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$201+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — CHI
Sep 1 — Sep 81
Tue 9/1
Tue 9/8
1 adult, Economy
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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”

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Cheapflights Tip: The best prices from Cancun to Chicago are usually found in April or January, booked 64 days in advance, depart on a Thursday or Sunday and return on a Sunday

Cheap 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 August 2, 2026.

This CheapOair deal was found by Cheapflights users on 7/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2412:35 pm
CUN
-
ORD
1 stop11h 05m
Multiple Airlines
Mon 9/287:35 am
ORD
-
CUN
1 stop13h 28m
Multiple Airlines
Deal found 7/30$295
This Kissandfly.com deal was found by Cheapflights users on 7/29. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:35 pm
CUN
-
ORD
1 stop11h 05m
Multiple Airlines
Tue 9/81:40 am
ORD
-
CUN
1 stop12h 48m
Multiple Airlines
Deal found 7/29$299
This Booking.com deal was found by Cheapflights users on 7/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:35 pm
CUN
-
ORD
1 stop11h 05m
Arajet
Mon 9/145:30 am
ORD
-
CUN
1 stop11h 42m
Arajet
Deal found 7/29$301
This Viva deal was found by Cheapflights users on 7/29. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/911:30 am
CUN
-
ORD
1 stop25h 40m
Viva
Sat 10/172:40 pm
ORD
-
CUN
1 stop7h 35m
Viva
Deal found 7/29$310
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 9/2412:35 pm
CUN
-
ORD
1 stop11h 05m
Multiple Airlines
Sat 9/261:40 am
ORD
-
CUN
1 stop8h 23m
Multiple Airlines
Deal found 8/1$318
This Viva deal was found by Cheapflights users on 7/31. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:00 am
CUN
-
ORD
1 stop8h 50m
Viva
Sat 10/242:40 pm
ORD
-
CUN
1 stop26h 05m
Viva
Deal found 7/31$320
This Gotogate deal was found by Cheapflights users on 7/29. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:35 pm
CUN
-
ORD
1 stop11h 05m
Multiple Airlines
Mon 9/71:40 am
ORD
-
CUN
1 stop12h 48m
Multiple Airlines
Deal found 7/29$321
This Super.com deal was found by Cheapflights users on 7/29. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/110:40 am
CUN
-
ORD
1 stop14h 15m
Volaris
Wed 9/27:35 am
ORD
-
CUN
1 stop13h 28m
Volaris
Deal found 7/29$323
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/29:50 pm
CUN
-
ORD
1 stop8h 02m
Volaris
Fri 10/97:35 am
ORD
-
CUN
1 stop13h 28m
Volaris
Deal found 7/30$324
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2410:50 am
CUN
-
ORD
1 stop12h 57m
Volaris
Mon 9/287:35 am
ORD
-
CUN
1 stop13h 28m
Volaris
Deal found 7/29$325
This Frontier deal was found by Cheapflights users on 7/29. 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.
Thu 10/292:24 pm
CUN
-
MDW
1 stop7h 29m
Frontier
Fri 11/137:25 am
MDW
-
CUN
1 stop5h 49m
Frontier
Deal found 7/29$393
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/53:24 pm
CUN
-
MDW
1 stop7h 29m
Frontier
Sun 11/87:25 am
MDW
-
CUN
1 stop5h 49m
Frontier
Deal found 7/30$394

Find 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 August 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$295
(CheapOair)

One-way from

$201
(Kiwi.com)

Popular in

September

Cheapest in

April

Average price

$353

Good round-trip deal

$305 or less

Good one-way deal

$274 or less
Provider with most accurate pricing for Cancun-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Cancun-Chicago (CHI) flights.
Search Deals
From Cancun to Chicago (CHI)
Search Deals
One-way flight from Cancun to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($69 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
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

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 August 2, 2026.
Use the filters below to find and compare flights from Cancún to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 10/1

9:50 pm-5:52 am

1 stop8h 02m

Chicago O'Hare Intl

Sat 10/3

1:40 am-10:03 am

1 stop8h 23m

$358

CancúnChicago

CUN - ORD

CUNORD

Cancun

Wed 12/30

12:30 pm-10:50 pm

1 stop11h 20m

Chicago O'Hare Intl

Thu 1/7

12:30 am-11:40 pm

1 stop22h 10m

$362

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 9/25

3:40 pm-11:59 pm

1 stop8h 19m

Chicago O'Hare Intl

Tue 9/29

7:05 am-7:50 pm

2 stops12h 45m

$395

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 10/8

3:38 pm-7:35 pm

Nonstop3h 57m

Chicago O'Hare Intl

Tue 10/13

5:30 am-7:19 pm

1 stop13h 49m

$396

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 10/9

12:11 pm-4:04 pm

Nonstop3h 53m

Chicago O'Hare Intl

Mon 10/12

9:38 pm-10:06 am

1 stop12h 28m

$398

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 9/25

3:38 pm-7:35 pm

Nonstop3h 57m

Chicago O'Hare Intl

Tue 9/29

6:00 am-2:40 pm

1 stop8h 40m

$398

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 9/25

9:20 am-10:44 pm

2 stops13h 24m

Chicago Midway

Tue 9/29

10:48 am-7:50 pm

1 stop9h 02m

$401

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 8/20

5:22 pm-12:59 am

1 stop7h 37m

Chicago O'Hare Intl

Mon 8/24

9:35 pm-10:06 am

1 stop12h 31m

$401

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 10/1

12:40 pm-12:01 am

1 stop11h 21m

Chicago O'Hare Intl

Sun 10/4

6:40 am-6:48 pm

2 stops12h 08m

$407

CancúnChicago

CUN - ORD

CUNORD

Cancun

Tue 10/27

1:55 pm-5:59 pm

Nonstop4h 04m

Chicago O'Hare Intl

Tue 11/3

7:30 am-3:24 pm

1 stop6h 54m

$407

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 41 resultsSorted by cheapest first
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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 August.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
Super.comPrice Accuracy-Trust Score*3 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Cancún-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.

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

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

Currently, January is the cheapest month in which you can book a flight from Cancún to Chicago (average of $221). Flying from Cancún to Chicago in September is currently the most expensive (average of $418). 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 August 2, 2026.

When flying from Cancún to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 August 2, 2026.

The most flights from CUN to CHI are scheduled on a Friday (11 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (6 on average).

How much does it cost to fly round-trip from Cancún to Chicago?

Airfare is typical for this route at the moment.
Cancún to Chicago flights typically cost between $260 and $433 in September.
The cheapest round-trip price found within the last 5 days was $295 on Multiple Airlines (Sep 24-Sep 28).

How often are flights from Cancún to Chicago delayed?

About 17% of weekly flights between Cancún and Chicago have experienced delays in the past year, with the average delay time being 152 minutes.

What is the most punctual flight time for Cancún to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Cancún to Chicago flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 15% of flights being delayed.

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

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 52 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

The best insider tips for Cancún to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Cancún to Chicago trip
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

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 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

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

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 August 2, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican 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
4,229 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,229 reviews
Southwest
8.0
Very good
4,229 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
10,061 reviews
Southwest
8.0
Very good
4,229 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,846 reviews
Southwest
8.0
Very good
4,229 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Frontier
5.6
Fair
2,741 reviews
Southwest
8.0
Very good
4,229 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

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 3 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 $358, Volaris can have you in Chicago from Cancún in 8h 02m. 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 $142, was found to be the cheapest airline from Cancún to Chicago.Alternate airlines to your destination round-trip include United Airlines and Volaris. Users have found that Frontier is 55% 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 Frontier, which is currently one of the cheapest options available, starting at $107. Southwest flights start at $144 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 Frontier (87%), Volaris (87%) or American Airlines (83%) 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 $362 for a flight from Cancún to Chicago. The cheapest flight overall is $197 while the most popular route, (Cancun - Chicago O'Hare Intl) is currently priced at $282.

  • 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, January is the cheapest month in which you can book a flight from Cancún to Chicago (average of $221). Flying from Cancún to Chicago in September is currently the most expensive (average of $418). 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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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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 2 airlines flying from Cancún to Chicago

Discover the top 2 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 August 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$142Average$184FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$209Average$251FlexibilityNo cancel feeOn-time69%

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