Southwest Airlines
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Cancún International Airport
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Midway International Airport
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Scan through all non-stop flights from Cancún to Chicago. The full flight schedule below gives an overview of all non-stop flights from CUN to MDW, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Known for its continental climate, Chicago features hot, humid summers with temperatures above 30°C (86°F) and cold, snowy winters that often drop below 0°C (32°F). This striking seasonal contrast offers travelers a variety of activities, from summer hiking to winter sports, ensuring year-round appeal.
The best time to visit Chicago is from March to November, covering spring, summer, and fall. While summer can be hot, it also sees slightly more rainfall than other seasons.
In total there are 2 airlines operating nonstop flights from Cancún CUN to Chicago MDW. This section gives an overview of the flight schedules and timetables of every airline with direct flights for this route.
Click an airline below to view their CUN MDW flight schedule.
Flights from CUN to MDW are operated 10 times a week, with an average of 1 flight per day. Departure times vary between 08:30 - 17:15. The earliest flight departs at 08:30, the last flight departs at 17:15. However, this depends on the date you are flying so please check with the full flight schedule above to see which departure times are available on your preferred date(s) of travel.
On this non-stop route, you can fly in Economy only.
The fastest direct flight from Cancún to Chicago takes 3 hours and 45 minutes. The flight distance between Cancún and Chicago is 1,433 miles (or 2,306 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (ORD).
There are 10 flights per week flying from Cancún to Chicago (as of April 2026).
3 hours and 45 minutes is the average flight time from Cancún to Chicago.
The distance from Cancún to Chicago is 1,433 miles (2,306 kilometers).
Frontier Airlines and Southwest Airlines are flying nonstop from Cancún to Chicago.
There are no alliances flying direct from Cancún to Chicago at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Cancún to Chicago:
The earliest flight departs at 08:30 from Cancún and arrives at 12:10 at Chicago.
The latest flight departs at 17:15 from Cancún and arrives at 20:55 at Chicago.
1,433 miles (2,306 km) · 3h 45m
08:30
12:10
Southwest Airlines
WN 217
Southwest Airlines
Boeing 757
Y
W
J
F
09:25
13:05
Southwest Airlines
WN 217
Southwest Airlines
Boeing 757
Y
W
J
F
09:55
13:40
Southwest Airlines
WN 217
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
10:50
14:30
Southwest Airlines
WN 219
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
13:20
17:05
Frontier Airlines
F9 234
Frontier Airlines
Airbus A320neo
Y
W
J
F
13:50
17:30
Southwest Airlines
WN 219
Southwest Airlines
Boeing 757
Y
W
J
F
14:05
17:50
Southwest Airlines
WN 219
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
15:15
18:55
Southwest Airlines
WN 219
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
15:25
19:10
Southwest Airlines
WN 219
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
16:00
19:40
Southwest Airlines
WN 217
Southwest Airlines
Boeing 757
Y
W
J
F
16:10
19:50
Southwest Airlines
WN 217
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
17:15
20:55
Southwest Airlines
WN 219
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
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