Cheap Flight Tickets from Chicago (MDW) to Cancún (CUN), Starting at $523

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

$538

AM Aeromexico • 1 stop • 23h 20m

Aug 31 – Sep 04

The cheapest round trip flight from Chicago to Cancún (MDW-CUN-MDW) is currently $538

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Cheapest Direct Flight

$523

WN Southwest Airlines • nonstop • 5h 35m

Aug 31

The cheapest nonstop flight from Chicago to Cancún (MDW-CUN) is currently $523

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Fastest Flight

5h 35m

The fastest nonstop flight from Chicago to Cancún (MDW-CUN) takes 5h 35m

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.

Aug 31 - Sep 04, Economy
AM
Chicago → Cancún
23h 20m
6:05 AM - 8:05 PM • 1 stop
AM
Chicago → Cancún
25h 52m
8:05 AM - 11:57 PM • 1 stop
$538
Aeromexico
Aug 30 - Sep 03, Economy
AM
Chicago → Cancún
10h 55m
6:05 AM - 1:00 PM • 1 stop
AM
Chicago → Cancún
15h 47m
2:10 PM - 11:57 PM • 1 stop
$561
Aeromexico
Aug 30 - Sep 03, Economy
WN
Chicago → Cancún
25h 55m
8:05 PM - 12:00 PM • 1 stop
WN
Chicago → Cancún
5h 35m
1:05 PM - 4:40 PM • nonstop
$570
Southwest Airlines
Aug 31 - Sep 04, Economy
WN
Chicago → Cancún
26h 40m
8:40 PM - 12:40 PM • 1 stop
WN
Chicago → Cancún
28h 35m
4:05 PM - 9:20 AM • 1 stop
$584
Southwest Airlines
Aug 30 - Sep 03, Economy
WN
Chicago → Cancún
12h 15m
7:55 AM - 3:30 PM • 1 stop
WN
Chicago → Cancún
17h 25m
11:35 AM - 10:20 PM • 1 stop
$584
Southwest Airlines
Aug 30 - Sep 03, Economy
WN
Chicago → Cancún
31h 55m
8:45 PM - 4:00 PM • 1 stop
WN
Chicago → Cancún
5h 35m
1:05 PM - 4:40 PM • nonstop
$586
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 6:05 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 584
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 8:45 pm

Hotels in Cancún (CUN)

5 hotels near Cancún International — compare rates from top booking sites.

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5.0-star hotel 5-star hotel

The Westin Lagunamar Ocean Resort And Villas

📍 Blvd Kukulcan Km 12,5 Lote 18 Zona Hotelera, Cancún 77500

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5.0-star hotel 5-star hotel

Beach Palace All Inclusive

📍 Blvd. Kukulcan Km 11.5 - Zona Hotelera, Cancun 77500

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5.0-star hotel 5-star hotel

Beloved Playa Mujeres By Excellence Group

📍 Lt 34, Mza 1 Condominio Playa Mujeres, Cancun 77400

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5.0-star hotel 5-star hotel

Casamagna Marriott Cancun Resort

📍 Blvd.kukulkan Km.14.5 Retorno Chac.mz.23,Lote 41, Cancun 77500

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5.0-star hotel 5-star hotel

Crown Paradise Club Cancun All Inclusive

📍 Boulevard Kukulcan Km 18.5, Cancun 77500

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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)

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