Cheap Flight Tickets from Chicago (MDW) to Cancún (CUN), Starting at $176

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

$488

WN Southwest Airlines • nonstop • 5h 45m

Mar 24 – Mar 24

The cheapest round trip flight from Chicago to Cancún (MDW-CUN-MDW) is currently $488

🔍 Search Flights

Cheapest Direct Flight

$478

WN Southwest Airlines • nonstop • 5h 45m

Mar 24

The cheapest nonstop flight from Chicago to Cancún (MDW-CUN) is currently $478

🔍 Search Flights

Fastest Flight

5h 45m

The fastest nonstop flight from Chicago to Cancún (MDW-CUN) takes 5h 45m

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 24 - Mar 24, Economy
WN
Chicago → Cancún
5h 45m
9:35 AM - 1:20 PM • nonstop
WN
Chicago → Cancún
25h 50m
3:45 PM - 7:35 AM • 1 stop
$488
Southwest Airlines
Mar 24 - Mar 30, Economy
DL
Chicago → Cancún
13h 35m
6:00 AM - 2:15 PM • 1 stop
DL
Chicago → Cancún
12h 22m
4:28 PM - 12:10 AM • 1 stop
$597
Delta Airlines
Mar 24 - Mar 30, Economy
DL
Chicago → Cancún
8h 55m
6:00 AM - 11:35 AM • 1 stop
DL
Chicago → Cancún
12h 22m
4:28 PM - 12:10 AM • 1 stop
$597
Delta Airlines
Mar 24 - Mar 30, Economy
WN
Chicago → Cancún
30h 35m
8:50 PM - 3:25 PM • 1 stop
WN
Chicago → Cancún
29h 5m
3:45 PM - 9:30 AM • 1 stop
$601
Southwest Airlines
Mar 24 - Mar 30, Economy
WN
Chicago → Cancún
13h 40m
5:50 AM - 2:10 PM • 1 stop
WN
Chicago → Cancún
29h 5m
3:45 PM - 9:30 AM • 1 stop
$601
Southwest Airlines
Mar 24 - Mar 30, Economy
WN
Chicago → Cancún
21h 40m
7:45 AM - 8:45 PM • 2 stops
WN
Chicago → Cancún
30h 30m
5:05 PM - 11:35 AM • 2 stops
$633
Southwest 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 5:00 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 DL : USD 597
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 8:50 pm

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

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

More Flight Options for Chicago (MDW) and Cancún (CUN)

Why Fareleaders for MDW to CUN Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Chicago to Cancún flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on MDW to CUN flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Chicago to Cancún flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Chicago (MDW) to Cancún (CUN)
Terms and Conditions*