HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$136+ Cheap flights from Cancún (CUN) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Cancún to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Cancun to Chicago are usually found in January or February, booked 48 days in advance, depart on a Friday or Sunday and return on a Monday

Cheap flight deals from Cancún to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Cancún (CUN) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 12, 2025.

Round-trip from

$220
(SmartFares)

One-way from

$136
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$344

Good round-trip deal

$179 or less

Good one-way deal

$167 or less
From Cancun to Chicago (CHI)
Search Deals
One-way flight from Cancun to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals
Price to beat on a round-trip flight from Cancun to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Cancun to Chicago (CHI).
Search Deals

Find flight deals from Cancún to Chicago

Cheapest flights from Cancún to Chicago
Explore the most affordable flight options available from Cancún to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This SmartFares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1110:55 amCUN - ORD
Nonstop3h 54mSpirit Airlines
Mon 7/146:00 amORD - CUN
Nonstop3h 50mSpirit Airlines
Deal found 6/10$220
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/113:38 pmCUN - ORD
Nonstop3h 58mUnited Airlines
Sat 9/2010:43 amORD - CUN
Nonstop3h 45mUnited Airlines
Deal found 6/10$230
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/112:50 pmCUN - ORD
Nonstop4h 00mAmerican Airlines
Sat 9/208:47 pmORD - CUN
1 stop14h 30mAmerican Airlines
Deal found 6/12$256
This Gotogate deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1110:55 amCUN - ORD
Nonstop3h 54mMultiple Airlines
Fri 7/1812:25 pmORD - CUN
1 stop7h 40mMultiple Airlines
Deal found 6/11$262
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/21:51 pmCUN - ORD
1 stop10h 38mDelta
Tue 10/71:16 pmORD - CUN
1 stop6h 48mDelta
Deal found 6/10$270
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/251:45 pmCUN - MDW
1 stop7h 59mDelta
Tue 9/301:05 pmMDW - CUN
1 stop6h 57mDelta
Deal found 6/10$275
This Priceline deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/129:09 amCUN - MDW
1 stop11h 13mFrontier
Mon 7/146:20 amMDW - CUN
1 stop6h 07mFrontier
Deal found 6/12$290
This Arajet deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/215:49 pmCUN - ORD
1 stop16h 08mArajet
Sun 11/233:30 amORD - CUN
1 stop12h 27mArajet
Deal found 6/11$312
This Aeromexico deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/101:54 pmCUN - ORD
1 stop7h 58mAeromexico
Sat 10/1811:19 amORD - CUN
1 stop8h 50mAeromexico
Deal found 6/10$316
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/211:31 amCUN - ORD
Nonstop3h 55mVolaris
Mon 10/61:40 amORD - CUN
1 stop13h 18mVolaris
Deal found 6/10$351
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/118:30 amCUN - MDW
Nonstop3h 35mSouthwest
Mon 7/144:35 pmMDW - CUN
Nonstop3h 35mSouthwest
Deal found 6/11$361
This Aeromexico deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1311:10 amCUN - MDW
1 stop10h 34mAeromexico
Sat 9/2010:35 amMDW - CUN
1 stop9h 27mAeromexico
Deal found 6/10$367

Cheapflights Fare Finder

Customize your flight search to find flights from Cancún to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
Use the filters below to find and compare flights from Cancún to Chicago that are best for you.

Fly from

Cancún

Fly to

Chicago

Route

Depart

Return

Price

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 7/11

10:55 am-2:49 pm

Nonstop3h 54m

Chicago O'Hare Intl

Mon 7/14

6:00 am-9:50 am

Nonstop3h 50m

$220

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 9/11

3:38 pm-7:36 pm

Nonstop3h 58m

Chicago O'Hare Intl

Sat 9/20

10:43 am-2:28 pm

Nonstop3h 45m

$230

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 9/11

2:50 pm-6:50 pm

Nonstop4h 00m

Chicago O'Hare Intl

Sat 9/20

8:47 pm-11:17 am

1 stop14h 30m

$256

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 7/11

10:55 am-2:49 pm

Nonstop3h 54m

Chicago O'Hare Intl

Fri 7/18

12:25 pm-8:05 pm

1 stop7h 40m

$262

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 10/2

1:51 pm-12:29 am

1 stop10h 38m

Chicago O'Hare Intl

Tue 10/7

1:16 pm-8:04 pm

1 stop6h 48m

$270

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 9/25

1:45 pm-9:44 pm

1 stop7h 59m

Chicago Midway

Tue 9/30

1:05 pm-8:02 pm

1 stop6h 57m

$275

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 7/12

9:09 am-8:22 pm

1 stop11h 13m

Chicago Midway

Mon 7/14

6:20 am-12:27 pm

1 stop6h 07m

$290

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 11/21

5:49 pm-8:57 am

1 stop16h 08m

Chicago O'Hare Intl

Sun 11/23

3:30 am-4:57 pm

1 stop12h 27m

$312

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 10/10

1:54 pm-9:52 pm

1 stop7h 58m

Chicago O'Hare Intl

Sat 10/18

11:19 am-8:09 pm

1 stop8h 50m

$316

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 10/2

11:31 am-3:26 pm

Nonstop3h 55m

Chicago O'Hare Intl

Mon 10/6

1:40 am-2:58 pm

1 stop13h 18m

$351

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

Showing 1-10 of 33 results
1
2
3
4

The best insider tips for Cancún to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Cancún to Chicago trip
Airlines
United Airlines

United's Economy Plus offers extra legroom and priority boarding for a more comfortable journey.


United's Polaris Business Class features lie-flat seats and upscale amenities for premium comfort.

Read more about United Airlinesby Harriet Baskas
Spirit Airlines

Spirit's Big Front Seats offer 11 extra inches of legroom, ideal for added comfort.


Spirit's self-service bag drop saves time; print your boarding pass beforehand to avoid fees.

Read more about Spirit Airlinesby Daniel Scheffler
Frontier

Frontier's UpFront Plus guarantees an empty middle seat for extra comfort.


Frontier's Economy Bundle includes a carry-on, seat selection, and no change fees.

Read more about Frontierby Marisa Garcia
Airports
CUN

Check your departure terminal at CUN; terminals aren't connected. A bus runs every ten minutes between them.

Read more about CUNby Ramsey Qubein
ORD

For international arrivals at ORD, expect long walks to immigration in Terminal 5. No moving walkways available.

Read more about ORDby Ramsey Qubein
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

Daniel Scheffler

Daniel Scheffler

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more
Marisa Garcia

Marisa Garcia

Expert on Frontier

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD and CUN

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

Best time to book a flight from Cancún to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Cancún with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Cancún to Chicago

How far ahead should I book a flight from Cancún to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Cancún to Chicago. Price data was last updated on June 9, 2025.

The price you pay for your flight from Cancún to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 48 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Cancún to Chicago?

Currently, August is the cheapest month in which you can book a flight from Cancún to Chicago (average of $245). Flying from Cancún to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CUN to CHI?

Find hourly flight availability from Cancún to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.

It’s optimal to fly from Cancún to Chicago in the afternoon. By choosing this option you can save up to 25% on the cost of your flight, compared to a flight at noon.

Weekly flight availability from Cancún to Chicago

Explore weekly flight availability from Cancún to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 12, 2025.

The most flights from CUN to CHI are scheduled on a Monday (10 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (7 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 12, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Air Transat from Cancún to Chicago by reading reviews from past customers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Air Transat
7.8
Good
396 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Aeromexico
7.5
Good
1,706 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

Find useful and relevant information for your journey from Cancún to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Cancún to Chicago?

    Most people fly from Cancun (CUN) if they book a flight from Cancún to Chicago. On average, Cancun has 9 outbound flights to Chicago per day from 4 airlines. Cancun is conveniently located just 8.9 mi from Cancún’s city center.

  • What are the cheapest airlines flying from Cancún to Chicago round-trip?

    Spirit Airlines, at $220, was found to be the cheapest airline from Cancún to Chicago.Alternate airlines to your destination round-trip include United Airlines and Delta. Users have found that Spirit Airlines is 14% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Cancún to Chicago one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $136. Southwest flights start at $148 while deals on United Airlines start at $148 one-way.

  • What are the most reliable airlines from Cancún to Chicago?

    No one likes to see their flight delayed. When booking a flight from Cancún to Chicago consider choosing Emirates (83%), United Airlines (83%) or Frontier (75%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Cancún to Chicago?

    On average you can expect to pay $256 for a flight from Cancún to Chicago. The cheapest flight overall is $117 while the most popular route, (Cancun - Chicago O'Hare Intl) is currently priced at $259.

  • Can I find deals for flights from Cancún to Chicago that include hotel bookings?

    Yes. In addition to deals on Cancún to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Cancún to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Cancún to Chicago.

  • Can I find deals for business class flights from Cancún to Chicago?

    Yes. Cheapflights offers flight deals from Cancún to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Cancún to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Cancún to Chicago (average of $245). Flying from Cancún to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Cancún?

Book flights to Cancún if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Cancún to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Cancún to O'Hare Intl flights
Cancún to Midway flights
Cozumel to O'Hare Intl flights
Cancún to St. Louis flights
Cozumel to St. Louis flights

Top 4 airlines flying from Cancún to Chicago

Discover the top 4 airlines that operate flights from Cancún to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$170FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$177Average$241FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$212Average$319FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$310Average$428FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.