Cheap Flight Tickets from Chicago (MDW) to Cancún (CUN), Starting at $440

Good to Know: Cheapest and Fastest MDW - CUN Flights

Useful information for finding best airline tickets from Chicago Midway International to Cancún International on your next trip.

Cheapest Round Trip Flight

$440

WN Southwest Airlines • nonstop • 5h 40m

Mar 21 – Mar 23

The cheapest round trip flight from Chicago to Cancún (MDW-CUN-MDW) is currently $440

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Cheapest Direct Flight

$440

WN Southwest Airlines • nonstop • 5h 40m

Mar 21

The cheapest nonstop flight from Chicago to Cancún (MDW-CUN) is currently $440

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Fastest Flight

5h 40m

The fastest nonstop flight from Chicago to Cancún (MDW-CUN) takes 5h 40m

Top Airlines Flying from Chicago to Cancún

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

Aeromexico Airline (AM)

Aeromexico

Latest Flight Deals from Chicago (MDW) to Cancún (CUN)

Compare and book low fare round-trip air tickets from Chicago to Cancún. Ideal for travelers with confirmed return itineraries.

Mar 21 - Mar 23, Economy
WN
Chicago → Cancún
5h 40m
5:05 PM - 8:45 PM • nonstop
WN
Chicago → Cancún
5h 50m
10:50 AM - 2:40 PM • nonstop
$440
Southwest Airlines
Mar 18 - Mar 24, Economy
WN
Chicago → Cancún
12h 35m
12:50 PM - 8:45 PM • 2 stops
WN
Chicago → Cancún
5h 50m
10:50 AM - 2:40 PM • nonstop
$444
Southwest Airlines
Mar 18 - Mar 24, Economy
WN
Chicago → Cancún
15h 45m
5:40 AM - 3:25 PM • 1 stop
WN
Chicago → Cancún
5h 50m
2:00 PM - 5:50 PM • nonstop
$444
Southwest Airlines
Mar 21 - Mar 23, Economy
WN
Chicago → Cancún
5h 40m
5:05 PM - 8:45 PM • nonstop
WN
Chicago → Cancún
13h 25m
11:20 AM - 7:25 PM • 1 stop
$450
Southwest Airlines
Mar 21 - Mar 23, Economy
WN
Chicago → Cancún
8h 40m
8:00 AM - 1:20 PM • 1 stop
WN
Chicago → Cancún
10h 30m
1:10 PM - 7:40 PM • 1 stop
$455
Southwest Airlines
Mar 18 - Mar 24, Economy
DL
Chicago → Cancún
10h 55m
6:00 AM - 12:55 PM • 1 stop
DL
Chicago → Cancún
12h 14m
6:06 AM - 1:40 PM • 1 stop
$489
Delta Airlines

Fly from Chicago to Cancún with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to Cancún? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Chicago to Cancún Flights

What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from MDW to CUN?
The most popular airline flying from Chicago to Cancún are
Can I fly from MDW to CUN non-stop?
Yes, you can fly MDW to CUN non-stop on
Which airlines fly nonstop between Chicago and Cancún?
The non-stop flights between Chicago and Cancún are .
What’s the earliest departure time from MDW to CUN Airport?
The earliest flight leaves MDW at 5:40 am and lands in CUN - Cancún International
What are the airports in Cancún?
CUN
Can I make changes to my Chicago to Cancún flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from MDW to CUN?
Read the fare rules of the Chicago to Cancún air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Chicago and Cancún?
operate flights between Chicago and Cancún
How long does a flight from Chicago to Cancún take?
It takes approximately 3 hour to fly non-stop from MDW to CUN, which is 1430.53 miles by air.
Which airlines provide the cheapest flights from Chicago (MDW) to Cancún (CUN) ?
In the past couple of days, the cheapest tickets to CUN from MDW were found on WN : USD 444
Do I need a passport to fly between MDW and CUN?
Yes
What’s the latest departure time from MDW to CUN ?
The last flight leaves MDW at 5:05 pm

Chicago (MDW) to Cancún (CUN): Airport Information

Origin Airport Chicago Midway International , Chicago, US
Destination Airport Cancún International , Cancún, MX
Distance 1431 miles

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