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$131+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — CHI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Cancun to Chicago are usually found in January or December, booked 49 days in advance, depart on a Friday or Saturday 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 September 16, 2025.

Round-trip from

$158
(Frontier)

One-way from

$131
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$337

Good round-trip deal

$191 or less

Good one-way deal

$154 or less
From Cancun to Chicago (CHI)
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One-way flight from Cancun to Chicago (CHI)
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Highest demand for flights based on searches. 10% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Cancun to Chicago (CHI).
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Price to beat on a one-way flight from Cancun to Chicago (CHI).
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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 September 16, 2025.

This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/511:38 amCUN - ORD
Nonstop4h 03mFrontier
Tue 12/96:45 amORD - CUN
Nonstop4h 01mFrontier
Deal found 9/15$158
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1611:25 amCUN - ORD
Nonstop3h 55mFrontier
Tue 10/216:30 amORD - CUN
Nonstop3h 45mFrontier
Deal found 9/15$170
This eDestinos deal was found by Cheapflights users on 9/14. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/269:16 amCUN - ORD
1 stop12h 42mSpirit Airlines
Tue 9/305:05 amORD - CUN
1 stop7h 54mSpirit Airlines
Deal found 9/14$199
This eDestinos deal was found by Cheapflights users on 9/14. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/249:16 amCUN - ORD
1 stop12h 42mSpirit Airlines
Sat 9/276:10 amORD - CUN
Nonstop3h 37mSpirit Airlines
Deal found 9/14$217
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Sat 12/611:42 amCUN - ORD
Nonstop4h 08mSpirit Airlines
Mon 12/85:05 amORD - CUN
1 stop6h 22mSpirit Airlines
Deal found 9/14$219
This United Airlines deal was found by Cheapflights users on 9/16. 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 11/131:27 pmCUN - ORD
Nonstop4h 00mUnited Airlines
Tue 11/187:10 amORD - CUN
1 stop7h 49mUnited Airlines
Deal found 9/16$221
This Expedia deal was found by Cheapflights users on 9/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/119:09 amCUN - ORD
1 stop8h 44mMultiple Airlines
Sun 10/196:30 amORD - CUN
Nonstop3h 45mMultiple Airlines
Deal found 9/15$224
This Orbitz deal was found by Cheapflights users on 9/15. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1611:25 amCUN - ORD
Nonstop3h 55mMultiple Airlines
Tue 10/215:05 amORD - CUN
1 stop7h 39mMultiple Airlines
Deal found 9/15$225
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/167:51 amCUN - ORD
1 stop16h 23mUnited Airlines
Mon 10/205:01 amORD - CUN
1 stop7h 59mUnited Airlines
Deal found 9/15$226
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Fri 10/1012:11 pmCUN - ORD
1 stop8h 00mSpirit Airlines
Tue 10/146:58 pmORD - CUN
1 stop13h 06mSpirit Airlines
Deal found 9/14$227
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Fri 12/53:18 pmCUN - ORD
Nonstop3h 51mUnited Airlines
Tue 12/98:49 amORD - CUN
1 stop8h 01mUnited Airlines
Deal found 9/16$229
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2411:16 amCUN - MDW
1 stop12h 04mFrontier
Fri 10/316:20 amMDW - CUN
1 stop5h 59mFrontier
Deal found 9/14$270

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 September 16, 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 12/5

11:38 am-2:41 pm

Nonstop4h 03m

Chicago O'Hare Intl

Tue 12/9

6:45 am-11:46 am

Nonstop4h 01m

$158

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 11/6

1:27 pm-4:27 pm

Nonstop4h 00m

Chicago O'Hare Intl

Tue 11/11

7:10 am-3:59 pm

1 stop7h 49m

$220

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 11/13

1:27 pm-4:27 pm

Nonstop4h 00m

Chicago O'Hare Intl

Tue 11/18

7:10 am-3:59 pm

1 stop7h 49m

$221

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 11/14

4:51 pm-12:15 am

1 stop8h 24m

Chicago O'Hare Intl

Wed 11/19

7:10 am-8:18 pm

1 stop12h 08m

$226

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 10/16

7:51 am-12:14 am

1 stop16h 23m

Chicago O'Hare Intl

Mon 10/20

5:01 am-1:00 pm

1 stop7h 59m

$226

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 9/26

9:16 am-9:58 pm

1 stop12h 42m

Chicago O'Hare Intl

Tue 9/30

5:05 am-12:59 pm

1 stop7h 54m

$228

CancúnChicago

CUN - ORD

CUNORD

Cancun

Wed 12/24

4:47 pm-7:47 pm

Nonstop4h 00m

Chicago O'Hare Intl

Sat 1/3

10:35 am-3:35 pm

Nonstop4h 00m

$231

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 2/13

5:55 pm-12:30 am

1 stop7h 35m

Chicago O'Hare Intl

Tue 2/17

7:34 am-12:30 pm

Nonstop3h 56m

$247

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 10/10

3:38 pm-7:36 pm

Nonstop3h 58m

Chicago O'Hare Intl

Sun 10/19

10:43 am-2:28 pm

Nonstop3h 45m

$252

CancúnChicago

CUN - ORD

CUNORD

Cancun

Sat 10/4

9:16 am-9:58 pm

1 stop12h 42m

Chicago O'Hare Intl

Sat 10/11

7:43 pm-12:44 pm

1 stop17h 01m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 35 results
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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
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
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
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
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
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
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 September 12, 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 49 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 September 16, 2025.

It’s optimal to fly from Cancún to Chicago in the afternoon. By choosing this option you can save up to 11% 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 September 16, 2025.

The most flights from CUN to CHI are scheduled on a Thursday (7 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (5 on average).

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 September 16, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and Spirit Airlines from Cancún to Chicago. 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
4,242 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,019 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 6 outbound flights to Chicago per day from 4 airlines. Cancun is conveniently located just 8.9 mi from Cancún’s city center.

  • How long is the flight from Cancún to Chicago?

    For as low as $220, Frontier can have you in Chicago from Cancún in 4h. Cancún and Chicago are separated by a distance of 1447 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Frontier, at $167, was found to be the cheapest airline from Cancún to Chicago.Alternate airlines to your destination round-trip include Spirit Airlines and United Airlines. Users have found that Frontier is 39% cheaper than the other options available to this destination.

  • 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 Qatar Airways (79%), American Airlines (75%) or Emirates (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 $347 for a flight from Cancún to Chicago. The cheapest flight overall is $110 while the most popular route, (Cancun - Chicago O'Hare Intl) is currently priced at $221.

  • 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 Chicago?

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

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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$167Average$202FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$194Average$283FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$212Average$320FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$272Average$352FlexibilityNo cancel feeOn-time71%

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