Cheap Flight Tickets from Chicago (MDW) to Cancún (CUN), Starting at $95

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

$95

WN Southwest Airlines • 1 stop • 10h

Oct 26 – Nov 01

The cheapest round trip flight from Chicago to Cancún (MDW-CUN-MDW) is currently $95

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Cheapest One way Flight

$122

WN Southwest Airlines • 2 stops • 27h 25m

Oct 26

The cheapest one way flight from Chicago to Cancún (MDW-CUN) is currently $122

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Cheapest Direct Flight

$543

WN Southwest Airlines • nonstop • 5h 45m

Nov 24

The cheapest nonstop flight from Chicago to Cancún (MDW-CUN) is currently $543

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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

Avianca Airline - AV

Avianca

Air Canada-AC

Air Canada

Aeromexico Airline (AM)

Aeromexico

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

WestJet Airlines

WestJet Airlines

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.

Oct 26 - Nov 01, Economy
WN
Chicago → Cancún
10h
7:05 AM - 1:05 PM • 1 stop
WN
Chicago → Cancún
5h 40m
1:50 PM - 4:30 PM • nonstop
$95
Southwest Airlines
Oct 25 - Oct 31, Economy
F9
Chicago → Cancún
- • 1 stop
F9
Chicago → Cancún
- • 1 stop
$299
Frontier Airlines
Oct 25 - Oct 31, Economy
DL
Chicago → Cancún
- • 1 stop
DL
Chicago → Cancún
- • 1 stop
$601
Delta Airlines
Oct 26 - Nov 01, Economy
DL
Chicago → Cancún
13h 41m
6:04 AM - 2:25 PM • 1 stop
DL
Chicago → Cancún
18h 20m
8:00 AM - 6:00 PM • 2 stops
$657
Delta Airlines
Oct 26 - Nov 01, Economy
WN
Chicago → Cancún
15h
7:15 AM - 4:15 PM • 2 stops
WN
Chicago → Cancún
5h 40m
1:50 PM - 4:30 PM • nonstop
$749
Southwest Airlines
Oct 26 - Nov 01, Economy
TS
Chicago → Cancún
25h 10m
6:20 PM - 9:30 AM • 1 stop
F8
Chicago → Cancún
14h 13m
12:55 PM - 8:48 PM • 1 stop
$2213
Air Transat

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 6:04 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 124
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 6:4000 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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