737 700 - 13h 55m
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
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07:25 - 12:40MDW - MCO
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07:25 (MDW)Chicago Midway Airport
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12:40 (MCO)Orlando International Airport
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(WN 4910)Boeing 737 700 - 4h 15m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
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07:50 - 11:20MDW - MCO
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07:50 (MDW)Chicago Midway Airport
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11:20 (MCO)Orlando International Airport
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(WN 2966)Boeing 737 700 - 2h 30m
- Direct
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- -
- T
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- -
- -
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- Boeing 737 700
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08:00 - 11:35MDW - MCO
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08:00 (MDW)Chicago Midway Airport
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11:35 (MCO)Orlando International Airport
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(WN 2966)Boeing 737 Max 8 Passenger - 2h 35m
- Direct
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- -
- -
- -
- -
- -
- S
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- Boeing 737 Max 8 Passenger
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08:00 - 11:35MDW - MCO
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08:00 (MDW)Chicago Midway Airport
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11:35 (MCO)Orlando International Airport
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(WN 2966)Boeing 737 800 - 2h 35m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 800
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08:10 - 11:45MDW - MCO
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08:10 (MDW)Chicago Midway Airport
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11:45 (MCO)Orlando International Airport
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(WN 2966)Boeing 737 700 - 2h 35m
- Direct
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- M
- -
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- T
- F
- -
- -
- Boeing 737 700
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08:20 - 11:59ORD - MCO
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08:20 (ORD)Chicago O'Hare International Airport
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11:59 (MCO)Orlando International Airport
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American Airlines (AA 2119)Boeing 737 800 - 2h 39m
- Direct
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- M
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- T
- F
- S
- S
- Boeing 737 800
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09:00 - 14:10MDW - MCO
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09:00 (MDW)Chicago Midway Airport
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14:10 (MCO)Orlando International Airport
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(WN 1171)Boeing 737 700 - 4h 10m
- Direct
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- -
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- -
- S
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- Boeing 737 700
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09:10 - 13:05ORD - MCO
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09:10 (ORD)Chicago O'Hare International Airport
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13:05 (MCO)Orlando International Airport
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(WN 2985)Boeing 737 800 - 2h 55m
- Direct
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- -
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- -
- S
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- Boeing 737 800
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09:10 - 13:05ORD - MCO
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09:10 (ORD)Chicago O'Hare International Airport
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13:05 (MCO)Orlando International Airport
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(WN 2985)Boeing 737 700 - 2h 55m
- Direct
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- M
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- F
- -
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- Boeing 737 700
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09:20 - 13:05ORD - MCO
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09:20 (ORD)Chicago O'Hare International Airport
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13:05 (MCO)Orlando International Airport
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United Airlines (UA 281)Boeing 737 900 - 2h 45m
- Direct
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- M
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- T
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- Boeing 737 900
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09:45 - 13:20MDW - MCO
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09:45 (MDW)Chicago Midway Airport
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13:20 (MCO)Orlando International Airport
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(WN 2967)Boeing 737 800 - 2h 35m
- Direct
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- M
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- Boeing 737 800
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10:10 - 13:45MDW - MCO
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10:10 (MDW)Chicago Midway Airport
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13:45 (MCO)Orlando International Airport
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(WN 2967)Boeing 737 800 - 2h 35m
- Direct
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- Boeing 737 800
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10:10 - 13:45MDW - MCO
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10:10 (MDW)Chicago Midway Airport
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13:45 (MCO)Orlando International Airport
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(WN 2967)Boeing 737 Max 8 Passenger - 2h 35m
- Direct
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- Boeing 737 Max 8 Passenger
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11:05 - 14:45ORD - MCO
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11:05 (ORD)Chicago O'Hare International Airport
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14:45 (MCO)Orlando International Airport
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United Airlines (UA 2340)Boeing 737 900 - 2h 40m
- Direct
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- M
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- S
- Boeing 737 900
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11:10 - 14:45MDW - MCO
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11:10 (MDW)Chicago Midway Airport
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14:45 (MCO)Orlando International Airport
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(WN 1575)Boeing 737 800 - 2h 35m
- Direct
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- -
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- S
- Boeing 737 800
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11:10 - 14:45MDW - MCO
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11:10 (MDW)Chicago Midway Airport
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14:45 (MCO)Orlando International Airport
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(WN 1575)Boeing 737 700 - 2h 35m
- Direct
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- -
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- Boeing 737 700
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11:40 - 16:55MDW - MCO
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11:40 (MDW)Chicago Midway Airport
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16:55 (MCO)Orlando International Airport
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(WN 4910)Boeing 737 700 - 4h 15m
- Direct
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- Boeing 737 700
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11:55 - 15:30MDW - MCO
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11:55 (MDW)Chicago Midway Airport
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15:30 (MCO)Orlando International Airport
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(WN 879)Boeing 737 700 - 2h 35m
- Direct
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- M
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- Boeing 737 700
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12:40 - 16:25ORD - MCO
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12:40 (ORD)Chicago O'Hare International Airport
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16:25 (MCO)Orlando International Airport
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(WN 5404)Boeing 737 700 - 2h 45m
- Direct
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- M
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- T
- F
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- Boeing 737 700
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12:59 - 16:39ORD - MCO
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12:59 (ORD)Chicago O'Hare International Airport
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16:39 (MCO)Orlando International Airport
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United Airlines (UA 561)Boeing 737 800 - 2h 40m
- Direct
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- M
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- S
- Boeing 737 800
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13:00 - 16:35MDW - MCO
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13:00 (MDW)Chicago Midway Airport
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16:35 (MCO)Orlando International Airport
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(WN 3048)Boeing 737 700 - 2h 35m
- Direct
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- S
- Boeing 737 700
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13:20 - 16:59ORD - MCO
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13:20 (ORD)Chicago O'Hare International Airport
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16:59 (MCO)Orlando International Airport
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American Airlines (AA 1782)Boeing 737 800 - 2h 39m
- Direct
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- M
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- S
- S
- Boeing 737 800
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13:30 - 17:20ORD - MCO
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13:30 (ORD)Chicago O'Hare International Airport
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17:20 (MCO)Orlando International Airport
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(WN 5404)Boeing 737 700 - 2h 50m
- Direct
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- Boeing 737 700
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13:40 - 17:15MDW - MCO
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13:40 (MDW)Chicago Midway Airport
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17:15 (MCO)Orlando International Airport
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(WN 879)Boeing 737 Max 8 Passenger - 2h 35m
- Direct
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- -
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- W
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- Boeing 737 Max 8 Passenger
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13:50 - 19:05MDW - MCO
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13:50 (MDW)Chicago Midway Airport
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19:05 (MCO)Orlando International Airport
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(WN 3263)Boeing 737 700 - 4h 15m
- Direct
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- -
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- -
- -
- S
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- Boeing 737 700
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13:55 - 17:35MDW - MCO
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13:55 (MDW)Chicago Midway Airport
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17:35 (MCO)Orlando International Airport
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(WN 879)Boeing 737 800 - 2h 40m
- Direct
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- -
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- -
- -
- S
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- Boeing 737 800
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14:00 - 20:45MDW - MCO
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14:00 (MDW)Chicago Midway Airport
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20:45 (MCO)Orlando International Airport
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(WN 1888)Boeing 737 Max 8 Passenger - 5h 45m
- Direct
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- M
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- Boeing 737 Max 8 Passenger
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14:20 - 18:00ORD - MCO
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14:20 (ORD)Chicago O'Hare International Airport
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18:00 (MCO)Orlando International Airport
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United Airlines (UA 2463)Boeing 737 800 - 2h 40m
- Direct
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- M
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- S
- Boeing 737 800
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14:45 - 18:30ORD - MCO
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14:45 (ORD)Chicago O'Hare International Airport
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18:30 (MCO)Orlando International Airport
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(WN 370)Boeing 737 800 - 2h 45m
- Direct
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- -
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- -
- -
- -
- -
- S
- Boeing 737 800
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15:00 - 18:30MDW - MCO
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15:00 (MDW)Chicago Midway Airport
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18:30 (MCO)Orlando International Airport
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(WN 2969)Boeing 737 800 - 2h 30m
- Direct
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- -
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- S
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- Boeing 737 800
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15:40 - 19:15MDW - MCO
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15:40 (MDW)Chicago Midway Airport
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19:15 (MCO)Orlando International Airport
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(WN 2969)Boeing 737 700 - 2h 35m
- Direct
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- -
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- Boeing 737 700
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16:00 - 19:35MDW - MCO
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16:00 (MDW)Chicago Midway Airport
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19:35 (MCO)Orlando International Airport
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(WN 2969)Boeing 737 700 - 2h 35m
- Direct
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- M
- -
- -
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- F
- -
- -
- Boeing 737 700
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16:00 - 19:45ORD - MCO
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16:00 (ORD)Chicago O'Hare International Airport
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19:45 (MCO)Orlando International Airport
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(WN 370)Boeing 737 700 - 2h 45m
- Direct
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- -
- T
- W
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- -
- -
- -
- Boeing 737 700
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16:00 - 19:45ORD - MCO
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16:00 (ORD)Chicago O'Hare International Airport
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19:45 (MCO)Orlando International Airport
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(WN 370)Boeing 737 800 - 2h 45m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
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16:35 - 20:10MDW - MCO
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16:35 (MDW)Chicago Midway Airport
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20:10 (MCO)Orlando International Airport
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(WN 1584)Boeing 737 Max 8 Passenger - 2h 35m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
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16:50 - 20:27ORD - MCO
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16:50 (ORD)Chicago O'Hare International Airport
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20:27 (MCO)Orlando International Airport
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American Airlines (AA 1075)Boeing 737 800 - 2h 37m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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17:15 - 20:50MDW - MCO
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17:15 (MDW)Chicago Midway Airport
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20:50 (MCO)Orlando International Airport
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(WN 2970)Boeing 737 700 - 2h 35m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
-
17:20 - 20:55MDW - MCO
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17:20 (MDW)Chicago Midway Airport
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20:55 (MCO)Orlando International Airport
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(WN 2970)Boeing 737 Max 8 Passenger - 2h 35m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
-
17:50 - 21:25MDW - MCO
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17:50 (MDW)Chicago Midway Airport
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21:25 (MCO)Orlando International Airport
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(WN 2970)Boeing 737 700 - 2h 35m
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
-
18:00 - 21:53ORD - MCO
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18:00 (ORD)Chicago O'Hare International Airport
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21:53 (MCO)Orlando International Airport
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United Airlines (UA 1840)Airbus A321 Neo - 2h 53m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Airbus A321 Neo
-
18:00 - 21:35MDW - MCO
-
18:00 (MDW)Chicago Midway Airport
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21:35 (MCO)Orlando International Airport
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(WN 2971)Boeing 737 700 - 2h 35m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
18:50 - 22:25MDW - MCO
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18:50 (MDW)Chicago Midway Airport
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22:25 (MCO)Orlando International Airport
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(WN 2971)Boeing 737 700 - 2h 35m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
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18:55 - 22:25MDW - MCO
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18:55 (MDW)Chicago Midway Airport
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22:25 (MCO)Orlando International Airport
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(WN 2971)Boeing 737 700 - 2h 30m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
Connecting Flights
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05:30 - 08:10MDW - AUS09:25 - 13:05AUS - MCO
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05:30 (MDW)Chicago Midway Airport09:25 (AUS)Austin-Bergstrom International Airport
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08:10 (AUS)Austin-Bergstrom International Airport13:05 (MCO)Orlando International Airport
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(WN 5387)Boeing 737 Max 8 Passenger (WN 5905)Boeing 737 700 - 6h 35m (1h 15m)
- AUS Austin 1h 15m
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- M
- -
- -
- T
- F
- -
- -
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05:45 - 07:10MDW - BNA07:50 - 10:45BNA - MCO
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05:45 (MDW)Chicago Midway Airport07:50 (BNA)Nashville Airport
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07:10 (BNA)Nashville Airport10:45 (MCO)Orlando International Airport
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(WN 270)Boeing 737 700 (WN 569)Boeing 737 Max 8 Passenger - 4h (40m)
- BNA Nashville 40m
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- -
- -
- -
- -
- -
- S
- -
-
05:45 - 07:10MDW - BNA10:20 - 13:15BNA - MCO
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05:45 (MDW)Chicago Midway Airport10:20 (BNA)Nashville Airport
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07:10 (BNA)Nashville Airport13:15 (MCO)Orlando International Airport
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(WN 270)Boeing 737 700 (WN 2906)Boeing 737 Max 8 Passenger - 6h 30m (3h 10m)
- BNA Nashville 3h 10m
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- -
- -
- -
- -
- -
- S
- -
-
05:55 - 07:05MDW - STL08:10 - 11:30STL - MCO
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05:55 (MDW)Chicago Midway Airport08:10 (STL)St Louis Lambert Intl Airport
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07:05 (STL)St Louis Lambert Intl Airport11:30 (MCO)Orlando International Airport
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(WN 5846)Boeing 737 Max 8 Passenger (WN 3016)Boeing 737 Max 8 Passenger - 4h 35m (1h 05m)
- STL Saint Louis 1h 05m
-
- -
- -
- -
- -
- -
- S
- -
-
06:00 - 08:55MDW - BWI10:00 - 12:15BWI - MCO
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06:00 (MDW)Chicago Midway Airport10:00 (BWI)Baltimore Washington International Airport
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08:55 (BWI)Baltimore Washington International Airport12:15 (MCO)Orlando International Airport
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(WN 1823)Boeing 737 800 (WN 1929)Boeing 737 800 - 5h 15m (1h 05m)
- BWI Baltimore 1h 05m
-
- -
- T
- W
- -
- -
- -
- -
-
06:05 - 08:55MDW - ATL11:30 - 13:00ATL - MCO
-
06:05 (MDW)Chicago Midway Airport11:30 (ATL)Atlanta Hartsfield-Jackson Intl Airport
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08:55 (ATL)Atlanta Hartsfield-Jackson Intl Airport13:00 (MCO)Orlando International Airport
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(WN 925)Boeing 737 800 (WN 2891)Boeing 737 700 - 5h 55m (2h 35m)
- ATL Atlanta 2h 35m
-
- M
- -
- -
- T
- F
- -
- -
-
06:05 - 08:55MDW - ATL10:40 - 12:15ATL - MCO
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06:05 (MDW)Chicago Midway Airport10:40 (ATL)Atlanta Hartsfield-Jackson Intl Airport
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08:55 (ATL)Atlanta Hartsfield-Jackson Intl Airport12:15 (MCO)Orlando International Airport
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(WN 925)Boeing 737 700 (WN 2891)Boeing 737 800 - 5h 10m (1h 45m)
- ATL Atlanta 1h 45m
-
- -
- -
- -
- -
- -
- -
- S
-
06:20 - 07:45MDW - BNA09:20 - 12:15BNA - MCO
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06:20 (MDW)Chicago Midway Airport09:20 (BNA)Nashville Airport
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07:45 (BNA)Nashville Airport12:15 (MCO)Orlando International Airport
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(WN 270)Boeing 737 Max 8 Passenger (WN 2906)Boeing 737 Max 8 Passenger - 4h 55m (1h 35m)
- BNA Nashville 1h 35m
-
- -
- T
- W
- -
- -
- -
- -
-
06:30 - 07:45MDW - STL08:40 - 12:00STL - MCO
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06:30 (MDW)Chicago Midway Airport08:40 (STL)St Louis Lambert Intl Airport
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07:45 (STL)St Louis Lambert Intl Airport12:00 (MCO)Orlando International Airport
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(WN 5846)Boeing 737 800 (WN 3016)Boeing 737 Max 8 Passenger - 4h 30m (55m)
- STL Saint Louis 55m
-
- -
- -
- -
- -
- -
- -
- S
-
06:55 - 08:30MDW - MCI10:05 - 13:50MCI - MCO
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06:55 (MDW)Chicago Midway Airport10:05 (MCI)Kansas City International Airport
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08:30 (MCI)Kansas City International Airport13:50 (MCO)Orlando International Airport
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(WN 1942)Boeing 737 700 (WN 5293)Boeing 737 700 - 5h 55m (1h 35m)
- MCI Kansas City 1h 35m
-
- -
- -
- -
- -
- -
- S
- -
-
07:05 - 09:55MDW - ATL10:35 - 12:00ATL - MCO
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07:05 (MDW)Chicago Midway Airport10:35 (ATL)Atlanta Hartsfield-Jackson Intl Airport
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09:55 (ATL)Atlanta Hartsfield-Jackson Intl Airport12:00 (MCO)Orlando International Airport
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(WN 1572)Boeing 737 800 (WN 2891)Boeing 737 700 - 3h 55m (40m)
- ATL Atlanta 40m
-
- -
- T
- W
- -
- -
- -
- -
-
07:10 - 08:35MDW - MCI10:25 - 14:05MCI - MCO
-
07:10 (MDW)Chicago Midway Airport10:25 (MCI)Kansas City International Airport
-
08:35 (MCI)Kansas City International Airport14:05 (MCO)Orlando International Airport
-
(WN 352)Boeing 737 700 (WN 5293)Boeing 737 800 - 5h 55m (1h 50m)
- MCI Kansas City 1h 50m
-
- -
- -
- -
- -
- -
- -
- S
-
07:20 - 10:00MDW - HOU10:40 - 14:00HOU - MCO
-
07:20 (MDW)Chicago Midway Airport10:40 (HOU)Houston Hobby Airport
-
10:00 (HOU)Houston Hobby Airport14:00 (MCO)Orlando International Airport
-
(WN 5171)Boeing 737 800 (WN 931)Boeing 737 700 - 5h 40m (40m)
- HOU Houston 40m
-
- M
- -
- -
- T
- F
- -
- -
-
07:25 - 10:25MDW - PHL12:30 - 14:50PHL - MCO
-
07:25 (MDW)Chicago Midway Airport12:30 (PHL)Philadelphia International Airport
-
10:25 (PHL)Philadelphia International Airport14:50 (MCO)Orlando International Airport
-
(WN 3706)Boeing 737 700 (WN 3710)Boeing 737 800 - 6h 25m (2h 05m)
- PHL Philadelphia 2h 05m
-
- M
- -
- -
- T
- F
- -
- -
-
07:30 - 09:05ORD - BNA10:20 - 13:15BNA - MCO
-
07:30 (ORD)Chicago O'Hare International Airport10:20 (BNA)Nashville Airport
-
09:05 (BNA)Nashville Airport13:15 (MCO)Orlando International Airport
-
(WN 658)Boeing 737 700 (WN 2906)Boeing 737 Max 8 Passenger - 4h 45m (1h 15m)
- BNA Nashville 1h 15m
-
- -
- -
- -
- -
- -
- S
- -
-
07:30 - 10:00ORD - DAL10:55 - 14:30DAL - MCO
-
07:30 (ORD)Chicago O'Hare International Airport10:55 (DAL)Dallas/Fort Worth Love Field Airport
-
10:00 (DAL)Dallas/Fort Worth Love Field Airport14:30 (MCO)Orlando International Airport
-
(WN 5820)Boeing 737 Max 8 Passenger (WN 278)Boeing 737 Max 8 Passenger - 6h (55m)
- DAL Dallas 55m
-
- -
- -
- -
- -
- -
- -
- S
-
07:30 - 09:05ORD - BNA12:10 - 15:05BNA - MCO
-
07:30 (ORD)Chicago O'Hare International Airport12:10 (BNA)Nashville Airport
-
09:05 (BNA)Nashville Airport15:05 (MCO)Orlando International Airport
-
(WN 658)Boeing 737 700 (WN 1504)Boeing 737 800 - 6h 35m (3h 05m)
- BNA Nashville 3h 05m
-
- -
- -
- -
- -
- -
- S
- -
-
07:40 - 09:10MDW - MCI10:45 - 14:30MCI - MCO
-
07:40 (MDW)Chicago Midway Airport10:45 (MCI)Kansas City International Airport
-
09:10 (MCI)Kansas City International Airport14:30 (MCO)Orlando International Airport
-
(WN 2862)Boeing 737 700 (WN 5293)Boeing 737 800 - 5h 50m (1h 35m)
- MCI Kansas City 1h 35m
-
- M
- -
- -
- T
- F
- -
- -
-
08:00 - 09:25MDW - BNA10:40 - 13:35BNA - MCO
-
08:00 (MDW)Chicago Midway Airport10:40 (BNA)Nashville Airport
-
09:25 (BNA)Nashville Airport13:35 (MCO)Orlando International Airport
-
(WN 433)Boeing 737 Max 8 Passenger (WN 2906)Boeing 737 800 - 4h 35m (1h 15m)
- BNA Nashville 1h 15m
-
- M
- -
- -
- T
- F
- -
- -
-
08:05 - 10:50MDW - BWI13:10 - 15:30BWI - MCO
-
08:05 (MDW)Chicago Midway Airport13:10 (BWI)Baltimore Washington International Airport
-
10:50 (BWI)Baltimore Washington International Airport15:30 (MCO)Orlando International Airport
-
(WN 5903)Boeing 737 700 (WN 5233)Boeing 737 Max 8 Passenger - 6h 25m (2h 20m)
- BWI Baltimore 2h 20m
-
- -
- -
- -
- -
- -
- -
- S
-
08:15 - 11:10MDW - BWI12:00 - 14:15BWI - MCO
-
08:15 (MDW)Chicago Midway Airport12:00 (BWI)Baltimore Washington International Airport
-
11:10 (BWI)Baltimore Washington International Airport14:15 (MCO)Orlando International Airport
-
(WN 5903)Boeing 737 800 (WN 2341)Boeing 737 800 - 5h (50m)
- BWI Baltimore 50m
-
- M
- -
- -
- T
- F
- -
- -
-
08:15 - 09:45MDW - MCI12:00 - 15:45MCI - MCO
-
08:15 (MDW)Chicago Midway Airport12:00 (MCI)Kansas City International Airport
-
09:45 (MCI)Kansas City International Airport15:45 (MCO)Orlando International Airport
-
(WN 2862)Boeing 737 700 (WN 5293)Boeing 737 Max 8 Passenger - 6h 30m (2h 15m)
- MCI Kansas City 2h 15m
-
- -
- T
- W
- -
- -
- -
- -
-
08:25 - 10:45MDW - DAL11:30 - 15:05DAL - MCO
-
08:25 (MDW)Chicago Midway Airport11:30 (DAL)Dallas/Fort Worth Love Field Airport
-
10:45 (DAL)Dallas/Fort Worth Love Field Airport15:05 (MCO)Orlando International Airport
-
(WN 5610)Boeing 737 Max 8 Passenger (WN 5633)Boeing 737 800 - 5h 40m (45m)
- DAL Dallas 45m
-
- -
- T
- W
- -
- -
- -
- -
-
08:30 - 10:35MDW - CMH11:35 - 13:55CMH - MCO
-
08:30 (MDW)Chicago Midway Airport11:35 (CMH)Columbus Port Columbus Intl Airport
-
10:35 (CMH)Columbus Port Columbus Intl Airport13:55 (MCO)Orlando International Airport
-
(WN 1222)Boeing 737 700 (WN 820)Boeing 737 700 - 4h 25m (1h)
- CMH Columbus 1h
-
- -
- T
- W
- -
- -
- -
- -
-
08:30 - 10:35MDW - CMH11:20 - 13:40CMH - MCO
-
08:30 (MDW)Chicago Midway Airport11:20 (CMH)Columbus Port Columbus Intl Airport
-
10:35 (CMH)Columbus Port Columbus Intl Airport13:40 (MCO)Orlando International Airport
-
(WN 1222)Boeing 737 800 (WN 820)Boeing 737 800 - 4h 10m (45m)
- CMH Columbus 45m
-
- M
- -
- -
- T
- F
- -
- -
-
08:35 - 11:30MDW - BWI13:30 - 15:50BWI - MCO
-
08:35 (MDW)Chicago Midway Airport13:30 (BWI)Baltimore Washington International Airport
-
11:30 (BWI)Baltimore Washington International Airport15:50 (MCO)Orlando International Airport
-
(WN 5903)Boeing 737 700 (WN 3480)Boeing 737 Max 8 Passenger - 6h 15m (2h)
- BWI Baltimore 2h
-
- -
- T
- W
- -
- -
- -
- -
-
08:45 - 10:55MDW - CLE11:40 - 14:05CLE - MCO
-
08:45 (MDW)Chicago Midway Airport11:40 (CLE)Cleveland Hopkins International Airport
-
10:55 (CLE)Cleveland Hopkins International Airport14:05 (MCO)Orlando International Airport
-
(WN 402)Boeing 737 800 (WN 1171)Boeing 737 800 - 4h 20m (45m)
- CLE Cleveland 45m
-
- -
- -
- -
- -
- -
- -
- S
-
08:55 - 11:30MDW - HOU12:35 - 16:00HOU - MCO
-
08:55 (MDW)Chicago Midway Airport12:35 (HOU)Houston Hobby Airport
-
11:30 (HOU)Houston Hobby Airport16:00 (MCO)Orlando International Airport
-
(WN 3596)Boeing 737 Max 8 Passenger (WN 931)Boeing 737 800 - 6h 05m (1h 05m)
- HOU Houston 1h 05m
-
- -
- T
- W
- -
- -
- -
- -
-
09:00 - 11:20MDW - DAL12:50 - 16:25DAL - MCO
-
09:00 (MDW)Chicago Midway Airport12:50 (DAL)Dallas/Fort Worth Love Field Airport
-
11:20 (DAL)Dallas/Fort Worth Love Field Airport16:25 (MCO)Orlando International Airport
-
(WN 5610)Boeing 737 800 (WN 2932)Boeing 737 800 - 6h 25m (1h 30m)
- DAL Dallas 1h 30m
-
- M
- -
- -
- T
- F
- -
- -
-
09:10 - 12:00MDW - DCA13:00 - 15:25DCA - MCO
-
09:10 (MDW)Chicago Midway Airport13:00 (DCA)Washington Ronald Reagan National Airport
-
12:00 (DCA)Washington Ronald Reagan National Airport15:25 (MCO)Orlando International Airport
-
(WN 1698)Boeing 737 Max 8 Passenger (WN 1843)Boeing 737 700 - 5h 15m (1h)
- DCA Washington 1h
-
- M
- -
- -
- T
- F
- -
- -
-
09:15 - 12:05MDW - ATL13:20 - 14:45ATL - MCO
-
09:15 (MDW)Chicago Midway Airport13:20 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
12:05 (ATL)Atlanta Hartsfield-Jackson Intl Airport14:45 (MCO)Orlando International Airport
-
(WN 2174)Boeing 737 Max 8 Passenger (WN 3293)Boeing 737 800 - 4h 30m (1h 15m)
- ATL Atlanta 1h 15m
-
- -
- T
- W
- -
- -
- -
- -
-
09:15 - 11:05MDW - GRR13:20 - 16:05GRR - MCO
-
09:15 (MDW)Chicago Midway Airport13:20 (GRR)Grand Rapids Airport
-
11:05 (GRR)Grand Rapids Airport16:05 (MCO)Orlando International Airport
-
(WN 2540)Boeing 737 700 (WN 1756)Boeing 737 800 - 5h 50m (2h 15m)
- GRR 2h 15m
-
- -
- -
- -
- -
- -
- S
- -
-
09:35 - 12:25MDW - DCA13:05 - 15:30DCA - MCO
-
09:35 (MDW)Chicago Midway Airport13:05 (DCA)Washington Ronald Reagan National Airport
-
12:25 (DCA)Washington Ronald Reagan National Airport15:30 (MCO)Orlando International Airport
-
(WN 1698)Boeing 737 700 (WN 1843)Boeing 737 700 - 4h 55m (40m)
- DCA Washington 40m
-
- -
- T
- W
- -
- -
- -
- -
-
09:35 - 12:20MDW - IAH13:15 - 16:35IAH - MCO
-
09:35 (MDW)Chicago Midway Airport13:15 (IAH)Houston George Bush Intercontinental Airport
-
12:20 (IAH)Houston George Bush Intercontinental Airport16:35 (MCO)Orlando International Airport
-
(WN 833)Boeing 737 Max 8 Passenger (WN 324)Boeing 737 Max 8 Passenger - 6h (55m)
- IAH 55m
-
- -
- -
- -
- -
- -
- -
- S
-
09:40 - 12:15MDW - HOU13:00 - 16:25HOU - MCO
-
09:40 (MDW)Chicago Midway Airport13:00 (HOU)Houston Hobby Airport
-
12:15 (HOU)Houston Hobby Airport16:25 (MCO)Orlando International Airport
-
(WN 3596)Boeing 737 Max 8 Passenger (WN 931)Boeing 737 800 - 5h 45m (45m)
- HOU Houston 45m
-
- -
- -
- -
- -
- -
- S
- -
-
09:40 - 10:50MDW - STL13:15 - 16:40STL - MCO
-
09:40 (MDW)Chicago Midway Airport13:15 (STL)St Louis Lambert Intl Airport
-
10:50 (STL)St Louis Lambert Intl Airport16:40 (MCO)Orlando International Airport
-
(WN 5846)Boeing 737 Max 8 Passenger (WN 4658)Boeing 737 800 - 6h (2h 25m)
- STL Saint Louis 2h 25m
-
- M
- -
- -
- T
- F
- -
- -
-
09:45 - 12:25MDW - AUS13:35 - 17:15AUS - MCO
-
09:45 (MDW)Chicago Midway Airport13:35 (AUS)Austin-Bergstrom International Airport
-
12:25 (AUS)Austin-Bergstrom International Airport17:15 (MCO)Orlando International Airport
-
(WN 6041)Boeing 737 Max 8 Passenger (WN 2897)Boeing 737 700 - 6h 30m (1h 10m)
- AUS Austin 1h 10m
-
- -
- T
- W
- -
- -
- -
- -
-
09:45 - 11:50MDW - OKC13:20 - 17:05OKC - MCO
-
09:45 (MDW)Chicago Midway Airport13:20 (OKC)Oklahoma City Will Rogers Airport
-
11:50 (OKC)Oklahoma City Will Rogers Airport17:05 (MCO)Orlando International Airport
-
(WN 1670)Boeing 737 700 (WN 2849)Boeing 737 Max 8 Passenger - 6h 20m (1h 30m)
- OKC Oklahoma City 1h 30m
-
- M
- -
- -
- T
- F
- -
- -
-
09:45 - 12:35MDW - DCA13:10 - 15:30DCA - MCO
-
09:45 (MDW)Chicago Midway Airport13:10 (DCA)Washington Ronald Reagan National Airport
-
12:35 (DCA)Washington Ronald Reagan National Airport15:30 (MCO)Orlando International Airport
-
(WN 1698)Boeing 737 700 (WN 1843)Boeing 737 800 - 4h 45m (35m)
- DCA Washington 35m
-
- -
- -
- -
- -
- -
- -
- S
-
09:50 - 11:00MDW - STL12:50 - 16:10STL - MCO
-
09:50 (MDW)Chicago Midway Airport12:50 (STL)St Louis Lambert Intl Airport
-
11:00 (STL)St Louis Lambert Intl Airport16:10 (MCO)Orlando International Airport
-
(WN 5846)Boeing 737 Max 8 Passenger (WN 349)Boeing 737 700 - 5h 20m (1h 50m)
- STL Saint Louis 1h 50m
-
- -
- T
- W
- -
- -
- -
- -
-
10:00 - 12:15MDW - DAL13:40 - 17:20DAL - MCO
-
10:00 (MDW)Chicago Midway Airport13:40 (DAL)Dallas/Fort Worth Love Field Airport
-
12:15 (DAL)Dallas/Fort Worth Love Field Airport17:20 (MCO)Orlando International Airport
-
(WN 1207)Boeing 737 800 (WN 2932)Boeing 737 800 - 6h 20m (1h 25m)
- DAL Dallas 1h 25m
-
- -
- T
- W
- -
- -
- -
- -
-
10:05 - 11:15MDW - STL12:50 - 16:10STL - MCO
-
10:05 (MDW)Chicago Midway Airport12:50 (STL)St Louis Lambert Intl Airport
-
11:15 (STL)St Louis Lambert Intl Airport16:10 (MCO)Orlando International Airport
-
(WN 3487)Boeing 737 800 (WN 349)Boeing 737 800 - 5h 05m (1h 35m)
- STL Saint Louis 1h 35m
-
- -
- -
- -
- -
- -
- -
- S
-
10:05 - 11:30MDW - BNA12:10 - 15:05BNA - MCO
-
10:05 (MDW)Chicago Midway Airport12:10 (BNA)Nashville Airport
-
11:30 (BNA)Nashville Airport15:05 (MCO)Orlando International Airport
-
(WN 433)Boeing 737 800 (WN 1504)Boeing 737 800 - 4h (40m)
- BNA Nashville 40m
-
- -
- -
- -
- -
- -
- S
- -
-
10:10 - 12:25MDW - MSY13:05 - 15:50MSY - MCO
-
10:10 (MDW)Chicago Midway Airport13:05 (MSY)New Orleans Louis Armstrong Intl Airport
-
12:25 (MSY)New Orleans Louis Armstrong Intl Airport15:50 (MCO)Orlando International Airport
-
(WN 3389)Boeing 737 800 (WN 1255)Boeing 737 Max 8 Passenger - 4h 40m (40m)
- MSY New Orleans 40m
-
- -
- -
- -
- -
- -
- -
- S
-
10:15 - 12:25MDW - CMH13:20 - 15:35CMH - MCO
-
10:15 (MDW)Chicago Midway Airport13:20 (CMH)Columbus Port Columbus Intl Airport
-
12:25 (CMH)Columbus Port Columbus Intl Airport15:35 (MCO)Orlando International Airport
-
(WN 1223)Boeing 737 700 (WN 527)Boeing 737 700 - 4h 20m (55m)
- CMH Columbus 55m
-
- -
- -
- -
- -
- -
- S
- -
-
10:20 - 13:00MDW - IAH14:20 - 17:40IAH - MCO
-
10:20 (MDW)Chicago Midway Airport14:20 (IAH)Houston George Bush Intercontinental Airport
-
13:00 (IAH)Houston George Bush Intercontinental Airport17:40 (MCO)Orlando International Airport
-
(WN 1764)Boeing 737 800 (WN 2975)Boeing 737 Max 8 Passenger - 6h 20m (1h 20m)
- IAH 1h 20m
-
- -
- T
- W
- -
- -
- -
- -
-
10:25 - 13:05MDW - IAH14:10 - 17:30IAH - MCO
-
10:25 (MDW)Chicago Midway Airport14:10 (IAH)Houston George Bush Intercontinental Airport
-
13:05 (IAH)Houston George Bush Intercontinental Airport17:30 (MCO)Orlando International Airport
-
(WN 1764)Boeing 737 800 (WN 2975)Boeing 737 700 - 6h 05m (1h 05m)
- IAH 1h 05m
-
- M
- -
- -
- T
- F
- -
- -
-
10:35 - 13:20MDW - BWI15:45 - 18:05BWI - MCO
-
10:35 (MDW)Chicago Midway Airport15:45 (BWI)Baltimore Washington International Airport
-
13:20 (BWI)Baltimore Washington International Airport18:05 (MCO)Orlando International Airport
-
(WN 575)Boeing 737 Max 8 Passenger (WN 5438)Boeing 737 Max 8 Passenger - 6h 30m (2h 25m)
- BWI Baltimore 2h 25m
-
- -
- T
- W
- -
- -
- -
- -
-
10:35 - 13:20MDW - BWI14:25 - 16:45BWI - MCO
-
10:35 (MDW)Chicago Midway Airport14:25 (BWI)Baltimore Washington International Airport
-
13:20 (BWI)Baltimore Washington International Airport16:45 (MCO)Orlando International Airport
-
(WN 575)Boeing 737 Max 8 Passenger (WN 5233)Boeing 737 Max 8 Passenger - 5h 10m (1h 05m)
- BWI Baltimore 1h 05m
-
- -
- T
- W
- -
- -
- -
- -
-
11:00 - 13:10MDW - CMH16:25 - 18:35CMH - MCO
-
11:00 (MDW)Chicago Midway Airport16:25 (CMH)Columbus Port Columbus Intl Airport
-
13:10 (CMH)Columbus Port Columbus Intl Airport18:35 (MCO)Orlando International Airport
-
(WN 1223)Boeing 737 700 (WN 527)Boeing 737 800 - 6h 35m (3h 15m)
- CMH Columbus 3h 15m
-
- M
- -
- -
- T
- F
- -
- -
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What’s the fastest flight time from Chicago to Orlando?
The fastest flight time for direct flights from Chicago to Orlando is 2 hours 30 minutes. Check latest flight schedules & prices on Wego.
What’s the most popular airline flying from Chicago to Orlando?
The most popular airline flying from Chicago to Orlando is American Airlines. Find the latest flight deals on Wego.
How far is Orlando from Chicago?
The flight distance between Chicago and Orlando is 1587km. Check all available flights on Wego.
When is the earliest and latest flight of the day?
The earliest flight of the day departs at 05:30. The last flight of the day departs at 19:47. See the full list of flight times on Wego.
How many airlines offer direct flights from Chicago to Orlando?
There are 4 airlines that offer direct flights from Chicago to Orlando. Find out the list of airlines on Wego.
All Airports in Chicago
Popular Airlines flying from Chicago to Orlando
Popular destinations from Orlando
Popular destinations from Chicago
Popular Hotels in Orlando
- Element Orlando International Drive
- Hyatt House Orlando Airport
- Hyatt Regency Grand Cypress
- Courtyard by Marriott Lake Buena Vista at Vista Centre
- Westgate Leisure Resort
- Aloft Orlando International Drive
- Hilton Orlando
- Hampton Inn Orlando International Drive Convention Center
- SpringHill Suites Orlando Lake Buena Vista in the Marriott Village
- Rosen Centre Hotel