Skip to main content
Beginning of main content

Cheap Flights from Cancun to Chicago $318.33

Search over 321,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia's Price Guarantee.
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheapest Flights from Cancun to Chicago (CUN to MDW)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Cancun to Chicago (CUN to MDW)

Question : Looking for the quickest flight from CUN to MDW?
Answer : Southwest Airlines can get you there in three hours and 45 minutes. So, if you were to leave Cancun at 3:00 PM EST, you would arrive in Chicago at 5:45 PM CDT (remember, there is a one-hour time difference).

Question : What's the expected flight time for CUN to MDW?
Answer : Flying from CUN to MDW typically takes about three hours and 45 minutes.

Question : If your plans are flexible, have you considered changing your departure day?
Answer : The best day to fly on a budget this month is Tuesday. Having flexibility in your travel plans means you can save more, so be sure to plan ahead when possible.

Question : If you’re booking CUN to MDW, how many different options of departure times do you have?
Answer : It does differ by the day of the week, but on average, you can expect only one flight time when you book. You won't have as many options on this route as most others departing Mexico.

Question : Do prices fluctuate more for this route than others?
Answer : Prices for this trip tend to fluctuate a lot more than other flights from Mexico. They can vary anywhere from $310 to $766. However, the sooner you book, the more you'll be able to save.

Question : In terms of overall promptness, how does CUN to MDW rank compared to the rest of the world?
Answer : The best measurement of overall promptness combines both on-time percentage and total delay minutes. CUN to MDW currently has 3 stars out of 5, an average score at best.

Question : Interested in traveling in the next 30 days and want to get the lowest fare?
Answer : Since low prices are preferred, look at Apr 4th. As of Mar 27th, it's showing the cheapest ticket sales at $311. That is 31% below the average price for this route, so you can spend that extra money on a fun experience in Chicago.