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Flights from Cancun to Chicago – Direct & connecting routes

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CUN to MDW flights and routes map CUN to MDW – All flight route options from Cancun International Airport, Mexico to Chicago Midway International, Illinois, USA. These flights are operated by 4 airlines. Fly non-stop with Southwest Airlines or choose from 13 different transit flights. The shortest flight time is 3 hours and 45 minutes. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.

From
To
Mexico CUN Cancun Airport Cancun, Mexico
USA MDW Chicago Midway , IL, USA
CUN
Cancun Airport
MexicoCancun, Mexico
Chicago Midway
USAChicago, IL, USA
MDW
1 direct route found »
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16 routes with 1 stop found »
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Non-stop route options:

Duration

Southwest Airlines
Non-stop with Southwest Airlines. 2 flights per day.

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3h 45m

Southwest Airlines
Non-stop with Southwest Airlines.
3h 45m
2 flights per day.
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1 stop route options with the same airline:

Duration

Via New Orleans MSY
1 stop with Southwest Airlines. 0-1 flights per day.
Only sundays

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6h 05m

Only sundays
Via New Orleans MSY
1 stop with Southwest Airlines.
6h 05m
0-1 flights per day.
Only sundays
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Via Pittsburgh PIT
1 stop with Southwest Airlines. 0-1 flights per day.
Only saturdays

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6h 55m

Only saturdays
Via Pittsburgh PIT
1 stop with Southwest Airlines.
6h 55m
0-1 flights per day.
Only saturdays
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Via Saint Louis STL
1 stop with Southwest Airlines. 1-2 flights per day.

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6h 55m

Via Saint Louis STL
1 stop with Southwest Airlines.
6h 55m
1-2 flights per day.
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Via Nashville BNA
1 stop with Southwest Airlines. 0-1 flights per day.

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7h 08m

Via Nashville BNA
1 stop with Southwest Airlines.
7h 08m
0-1 flights per day.
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Via Austin AUS
1 stop with Southwest Airlines. 0-2 flights per day.

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7h 25m

Via Austin AUS
1 stop with Southwest Airlines.
7h 25m
0-2 flights per day.
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Via Atlanta ATL
1 stop with Southwest Airlines. 0-1 flights per day.
Only sundays

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7h 30m

Only sundays
Via Atlanta ATL
1 stop with Southwest Airlines.
7h 30m
0-1 flights per day.
Only sundays
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Via Detroit DTW
1 stop with Delta Air Lines. 0-1 flights per day.
Begins in 8/11

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7h 31m

Begins in 8/11
Via Detroit DTW
1 stop with Delta Air Lines.
7h 31m
0-1 flights per day.
Begins in 8/11
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Via Atlanta ATL
1 stop with Delta Air Lines. 4-6 flights per day.

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7h 49m

Via Atlanta ATL
1 stop with Delta Air Lines.
7h 49m
4-6 flights per day.
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Via Kansas City MCI
1 stop with Southwest Airlines. 0-1 flights per day.

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7h 53m

Via Kansas City MCI
1 stop with Southwest Airlines.
7h 53m
0-1 flights per day.
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Via Orlando MCO
1 stop with Southwest Airlines. 0-1 flights per day.

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8h 05m

Via Orlando MCO
1 stop with Southwest Airlines.
8h 05m
0-1 flights per day.
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Via Houston HOU
1 stop with Southwest Airlines. 3-4 flights per day.

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8h 18m

Via Houston HOU
1 stop with Southwest Airlines.
8h 18m
3-4 flights per day.
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Via Columbus CMH
1 stop with Southwest Airlines. 0-1 flights per day.
Sat & Sun

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8h 35m

Sat & Sun
Via Columbus CMH
1 stop with Southwest Airlines.
8h 35m
0-1 flights per day.
Sat & Sun
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Via Baltimore BWI
1 stop with Southwest Airlines. 2-3 flights per day.

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8h 40m

Via Baltimore BWI
1 stop with Southwest Airlines.
8h 40m
2-3 flights per day.
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Via Indianapolis IND
1 stop with Southwest Airlines.
Begins in 8/11

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9h 05m

Begins in 8/11
Via Indianapolis IND
1 stop with Southwest Airlines.
9h 05m
Begins in 8/11
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Via Atlanta ATL
1 stop with Frontier Airlines. 0-1 flights per day.

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9h 28m

Via Atlanta ATL
1 stop with Frontier Airlines.
9h 28m
0-1 flights per day.
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1 stop route options with codeshare or different airlines:

Duration

Via Atlanta ATL 1 stop with Aeromexico. 4-6 flights per day.
CODESHARE

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7h 47m

Via Atlanta ATL
7h 47m
1 stop with Aeromexico. 4-6 flights per day.
CODESHARE
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Cancun to Chicago flights

There are over 14 airlines and as many as 219 flights every week to this destination. You can fly non-stop to Chicago (MDW) from Cancun (CUN) with Southwest Airlines but if a stopover option suits you better you can choose to fly via New Orleans, Pittsburgh or any other of the 13 alternatives with connectiing airports.

Cancun to Chicago with Southwest Airlines

You can fly non-stop every weekday with flights departing between 8:00 am and 4:00 pm. You can also catch a transit flight via New Orleans or Saint Louis.

With Delta Air Lines

If you choose to fly with Delta Air Lines from Cancun to Chicago you can make a transit either via Detroit or via Atlanta. The route via Detroit is 18 minutes faster. Delta Air Lines is a member of SkyTeam.

Distance & flight times: Cancun International Airport to Midway International Airport

The shortest flight time between CUN and MDW is 3 hours and 45 minutes.

ViaTotal flight timeLayover timeDistance
Direct3h 45m-1442 miles (2320 km)
MSY New Orleans6h 5m1h 50m1488 miles (2394 km)
PIT Pittsburgh6h 55m1h 45m1810 miles (2912 km)
STL Saint Louis6h 55m1h 35m1500 miles (2414 km)
BNA Nashville7h 8m2h 30m1445 miles (2325 km)
AUS Austin7h 25m2h 40m1905 miles (3065 km)
DTW Detroit7h 31m2h 21m1715 miles (2759 km)
ATL Atlanta7h 47m3h 22m1482 miles (2385 km)
MCI Kansas City7h 53m4h 45m1758 miles (2829 km)
MCO Orlando8h 5m3h 30m1617 miles (2602 km)
HOU Houston8h 18m2h 0m1740 miles (2800 km)
CMH Columbus8h 35m3h 15m1622 miles (2610 km)
BWI Baltimore8h 40m3h 20m2011 miles (3236 km)
IND Indianapolis9h 5m4h 40m1460 miles (2349 km)
The flight times and layover times in the table above are approximate and may vary depending on flight number, aircraft, airline, weather, and time of day.CUN-MDW flight routesCancun to Chicago flight routes illustrated on a map.
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Cancun - Chicago route map and flight paths
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From Cancun to USA

Below is a list of other destinations to USA from Cancun International Airport with either direct flights or 1 stop connections.

From Mexico to Chicago

Below is a list of other cities in Mexico with flights to Chicago with either non-stop or connecting flights.

You can fly non-stop from Cancun (CUN) to Chicago (MDW) with Southwest Airlines. The flight takes approximately 3 hours and 45 minutes. If you travel with a connecting flight instead, for example via New Orleans, the total flight time will be 6 hours and 5 minutes.

If you're interested in direct flights, Southwest Airlines is available. For flights with stopovers, Southwest Airlines, Delta Air Lines or Aeromexico is also an option.

The flight time between Cancun Airport (CUN) and Chicago Midway International (MDW) is approximately 3 hours and 45 minutes. The distance between the two airports is 1482 miles (or 2385 kilometers).

Yes, you can fly non-stop to MDW from CUN with Southwest Airlines.

A codeshare agreement means that cooperating airlines are able to sell seats on each other’s flights. This means that you are able to travel to more destinations than your airline of choice normally offers. Codeshare flights are also beneficial because of the seamless transits you can get with connecting flights from the same airline. The downside of choosing a codeshare flight can be that you in some cases can’t upgrade codeshare flights or use elite benefits.

A connecting or transit flight means that you reach your final destination through two or more flights – in other words a non-direct flight. You will change to a new aircraft after your first flight, this may include moving to another terminal at the airport aswell. The time required to transfer passengers and luggage between flights is called Minimum Connecting Time (MCT) and are always taken into account here on Flightroutes.com.

If you bought your whole flight on a single ticket, the airline will book you on the next available connecting flight.

With connecting flights, checked in luggage is most commonly forwarded to your final destination when buying a single ticket for both flights.

If you miss your connecting flight due to circumstances outside your control such as your first flight being delayed, you should turn to your airline who will provide you with a seat on the next available flight. This is usually done free of charge, and only applies if you purchased your trip as one ticket. If the next connecting flight is the following day, the airline usually provides accommodation and meals.
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