Fare Guide
Estimated lowest fares found within 7 days
Cheapest Airline
The cheapest airline(s) flying from Orlando to Chicago is Spirit Airlines.
Cheapest Month
May
Travel Period: May 2024 - April 2025
The cheapest month(s) to fly from Orlando to Chicago 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
Thursday
The cheapest day(s) of the week to fly from Orlando to Chicago is Thursday.
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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 Orlando to Chicago 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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Total Duration
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Availability
- M
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- S
- S
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20:40 - 22:25MCO - MDW
-
20:40 (MCO)Orlando International Airport
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22:25 (MDW)Chicago Midway Airport
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(WN 1328)Boeing 737 700 - 2h 45m
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
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21:20 - 23:10MCO - MDW
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21:20 (MCO)Orlando International Airport
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23:10 (MDW)Chicago Midway Airport
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(WN 1328)Boeing 737 800 - 2h 50m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 800
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21:30 - 23:20MCO - MDW
-
21:30 (MCO)Orlando International Airport
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23:20 (MDW)Chicago Midway Airport
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(WN 1328)Boeing 737 Max 8 Passenger - 2h 50m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
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21:45 - 23:30MCO - MDW
-
21:45 (MCO)Orlando International Airport
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23:30 (MDW)Chicago Midway Airport
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(WN 1328)Boeing 737 Max 8 Passenger - 2h 45m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
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06:25 - 08:15MCO - MDW
-
06:25 (MCO)Orlando International Airport
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08:15 (MDW)Chicago Midway Airport
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(WN 6125)Boeing 737 800 - 2h 50m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
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06:45 - 08:45MCO - ORD
-
06:45 (MCO)Orlando International Airport
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08:45 (ORD)Chicago O'Hare International Airport
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(WN 3648)Boeing 737 700 - 3h
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
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06:55 - 09:55MCO - MDW
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06:55 (MCO)Orlando International Airport
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09:55 (MDW)Chicago Midway Airport
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(WN 5590)Boeing 737 700 - 4h
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
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07:02 - 09:15MCO - ORD
-
07:02 (MCO)Orlando International Airport
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09:15 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 557)Boeing 737 800 - 3h 13m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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07:15 - 09:25MCO - ORD
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07:15 (MCO)Orlando International Airport
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09:25 (ORD)Chicago O'Hare International Airport
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(WN 3648)Boeing 737 700 - 3h 10m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
-
07:15 - 09:05MCO - MDW
-
07:15 (MCO)Orlando International Airport
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09:05 (MDW)Chicago Midway Airport
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(WN 5117)Boeing 737 800 - 2h 50m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 800
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07:30 - 09:20MCO - MDW
-
07:30 (MCO)Orlando International Airport
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09:20 (MDW)Chicago Midway Airport
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(WN 5117)Boeing 737 700 - 2h 50m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
07:40 - 09:30MCO - MDW
-
07:40 (MCO)Orlando International Airport
-
09:30 (MDW)Chicago Midway Airport
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(WN 5117)Boeing 737 700 - 2h 50m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
-
07:45 - 09:45MCO - ORD
-
07:45 (MCO)Orlando International Airport
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09:45 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1957)Boeing 737 900 - 3h
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 900
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07:55 - 09:45MCO - MDW
-
07:55 (MCO)Orlando International Airport
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09:45 (MDW)Chicago Midway Airport
-
(WN 5117)Boeing 737 700 - 2h 50m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
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09:10 - 10:55MCO - MDW
-
09:10 (MCO)Orlando International Airport
-
10:55 (MDW)Chicago Midway Airport
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(WN 3156)Boeing 737 700 - 2h 45m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
09:30 - 11:30MCO - ORD
-
09:30 (MCO)Orlando International Airport
-
11:30 (ORD)Chicago O'Hare International Airport
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(WN 934)Boeing 737 800 - 3h
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 800
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09:40 - 11:25MCO - MDW
-
09:40 (MCO)Orlando International Airport
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11:25 (MDW)Chicago Midway Airport
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(WN 3156)Boeing 737 800 - 2h 45m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
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09:45 - 11:30MCO - MDW
-
09:45 (MCO)Orlando International Airport
-
11:30 (MDW)Chicago Midway Airport
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(WN 3156)Boeing 737 800 - 2h 45m
- Direct
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- -
- T
- W
- -
- -
- S
- -
- Boeing 737 800
-
09:50 - 11:53MCO - ORD
-
09:50 (MCO)Orlando International Airport
-
11:53 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1941)Airbus A321 Neo - 3h 03m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus A321 Neo
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10:35 - 12:25MCO - MDW
-
10:35 (MCO)Orlando International Airport
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12:25 (MDW)Chicago Midway Airport
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(WN 6125)Boeing 737 800 - 2h 50m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 800
-
10:45 - 14:00MCO - MDW
-
10:45 (MCO)Orlando International Airport
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14:00 (MDW)Chicago Midway Airport
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(WN 2557)Boeing 737 700 - 4h 15m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
11:00 - 14:20MCO - MDW
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11:00 (MCO)Orlando International Airport
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14:20 (MDW)Chicago Midway Airport
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(WN 3207)Boeing 737 700 - 4h 20m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
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11:00 - 13:00MCO - ORD
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11:00 (MCO)Orlando International Airport
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13:00 (ORD)Chicago O'Hare International Airport
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(WN 934)Boeing 737 800 - 3h
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
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11:05 - 14:05MCO - MDW
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11:05 (MCO)Orlando International Airport
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14:05 (MDW)Chicago Midway Airport
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(WN 6025)Boeing 737 700 - 4h
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
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11:15 - 13:15MCO - ORD
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11:15 (MCO)Orlando International Airport
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13:15 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 2421)Boeing 737 800 - 3h
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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11:15 - 13:00MCO - MDW
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11:15 (MCO)Orlando International Airport
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13:00 (MDW)Chicago Midway Airport
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(WN 6125)Boeing 737 Max 8 Passenger - 2h 45m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 Max 8 Passenger
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11:55 - 14:00MCO - ORD
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11:55 (MCO)Orlando International Airport
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14:00 (ORD)Chicago O'Hare International Airport
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(WN 3648)Boeing 737 800 - 3h 05m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 800
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12:20 - 14:24MCO - ORD
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12:20 (MCO)Orlando International Airport
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14:24 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 2475)Boeing 737 900 - 3h 04m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 900
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12:20 - 14:25MCO - ORD
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12:20 (MCO)Orlando International Airport
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14:25 (ORD)Chicago O'Hare International Airport
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(WN 934)Boeing 737 800 - 3h 05m
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Boeing 737 800
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12:40 - 14:25MCO - MDW
-
12:40 (MCO)Orlando International Airport
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14:25 (MDW)Chicago Midway Airport
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(WN 3157)Boeing 737 Max 8 Passenger - 2h 45m
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Boeing 737 Max 8 Passenger
-
12:45 - 15:45MCO - MDW
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12:45 (MCO)Orlando International Airport
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15:45 (MDW)Chicago Midway Airport
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(WN 1219)Boeing 737 700 - 4h
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
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12:50 - 14:35MCO - MDW
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12:50 (MCO)Orlando International Airport
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14:35 (MDW)Chicago Midway Airport
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(WN 3157)Boeing 737 800 - 2h 45m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
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13:05 - 16:25MCO - MDW
-
13:05 (MCO)Orlando International Airport
-
16:25 (MDW)Chicago Midway Airport
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(WN 3207)Boeing 737 700 - 4h 20m
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
-
13:05 - 14:50MCO - MDW
-
13:05 (MCO)Orlando International Airport
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14:50 (MDW)Chicago Midway Airport
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(WN 3157)Boeing 737 Max 8 Passenger - 2h 45m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 Max 8 Passenger
-
13:25 - 15:15MCO - MDW
-
13:25 (MCO)Orlando International Airport
-
15:15 (MDW)Chicago Midway Airport
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(WN 3157)Boeing 737 800 - 2h 50m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 800
-
14:06 - 16:10MCO - ORD
-
14:06 (MCO)Orlando International Airport
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16:10 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 2119)Boeing 737 800 - 3h 04m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
14:28 - 16:27MCO - ORD
-
14:28 (MCO)Orlando International Airport
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16:27 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 2419)Boeing 737 800 - 2h 59m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
14:30 - 17:35MCO - MDW
-
14:30 (MCO)Orlando International Airport
-
17:35 (MDW)Chicago Midway Airport
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(WN 5489)Boeing 737 700 - 4h 05m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
14:40 - 16:45MCO - ORD
-
14:40 (MCO)Orlando International Airport
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16:45 (ORD)Chicago O'Hare International Airport
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(WN 3650)Boeing 737 Max 8 Passenger - 3h 05m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
-
14:40 - 16:45MCO - ORD
-
14:40 (MCO)Orlando International Airport
-
16:45 (ORD)Chicago O'Hare International Airport
-
(WN 3650)Boeing 737 700 - 3h 05m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
-
14:45 - 16:30MCO - MDW
-
14:45 (MCO)Orlando International Airport
-
16:30 (MDW)Chicago Midway Airport
-
(WN 3313)Boeing 737 700 - 2h 45m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
-
14:55 - 18:30MCO - MDW
-
14:55 (MCO)Orlando International Airport
-
18:30 (MDW)Chicago Midway Airport
-
(WN 2282)Boeing 737 700 - 4h 35m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
-
15:25 - 18:20MCO - MDW
-
15:25 (MCO)Orlando International Airport
-
18:20 (MDW)Chicago Midway Airport
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(WN 2686)Boeing 737 700 - 3h 55m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
-
15:35 - 17:25MCO - MDW
-
15:35 (MCO)Orlando International Airport
-
17:25 (MDW)Chicago Midway Airport
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(WN 3313)Boeing 737 800 - 2h 50m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 800
-
15:50 - 17:40MCO - MDW
-
15:50 (MCO)Orlando International Airport
-
17:40 (MDW)Chicago Midway Airport
-
(WN 3313)Boeing 737 800 - 2h 50m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 800
-
16:29 - 18:30MCO - ORD
-
16:29 (MCO)Orlando International Airport
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18:30 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 1828)Boeing 737 900 - 3h 01m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 900
-
16:55 - 21:25MCO - MDW
-
16:55 (MCO)Orlando International Airport
-
21:25 (MDW)Chicago Midway Airport
-
(WN 3194)Boeing 737 800 - 5h 30m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 800
-
17:00 - 18:55MCO - MDW
-
17:00 (MCO)Orlando International Airport
-
18:55 (MDW)Chicago Midway Airport
-
(WN 998)Boeing 737 800 - 2h 55m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 800
-
17:08 - 18:57SFB - RFD
-
17:08 (SFB)Orlando Sanford International Airport
-
18:57 (RFD)Chicago Rockford Airport
-
Allegiant Air LLC (G4 2815)Airbus - 2h 49m
- Direct
-
- M
- -
- -
- -
- F
- -
- -
- Airbus
-
17:15 - 20:15MCO - MDW
-
17:15 (MCO)Orlando International Airport
-
20:15 (MDW)Chicago Midway Airport
-
(WN 3768)Boeing 737 700 - 4h
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
17:36 - 19:40MCO - ORD
-
17:36 (MCO)Orlando International Airport
-
19:40 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 1782)Boeing 737 800 - 3h 04m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
18:00 - 19:50MCO - MDW
-
18:00 (MCO)Orlando International Airport
-
19:50 (MDW)Chicago Midway Airport
-
(WN 3158)Boeing 737 Max 8 Passenger - 2h 50m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
-
18:05 - 20:00MCO - MDW
-
18:05 (MCO)Orlando International Airport
-
20:00 (MDW)Chicago Midway Airport
-
(WN 3158)Boeing 737 700 - 2h 55m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
-
18:20 - 22:10MCO - MDW
-
18:20 (MCO)Orlando International Airport
-
22:10 (MDW)Chicago Midway Airport
-
(WN 2302)Boeing 737 700 - 4h 50m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
-
18:30 - 20:20MCO - MDW
-
18:30 (MCO)Orlando International Airport
-
20:20 (MDW)Chicago Midway Airport
-
(WN 3158)Boeing 737 Max 8 Passenger - 2h 50m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 Max 8 Passenger
-
18:50 - 20:55MCO - ORD
-
18:50 (MCO)Orlando International Airport
-
20:55 (ORD)Chicago O'Hare International Airport
-
(WN 3650)Boeing 737 Max 8 Passenger - 3h 05m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
-
18:55 - 20:50MCO - MDW
-
18:55 (MCO)Orlando International Airport
-
20:50 (MDW)Chicago Midway Airport
-
(WN 3159)Boeing 737 700 - 2h 55m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
19:20 - 21:10MCO - MDW
-
19:20 (MCO)Orlando International Airport
-
21:10 (MDW)Chicago Midway Airport
-
(WN 3159)Boeing 737 800 - 2h 50m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
Connecting Flights
-
20:15 - 21:55MCO - STL22:50 - 23:55STL - MDW
-
20:15 (MCO)Orlando International Airport22:50 (STL)St Louis Lambert Intl Airport
-
21:55 (STL)St Louis Lambert Intl Airport23:55 (MDW)Chicago Midway Airport
-
(WN 4942)Boeing 737 800 (WN 3244)Boeing 737 800 - 4h 40m (55m)
- STL Saint Louis 55m
-
- -
- -
- -
- -
- -
- -
- S
-
06:05 - 08:05MCO - MCI10:20 - 11:45MCI - MDW
-
06:05 (MCO)Orlando International Airport10:20 (MCI)Kansas City International Airport
-
08:05 (MCI)Kansas City International Airport11:45 (MDW)Chicago Midway Airport
-
(WN 853)Boeing 737 700 (WN 4988)Boeing 737 700 - 6h 40m (2h 15m)
- MCI Kansas City 2h 15m
-
- -
- T
- W
- -
- -
- -
- -
-
06:10 - 07:45MCO - ATL09:50 - 10:45ATL - MDW
-
06:10 (MCO)Orlando International Airport09:50 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
07:45 (ATL)Atlanta Hartsfield-Jackson Intl Airport10:45 (MDW)Chicago Midway Airport
-
(WN 263)Boeing 737 800 (WN 5518)Boeing 737 Max 8 Passenger - 5h 35m (2h 05m)
- ATL Atlanta 2h 05m
-
- -
- -
- -
- -
- -
- -
- S
-
06:15 - 07:50MCO - ATL10:40 - 11:35ATL - MDW
-
06:15 (MCO)Orlando International Airport10:40 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
07:50 (ATL)Atlanta Hartsfield-Jackson Intl Airport11:35 (MDW)Chicago Midway Airport
-
(WN 263)Boeing 737 Max 8 Passenger (WN 5518)Boeing 737 Max 8 Passenger - 6h 20m (2h 50m)
- ATL Atlanta 2h 50m
-
- -
- -
- -
- -
- -
- S
- -
-
06:20 - 08:10MCO - AUS09:05 - 11:35AUS - MDW
-
06:20 (MCO)Orlando International Airport09:05 (AUS)Austin-Bergstrom International Airport
-
08:10 (AUS)Austin-Bergstrom International Airport11:35 (MDW)Chicago Midway Airport
-
(WN 6146)Boeing 737 700 (WN 3033)Boeing 737 700 - 6h 15m (55m)
- AUS Austin 55m
-
- -
- -
- -
- -
- -
- -
- S
-
06:20 - 08:10MCO - DAL09:10 - 11:30DAL - ORD
-
06:20 (MCO)Orlando International Airport09:10 (DAL)Dallas/Fort Worth Love Field Airport
-
08:10 (DAL)Dallas/Fort Worth Love Field Airport11:30 (ORD)Chicago O'Hare International Airport
-
(WN 1389)Boeing 737 700 (WN 4903)Boeing 737 800 - 6h 10m (1h)
- DAL Dallas 1h
-
- M
- -
- -
- T
- F
- -
- -
-
06:45 - 07:45MCO - BNA09:45 - 11:15BNA - MDW
-
06:45 (MCO)Orlando International Airport09:45 (BNA)Nashville Airport
-
07:45 (BNA)Nashville Airport11:15 (MDW)Chicago Midway Airport
-
(WN 3287)Boeing 737 700 (WN 2119)Boeing 737 700 - 5h 30m (2h)
- BNA Nashville 2h
-
- -
- T
- W
- -
- -
- -
- -
-
06:45 - 07:45MCO - BNA09:00 - 10:45BNA - ORD
-
06:45 (MCO)Orlando International Airport09:00 (BNA)Nashville Airport
-
07:45 (BNA)Nashville Airport10:45 (ORD)Chicago O'Hare International Airport
-
(WN 3287)Boeing 737 700 (WN 510)Boeing 737 700 - 5h (1h 15m)
- BNA Nashville 1h 15m
-
- -
- T
- W
- -
- -
- -
- -
-
07:00 - 09:20MCO - CMH10:50 - 11:05CMH - MDW
-
07:00 (MCO)Orlando International Airport10:50 (CMH)Columbus Port Columbus Intl Airport
-
09:20 (CMH)Columbus Port Columbus Intl Airport11:05 (MDW)Chicago Midway Airport
-
(WN 1218)Boeing 737 700 (WN 5203)Boeing 737 700 - 5h 05m (1h 30m)
- CMH Columbus 1h 30m
-
- M
- -
- -
- T
- F
- -
- -
-
07:05 - 09:20MCO - CMH11:10 - 11:25CMH - MDW
-
07:05 (MCO)Orlando International Airport11:10 (CMH)Columbus Port Columbus Intl Airport
-
09:20 (CMH)Columbus Port Columbus Intl Airport11:25 (MDW)Chicago Midway Airport
-
(WN 1218)Boeing 737 700 (WN 3279)Boeing 737 700 - 5h 20m (1h 50m)
- CMH Columbus 1h 50m
-
- -
- T
- W
- -
- -
- -
- -
-
07:05 - 09:30MCO - PIT11:25 - 11:50PIT - MDW
-
07:05 (MCO)Orlando International Airport11:25 (PIT)Pittsburgh International Airport
-
09:30 (PIT)Pittsburgh International Airport11:50 (MDW)Chicago Midway Airport
-
(WN 3930)Boeing 737 Max 8 Passenger (WN 472)Boeing 737 700 - 5h 45m (1h 55m)
- PIT Pittsburgh 1h 55m
-
- M
- -
- -
- T
- F
- -
- -
-
07:10 - 08:50MCO - STL10:00 - 11:05STL - MDW
-
07:10 (MCO)Orlando International Airport10:00 (STL)St Louis Lambert Intl Airport
-
08:50 (STL)St Louis Lambert Intl Airport11:05 (MDW)Chicago Midway Airport
-
(WN 4676)Boeing 737 700 (WN 5866)Boeing 737 Max 8 Passenger - 4h 55m (1h 10m)
- STL Saint Louis 1h 10m
-
- -
- -
- -
- -
- -
- -
- S
-
07:20 - 09:15MCO - DAL11:00 - 13:10DAL - MDW
-
07:20 (MCO)Orlando International Airport11:00 (DAL)Dallas/Fort Worth Love Field Airport
-
09:15 (DAL)Dallas/Fort Worth Love Field Airport13:10 (MDW)Chicago Midway Airport
-
(WN 365)Boeing 737 700 (WN 2148)Boeing 737 Max 8 Passenger - 6h 50m (1h 45m)
- DAL Dallas 1h 45m
-
- M
- -
- -
- T
- F
- -
- -
-
07:25 - 09:45MCO - BWI11:55 - 13:05BWI - ORD
-
07:25 (MCO)Orlando International Airport11:55 (BWI)Baltimore Washington International Airport
-
09:45 (BWI)Baltimore Washington International Airport13:05 (ORD)Chicago O'Hare International Airport
-
(WN 350)Boeing 737 Max 8 Passenger (WN 1090)Boeing 737 700 - 6h 40m (2h 10m)
- BWI Baltimore 2h 10m
-
- M
- -
- -
- T
- F
- -
- -
-
07:50 - 09:50MCO - MCI12:15 - 13:40MCI - MDW
-
07:50 (MCO)Orlando International Airport12:15 (MCI)Kansas City International Airport
-
09:50 (MCI)Kansas City International Airport13:40 (MDW)Chicago Midway Airport
-
(WN 853)Boeing 737 800 (WN 5424)Boeing 737 700 - 6h 50m (2h 25m)
- MCI Kansas City 2h 25m
-
- M
- -
- -
- T
- F
- -
- -
-
07:50 - 09:50MCO - MCI10:40 - 12:05MCI - MDW
-
07:50 (MCO)Orlando International Airport10:40 (MCI)Kansas City International Airport
-
09:50 (MCI)Kansas City International Airport12:05 (MDW)Chicago Midway Airport
-
(WN 853)Boeing 737 800 (WN 4988)Boeing 737 700 - 5h 15m (50m)
- MCI Kansas City 50m
-
- M
- -
- -
- T
- F
- -
- -
-
08:10 - 09:10MCO - BNA10:15 - 12:00BNA - ORD
-
08:10 (MCO)Orlando International Airport10:15 (BNA)Nashville Airport
-
09:10 (BNA)Nashville Airport12:00 (ORD)Chicago O'Hare International Airport
-
(WN 3287)Boeing 737 Max 8 Passenger (WN 3624)Boeing 737 700 - 4h 50m (1h 05m)
- BNA Nashville 1h 05m
-
- -
- -
- -
- -
- -
- S
- -
-
08:15 - 10:30MCO - BWI11:55 - 13:05BWI - ORD
-
08:15 (MCO)Orlando International Airport11:55 (BWI)Baltimore Washington International Airport
-
10:30 (BWI)Baltimore Washington International Airport13:05 (ORD)Chicago O'Hare International Airport
-
(WN 5078)Boeing 737 700 (WN 1090)Boeing 737 700 - 5h 50m (1h 25m)
- BWI Baltimore 1h 25m
-
- M
- -
- -
- T
- F
- -
- -
-
08:20 - 09:50MCO - STL12:20 - 13:25STL - MDW
-
08:20 (MCO)Orlando International Airport12:20 (STL)St Louis Lambert Intl Airport
-
09:50 (STL)St Louis Lambert Intl Airport13:25 (MDW)Chicago Midway Airport
-
(WN 4676)Boeing 737 700 (WN 1268)Boeing 737 700 - 6h 05m (2h 30m)
- STL Saint Louis 2h 30m
-
- -
- T
- W
- -
- -
- -
- -
-
08:25 - 09:35MCO - FLL10:25 - 12:35FLL - MDW
-
08:25 (MCO)Orlando International Airport10:25 (FLL)Fort Lauderdale/Hollywood Intl Airport
-
09:35 (FLL)Fort Lauderdale/Hollywood Intl Airport12:35 (MDW)Chicago Midway Airport
-
(WN 5290)Boeing 737 Max 8 Passenger (WN 3684)Boeing 737 800 - 5h 10m (50m)
- FLL Miami 50m
-
- -
- -
- -
- -
- -
- -
- S
-
08:35 - 09:25MCO - MSY10:10 - 12:30MSY - MDW
-
08:35 (MCO)Orlando International Airport10:10 (MSY)New Orleans Louis Armstrong Intl Airport
-
09:25 (MSY)New Orleans Louis Armstrong Intl Airport12:30 (MDW)Chicago Midway Airport
-
(WN 5382)Boeing 737 700 (WN 1704)Boeing 737 700 - 4h 55m (45m)
- MSY New Orleans 45m
-
- -
- -
- -
- -
- -
- S
- -
-
08:40 - 10:35MCO - MCI11:15 - 12:35MCI - MDW
-
08:40 (MCO)Orlando International Airport11:15 (MCI)Kansas City International Airport
-
10:35 (MCI)Kansas City International Airport12:35 (MDW)Chicago Midway Airport
-
(WN 853)Boeing 737 700 (WN 4988)Boeing 737 700 - 4h 55m (40m)
- MCI Kansas City 40m
-
- -
- -
- -
- -
- -
- S
- -
-
08:45 - 09:50MCO - FLL10:55 - 13:00FLL - MDW
-
08:45 (MCO)Orlando International Airport10:55 (FLL)Fort Lauderdale/Hollywood Intl Airport
-
09:50 (FLL)Fort Lauderdale/Hollywood Intl Airport13:00 (MDW)Chicago Midway Airport
-
(WN 5290)Boeing 737 800 (WN 3684)Boeing 737 800 - 5h 15m (1h 05m)
- FLL Miami 1h 05m
-
- -
- -
- -
- -
- -
- S
- -
-
08:45 - 09:45MCO - BNA12:30 - 14:15BNA - ORD
-
08:45 (MCO)Orlando International Airport12:30 (BNA)Nashville Airport
-
09:45 (BNA)Nashville Airport14:15 (ORD)Chicago O'Hare International Airport
-
(WN 366)Boeing 737 800 (WN 3623)Boeing 737 700 - 6h 30m (2h 45m)
- BNA Nashville 2h 45m
-
- M
- -
- -
- T
- F
- -
- -
-
08:50 - 11:10MCO - BWI13:05 - 14:05BWI - MDW
-
08:50 (MCO)Orlando International Airport13:05 (BWI)Baltimore Washington International Airport
-
11:10 (BWI)Baltimore Washington International Airport14:05 (MDW)Chicago Midway Airport
-
(WN 420)Boeing 737 800 (WN 5950)Boeing 737 800 - 6h 15m (1h 55m)
- BWI Baltimore 1h 55m
-
- -
- T
- W
- -
- -
- -
- -
-
08:50 - 11:10MCO - BWI13:05 - 14:15BWI - ORD
-
08:50 (MCO)Orlando International Airport13:05 (BWI)Baltimore Washington International Airport
-
11:10 (BWI)Baltimore Washington International Airport14:15 (ORD)Chicago O'Hare International Airport
-
(WN 420)Boeing 737 800 (WN 3191)Boeing 737 700 - 6h 25m (1h 55m)
- BWI Baltimore 1h 55m
-
- -
- T
- W
- -
- -
- -
- -
-
08:55 - 10:45MCO - DAL11:55 - 14:10DAL - MDW
-
08:55 (MCO)Orlando International Airport11:55 (DAL)Dallas/Fort Worth Love Field Airport
-
10:45 (DAL)Dallas/Fort Worth Love Field Airport14:10 (MDW)Chicago Midway Airport
-
(WN 5530)Boeing 737 800 (WN 473)Boeing 737 800 - 6h 15m (1h 10m)
- DAL Dallas 1h 10m
-
- -
- T
- W
- -
- -
- -
- -
-
09:00 - 11:15MCO - BWI13:15 - 14:15BWI - MDW
-
09:00 (MCO)Orlando International Airport13:15 (BWI)Baltimore Washington International Airport
-
11:15 (BWI)Baltimore Washington International Airport14:15 (MDW)Chicago Midway Airport
-
(WN 1477)Boeing 737 Max 8 Passenger (WN 5950)Boeing 737 Max 8 Passenger - 6h 15m (2h)
- BWI Baltimore 2h
-
- -
- -
- -
- -
- -
- -
- S
-
09:10 - 10:45MCO - HOU11:40 - 14:10HOU - MDW
-
09:10 (MCO)Orlando International Airport11:40 (HOU)Houston Hobby Airport
-
10:45 (HOU)Houston Hobby Airport14:10 (MDW)Chicago Midway Airport
-
(WN 2152)Boeing 737 Max 8 Passenger (WN 460)Boeing 737 700 - 6h (55m)
- HOU Houston 55m
-
- M
- -
- -
- T
- F
- -
- -
-
09:20 - 11:40MCO - BWI13:45 - 14:45BWI - MDW
-
09:20 (MCO)Orlando International Airport13:45 (BWI)Baltimore Washington International Airport
-
11:40 (BWI)Baltimore Washington International Airport14:45 (MDW)Chicago Midway Airport
-
(WN 420)Boeing 737 800 (WN 5950)Boeing 737 800 - 6h 25m (2h 05m)
- BWI Baltimore 2h 05m
-
- M
- -
- -
- T
- F
- -
- -
-
09:25 - 11:20MCO - DAL12:35 - 15:00DAL - ORD
-
09:25 (MCO)Orlando International Airport12:35 (DAL)Dallas/Fort Worth Love Field Airport
-
11:20 (DAL)Dallas/Fort Worth Love Field Airport15:00 (ORD)Chicago O'Hare International Airport
-
(WN 5530)Boeing 737 800 (WN 5556)Boeing 737 800 - 6h 35m (1h 15m)
- DAL Dallas 1h 15m
-
- M
- -
- -
- T
- F
- -
- -
-
09:25 - 11:20MCO - DAL12:35 - 14:45DAL - MDW
-
09:25 (MCO)Orlando International Airport12:35 (DAL)Dallas/Fort Worth Love Field Airport
-
11:20 (DAL)Dallas/Fort Worth Love Field Airport14:45 (MDW)Chicago Midway Airport
-
(WN 5530)Boeing 737 800 (WN 473)Boeing 737 Max 8 Passenger - 6h 20m (1h 15m)
- DAL Dallas 1h 15m
-
- M
- -
- -
- T
- F
- -
- -
-
09:35 - 11:30MCO - ORF14:00 - 15:10ORF - MDW
-
09:35 (MCO)Orlando International Airport14:00 (ORF)Norfolk International Airport
-
11:30 (ORF)Norfolk International Airport15:10 (MDW)Chicago Midway Airport
-
(WN 6159)Boeing 737 Max 8 Passenger (WN 2240)Boeing 737 700 - 6h 35m (2h 30m)
- ORF 2h 30m
-
- -
- -
- -
- -
- -
- -
- S
-
09:40 - 11:15MCO - ATL13:00 - 13:55ATL - MDW
-
09:40 (MCO)Orlando International Airport13:00 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
11:15 (ATL)Atlanta Hartsfield-Jackson Intl Airport13:55 (MDW)Chicago Midway Airport
-
(WN 1269)Boeing 737 700 (WN 1751)Boeing 737 Max 8 Passenger - 5h 15m (1h 45m)
- ATL Atlanta 1h 45m
-
- -
- -
- -
- -
- -
- -
- S
-
09:40 - 12:00MCO - BWI12:45 - 13:40BWI - MDW
-
09:40 (MCO)Orlando International Airport12:45 (BWI)Baltimore Washington International Airport
-
12:00 (BWI)Baltimore Washington International Airport13:40 (MDW)Chicago Midway Airport
-
(WN 1002)Boeing 737 800 (WN 5950)Boeing 737 800 - 5h (45m)
- BWI Baltimore 45m
-
- -
- -
- -
- -
- -
- S
- -
-
10:05 - 11:05MCO - BNA13:10 - 14:45BNA - MDW
-
10:05 (MCO)Orlando International Airport13:10 (BNA)Nashville Airport
-
11:05 (BNA)Nashville Airport14:45 (MDW)Chicago Midway Airport
-
(WN 366)Boeing 737 700 (WN 743)Boeing 737 700 - 5h 40m (2h 05m)
- BNA Nashville 2h 05m
-
- -
- -
- -
- -
- -
- -
- S
-
10:10 - 12:20MCO - BWI13:05 - 14:05BWI - MDW
-
10:10 (MCO)Orlando International Airport13:05 (BWI)Baltimore Washington International Airport
-
12:20 (BWI)Baltimore Washington International Airport14:05 (MDW)Chicago Midway Airport
-
(WN 1002)Boeing 737 700 (WN 5950)Boeing 737 800 - 4h 55m (45m)
- BWI Baltimore 45m
-
- -
- T
- W
- -
- -
- -
- -
-
10:10 - 11:50MCO - ATL14:35 - 15:25ATL - MDW
-
10:10 (MCO)Orlando International Airport14:35 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
11:50 (ATL)Atlanta Hartsfield-Jackson Intl Airport15:25 (MDW)Chicago Midway Airport
-
(WN 264)Boeing 737 700 (WN 1751)Boeing 737 Max 8 Passenger - 6h 15m (2h 45m)
- ATL Atlanta 2h 45m
-
- M
- -
- -
- T
- F
- -
- -
-
10:10 - 12:20MCO - BWI13:05 - 14:15BWI - ORD
-
10:10 (MCO)Orlando International Airport13:05 (BWI)Baltimore Washington International Airport
-
12:20 (BWI)Baltimore Washington International Airport14:15 (ORD)Chicago O'Hare International Airport
-
(WN 1002)Boeing 737 700 (WN 3191)Boeing 737 700 - 5h 05m (45m)
- BWI Baltimore 45m
-
- -
- T
- W
- -
- -
- -
- -
-
10:15 - 11:50MCO - STL12:35 - 13:40STL - MDW
-
10:15 (MCO)Orlando International Airport12:35 (STL)St Louis Lambert Intl Airport
-
11:50 (STL)St Louis Lambert Intl Airport13:40 (MDW)Chicago Midway Airport
-
(WN 4677)Boeing 737 800 (WN 3241)Boeing 737 700 - 4h 25m (45m)
- STL Saint Louis 45m
-
- M
- -
- -
- T
- F
- -
- -
-
10:15 - 12:00MCO - IAH12:40 - 15:05IAH - MDW
-
10:15 (MCO)Orlando International Airport12:40 (IAH)Houston George Bush Intercontinental Airport
-
12:00 (IAH)Houston George Bush Intercontinental Airport15:05 (MDW)Chicago Midway Airport
-
(WN 2242)Boeing 737 700 (WN 549)Boeing 737 700 - 5h 50m (40m)
- IAH Houston 40m
-
- -
- -
- -
- -
- -
- S
- -
-
10:20 - 11:50MCO - STL14:20 - 15:25STL - MDW
-
10:20 (MCO)Orlando International Airport14:20 (STL)St Louis Lambert Intl Airport
-
11:50 (STL)St Louis Lambert Intl Airport15:25 (MDW)Chicago Midway Airport
-
(WN 4677)Boeing 737 800 (WN 2732)Boeing 737 700 - 6h 05m (2h 30m)
- STL Saint Louis 2h 30m
-
- -
- -
- -
- -
- -
- -
- S
-
10:25 - 12:45MCO - PIT14:45 - 15:10PIT - MDW
-
10:25 (MCO)Orlando International Airport14:45 (PIT)Pittsburgh International Airport
-
12:45 (PIT)Pittsburgh International Airport15:10 (MDW)Chicago Midway Airport
-
(WN 1592)Boeing 737 Max 8 Passenger (WN 887)Boeing 737 700 - 5h 45m (2h)
- PIT Pittsburgh 2h
-
- -
- -
- -
- -
- -
- -
- S
-
10:35 - 12:20MCO - AUS13:25 - 16:00AUS - MDW
-
10:35 (MCO)Orlando International Airport13:25 (AUS)Austin-Bergstrom International Airport
-
12:20 (AUS)Austin-Bergstrom International Airport16:00 (MDW)Chicago Midway Airport
-
(WN 5490)Boeing 737 800 (WN 2496)Boeing 737 800 - 6h 25m (1h 05m)
- AUS Austin 1h 05m
-
- -
- -
- -
- -
- -
- S
- -
-
10:40 - 12:10MCO - STL14:40 - 15:45STL - MDW
-
10:40 (MCO)Orlando International Airport14:40 (STL)St Louis Lambert Intl Airport
-
12:10 (STL)St Louis Lambert Intl Airport15:45 (MDW)Chicago Midway Airport
-
(WN 4677)Boeing 737 800 (WN 3242)Boeing 737 Max 8 Passenger - 6h 05m (2h 30m)
- STL Saint Louis 2h 30m
-
- -
- T
- W
- -
- -
- -
- -
-
10:45 - 12:20MCO - HOU13:35 - 16:00HOU - MDW
-
10:45 (MCO)Orlando International Airport13:35 (HOU)Houston Hobby Airport
-
12:20 (HOU)Houston Hobby Airport16:00 (MDW)Chicago Midway Airport
-
(WN 2152)Boeing 737 Max 8 Passenger (WN 5388)Boeing 737 700 - 6h 15m (1h 15m)
- HOU Houston 1h 15m
-
- -
- -
- -
- -
- -
- -
- S
-
10:45 - 12:50MCO - SDF14:35 - 14:50SDF - MDW
-
10:45 (MCO)Orlando International Airport14:35 (SDF)Louisville International Airport
-
12:50 (SDF)Louisville International Airport14:50 (MDW)Chicago Midway Airport
-
(WN 3565)Boeing 737 700 (WN 4247)Boeing 737 700 - 5h 05m (1h 45m)
- SDF Louisville 1h 45m
-
- -
- -
- -
- -
- -
- -
- S
-
10:45 - 12:30MCO - AUS13:15 - 15:45AUS - MDW
-
10:45 (MCO)Orlando International Airport13:15 (AUS)Austin-Bergstrom International Airport
-
12:30 (AUS)Austin-Bergstrom International Airport15:45 (MDW)Chicago Midway Airport
-
(WN 5490)Boeing 737 Max 8 Passenger (WN 2496)Boeing 737 Max 8 Passenger - 6h (45m)
- AUS Austin 45m
-
- M
- -
- -
- T
- F
- -
- -
-
10:50 - 11:45MCO - MSY12:35 - 14:55MSY - MDW
-
10:50 (MCO)Orlando International Airport12:35 (MSY)New Orleans Louis Armstrong Intl Airport
-
11:45 (MSY)New Orleans Louis Armstrong Intl Airport14:55 (MDW)Chicago Midway Airport
-
(WN 2134)Boeing 737 700 (WN 2055)Boeing 737 Max 8 Passenger - 5h 05m (50m)
- MSY New Orleans 50m
-
- -
- T
- W
- -
- -
- -
- -
-
11:00 - 12:50MCO - AUS13:45 - 16:25AUS - ORD
-
11:00 (MCO)Orlando International Airport13:45 (AUS)Austin-Bergstrom International Airport
-
12:50 (AUS)Austin-Bergstrom International Airport16:25 (ORD)Chicago O'Hare International Airport
-
(WN 5490)Boeing 737 800 (WN 3621)Boeing 737 800 - 6h 25m (55m)
- AUS Austin 55m
-
- -
- -
- -
- -
- -
- -
- S
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What’s the fastest flight time from Orlando to Chicago?
The fastest flight time for direct flights from Orlando to Chicago is 2 hours 45 minutes. Check latest flight schedules & prices on Wego.
What’s the most popular airline flying from Orlando to Chicago?
The most popular airline flying from Orlando to Chicago is Spirit Airlines. Find the latest flight deals on Wego.
How far is Chicago from Orlando?
The flight distance between Orlando and Chicago 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 06:05. The last flight of the day departs at 20:15. See the full list of flight times on Wego.
How many airlines offer direct flights from Orlando to Chicago?
There are 4 airlines that offer direct flights from Orlando to Chicago. Find out the list of airlines on Wego.
All Airports in Chicago
Popular Airlines flying from Orlando to Chicago
Popular destinations from Chicago
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- Swissôtel Chicago
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