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Flights from Chicago to Cancun – Direct & connecting routes

Non-stop airlines Connecting flights Show map Price search

MDW to CUN flights and routes map MDW to CUN – All flight route options from Chicago Midway International, Illinois, USA to Cancun International Airport, Mexico. These flights are operated by 4 airlines. Fly non-stop with Southwest Airlines or choose from 9 different transit flights. The shortest flight time is 3 hours and 40 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
USA MDW Chicago Midway Chicago, IL, USA
Mexico CUN Cancun Airport, Mexico
MDW
Chicago Midway
USAChicago, IL, USA
Cancun Airport
MexicoCancun, Mexico
CUN
1 direct route found »
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12 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 40m

Southwest Airlines
Non-stop with Southwest Airlines.
3h 40m
2 flights per day.
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1 stop route options with the same airline:

Duration

Via Atlanta ATL
1 stop with Frontier Airlines. 0-1 flights per day.

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6h 11m

Via Atlanta ATL
1 stop with Frontier Airlines.
6h 11m
0-1 flights per day.
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Via Kansas City MCI
1 stop with Southwest Airlines. 0-1 flights per day.
Begins in 2/10

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6h 30m

Begins in 2/10
Via Kansas City MCI
1 stop with Southwest Airlines.
6h 30m
0-1 flights per day.
Begins in 2/10
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Via Atlanta ATL
1 stop with Southwest Airlines. 0-2 flights per day.
Only sundays

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6h 40m

Only sundays
Via Atlanta ATL
1 stop with Southwest Airlines.
6h 40m
0-2 flights per day.
Only sundays
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Via Orlando MCO
1 stop with Southwest Airlines. 2 flights per day.

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6h 40m

Via Orlando MCO
1 stop with Southwest Airlines.
6h 40m
2 flights per day.
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Via Nashville BNA
1 stop with Southwest Airlines. 0-2 flights per day.

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6h 40m

Via Nashville BNA
1 stop with Southwest Airlines.
6h 40m
0-2 flights per day.
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Via Saint Louis STL
1 stop with Southwest Airlines. 1-2 flights per day.

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6h 40m

Via Saint Louis STL
1 stop with Southwest Airlines.
6h 40m
1-2 flights per day.
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Via Atlanta ATL
1 stop with Delta Air Lines. 2 flights per day.

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6h 57m

Via Atlanta ATL
1 stop with Delta Air Lines.
6h 57m
2 flights per day.
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Via Baltimore BWI
1 stop with Southwest Airlines. 2 flights per day.

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7h 05m

Via Baltimore BWI
1 stop with Southwest Airlines.
7h 05m
2 flights per day.
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Via Houston HOU
1 stop with Southwest Airlines. 2 flights per day.

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7h 40m

Via Houston HOU
1 stop with Southwest Airlines.
7h 40m
2 flights per day.
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Via Austin AUS
1 stop with Southwest Airlines. 0-1 flights per day.
Mon,Thu & Fri

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8h 10m

Mon,Thu & Fri
Via Austin AUS
1 stop with Southwest Airlines.
8h 10m
0-1 flights per day.
Mon,Thu & Fri
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Via Dallas DFW
1 stop with Frontier Airlines. 0-1 flights per day.
Thu,Sat & Sun

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8h 26m

Thu,Sat & Sun
Via Dallas DFW
1 stop with Frontier Airlines.
8h 26m
0-1 flights per day.
Thu,Sat & Sun
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1 stop route options with codeshare or different airlines:

Duration

Via Atlanta ATL 1 stop with Aeromexico. 2 flights per day.
CODESHARE

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7h 36m

Via Atlanta ATL
7h 36m
1 stop with Aeromexico. 2 flights per day.
CODESHARE
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Find the best prices on hotels and car rental near Cancun Airport

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Chicago to Cancun flights

With over 166 flights every week and 10 different airlines you have a wide range of options. You can fly non-stop to Cancun (CUN) from Chicago (MDW) with Southwest Airlines but if a stopover option suits you better you can choose to fly via Kansas City, Orlando or any other of the 9 alternatives with connectiing airports.

Chicago to Cancun with Southwest Airlines

You can fly non-stop every weekday with flights departing from 6:00 am to 5:00 pm. You can also catch a transit flight via Kansas City or Atlanta.

With Frontier Airlines

If you choose to fly with Frontier Airlines from Chicago to Cancun you can make a transit either via Atlanta or via Dallas. The route via Atlanta is 2 hours and 15 minutes faster.

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

The shortest flight time between MDW and CUN is 3 hours and 40 minutes.

ViaTotal flight timeLayover timeDistance
Direct3h 40m-1442 miles (2320 km)
MCI Kansas City6h 30m1h 40m1758 miles (2829 km)
MCO Orlando6h 40m2h 35m1617 miles (2602 km)
STL Saint Louis6h 40m1h 5m1500 miles (2414 km)
BNA Nashville6h 40m1h 55m1445 miles (2325 km)
BWI Baltimore7h 5m3h 25m2011 miles (3236 km)
ATL Atlanta7h 36m59m1482 miles (2385 km)
HOU Houston7h 40m2h 45m1740 miles (2800 km)
AUS Austin8h 10m3h 10m1905 miles (3065 km)
DFW Dallas8h 26m3h 32m1837 miles (2956 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.MDW-CUN flight routesChicago to Cancun flight routes illustrated on a map.
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Chicago - Cancun route map and flight paths
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Show all destinations from MDW Show all destinations from CUN
From Chicago to Mexico

Below is a list of other destinations to Mexico from Chicago Midway International with either direct flights or 1 stop connections.

From USA to Cancun

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

You can fly non-stop from Chicago (MDW) to Cancun (CUN) with Southwest Airlines. The flight takes approximately 3 hours and 40 minutes. If you travel with a connecting flight instead, for example via Kansas City, the total flight time will be 6 hours and 30 minutes.

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

The flight time between Chicago Midway (MDW) and Cancun International Airport (CUN) is approximately 3 hours and 40 minutes. The distance between the two airports is 1482 miles (or 2385 kilometers).

Yes, you can fly non-stop to CUN from MDW 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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