S$197 Cheap Flights from Chicago to Cancun

View S$197 flight on Tue, 17 Mar, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Cancun Intl. Airport (CUN)

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Cheap Flights from Chicago to Cancun (MDW-CUN)

Prices were available within the past 7 days and start at S$197 for one-way flights and S$711 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, 17 Mar - Sun, 22 Mar
MDW
Chicago
CUN
Cancun
S$711 Return, found 3 days ago
S$711
Return
found 3 days ago
Select Delta flight, departing Tue, 17 Mar from Chicago to Cancun, returning Sun, 22 Mar, priced at S$711 found 3 days ago
Delta
Tue, 17 Mar - Sun, 22 Mar
MDW
Chicago
CUN
Cancun
S$712 Return, found 2 days ago
S$712
Return
found 2 days ago
Select Delta flight, departing Tue, 17 Mar from Chicago to Cancun, returning Sun, 22 Mar, priced at S$712 found 2 days ago
Delta
Tue, 17 Mar - Sun, 22 Mar
MDW
Chicago
CUN
Cancun
S$794 Return, found 3 days ago
S$794
Return
found 3 days ago
Select Delta flight, departing Tue, 17 Mar from Chicago to Cancun, returning Sun, 22 Mar, priced at S$794 found 3 days ago
Delta
Wed, 4 Feb - Sun, 8 Feb
MDW
Chicago
CUN
Cancun
S$795 Return, found 1 day ago
S$795
Return
found 1 day ago
Select Delta flight, departing Wed, 4 Feb from Chicago to Cancun, returning Sun, 8 Feb, priced at S$795 found 1 day ago
Delta
Tue, 17 Mar - Sun, 22 Mar
MDW
Chicago
CUN
Cancun
S$808 Return, found 2 days ago
S$808
Return
found 2 days ago
Select Delta flight, departing Tue, 17 Mar from Chicago to Cancun, returning Sun, 22 Mar, priced at S$808 found 2 days ago
Delta
Tue, 17 Mar - Sun, 22 Mar
MDW
Chicago
CUN
Cancun
S$878 Return, found 3 days ago
S$878
Return
found 3 days ago
Select Delta flight, departing Tue, 17 Mar from Chicago to Cancun, returning Sun, 22 Mar, priced at S$878 found 3 days ago
Delta
Tue, 17 Mar - Sun, 22 Mar
MDW
Chicago
CUN
Cancun
S$879 Return, found 2 days ago
S$879
Return
found 2 days ago
Select Delta flight, departing Tue, 17 Mar from Chicago to Cancun, returning Sun, 22 Mar, priced at S$879 found 2 days ago
Delta
Tue, 17 Mar - Sun, 22 Mar
MDW
Chicago
CUN
Cancun
S$969 Return, found 2 days ago
S$969
Return
found 2 days ago
Select Delta flight, departing Tue, 17 Mar from Chicago to Cancun, returning Sun, 22 Mar, priced at S$969 found 2 days ago
Delta
Tue, 17 Mar - Sun, 22 Mar
MDW
Chicago
CUN
Cancun
S$982 Return, found 2 days ago
S$982
Return
found 2 days ago
Select Delta flight, departing Tue, 17 Mar from Chicago to Cancun, returning Sun, 22 Mar, priced at S$982 found 2 days ago
Delta
Tue, 17 Mar - Sun, 22 Mar
MDW
Chicago
CUN
Cancun
S$1,052 Return, found 2 days ago
S$1,052
Return
found 2 days ago
Select Delta flight, departing Tue, 17 Mar from Chicago to Cancun, returning Sun, 22 Mar, priced at S$1,052 found 2 days ago

Find the cheapest month to fly from Chicago (MDW) to Cancun (CUN)

July is typically the cheapest month to fly

From S$318 - S$847 per traveller.

Frequently asked questions

How much is a flight from Midway Intl. Airport (MDW) to Cancun Intl. Airport (CUN)?
The lowest price advertised for a round-trip flight between Midway Airport and CUN is S$711. But you better act soon. This price is based on fares listed within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from MDW to Cancun Intl. Airport (CUN)?
Most flights can be cancelled online, but each airline has its own set of terms and conditions. If you do have to cancel your flight, check out our Customer Service Portal and follow the instructions.
How do I find cheap flights from Midway Airport to Cancun Intl. Airport (CUN) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Chicago Airport to Cancun Intl. Airport (CUN) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Midway Airport to CUN?
The flight distance from Chicago Airport to Cancun Intl. Airport (CUN) is 2,300 kilometres. Listen to your favourite tunes or get stuck into a book and the trip will fly by.
Which airlines fly direct from Chicago Airport to Cancun Airport?
Southwest Airlines (WN) will fly you from Chicago Airport to Cancun Intl. Airport (CUN) comfortably and reliably. Choose from 34 direct flights each month on this route.
Are Midway Airport to Cancun Intl. Airport (CUN) flight tickets cheaper when they're purchased at the last minute?
It is possible to score a great last-minute deal from Midway Airport to Cancun Airport, but there's no guarantee. As many airlines release prices up to 12 months in advance, it's worth keeping an eye on fares early and being ready to book when you spot a good bargain. Expedia compares air carrier prices and updates flight deals frequently, so you can feel confident knowing you're always seeing the latest offers.

Travel information

Origin airport
Midway Intl.
Destination airport
Cancun Intl.
Airlines serving
Delta
Return price
S$710
Distance
2294 km
Average flight time
3 hours 40 mins

Book with confidence

Perfect flights from Chicago to Cancun

Your Journey from Chicago to Cancun

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With Expedia, you have access to a wide range of airlines, including Delta. Our selection of flights from Midway Intl. to Cancun Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

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Experience the joy of finding cheap flights from Midway Intl. to Cancun Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$197 and roundtrip prices from S$711*.
 

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*Note: Prices may vary based on availability and are subject to change.
Perfect flights from Chicago to Cancun

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