$101 Cheap Flights from Chicago (ORD) to Cancun (CUN)

View $101 flight on Wed, Aug 6, 2025Opens in a new window

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

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Cheap Flights from Chicago to Cancun (ORD-CUN)

Prices were available within the past 7 days and start at $101 for one-way flights and $221 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Sat, Aug 16 - Sat, Aug 23
ORD
Chicago
CUN
Cancun
$221 Roundtrip, just found
$221
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Aug 16 from Chicago to Cancun, returning Sat, Aug 23, priced at $221 just found
Spirit Airlines
Wed, Aug 6 - Fri, Aug 22
ORD
Chicago
CUN
Cancun
$227 Roundtrip, found 19 hours ago
$227
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Wed, Aug 6 from Chicago to Cancun, returning Fri, Aug 22, priced at $227 found 19 hours ago
Funjet Vacations
Sat, Sep 13 - Sat, Sep 20
ORD
Chicago
CUN
Cancun
$229 Roundtrip, just found
$229
Roundtrip
just found
Select Funjet Vacations flight, departing Sat, Sep 13 from Chicago to Cancun, returning Sat, Sep 20, priced at $229 just found
Spirit Airlines
Sat, Aug 16 - Sat, Aug 23
ORD
Chicago
CUN
Cancun
$234 Roundtrip, just found
$234
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Aug 16 from Chicago to Cancun, returning Sat, Aug 23, priced at $234 just found
Spirit Airlines
Wed, Aug 6 - Wed, Aug 13
ORD
Chicago
CUN
Cancun
$239 Roundtrip, just found
$239
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Aug 6 from Chicago to Cancun, returning Wed, Aug 13, priced at $239 just found
Spirit Airlines
Sat, Oct 18 - Fri, Oct 24
ORD
Chicago
CUN
Cancun
$241 Roundtrip, found 1 hour ago
$241
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Oct 18 from Chicago to Cancun, returning Fri, Oct 24, priced at $241 found 1 hour ago
United
Sat, Sep 20 - Sat, Sep 27
ORD
Chicago
CUN
Cancun
$243 Roundtrip, just found
$243
Roundtrip
just found
Select United flight, departing Sat, Sep 20 from Chicago to Cancun, returning Sat, Sep 27, priced at $243 just found
Frontier Airlines
Sat, Aug 16 - Sat, Aug 23
ORD
Chicago
CUN
Cancun
$269 Roundtrip, just found
$269
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Aug 16 from Chicago to Cancun, returning Sat, Aug 23, priced at $269 just found
United
Sat, Sep 20 - Sat, Sep 27
ORD
Chicago
CUN
Cancun
$270 Roundtrip, just found
$270
Roundtrip
just found
Select United flight, departing Sat, Sep 20 from Chicago to Cancun, returning Sat, Sep 27, priced at $270 just found
American Airlines
Tue, Jul 15 - Wed, Jul 16
ORD
Chicago
CUN
Cancun
$270 Roundtrip, just found
$270
Roundtrip
just found
Select American Airlines flight, departing Tue, Jul 15 from Chicago to Cancun, returning Wed, Jul 16, priced at $270 just found

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

January is typically the cheapest month to fly

From $185 - $444 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (ORD) to Cancun (CUN)
Origin airport
O'Hare Intl.
Destination airport
Cancun Intl.
Airlines serving
Aeromexico, Air Canada, Alaska Airlines, American Airlines, Arajet, Delta, Frontier Airlines, Funjet Vacations, JetBlue Airways, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United, Viva, Volaris, avianca
Roundtrip price
$220
Distance
1447 mi
Average flight time
3 hours 47 mins

Chicago to Cancun Flights

The cheapest times to fly from Chicago to Cancun

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 Chicago to Cancun are during the month of August. You can find some of the cheapest flights from Chicago to Cancun with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Cancun

Sunday is one of the best days to book for cheap flights from Chicago to Cancun: 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 Chicago to Cancun

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 Chicago to Cancun in 2025. You can also book with separate airlines for your outbound and return journeys, from $101 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 Chicago to Cancun 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 Chicago to Cancun 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 O'Hare Intl. Airport (ORD) to Cancun Intl. Airport (CUN) cost?
Grab cheap return tickets starting from $207 from O'Hare Intl. Airport (ORD) to Cancun Intl. Airport (CUN). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Spirit Airlines flight leaving ORD on July 12 2025 and touching down at CUN. The price was last updated on July 8 2025 and has not changed since.
What is the cheapest month to fly from ORD to CUN?
The cheapest flights from ORD to CUN are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Cancun Intl. Airport (CUN)?
Fly straight to Cancun Intl. Airport (CUN). 4 carriers offer direct routes from O'Hare Intl. Airport (ORD), including:

  • United Airlines
  • American Airlines
  • Frontier Airlines

What is the cheapest airline that flies from ORD to CUN?
Fly from ORD to CUN with Spirit Airlines. This carrier currently offers the lowest one-way fare on this route, starting at $88. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on July 12 2025. Prices were last updated on July 8 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Cancun Intl. Airport (CUN)?
Each day, an average of 6 nonstop flights take off from O'Hare Intl. Airport (ORD) to Cancun Intl. Airport (CUN). Choose the departure time that fits your schedule best.
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Cancun Intl. Airport (CUN)?
Flights between ORD and CUN are busiest at 8 AM. For a quieter experience and potentially cheaper tickets, look for a departure outside the usual busy windows.
What day of the week has the most flights from ORD to CUN?
Depart on a Friday if you're searching for the biggest selection of flights from O'Hare Intl. Airport (ORD) to Cancun Intl. Airport (CUN).
What is the earliest flight from O'Hare Intl. Airport (ORD) to Cancun Intl. Airport (CUN)?
O'Hare Intl. Airport (ORD)'s earliest flight to Cancun Intl. Airport (CUN) takes off at approximately 6:00AM UTC-6. With a flight time of 4h 19m, you'll land at around 11:19AM UTC-5.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Cancun Intl. Airport (CUN)?
The average flight time from ORD to CUN is 3 hours and 56 minutes, covering a distance of 1,450 mi.
What airline has the least delays from ORD to CUN?
Consider booking with Southwest Airlines if you'd like to fly straight from O'Hare Intl. Airport (ORD) to Cancun Intl. Airport (CUN) without any holdups. This carrier has the best track record for punctuality, with an on-time score of 100%. Want real-time updates? You can keep an eye on your flight status using the Expedia App.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Cancun Intl. Airport (CUN)?
To touch down at Cancun Intl. Airport (CUN) on schedule, select a flight that takes off from O'Hare Intl. Airport (ORD) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**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 Cancun from O'Hare Intl. Airport (ORD)?
If you're taking a direct flight from O'Hare Intl. Airport (ORD) to Cancun, you'll touch down at either Cancun Intl. Airport (CUN) or Cozumel Intl. Airport (CZM).
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Cancun Intl. Airport (CUN) last-minute?
Holding off until just before your trip to book a ticket from ORD to CUN generally means paying more. While you may come across some last-minute deals, there's no guarantee. Be flexible with your travel plans for a better chance of snagging a bargain.
Is it cheaper to book an ORD to CUN flight and hotel package?
Compared with arranging hotels and flights separately, booking an ORD to CUN flight and hotel package with Expedia could result in significant savings. Better yet, managing everything in one place will take the stress out of planning your trip. Simply secure your flights and select from our extensive range of hotels, then customize your trip with extras like tours, activities and car rentals.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Cancun Intl. Airport (CUN)?
Typically, it's possible to cancel or reschedule your ORD to CUN flight. However, if it's been more than 24 hours since booking, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more details on our Customer Service portal.

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