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Flight Schedules

Last Updated: Thu, 2 May, 2024

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- M
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- S
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12:20 - 16:19

CUN - ORD
12:20 (CUN)Cancun Airport
16:19 (ORD)Chicago O'Hare International Airport
United Airlines (UA 1196)Boeing 737 800
3h 59m
Direct
- M
- T
- W
- T
- F
- S
- S
Boeing 737 800

12:25 - 16:05

CUN - MDW
12:25 (CUN)Cancun Airport
16:05 (MDW)Chicago Midway Airport
(WN 219)Boeing 737 700
3h 40m
Direct
- -
- -
- -
- -
- -
- S
- -
Boeing 737 700

12:55 - 16:40

CUN - MDW
12:55 (CUN)Cancun Airport
16:40 (MDW)Chicago Midway Airport
(WN 219)Boeing 737 Max 8 Passenger
3h 45m
Direct
- -
- -
- -
- -
- -
- -
- S
Boeing 737 Max 8 Passenger

12:58 - 17:00

CUN - ORD
12:58 (CUN)Cancun Airport
17:00 (ORD)Chicago O'Hare International Airport
American Airlines (AA 1883)Boeing 737 800
4h 02m
Direct
- M
- T
- W
- T
- F
- S
- S
Boeing 737 800

13:55 - 17:55

CUN - ORD
13:55 (CUN)Cancun Airport
17:55 (ORD)Chicago O'Hare International Airport
(WN 1512)Boeing 737 Max 8 Passenger
4h
Direct
- -
- -
- -
- -
- -
- S
- -
Boeing 737 Max 8 Passenger

14:15 - 18:15

CUN - ORD
14:15 (CUN)Cancun Airport
18:15 (ORD)Chicago O'Hare International Airport
United Airlines (UA 1423)Boeing 737 800
4h
Direct
- M
- T
- W
- T
- -
- -
- -
Boeing 737 800

14:53 - 18:55

CUN - ORD
14:53 (CUN)Cancun Airport
18:55 (ORD)Chicago O'Hare International Airport
American Airlines (AA 1503)Boeing 737 800
4h 02m
Direct
- M
- T
- W
- T
- F
- S
- S
Boeing 737 800

15:25 - 19:05

CUN - MDW
15:25 (CUN)Cancun Airport
19:05 (MDW)Chicago Midway Airport
(WN 217)Boeing 737 700
3h 40m
Direct
- -
- -
- -
- -
- -
- S
- -
Boeing 737 700

15:38 - 19:37

CUN - ORD
15:38 (CUN)Cancun Airport
19:37 (ORD)Chicago O'Hare International Airport
United Airlines (UA 1667)Boeing 737 800
3h 59m
Direct
- M
- T
- W
- T
- F
- S
- S
Boeing 737 800

16:35 - 20:20

CUN - MDW
16:35 (CUN)Cancun Airport
20:20 (MDW)Chicago Midway Airport
(WN 219)Boeing 737 700
3h 45m
Direct
- M
- T
- W
- T
- F
- -
- -
Boeing 737 700

16:40 - 20:20

CUN - MDW
16:40 (CUN)Cancun Airport
20:20 (MDW)Chicago Midway Airport
(WN 217)Boeing 737 Max 8 Passenger
3h 40m
Direct
- -
- -
- -
- -
- -
- -
- S
Boeing 737 Max 8 Passenger

Connecting Flights

09:00 - 11:25

CUN - HOU

13:35 - 16:00

HOU - MDW
09:00 (CUN)Cancun Airport

13:35 (HOU)Houston Hobby Airport
11:25 (HOU)Houston Hobby Airport

16:00 (MDW)Chicago Midway Airport
(WN 316)Boeing 737 700

(WN 5388)Boeing 737 700
7h (2h 10m)
HOU Houston 2h 10m
- -
- -
- -
- -
- -
- -
- S

09:00 - 11:25

CUN - HOU

14:20 - 16:45

HOU - MDW
09:00 (CUN)Cancun Airport

14:20 (HOU)Houston Hobby Airport
11:25 (HOU)Houston Hobby Airport

16:45 (MDW)Chicago Midway Airport
(WN 316)Boeing 737 700

(WN 3970)Boeing 737 Max 8 Passenger
7h 45m (2h 55m)
HOU Houston 2h 55m
- -
- T
- W
- -
- -
- -
- -

11:30 - 16:00

CUN - BWI

18:45 - 19:45

BWI - MDW
11:30 (CUN)Cancun Airport

18:45 (BWI)Baltimore Washington International Airport
16:00 (BWI)Baltimore Washington International Airport

19:45 (MDW)Chicago Midway Airport
(WN 1608)Boeing 737 Max 8 Passenger

(WN 1789)Boeing 737 Max 8 Passenger
8h 15m (2h 45m)
BWI Baltimore 2h 45m
- -
- -
- -
- -
- -
- S
- -

11:40 - 15:20

CUN - ATL

17:05 - 18:00

ATL - MDW
11:40 (CUN)Cancun Airport

17:05 (ATL)Atlanta Hartsfield-Jackson Intl Airport
15:20 (ATL)Atlanta Hartsfield-Jackson Intl Airport

18:00 (MDW)Chicago Midway Airport
(WN 1135)Boeing 737 Max 8 Passenger

(WN 5042)Boeing 737 Max 8 Passenger
6h 20m (1h 45m)
ATL Atlanta 1h 45m
- -
- -
- -
- -
- -
- S
- -

12:15 - 15:45

CUN - DEN

17:25 - 20:55

DEN - ORD
12:15 (CUN)Cancun Airport

17:25 (DEN)Denver Intl Airport
15:45 (DEN)Denver Intl Airport

20:55 (ORD)Chicago O'Hare International Airport
(WN 1018)Boeing 737 700

(WN 1130)Boeing 737 800
8h 40m (1h 40m)
DEN Denver 1h 40m
- -
- -
- -
- -
- -
- S
- -

12:20 - 16:45

CUN - BWI

18:55 - 20:00

BWI - MDW
12:20 (CUN)Cancun Airport

18:55 (BWI)Baltimore Washington International Airport
16:45 (BWI)Baltimore Washington International Airport

20:00 (MDW)Chicago Midway Airport
(WN 1608)Boeing 737 Max 8 Passenger

(WN 1789)Boeing 737 800
7h 40m (2h 10m)
BWI Baltimore 2h 10m
- -
- -
- -
- -
- -
- -
- S

12:35 - 17:00

CUN - BWI

18:45 - 19:45

BWI - MDW
12:35 (CUN)Cancun Airport

18:45 (BWI)Baltimore Washington International Airport
17:00 (BWI)Baltimore Washington International Airport

19:45 (MDW)Chicago Midway Airport
(WN 1610)Boeing 737 Max 8 Passenger

(WN 1789)Boeing 737 Max 8 Passenger
7h 10m (1h 45m)
BWI Baltimore 1h 45m
- -
- -
- -
- -
- -
- S
- -

12:45 - 17:10

CUN - BWI

20:20 - 21:25

BWI - MDW
12:45 (CUN)Cancun Airport

20:20 (BWI)Baltimore Washington International Airport
17:10 (BWI)Baltimore Washington International Airport

21:25 (MDW)Chicago Midway Airport
(WN 1608)Boeing 737 700

(WN 3059)Boeing 737 700
8h 40m (3h 10m)
BWI Baltimore 3h 10m
- -
- T
- W
- -
- -
- -
- -

12:50 - 16:20

CUN - MCI

18:50 - 20:10

MCI - MDW
12:50 (CUN)Cancun Airport

18:50 (MCI)Kansas City International Airport
16:20 (MCI)Kansas City International Airport

20:10 (MDW)Chicago Midway Airport
(WN 750)Boeing 737 Max 8 Passenger

(WN 2051)Boeing 737 Max 8 Passenger
7h 20m (2h 30m)
MCI Kansas City 2h 30m
- -
- -
- -
- -
- -
- -
- S

12:55 - 15:25

CUN - HOU

16:55 - 19:30

HOU - MDW
12:55 (CUN)Cancun Airport

16:55 (HOU)Houston Hobby Airport
15:25 (HOU)Houston Hobby Airport

19:30 (MDW)Chicago Midway Airport
(WN 328)Boeing 737 Max 8 Passenger

(WN 3114)Boeing 737 Max 8 Passenger
6h 35m (1h 30m)
HOU Houston 1h 30m
- -
- T
- W
- -
- -
- -
- -

13:15 - 16:45

CUN - MCI

19:00 - 20:25

MCI - MDW
13:15 (CUN)Cancun Airport

19:00 (MCI)Kansas City International Airport
16:45 (MCI)Kansas City International Airport

20:25 (MDW)Chicago Midway Airport
(WN 750)Boeing 737 Max 8 Passenger

(WN 2051)Boeing 737 700
7h 10m (2h 15m)
MCI Kansas City 2h 15m
- -
- T
- W
- -
- -
- -
- -

13:15 - 16:45

CUN - MCI

19:05 - 20:30

MCI - MDW
13:15 (CUN)Cancun Airport

19:05 (MCI)Kansas City International Airport
16:45 (MCI)Kansas City International Airport

20:30 (MDW)Chicago Midway Airport
(WN 750)Boeing 737 Max 8 Passenger

(WN 2051)Boeing 737 700
7h 15m (2h 20m)
MCI Kansas City 2h 20m
- M
- -
- -
- T
- F
- -
- -

13:15 - 16:45

CUN - MCI

20:20 - 21:40

MCI - MDW
13:15 (CUN)Cancun Airport

20:20 (MCI)Kansas City International Airport
16:45 (MCI)Kansas City International Airport

21:40 (MDW)Chicago Midway Airport
(WN 750)Boeing 737 Max 8 Passenger

(WN 3312)Boeing 737 800
8h 25m (3h 35m)
MCI Kansas City 3h 35m
- -
- T
- W
- -
- -
- -
- -

13:45 - 17:15

CUN - MCI

18:55 - 20:15

MCI - MDW
13:45 (CUN)Cancun Airport

18:55 (MCI)Kansas City International Airport
17:15 (MCI)Kansas City International Airport

20:15 (MDW)Chicago Midway Airport
(WN 750)Boeing 737 Max 8 Passenger

(WN 2051)Boeing 737 800
6h 30m (1h 40m)
MCI Kansas City 1h 40m
- -
- -
- -
- -
- -
- S
- -

13:50 - 16:35

CUN - FLL

19:05 - 21:15

FLL - MDW
13:50 (CUN)Cancun Airport

19:05 (FLL)Fort Lauderdale/Hollywood Intl Airport
16:35 (FLL)Fort Lauderdale/Hollywood Intl Airport

21:15 (MDW)Chicago Midway Airport
(WN 521)Boeing 737 700

(WN 3107)Boeing 737 Max 8 Passenger
7h 25m (2h 30m)
FLL Miami 2h 30m
- -
- -
- -
- -
- -
- -
- S

13:55 - 16:40

CUN - FLL

19:10 - 21:25

FLL - MDW
13:55 (CUN)Cancun Airport

19:10 (FLL)Fort Lauderdale/Hollywood Intl Airport
16:40 (FLL)Fort Lauderdale/Hollywood Intl Airport

21:25 (MDW)Chicago Midway Airport
(WN 521)Boeing 737 Max 8 Passenger

(WN 3107)Boeing 737 800
7h 30m (2h 30m)
FLL Miami 2h 30m
- M
- -
- -
- T
- F
- -
- -

13:55 - 16:40

CUN - FLL

19:10 - 21:20

FLL - MDW
13:55 (CUN)Cancun Airport

19:10 (FLL)Fort Lauderdale/Hollywood Intl Airport
16:40 (FLL)Fort Lauderdale/Hollywood Intl Airport

21:20 (MDW)Chicago Midway Airport
(WN 521)Boeing 737 Max 8 Passenger

(WN 3107)Boeing 737 Max 8 Passenger
7h 25m (2h 30m)
FLL Miami 2h 30m
- -
- T
- W
- -
- -
- -
- -

14:05 - 17:40

CUN - DEN

19:10 - 22:35

DEN - ORD
14:05 (CUN)Cancun Airport

19:10 (DEN)Denver Intl Airport
17:40 (DEN)Denver Intl Airport

22:35 (ORD)Chicago O'Hare International Airport
(WN 1018)Boeing 737 Max 8 Passenger

(WN 3642)Boeing 737 700
8h 30m (1h 30m)
DEN Denver 1h 30m
- M
- -
- -
- T
- F
- -
- -

14:05 - 17:40

CUN - DEN

19:10 - 22:35

DEN - ORD
14:05 (CUN)Cancun Airport

19:10 (DEN)Denver Intl Airport
17:40 (DEN)Denver Intl Airport

22:35 (ORD)Chicago O'Hare International Airport
(WN 1018)Boeing 737 Max 8 Passenger

(WN 3642)Boeing 737 800
8h 30m (1h 30m)
DEN Denver 1h 30m
- -
- T
- W
- -
- -
- -
- -

14:10 - 17:00

CUN - FLL

19:00 - 21:15

FLL - MDW
14:10 (CUN)Cancun Airport

19:00 (FLL)Fort Lauderdale/Hollywood Intl Airport
17:00 (FLL)Fort Lauderdale/Hollywood Intl Airport

21:15 (MDW)Chicago Midway Airport
(WN 521)Boeing 737 700

(WN 3107)Boeing 737 Max 8 Passenger
7h 05m (2h)
FLL Miami 2h
- -
- -
- -
- -
- -
- S
- -

14:10 - 16:40

CUN - HOU

18:15 - 20:45

HOU - MDW
14:10 (CUN)Cancun Airport

18:15 (HOU)Houston Hobby Airport
16:40 (HOU)Houston Hobby Airport

20:45 (MDW)Chicago Midway Airport
(WN 328)Boeing 737 700

(WN 3114)Boeing 737 700
6h 35m (1h 35m)
HOU Houston 1h 35m
- -
- -
- -
- -
- -
- -
- S

14:55 - 17:50

CUN - BNA

20:35 - 22:10

BNA - MDW
14:55 (CUN)Cancun Airport

20:35 (BNA)Nashville Airport
17:50 (BNA)Nashville Airport

22:10 (MDW)Chicago Midway Airport
(WN 387)Boeing 737 Max 8 Passenger

(WN 3046)Boeing 737 800
7h 15m (2h 45m)
BNA Nashville 2h 45m
- -
- -
- -
- -
- -
- -
- S

15:15 - 18:25

CUN - STL

22:50 - 23:55

STL - MDW
15:15 (CUN)Cancun Airport

22:50 (STL)St Louis Lambert Intl Airport
18:25 (STL)St Louis Lambert Intl Airport

23:55 (MDW)Chicago Midway Airport
(WN 1996)Boeing 737 Max 8 Passenger

(WN 3244)Boeing 737 800
8h 40m (4h 25m)
STL Saint Louis 4h 25m
- -
- -
- -
- -
- -
- -
- S

15:25 - 19:50

CUN - BWI

21:55 - 22:55

BWI - MDW
15:25 (CUN)Cancun Airport

21:55 (BWI)Baltimore Washington International Airport
19:50 (BWI)Baltimore Washington International Airport

22:55 (MDW)Chicago Midway Airport
(WN 1610)Boeing 737 Max 8 Passenger

(WN 2775)Boeing 737 700
7h 30m (2h 05m)
BWI Baltimore 2h 05m
- -
- -
- -
- -
- -
- -
- S

15:45 - 19:00

CUN - STL

21:30 - 22:35

STL - MDW
15:45 (CUN)Cancun Airport

21:30 (STL)St Louis Lambert Intl Airport
19:00 (STL)St Louis Lambert Intl Airport

22:35 (MDW)Chicago Midway Airport
(WN 1996)Boeing 737 Max 8 Passenger

(WN 3244)Boeing 737 Max 8 Passenger
6h 50m (2h 30m)
STL Saint Louis 2h 30m
- -
- T
- W
- -
- -
- -
- -

16:25 - 20:00

CUN - ATL

21:50 - 22:45

ATL - MDW
16:25 (CUN)Cancun Airport

21:50 (ATL)Atlanta Hartsfield-Jackson Intl Airport
20:00 (ATL)Atlanta Hartsfield-Jackson Intl Airport

22:45 (MDW)Chicago Midway Airport
(WN 1135)Boeing 737 700

(WN 1245)Boeing 737 800
6h 20m (1h 50m)
ATL Atlanta 1h 50m
- -
- -
- -
- -
- -
- -
- S

16:40 - 19:05

CUN - HOU

20:50 - 23:25

HOU - MDW
16:40 (CUN)Cancun Airport

20:50 (HOU)Houston Hobby Airport
19:05 (HOU)Houston Hobby Airport

23:25 (MDW)Chicago Midway Airport
(WN 306)Boeing 737 Max 8 Passenger

(WN 3115)Boeing 737 Max 8 Passenger
6h 45m (1h 45m)
HOU Houston 1h 45m
- -
- -
- -
- -
- -
- S
- -

17:35 - 20:00+ 1

CUN - HOU

21:35 - 00:05+ 1

HOU - MDW
17:35 (CUN)Cancun Airport

21:35 (HOU)Houston Hobby Airport
20:00 (HOU)Houston Hobby Airport + 1

00:05 (MDW)Chicago Midway Airport
(WN 306)Boeing 737 Max 8 Passenger

(WN 3115)Boeing 737 800
6h 30m (1h 35m)
HOU Houston 1h 35m
- M
- -
- -
- T
- F
- -
- -

Sorry, there are no schedules matching your filters. Try removing one. reset

What’s the fastest flight time from Cancun to Chicago?

The fastest flight time for direct flights from Cancun to Chicago is 3 hours 40 minutes. Check latest flight schedules & prices on Wego.

How far is Chicago from Cancun?

The flight distance between Cancun and Chicago 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 09:00. The last flight of the day departs at 09:00. See the full list of flight times on Wego.

How many airlines offer direct flights from Cancun to Chicago?

There are 3 airlines that offer direct flights from Cancun to Chicago. Find out the list of airlines on Wego.

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