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$139+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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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 July 3, 2025.

Round-trip from

$205
(Cheapflightsfares)

One-way from

$139
(Priceline)

Popular in

June

Cheapest in

January

Average price

$273

Good round-trip deal

$179 or less

Good one-way deal

$148 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. 11% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/2. 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 7/1810:55 amCUN - ORD
Nonstop3h 54mSpirit Airlines
Mon 7/216:00 amORD - CUN
Nonstop3h 50mSpirit Airlines
Deal found 7/2$205
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 8/1511:05 amCUN - ORD
Nonstop4h 01mMultiple Airlines
Sat 8/236:10 amORD - CUN
Nonstop3h 29mMultiple Airlines
Deal found 7/3$208
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 8/1511:05 amCUN - ORD
Nonstop4h 01mVolaris
Sun 8/177:35 amORD - CUN
Nonstop3h 55mVolaris
Deal found 7/3$210
This United Airlines deal was found by Cheapflights users on 7/3. 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 10/3012:27 pmCUN - ORD
Nonstop4h 03mUnited Airlines
Sun 11/27:34 amORD - CUN
Nonstop3h 56mUnited Airlines
Deal found 7/3$230
This Priceline deal was found by Cheapflights users on 7/3. 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.
Thu 7/311:49 pmCUN - ORD
1 stop10h 33mFrontier
Thu 8/75:01 amORD - CUN
1 stop7h 26mFrontier
Deal found 7/3$238
This American Airlines deal was found by Cheapflights users on 7/1. 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 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 9/207:15 pmORD - CUN
1 stop16h 34mAmerican Airlines
Deal found 7/1$255
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/46:00 amCUN - ORD
1 stop8h 25mDelta
Tue 7/87:10 amORD - CUN
1 stop5h 50mDelta
Deal found 7/1$272
This Delta deal was found by Cheapflights users on 7/2. 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.
Wed 8/138:00 amCUN - MDW
1 stop13h 44mDelta
Wed 8/209:31 amMDW - CUN
2 stops10h 49mDelta
Deal found 7/2$276
This Priceline deal was found by Cheapflights users on 7/2. 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.
Thu 7/35:37 pmCUN - MDW
1 stop28h 41mFrontier
Thu 7/109:12 pmMDW - CUN
1 stop10h 36mFrontier
Deal found 7/2$283
This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/178:15 amCUN - MDW
Nonstop3h 35mSouthwest
Sun 7/205:25 pmMDW - CUN
Nonstop3h 35mSouthwest
Deal found 7/1$357
This CheapOair deal was found by Cheapflights users on 7/2. 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.
Sat 8/231:54 pmCUN - MDW
1 stop9h 14mMultiple Airlines
Mon 8/256:00 amMDW - CUN
1 stop6h 50mMultiple Airlines
Deal found 7/2$384

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 July 3, 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 7/18

10:55 am-2:49 pm

Nonstop3h 54m

Chicago O'Hare Intl

Mon 7/21

6:00 am-9:50 am

Nonstop3h 50m

$205

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 10/30

2:18 pm-6:13 pm

Nonstop3h 55m

Chicago O'Hare Intl

Sun 11/2

7:34 am-12:30 pm

Nonstop3h 56m

$231

CancúnChicago

CUN - ORD

CUNORD

Cancun

Sat 8/16

10:34 am-2:49 pm

Nonstop4h 15m

Chicago O'Hare Intl

Sat 8/23

12:25 pm-8:55 pm

1 stop8h 30m

$235

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 9/11

2:50 pm-6:50 pm

Nonstop4h 00m

Chicago O'Hare Intl

Sat 9/20

10:02 am-1:50 pm

Nonstop3h 48m

$236

CancúnChicago

CUN - ORD

CUNORD

Cancun

Wed 7/16

3:25 pm-12:10 am

1 stop8h 45m

Chicago O'Hare Intl

Wed 8/13

5:01 am-12:27 pm

1 stop7h 26m

$249

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 10/2

2:00 pm-11:52 pm

1 stop9h 52m

Chicago O'Hare Intl

Tue 10/7

9:30 am-8:04 pm

1 stop10h 34m

$275

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 8/13

8:00 am-9:44 pm

1 stop13h 44m

Chicago Midway

Wed 8/20

9:31 am-8:20 pm

2 stops10h 49m

$276

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 7/24

11:05 am-3:06 pm

Nonstop4h 01m

Chicago O'Hare Intl

Mon 8/4

7:35 am-11:30 am

Nonstop3h 55m

$283

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 8/16

1:49 pm-10:33 pm

1 stop8h 44m

Chicago Midway

Sat 8/23

6:10 am-12:39 pm

1 stop6h 29m

$326

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 7/17

8:15 am-11:50 am

Nonstop3h 35m

Chicago Midway

Sun 7/20

5:25 pm-9:00 pm

Nonstop3h 35m

$357

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 26 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
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 27, 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 July 3, 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 in the morning.

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 July 3, 2025.

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

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

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 July 3, 2025.
Read reviews from past customers who have flown Southwest, Delta, and KLM 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
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

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
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

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
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

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.
KLM
7.8
Good
1,367 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

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
1,718 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

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
8,861 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

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 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?

    Spirit Airlines, at $205, was found to be the cheapest airline from Cancún to Chicago.Alternate airlines to your destination round-trip include United Airlines and American Airlines. Users have found that Spirit Airlines is 20% 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 $139. Volaris flights start at $146 while deals on Southwest start at $149 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 (89%), American Airlines (84%) or Emirates (79%) 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 $388 for a flight from Cancún to Chicago. The cheapest flight overall is $119 while the most popular route, (Cancun - Chicago O'Hare Intl) is currently priced at $248.

  • 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

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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$170FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$177Average$277FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$214Average$319FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$310Average$428FlexibilityNo cancel feeOn-time71%

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