Fare Guide
Estimated lowest fares found within 7 days
Cheapest Airline
The cheapest airline(s) flying from Chicago to Cancun is Spirit Airlines.
Cheapest Month
May
Travel Period: May 2024 - April 2025
The cheapest month(s) to fly from Chicago to Cancun 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
Monday
The cheapest day(s) of the week to fly from Chicago to Cancun is Monday.
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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
6am
The cheapest time of the day to fly from Chicago to Cancun is in the early morning.
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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Arrive
- Earliest
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Airline
Filter by Airline
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Total Duration
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Stopover
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Availability
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07:49 - 11:31ORD - CUN
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07:49 (ORD)Chicago O'Hare International Airport
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11:31 (CUN)Cancun Airport
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United Airlines (UA 1198)Boeing 737 800 - 3h 42m
- Direct
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- M
- T
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- S
- Boeing 737 800
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08:20 - 11:56ORD - CUN
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08:20 (ORD)Chicago O'Hare International Airport
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11:56 (CUN)Cancun Airport
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American Airlines (AA 1193)Boeing 737 800 - 3h 36m
- Direct
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- M
- T
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- S
- Boeing 737 800
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08:35 - 12:10MDW - CUN
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08:35 (MDW)Chicago Midway Airport
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12:10 (CUN)Cancun Airport
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(WN 216)Boeing 737 Max 8 Passenger - 3h 35m
- Direct
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- -
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- S
- Boeing 737 Max 8 Passenger
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09:05 - 12:40MDW - CUN
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09:05 (MDW)Chicago Midway Airport
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12:40 (CUN)Cancun Airport
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(WN 216)Boeing 737 Max 8 Passenger - 3h 35m
- Direct
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- Boeing 737 Max 8 Passenger
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09:18 - 13:05ORD - CUN
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09:18 (ORD)Chicago O'Hare International Airport
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13:05 (CUN)Cancun Airport
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United Airlines (UA 1656)Boeing 737 800 - 3h 47m
- Direct
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- M
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- S
- S
- Boeing 737 800
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09:55 - 13:32ORD - CUN
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09:55 (ORD)Chicago O'Hare International Airport
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13:32 (CUN)Cancun Airport
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American Airlines (AA 1503)Boeing 737 800 - 3h 37m
- Direct
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- M
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- T
- F
- S
- S
- Boeing 737 800
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10:30 - 14:10ORD - CUN
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10:30 (ORD)Chicago O'Hare International Airport
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14:10 (CUN)Cancun Airport
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(WN 1510)Boeing 737 700 - 3h 40m
- Direct
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- S
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- Boeing 737 700
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10:41 - 14:28ORD - CUN
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10:41 (ORD)Chicago O'Hare International Airport
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14:28 (CUN)Cancun Airport
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United Airlines (UA 1659)Boeing 737 800 - 3h 47m
- Direct
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- M
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- F
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- S
- Boeing 737 800
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10:45 - 14:20MDW - CUN
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10:45 (MDW)Chicago Midway Airport
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14:20 (CUN)Cancun Airport
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(WN 218)Boeing 737 Max 8 Passenger - 3h 35m
- Direct
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- M
- T
- W
- T
- F
- -
- S
- Boeing 737 Max 8 Passenger
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11:00 - 14:40MDW - CUN
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11:00 (MDW)Chicago Midway Airport
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14:40 (CUN)Cancun Airport
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(WN 218)Boeing 737 700 - 3h 40m
- Direct
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- Boeing 737 700
Connecting Flights
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05:00 - 09:06ORD - MIA10:05 - 11:05MIA - CUN
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05:00 (ORD)Chicago O'Hare International Airport10:05 (MIA)Miami International Airport
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09:06 (MIA)Miami International Airport11:05 (CUN)Cancun Airport
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American Airlines (AA 2341)Boeing 737 Max 8 Passenger American Airlines (AA 1157)Boeing 737 Max 8 Passenger - 6h 05m (59m)
- MIA 59m
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- M
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- S
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05:30 - 07:10MDW - DEN08:15 - 13:10DEN - CUN
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05:30 (MDW)Chicago Midway Airport08:15 (DEN)Denver Intl Airport
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07:10 (DEN)Denver Intl Airport13:10 (CUN)Cancun Airport
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(WN 3101)Boeing 737 Max 8 Passenger (WN 601)Boeing 737 700 - 7h 40m (1h 05m)
- DEN Denver 1h 05m
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- S
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05:30 - 08:10MDW - AUS09:20 - 11:50AUS - CUN
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05:30 (MDW)Chicago Midway Airport09:20 (AUS)Austin-Bergstrom International Airport
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08:10 (AUS)Austin-Bergstrom International Airport11:50 (CUN)Cancun Airport
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(WN 5387)Boeing 737 Max 8 Passenger (WN 708)Boeing 737 Max 8 Passenger - 6h 20m (1h 10m)
- AUS Austin 1h 10m
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- M
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- -
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05:35 - 08:15MDW - AUS09:20 - 11:50AUS - CUN
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05:35 (MDW)Chicago Midway Airport09:20 (AUS)Austin-Bergstrom International Airport
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08:15 (AUS)Austin-Bergstrom International Airport11:50 (CUN)Cancun Airport
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(WN 5387)Boeing 737 Max 8 Passenger (WN 708)Boeing 737 Max 8 Passenger - 6h 15m (1h 05m)
- AUS Austin 1h 05m
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05:40 - 09:40MDW - FLL11:45 - 12:50FLL - CUN
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05:40 (MDW)Chicago Midway Airport11:45 (FLL)Fort Lauderdale/Hollywood Intl Airport
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09:40 (FLL)Fort Lauderdale/Hollywood Intl Airport12:50 (CUN)Cancun Airport
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(WN 2331)Boeing 737 700 (WN 828)Boeing 737 700 - 7h 10m (2h 05m)
- FLL Miami 2h 05m
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- S
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05:45 - 07:10MDW - BNA09:05 - 12:10BNA - CUN
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05:45 (MDW)Chicago Midway Airport09:05 (BNA)Nashville Airport
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07:10 (BNA)Nashville Airport12:10 (CUN)Cancun Airport
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(WN 270)Boeing 737 700 (WN 386)Boeing 737 Max 8 Passenger - 6h 25m (1h 55m)
- BNA Nashville 1h 55m
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05:55 - 07:05MDW - STL08:45 - 11:50STL - CUN
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05:55 (MDW)Chicago Midway Airport08:45 (STL)St Louis Lambert Intl Airport
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07:05 (STL)St Louis Lambert Intl Airport11:50 (CUN)Cancun Airport
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(WN 5846)Boeing 737 Max 8 Passenger (WN 1985)Boeing 737 Max 8 Passenger - 5h 55m (1h 40m)
- STL Saint Louis 1h 40m
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06:00 - 09:55MDW - FLL11:55 - 13:00FLL - CUN
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06:00 (MDW)Chicago Midway Airport11:55 (FLL)Fort Lauderdale/Hollywood Intl Airport
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09:55 (FLL)Fort Lauderdale/Hollywood Intl Airport13:00 (CUN)Cancun Airport
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(WN 2331)Boeing 737 Max 8 Passenger (WN 828)Boeing 737 Max 8 Passenger - 7h (2h)
- FLL Miami 2h
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06:05 - 10:05MDW - FLL12:05 - 13:10FLL - CUN
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06:05 (MDW)Chicago Midway Airport12:05 (FLL)Fort Lauderdale/Hollywood Intl Airport
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10:05 (FLL)Fort Lauderdale/Hollywood Intl Airport13:10 (CUN)Cancun Airport
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(WN 2331)Boeing 737 700 (WN 828)Boeing 737 700 - 7h 05m (2h)
- FLL Miami 2h
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06:05 - 08:55MDW - ATL12:10 - 13:50ATL - CUN
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06:05 (MDW)Chicago Midway Airport12:10 (ATL)Atlanta Hartsfield-Jackson Intl Airport
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08:55 (ATL)Atlanta Hartsfield-Jackson Intl Airport13:50 (CUN)Cancun Airport
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(WN 925)Boeing 737 700 (WN 1134)Boeing 737 Max 8 Passenger - 7h 45m (3h 15m)
- ATL Atlanta 3h 15m
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06:05 - 07:35MDW - MCI09:30 - 12:50MCI - CUN
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06:05 (MDW)Chicago Midway Airport09:30 (MCI)Kansas City International Airport
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07:35 (MCI)Kansas City International Airport12:50 (CUN)Cancun Airport
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(WN 1942)Boeing 737 700 (WN 751)Boeing 737 Max 8 Passenger - 6h 45m (1h 55m)
- MCI Kansas City 1h 55m
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06:10 - 10:05MDW - FLL11:55 - 13:00FLL - CUN
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06:10 (MDW)Chicago Midway Airport11:55 (FLL)Fort Lauderdale/Hollywood Intl Airport
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10:05 (FLL)Fort Lauderdale/Hollywood Intl Airport13:00 (CUN)Cancun Airport
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(WN 2331)Boeing 737 700 (WN 828)Boeing 737 Max 8 Passenger - 6h 50m (1h 50m)
- FLL Miami 1h 50m
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06:25 - 08:00MDW - DEN09:55 - 14:50DEN - CUN
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06:25 (MDW)Chicago Midway Airport09:55 (DEN)Denver Intl Airport
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08:00 (DEN)Denver Intl Airport14:50 (CUN)Cancun Airport
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(WN 1699)Boeing 737 Max 8 Passenger (WN 601)Boeing 737 700 - 8h 25m (1h 55m)
- DEN Denver 1h 55m
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06:25 - 08:00MDW - DEN08:55 - 13:50DEN - CUN
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06:25 (MDW)Chicago Midway Airport08:55 (DEN)Denver Intl Airport
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08:00 (DEN)Denver Intl Airport13:50 (CUN)Cancun Airport
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(WN 1699)Boeing 737 Max 8 Passenger (WN 131)Boeing 737 Max 8 Passenger - 7h 25m (55m)
- DEN Denver 55m
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06:30 - 08:10ORD - DEN09:55 - 14:50DEN - CUN
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06:30 (ORD)Chicago O'Hare International Airport09:55 (DEN)Denver Intl Airport
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08:10 (DEN)Denver Intl Airport14:50 (CUN)Cancun Airport
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(WN 1260)Boeing 737 800 (WN 601)Boeing 737 700 - 8h 20m (1h 45m)
- DEN Denver 1h 45m
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06:30 - 08:10ORD - DEN08:55 - 13:50DEN - CUN
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06:30 (ORD)Chicago O'Hare International Airport08:55 (DEN)Denver Intl Airport
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08:10 (DEN)Denver Intl Airport13:50 (CUN)Cancun Airport
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(WN 1260)Boeing 737 800 (WN 131)Boeing 737 Max 8 Passenger - 7h 20m (45m)
- DEN Denver 45m
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- -
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- S
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06:30 - 07:45MDW - STL11:35 - 14:40STL - CUN
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06:30 (MDW)Chicago Midway Airport11:35 (STL)St Louis Lambert Intl Airport
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07:45 (STL)St Louis Lambert Intl Airport14:40 (CUN)Cancun Airport
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(WN 5846)Boeing 737 800 (WN 1995)Boeing 737 700 - 8h 10m (3h 50m)
- STL Saint Louis 3h 50m
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- -
- -
- -
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- S
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06:55 - 08:30MDW - MCI11:10 - 14:25MCI - CUN
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06:55 (MDW)Chicago Midway Airport11:10 (MCI)Kansas City International Airport
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08:30 (MCI)Kansas City International Airport14:25 (CUN)Cancun Airport
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(WN 1942)Boeing 737 700 (WN 751)Boeing 737 700 - 7h 30m (2h 40m)
- MCI Kansas City 2h 40m
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- S
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07:15 - 10:05MDW - BWI12:55 - 15:35BWI - CUN
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07:15 (MDW)Chicago Midway Airport12:55 (BWI)Baltimore Washington International Airport
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10:05 (BWI)Baltimore Washington International Airport15:35 (CUN)Cancun Airport
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(WN 5903)Boeing 737 700 (WN 1609)Boeing 737 Max 8 Passenger - 8h 20m (2h 50m)
- BWI Baltimore 2h 50m
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- S
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07:15 - 08:45ORD - BNA12:20 - 15:25BNA - CUN
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07:15 (ORD)Chicago O'Hare International Airport12:20 (BNA)Nashville Airport
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08:45 (BNA)Nashville Airport15:25 (CUN)Cancun Airport
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(WN 658)Boeing 737 Max 8 Passenger (WN 386)Boeing 737 700 - 8h 10m (3h 35m)
- BNA Nashville 3h 35m
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- -
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- S
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07:20 - 10:00MDW - HOU13:25 - 15:35HOU - CUN
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07:20 (MDW)Chicago Midway Airport13:25 (HOU)Houston Hobby Airport
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10:00 (HOU)Houston Hobby Airport15:35 (CUN)Cancun Airport
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(WN 5171)Boeing 737 800 (WN 305)Boeing 737 700 - 8h 15m (3h 25m)
- HOU Houston 3h 25m
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- M
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07:35 - 10:05MDW - HOU13:25 - 15:35HOU - CUN
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07:35 (MDW)Chicago Midway Airport13:25 (HOU)Houston Hobby Airport
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10:05 (HOU)Houston Hobby Airport15:35 (CUN)Cancun Airport
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(WN 5171)Boeing 737 800 (WN 305)Boeing 737 Max 8 Passenger - 8h (3h 20m)
- HOU Houston 3h 20m
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- S
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07:50 - 10:40MDW - ATL12:10 - 13:50ATL - CUN
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07:50 (MDW)Chicago Midway Airport12:10 (ATL)Atlanta Hartsfield-Jackson Intl Airport
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10:40 (ATL)Atlanta Hartsfield-Jackson Intl Airport13:50 (CUN)Cancun Airport
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(WN 1572)Boeing 737 Max 8 Passenger (WN 1134)Boeing 737 Max 8 Passenger - 6h (1h 30m)
- ATL Atlanta 1h 30m
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- -
- -
- -
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- -
- S
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08:05 - 10:50MDW - BWI13:25 - 16:05BWI - CUN
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08:05 (MDW)Chicago Midway Airport13:25 (BWI)Baltimore Washington International Airport
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10:50 (BWI)Baltimore Washington International Airport16:05 (CUN)Cancun Airport
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(WN 5903)Boeing 737 700 (WN 1607)Boeing 737 700 - 8h (2h 35m)
- BWI Baltimore 2h 35m
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- -
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- S
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08:10 - 09:45MDW - DEN11:00 - 15:55DEN - CUN
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08:10 (MDW)Chicago Midway Airport11:00 (DEN)Denver Intl Airport
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09:45 (DEN)Denver Intl Airport15:55 (CUN)Cancun Airport
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(WN 1699)Boeing 737 700 (WN 131)Boeing 737 700 - 7h 45m (1h 15m)
- DEN Denver 1h 15m
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- M
- -
- -
- T
- F
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- -
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08:10 - 09:50MDW - DEN11:00 - 15:55DEN - CUN
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08:10 (MDW)Chicago Midway Airport11:00 (DEN)Denver Intl Airport
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09:50 (DEN)Denver Intl Airport15:55 (CUN)Cancun Airport
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(WN 5797)Boeing 737 700 (WN 131)Boeing 737 700 - 7h 45m (1h 10m)
- DEN Denver 1h 10m
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- S
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08:15 - 09:55MDW - DEN11:00 - 15:55DEN - CUN
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08:15 (MDW)Chicago Midway Airport11:00 (DEN)Denver Intl Airport
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09:55 (DEN)Denver Intl Airport15:55 (CUN)Cancun Airport
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(WN 1699)Boeing 737 Max 8 Passenger (WN 131)Boeing 737 700 - 7h 40m (1h 05m)
- DEN Denver 1h 05m
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- T
- W
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08:15 - 11:10MDW - BWI13:50 - 16:30BWI - CUN
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08:15 (MDW)Chicago Midway Airport13:50 (BWI)Baltimore Washington International Airport
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11:10 (BWI)Baltimore Washington International Airport16:30 (CUN)Cancun Airport
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(WN 5903)Boeing 737 800 (WN 1607)Boeing 737 Max 8 Passenger - 8h 15m (2h 40m)
- BWI Baltimore 2h 40m
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- M
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- T
- F
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08:20 - 09:35MDW - STL11:35 - 14:40STL - CUN
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08:20 (MDW)Chicago Midway Airport11:35 (STL)St Louis Lambert Intl Airport
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09:35 (STL)St Louis Lambert Intl Airport14:40 (CUN)Cancun Airport
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(WN 3487)Boeing 737 Max 8 Passenger (WN 1995)Boeing 737 Max 8 Passenger - 6h 20m (2h)
- STL Saint Louis 2h
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- T
- W
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- -
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- -
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08:35 - 11:30MDW - BWI13:50 - 16:30BWI - CUN
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08:35 (MDW)Chicago Midway Airport13:50 (BWI)Baltimore Washington International Airport
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11:30 (BWI)Baltimore Washington International Airport16:30 (CUN)Cancun Airport
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(WN 5903)Boeing 737 700 (WN 1607)Boeing 737 Max 8 Passenger - 7h 55m (2h 20m)
- BWI Baltimore 2h 20m
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- -
- T
- W
- -
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08:55 - 11:30MDW - HOU13:25 - 15:35HOU - CUN
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08:55 (MDW)Chicago Midway Airport13:25 (HOU)Houston Hobby Airport
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11:30 (HOU)Houston Hobby Airport15:35 (CUN)Cancun Airport
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(WN 3596)Boeing 737 Max 8 Passenger (WN 305)Boeing 737 700 - 6h 40m (1h 55m)
- HOU Houston 1h 55m
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- -
- T
- W
- -
- -
- -
- -
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09:30 - 12:35ORD - BWI13:25 - 16:05BWI - CUN
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09:30 (ORD)Chicago O'Hare International Airport13:25 (BWI)Baltimore Washington International Airport
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12:35 (BWI)Baltimore Washington International Airport16:05 (CUN)Cancun Airport
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(WN 5932)Boeing 737 800 (WN 1607)Boeing 737 700 - 6h 35m (50m)
- BWI Baltimore 50m
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- -
- -
- -
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- S
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09:40 - 10:50MDW - STL11:35 - 14:40STL - CUN
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09:40 (MDW)Chicago Midway Airport11:35 (STL)St Louis Lambert Intl Airport
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10:50 (STL)St Louis Lambert Intl Airport14:40 (CUN)Cancun Airport
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(WN 5846)Boeing 737 Max 8 Passenger (WN 1995)Boeing 737 Max 8 Passenger - 5h (45m)
- STL Saint Louis 45m
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- M
- -
- -
- T
- F
- -
- -
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09:40 - 12:15MDW - HOU13:45 - 15:55HOU - CUN
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09:40 (MDW)Chicago Midway Airport13:45 (HOU)Houston Hobby Airport
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12:15 (HOU)Houston Hobby Airport15:55 (CUN)Cancun Airport
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(WN 3596)Boeing 737 Max 8 Passenger (WN 305)Boeing 737 700 - 6h 15m (1h 30m)
- HOU Houston 1h 30m
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- -
- -
- -
- -
- -
- S
- -
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10:05 - 12:40MDW - HOU13:25 - 15:35HOU - CUN
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10:05 (MDW)Chicago Midway Airport13:25 (HOU)Houston Hobby Airport
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12:40 (HOU)Houston Hobby Airport15:35 (CUN)Cancun Airport
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(WN 2446)Boeing 737 800 (WN 305)Boeing 737 Max 8 Passenger - 5h 30m (45m)
- HOU Houston 45m
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- -
- -
- -
- -
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- S
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14:05 - 16:40MDW - HOU18:45 - 21:00HOU - CUN
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14:05 (MDW)Chicago Midway Airport18:45 (HOU)Houston Hobby Airport
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16:40 (HOU)Houston Hobby Airport21:00 (CUN)Cancun Airport
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(WN 2158)Boeing 737 Max 8 Passenger (WN 307)Boeing 737 700 - 6h 55m (2h 05m)
- HOU Houston 2h 05m
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- -
- -
- -
- -
- -
- -
- S
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15:00 - 17:40MDW - HOU18:45 - 21:00HOU - CUN
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15:00 (MDW)Chicago Midway Airport18:45 (HOU)Houston Hobby Airport
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17:40 (HOU)Houston Hobby Airport21:00 (CUN)Cancun Airport
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(WN 5165)Boeing 737 700 (WN 307)Boeing 737 700 - 6h (1h 05m)
- HOU Houston 1h 05m
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- M
- -
- -
- T
- F
- -
- -
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15:10 - 17:50MDW - HOU18:45 - 21:00HOU - CUN
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15:10 (MDW)Chicago Midway Airport18:45 (HOU)Houston Hobby Airport
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17:50 (HOU)Houston Hobby Airport21:00 (CUN)Cancun Airport
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(WN 2158)Boeing 737 800 (WN 307)Boeing 737 700 - 5h 50m (55m)
- HOU Houston 55m
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- -
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- -
- -
- S
- -
No Schedules
Sorry, there are no schedules matching your filters. Try removing one.
reset
What’s the fastest flight time from Chicago to Cancun?
The fastest flight time for direct flights from Chicago to Cancun is 3 hours 35 minutes. Check latest flight schedules & prices on Wego.
What’s the most popular airline flying from Chicago to Cancun?
The most popular airline flying from Chicago to Cancun is Spirit Airlines. Find the latest flight deals on Wego.
How far is Cancun from Chicago?
The flight distance between Chicago and Cancun is 2305km. Check all available flights on Wego.
When is the earliest and latest flight of the day?
The earliest flight of the day departs at 05:00. The last flight of the day departs at 05:00. See the full list of flight times on Wego.
How many airlines offer direct flights from Chicago to Cancun?
There are 3 airlines that offer direct flights from Chicago to Cancun. Find out the list of airlines on Wego.
All Airports in Chicago
All Airports in Cancun
Popular Airlines flying from Chicago to Cancun
Popular destinations from Cancun
Popular destinations from Chicago
Popular Hotels in Cancun
- The Smart Cancun
- Canopy by Hilton Cancun La Isla
- Renaissance Cancun Resort & Marina
- Moon Palace Cancun
- Hilton Garden Inn Cancun Airport
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