$111 Cheap Flights from Cancun (CUN) to Chicago (ORD)

View $111 flight on Sat, Sep 6, 2025Opens in a new window

Popular airlines from Cancun Intl. Airport (CUN) to Chicago O'Hare Intl. Airport (ORD)

Cheap Flights from Cancun to Chicago (CUN-ORD)

Prices were available within the past 7 days and start at $111 for one-way flights and $199 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Sat, Sep 13 - Sat, Sep 20
CUN
Cancun
ORD
Chicago
$199 Roundtrip, found 13 hours ago
$199
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Sat, Sep 13 from Cancun to Chicago, returning Sat, Sep 20, priced at $199 found 13 hours ago
Spirit Airlines
Sat, Sep 20 - Sat, Sep 27
CUN
Cancun
ORD
Chicago
$205 Roundtrip, found 11 hours ago
$205
Roundtrip
found 11 hours ago
Select Spirit Airlines flight, departing Sat, Sep 20 from Cancun to Chicago, returning Sat, Sep 27, priced at $205 found 11 hours ago
Spirit Airlines
Sat, Sep 13 - Sun, Sep 21
CUN
Cancun
ORD
Chicago
$209 Roundtrip, found 10 hours ago
$209
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Sat, Sep 13 from Cancun to Chicago, returning Sun, Sep 21, priced at $209 found 10 hours ago
Frontier Airlines
Sat, Sep 6 - Sat, Sep 13
CUN
Cancun
ORD
Chicago
$212 Roundtrip, found 3 hours ago
$212
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Sep 6 from Cancun to Chicago, returning Sat, Sep 13, priced at $212 found 3 hours ago
Frontier Airlines
Sat, Sep 27 - Sun, Sep 28
CUN
Cancun
ORD
Chicago
$216 Roundtrip, found 3 hours ago
$216
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Sep 27 from Cancun to Chicago, returning Sun, Sep 28, priced at $216 found 3 hours ago
Spirit Airlines
Wed, Sep 10 - Sat, Sep 20
CUN
Cancun
ORD
Chicago
$218 Roundtrip, found 6 hours ago
$218
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Wed, Sep 10 from Cancun to Chicago, returning Sat, Sep 20, priced at $218 found 6 hours ago
Frontier Airlines
Sat, Sep 6 - Tue, Sep 16
CUN
Cancun
ORD
Chicago
$219 Roundtrip, found 6 hours ago
$219
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sat, Sep 6 from Cancun to Chicago, returning Tue, Sep 16, priced at $219 found 6 hours ago
Southwest Airlines
Sat, Nov 22 - Sat, Nov 29
CUN
Cancun
ORD
Chicago
$275 Roundtrip, found 12 hours ago
$275
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Sat, Nov 22 from Cancun to Chicago, returning Sat, Nov 29, priced at $275 found 12 hours ago
United
Thu, Aug 21 - Mon, Aug 25
CUN
Cancun
ORD
Chicago
$275 Roundtrip, found 1 hour ago
$275
Roundtrip
found 1 hour ago
Select United flight, departing Thu, Aug 21 from Cancun to Chicago, returning Mon, Aug 25, priced at $275 found 1 hour ago
American Airlines
Thu, Oct 9 - Tue, Oct 14
CUN
Cancun
ORD
Chicago
$285 Roundtrip, just found
$285
Roundtrip
just found
Select American Airlines flight, departing Thu, Oct 9 from Cancun to Chicago, returning Tue, Oct 14, priced at $285 just found

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

January is typically the cheapest month to fly

From $188 - $481 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $994
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $994
Flights from Cancun (CUN) to Chicago (ORD)
Origin airport
Cancun Intl.
Destination airport
O'Hare Intl.
Airlines serving
Aeromexico, Air Canada, Alaska Airlines, American Airlines, Arajet, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United, Viva, Volaris, World Ticket Ltd
Roundtrip price
$199
Distance
1447 mi
Average flight time
3 hours 59 mins

Cancun to Chicago Flights

The cheapest times to fly from Cancun to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Cancun to Chicago are during the month of September. You can find some of the cheapest flights from Cancun to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Cancun to Chicago

Sunday is one of the best days to book for cheap flights from Cancun to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Cancun to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Cancun to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $111 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Cancun to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Cancun to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Cancun Intl. Airport (CUN) to O'Hare Intl. Airport (ORD) cost?
Snag a cheap one-way flight from $111 or cheap return flight from $199 from Cancun Intl. Airport (CUN) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Cancun Intl. Airport (CUN) to O'Hare Intl. Airport (ORD)?
September is the most affordable month to fly from CUN to ORD. Traveling outside of peak seasons is often the key to scoring lower fares.
Which airlines fly direct from Cancun Intl. Airport (CUN) to O'Hare Intl. Airport (ORD)?
Fly straight to O'Hare Intl. Airport (ORD). 4 carriers offer nonstop flights from Cancun Intl. Airport (CUN), including:

  • United Airlines
  • American Airlines
  • Frontier Airlines

What is the cheapest airline that flies from Cancun Intl. Airport (CUN) to O'Hare Intl. Airport (ORD)?
Spirit Airlines and Frontier Airlines are well-known airlines offering competitive fares. Remember that flight prices from Cancun Intl. Airport (CUN) to O'Hare Intl. Airport (ORD) can vary depending on travel dates, demand and how early you book. With Expedia's search tool, you can easily find a CUN to ORD flight that suits your plans and budget.
How many flights per day from Cancun Intl. Airport (CUN) to O'Hare Intl. Airport (ORD)?
With, on average, 6 direct flights departing from Cancun Intl. Airport (CUN) to O'Hare Intl. Airport (ORD) daily, you'll be taking off on vacation soon enough.
What are the most popular departure times for flights from Cancun Intl. Airport (CUN) to O'Hare Intl. Airport (ORD)?
More people fly between CUN and ORD at 3 PM than at any other time of day. Looking to skip the crowds? Try choosing a quieter departure window and there's a chance you'll save on your fare as well.
What day of the week has the most flights from CUN to ORD?
Depart on a Friday if you're after the best selection of flights from Cancun Intl. Airport (CUN) to O'Hare Intl. Airport (ORD).
What is the earliest flight from Cancun Intl. Airport (CUN) to O'Hare Intl. Airport (ORD)?
The first flight of the day taking off from Cancun Intl. Airport (CUN) is at around 11:45AM UTC-5. Catch this flight and you'll arrive at O'Hare Intl. Airport (ORD) at approximately 2:47PM UTC-6. The total flight duration is 4h 2m.
How long does it take to fly from Cancun Intl. Airport (CUN) to O'Hare Intl. Airport (ORD)?
Flights from CUN to ORD have an average travel time of 3 hours and 58 minutes. The total distance between the two is 1,450 mi.
What airline has the least delays from CUN to ORD?
With 87% of journeys usually arriving on time, American Airlines has the best on-time performance for nonstop flights from Cancun Intl. Airport (CUN) to O'Hare Intl. Airport (ORD). To check your flight status and get notifications if anything changes, use the Expedia App.
What is the best time to fly from Cancun Intl. Airport (CUN) to O'Hare Intl. Airport (ORD)?
To avoid potential delays on the Cancun Intl. Airport (CUN) to O'Hare Intl. Airport (ORD) route, aim to fly before 3 PM. Departures after this time have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Cancun Intl. Airport (CUN)?
Take a direct flight from Cancun Intl. Airport (CUN) to Chicago and arrive at O'Hare Intl. Airport (ORD). Another convenient entry point into this destination is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Cancun Intl. Airport (CUN) to O'Hare Intl. Airport (ORD) last-minute?
Booking your flight from CUN to ORD right before your trip is usually more expensive. But if there's some wiggle room with your travel dates and times, you could snag a cheap last-minute fare.
Is it cheaper to book a CUN to ORD flight and hotel package?
You'll generally save money by booking a CUN to ORD flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one convenient place. After choosing your preferred flights and accommodations, you can add extras such as tours, activities and car rentals.
Can I cancel or change the date of my flight from Cancun Intl. Airport (CUN) to O'Hare Intl. Airport (ORD)?
If you reserved your CUN to ORD flight within the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more details.

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*Available to One Key members.