$179 Cheap Delta flights Cancun (CUN) to Chicago (MDW)

View $179 flight on Fri, Sep 19, 2025Opens in a new window

$179 Cheap Delta flights Cancun (CUN) to Chicago (MDW)

Prices were available within the past 7 days and start at $179 for one-way flights and $303 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, Sep 5 - Sun, Sep 7
CUN
Cancun
MDW
Chicago
$303 Roundtrip, just found
$303
Roundtrip
just found
Select Delta flight, departing Fri, Sep 5 from Cancun to Chicago, returning Sun, Sep 7, priced at $303 just found
Delta
Fri, Sep 5 - Sun, Sep 7
CUN
Cancun
MDW
Chicago
$330 Roundtrip, just found
$330
Roundtrip
just found
Select Delta flight, departing Fri, Sep 5 from Cancun to Chicago, returning Sun, Sep 7, priced at $330 just found
Delta
Sat, Jul 5 - Wed, Jul 9
CUN
Cancun
MDW
Chicago
$348 Roundtrip, found 1 day ago
$348
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jul 5 from Cancun to Chicago, returning Wed, Jul 9, priced at $348 found 1 day ago
Delta
Fri, Sep 19 - Mon, Sep 22
CUN
Cancun
MDW
Chicago
$366 Roundtrip, found 2 hours ago
$366
Roundtrip
found 2 hours ago
Select Delta flight, departing Fri, Sep 19 from Cancun to Chicago, returning Mon, Sep 22, priced at $366 found 2 hours ago
Flights from Cancun (CUN) to Chicago (MDW)
Origin airport
Cancun Intl.
Destination airport
Midway Intl.
Airlines serving
Aeromexico, Delta, Frontier Airlines, Southwest Airlines, Volaris
Popular airline
Southwest Airlines
Distance
1434 mi
Average flight time
3 hours 40 mins

Frequently asked questions

How much is a Delta Air Lines flight from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW)?
Make use of the "Price (lowest to highest)" filter on Expedia to search for cheap Delta Air Lines round-trip flights from $303 from CUN to MDW. Affordable one-way tickets from $179 are also on offer.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly from CUN to MDW with Delta Air Lines?
January is one of the most affordable months to jet away to Chicago with Delta Air Lines. You could also find great prices on one-way and round-trip tickets in February.
What is the cheapest time to book flights from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW) with Delta Air Lines?
Check for Delta Air Lines flights from CUN to MDW about one month before you want to go. The most affordable time to reserve an international flight is generally 18 to 29 days ahead of your travel date when you can save 17% versus booking four to five months in advance. No matter your itinerary or ticket type, the best day of the week to book international airfare is usually Sunday. Friday can be the most expensive. Passengers who book on a Sunday can save 17% on average compared to those who book on a Friday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.
Does Delta Air Lines fly nonstop from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW)?
Use the "Nonstop" filter when looking for direct Delta Air Lines flights from CUN to MDW. You'll also be able to compare other airlines servicing the same direct trip.
What is the earliest Delta Air Lines flight from CUN to MDW?
Find Delta Air Lines's earliest flights from CUN to MDW by selecting our "Early Morning" and "Morning" filters. Not only will you arrive sooner, early departures also have a 20% less chance of being canceled.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports does Delta Air Lines fly into in Chicago?
Delta Air Lines flights from Cancun Intl. Airport (CUN) to Chicago come in to Midway Intl. Airport (MDW). This is the main gateway here.
Why fly with Delta Air Lines from CUN to MDW?
Offering a rewarding loyalty program and an excellent in-flight experience, Delta Air Lines is a top choice for many passengers heading from CUN to MDW. Also, if you're a Delta SkyMiles and One Key™ member booking with Expedia, you could earn OneKeyCash™* on eligible flights on top of your airline miles, which you can put toward future trips.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
Can I change or cancel my Delta Air Lines flight from Cancun Intl. Airport (CUN) to Midway Intl. Airport (MDW)?
Depending on the type of fare you purchased, a fee is typically charged if you cancel or reschedule your booking more than 24 hours after it's been confirmed. To secure flexible plane tickets, select our "Changes included" and "No cancel fee" boxes while looking for flights. To learn more about modifying or canceling your reservation, go to "Trips," select your flight and tick "Manage Booking."

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*Available to One Key members.