Chicago

$134+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — CHI
May 6 — May 131
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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

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Cheapflights Tip: The best prices from Cancun to Chicago are usually found in January or September, 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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$213
(Cheapflightsfares)

One-way from

$135
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$226

Good round-trip deal

$216 or less

Good one-way deal

$147 or less
Provider with most accurate pricing for Cancun-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Cancun-Chicago (CHI) flights.
From Cancun to Chicago (CHI)
One-way flight from Cancun to Chicago (CHI)
Highest demand for flights based on searches. 6% potential increase in price ($17 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Average for round-trip flights in May 2025
Price to beat on a round-trip flight from Cancun to Chicago (CHI).
Price to beat on a one-way flight from Cancun to Chicago (CHI).

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 May 1, 2025.

This eDestinos deal was found by Cheapflights users on 4/30. 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 5/1612:18 pmCUN - ORD
1 stop11h 47mSpirit Airlines
Mon 5/196:10 amORD - CUN
Nonstop3h 34mSpirit Airlines
Deal found 4/30$204
This Booking.com deal was found by Cheapflights users on 4/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/511:05 amCUN - ORD
Nonstop3h 59mFrontier
Tue 6/107:33 amORD - CUN
Nonstop3h 57mFrontier
Deal found 4/30$205
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
Tue 5/1311:05 amCUN - ORD
Nonstop3h 57mMultiple Airlines
Fri 5/166:10 amORD - CUN
Nonstop3h 34mMultiple Airlines
Deal found 4/30$213
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Sat 5/312:20 pmCUN - ORD
Nonstop4h 02mUnited Airlines
Mon 5/1210:42 amORD - CUN
Nonstop3h 46mUnited Airlines
Deal found 4/30$222
This Southwest deal was found by Cheapflights users on 4/29. 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.
Thu 7/318:15 amCUN - MDW
Nonstop3h 35mSouthwest
Sun 8/35:25 pmMDW - CUN
Nonstop3h 35mSouthwest
Deal found 4/29$249
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 5/710:35 amCUN - ORD
1 stop10h 50mAmerican Airlines
Sun 5/119:59 amORD - CUN
Nonstop3h 45mAmerican Airlines
Deal found 4/30$258
This Delta deal was found by Cheapflights users on 4/30. 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.
Sat 5/38:15 amCUN - MDW
1 stop9h 44mDelta
Fri 5/99:16 amMDW - CUN
2 stops11h 04mDelta
Deal found 4/30$274
This Delta deal was found by Cheapflights users on 4/30. 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.
Sat 5/311:03 amCUN - ORD
1 stop7h 57mDelta
Sat 5/1011:05 amORD - CUN
2 stops9h 15mDelta
Deal found 4/30$274
This Aeromexico deal was found by Cheapflights users on 4/30. 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.
Mon 6/91:01 amCUN - ORD
2 stops17h 48mAeromexico
Tue 6/171:45 pmORD - CUN
1 stop6h 35mAeromexico
Deal found 4/30$318
This eDestinos deal was found by Cheapflights users on 4/28. 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 5/1411:00 amCUN - MDW
1 stop10h 28mAeromexico
Tue 5/206:00 amMDW - CUN
1 stop6h 45mAeromexico
Deal found 4/28$325
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 8/163:19 pmCUN - ORD
1 stop13h 32mVolaris
Sat 8/237:25 amORD - CUN
1 stop13h 38mVolaris
Deal found 4/30$339
This Frontier deal was found by Cheapflights users on 4/29. 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.
Tue 5/272:20 pmCUN - MDW
1 stop7h 54mFrontier
Tue 6/36:40 amMDW - CUN
1 stop6h 20mFrontier
Deal found 4/29$391

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 May 1, 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 5/16

12:18 pm-12:05 am

1 stop11h 47m

Chicago O'Hare Intl

Mon 5/19

6:10 am-9:44 am

Nonstop3h 34m

$204

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 6/5

11:05 am-3:04 pm

Nonstop3h 59m

Chicago O'Hare Intl

Tue 6/10

7:33 am-11:30 am

Nonstop3h 57m

$205

CancúnChicago

CUN - ORD

CUNORD

Cancun

Tue 5/13

11:05 am-3:02 pm

Nonstop3h 57m

Chicago O'Hare Intl

Fri 5/16

6:10 am-9:44 am

Nonstop3h 34m

$213

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 7/31

8:15 am-11:50 am

Nonstop3h 35m

Chicago Midway

Sun 8/3

5:25 pm-9:00 pm

Nonstop3h 35m

$249

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 5/14

9:55 am-6:45 pm

2 stops8h 50m

Chicago Midway

Tue 5/20

6:00 am-11:25 am

1 stop5h 25m

$274

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 6/5

9:55 am-8:21 pm

2 stops10h 26m

Chicago O'Hare Intl

Tue 6/10

6:00 am-12:50 pm

1 stop6h 50m

$274

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 6/13

8:35 am-11:58 pm

2 stops15h 23m

Chicago O'Hare Intl

Tue 6/17

9:49 am-1:17 am

2 stops15h 28m

$279

CancúnChicago

CUN - ORD

CUNORD

Cancun

Tue 6/10

5:35 am-11:12 pm

1 stop17h 37m

Chicago O'Hare Intl

Tue 6/17

12:45 pm-7:20 pm

1 stop6h 35m

$317

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 5/14

11:00 am-9:28 pm

1 stop10h 28m

Chicago Midway

Tue 5/20

6:00 am-12:45 pm

1 stop6h 45m

$325

CancúnChicago

CUN - ORD

CUNORD

Cancun

Sat 8/16

3:19 pm-4:51 am

1 stop13h 32m

Chicago O'Hare Intl

Sat 8/23

7:25 am-9:03 pm

1 stop13h 38m

$339

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 36 results
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Compare providers for flights from Cancún to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Cancún to Chicago in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*2 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Cancún-Chicago flights, users find the pricing of AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Cancún-Chicago flight deals on Cheapflights vs. AranGrant >95% of the time. Price accuracy is based on data collected from Cancún-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Cancún-Chicago flights, Cheapflights users trust AranGrant the most. AranGrant has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Cancún-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

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.

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

Prepare for long security lines at CUN. Arrive early to navigate crowded terminals and ensure a smooth departure.

Read more about CUNby Ramsey Qubein
ORD

Expect long walks at ORD. Use the free shuttle train between terminals to ease your arrival journey.

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 April 25, 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 May 1, 2025.

It’s optimal to fly from Cancún to Chicago in the afternoon. By choosing this option you can save up to 33% 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 May 1, 2025.

The most flights from CUN to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 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 May 1, 2025.
Get a feel of what it's like to fly with Delta, Alaska Airlines and Southwest 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.
8.0
Very good

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
8.0
Very good
8.0
Very good

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
8.0
Very good

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
8.0
Very good

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
8.0
Very good

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
8.0
Very good

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 8 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?

    United Airlines, at $222, was found to be the cheapest airline from Cancún to Chicago.Alternate airlines to your destination round-trip include Spirit Airlines and Frontier. Users have found that United Airlines is 10% 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 $135. Southwest flights start at $137 while deals on Frontier start at $143 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 Qatar Airways (74%), American Airlines (72%) or Spirit Airlines (69%) 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 $302 for a flight from Cancún to Chicago. The cheapest flight overall is $135 while the most popular route, (Cancun - Chicago O'Hare Intl) is currently priced at $260.

  • 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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.

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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$167FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$177Average$246FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$212Average$309FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$262Average$426FlexibilityNo cancel feeOn-time71%

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