$178 Cheap Delta flights Cancun (CUN) to Chicago (MDW)

Make use of the “Price (lowest to highest)” filter on Expedia to search for cheap Delta Air Lines round-trip flights from $299 from CUN to MDW. Affordable one-way tickets from $178 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.

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.

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.

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.

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.

Delta Air Lines flights from Cancun Intl. Airport (CUN) to Chicago come in to Midway Intl. Airport (MDW). This is the main gateway here.

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.

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.”