What airlines fly to Chicago?

United Airlines, Frontier and Spirit Airlines are the top three most popular airlines that fly to Chicago from Cancún according to our data. United Airlines is the first choice among our users, with 56% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from Cancún to Chicago on average per week?

As of October 2025, there are 57 flights per week flying from Cancún to Chicago. The most common day of the week flights depart is Tue, with 16% of flights taking off on this day.

How many flights depart from Cancún to Chicago on average per day?

As of October 2025, there are 8 flights per day flying from Cancún to Chicago. The most common time of day flights depart is 3:00PM, with 95% of flights taking off in the afternoon.

What is the cheapest airline that flies from Cancun to Chicago?

Southwest, Frontier, and Spirit Airlines are the most popular carriers operating from Cancun to Chicago

When did momondo last update prices for flights from Cancun Airport to Chicago?

Prices for flights from Cancun Airport to Chicago refresh daily.

How many operators does momondo search for flights from Cancun Airport to Chicago?

As of October 2025, there are 4 operators available to choose from for flights from Cancun Airport to Chicago.

How old do you have to be to fly from Cancun Airport to Chicago?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Cancun Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$100 Cheap Flights from Cancún to Chicago in 2025/26

Q: What is the typical price of a round-trip flight between Cancún and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from $228 to $364. The lowest price recently found on this route was $142.

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Find the cheapest flights from Cancún to Chicago

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:30 pm - 9:31 pmCUN-ORD

4h 01mnonstop

10:32 am - 3:35 pmORD-CUN

4h 03mnonstop

$142Frontier

Find Deal

Sat, Nov 22 - Sat, Nov 29

6:02 pm - 9:12 pmCUN-ORD

4h 10mnonstop

11:43 am - 4:52 pmORD-CUN

4h 09mnonstop

$143Frontier

Find Deal

Thu, Dec 4 - Wed, Dec 10

11:53 am - 2:53 pmCUN-ORD

4h 00mnonstop

10:32 am - 3:35 pmORD-CUN

4h 03mnonstop

$198Multiple Airlines

Find Deal

Mon, Nov 24 - Mon, Dec 1

11:53 am - 2:53 pmCUN-ORD

4h 00mnonstop

10:32 am - 3:35 pmORD-CUN

4h 03mnonstop

$199Multiple Airlines

Find Deal

Mon, Nov 24 - Mon, Dec 1

1:27 pm - 4:27 pmCUN-ORD

4h 00mnonstop

8:43 am - 1:33 pmORD-CUN

3h 50mnonstop

$208United Airlines

Find Deal

Fri, Dec 5 - Tue, Dec 9

3:18 pm - 6:09 pmCUN-ORD

3h 51mnonstop

10:35 am - 3:35 pmORD-CUN

4h 00mnonstop

$209United Airlines

Find Deal

Thu, Feb 5 - Mon, Feb 9

11:53 am - 2:53 pmCUN-ORD

4h 00mnonstop

6:00 am - 10:44 amORD-CUN

3h 44mnonstop

$221Spirit Airlines

Find Deal

Fri, Nov 21 - Sun, Nov 23

2:44 pm - 12:27 amCUN-ORD

10h 43m1 stop

5:10 am - 1:35 pmORD-CUN

7h 25m1 stop

$236Spirit Airlines

Find Deal

Tue, Nov 4 - Tue, Nov 11

2:15 pm - 5:00 pmCUN-MDW

3h 45mnonstop

10:40 am - 3:25 pmMDW-CUN

3h 45mnonstop

$260Southwest

Find Deal

Fri, Nov 14 - Sun, Nov 16

2:15 pm - 5:00 pmCUN-MDW

3h 45mnonstop

8:40 am - 1:25 pmMDW-CUN

3h 45mnonstop

$265Southwest

Find Deal

Fri, Nov 14 - Mon, Nov 17

Frontier flights from Cancún to Chicago

Our best Frontier deals on Cancún to Chicago flight tickets

Frontier

Nov 22

CUN6:30 pmCancun

4h 01m

ORD9:31 pmChicago O'Hare Intl

Nov 29

ORD10:32 amChicago O'Hare Intl

4h 03m

CUN3:35 pmCancun

$142

Find similar

Frontier

Dec 4

CUN6:02 pmCancun

4h 10m

ORD9:12 pmChicago O'Hare Intl

Dec 10

ORD11:43 amChicago O'Hare Intl

4h 09m

CUN4:52 pmCancun

$143

Find similar

Frontier

Dec 5

CUN6:02 pmCancun

4h 10m

ORD9:12 pmChicago O'Hare Intl

Dec 10

ORD11:43 amChicago O'Hare Intl

4h 09m

CUN4:52 pmCancun

$181

Find similar

United Airlines flights from Cancún to Chicago

Our best United Airlines deals on Cancún to Chicago flight tickets

United Airlines

Dec 5

CUN1:27 pmCancun

4h 00m

ORD4:27 pmChicago O'Hare Intl

Dec 9

ORD8:43 amChicago O'Hare Intl

3h 50m

CUN1:33 pmCancun

$208

Find similar

United Airlines

Feb 5

CUN3:18 pmCancun

3h 51m

ORD6:09 pmChicago O'Hare Intl

Feb 9

ORD10:35 amChicago O'Hare Intl

4h 00m

CUN3:35 pmCancun

$209

Find similar

United Airlines

Feb 3

CUN4:47 pmCancun

4h 00m

ORD7:47 pmChicago O'Hare Intl

Feb 9

ORD9:05 pmChicago O'Hare Intl

13h 20m

1 stop

CUN11:25 amCancun

$227

Find similar

Fly from

Fly to

Route

Depart

Return

Price

CancúnChicago

CUN - ORD

CUNORD

Cancun

Sat 11/22

6:30 pm-9:31 pm

Nonstop4h 01m

Chicago O'Hare Intl

Sat 11/29

10:32 am-3:35 pm

Nonstop4h 03m

$142

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 12/4

6:02 pm-9:12 pm

Nonstop4h 10m

Chicago O'Hare Intl

Wed 12/10

11:43 am-4:52 pm

Nonstop4h 09m

$143

CancúnChicago

CUN - ORD

CUNORD

Cancun

Mon 11/24

11:53 am-2:53 pm

Nonstop4h 00m

Chicago O'Hare Intl

Mon 12/1

10:32 am-3:35 pm

Nonstop4h 03m

$198

CancúnChicago

CUN - ORD

CUNORD

Cancun

Mon 11/24

11:53 am-2:53 pm

Nonstop4h 00m

Chicago O'Hare Intl

Mon 12/1

10:32 am-3:35 pm

Nonstop4h 03m

$199

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 12/5

1:27 pm-4:27 pm

Nonstop4h 00m

Chicago O'Hare Intl

Tue 12/9

8:43 am-1:33 pm

Nonstop3h 50m

$208

CancúnChicago

CUN - ORD

CUNORD

Cancun

Thu 2/5

3:18 pm-6:09 pm

Nonstop3h 51m

Chicago O'Hare Intl

Mon 2/9

10:35 am-3:35 pm

Nonstop4h 00m

$209

CancúnChicago

CUN - ORD

CUNORD

Cancun

Fri 11/21

11:53 am-2:53 pm

Nonstop4h 00m

Chicago O'Hare Intl

Sun 11/23

6:00 am-10:44 am

Nonstop3h 44m

$221

CancúnChicago

CUN - ORD

CUNORD

Cancun

Tue 11/4

2:44 pm-12:27 am

1 stop10h 43m

Chicago O'Hare Intl

Tue 11/11

5:10 am-1:35 pm

1 stop7h 25m

$236

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 11/14

2:15 pm-5:00 pm

Nonstop3h 45m

Chicago Midway

Sun 11/16

10:40 am-3:25 pm

Nonstop3h 45m

$260

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 11/14

2:15 pm-5:00 pm

Nonstop3h 45m

Chicago Midway

Mon 11/17

8:40 am-1:25 pm

Nonstop3h 45m

$265

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Cancún to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the typical price of a round-trip flight between Cancún and Chicago?

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Cancún, with most prices found around $195. If you’re not able to fly to Chicago in January, then November is your next best option. Flight prices from Cancún to Chicago during November average around $238.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $186. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Cancún to Chicago for around $279.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Cancún to Chicago during this time can be as low as $215. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $268.

What is the cheapest Cancun to Chicago flight route?

Fly from Cancun to Chicago O'Hare Intl for the best Cancun - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Cancún when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $268 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Cancún for as low as $124 on momondo.

What cabin class options are available on Cancun to Chicago flights?

There are 3 cabin classes available to choose from on Cancun to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Cancún to Chicago flights?

No. A direct flight is the cheapest option for a flight between Cancún to Chicago.

How have Cancún to Chicago flight prices changed over time?

As of October 2025, prices for Cancún to Chicago flights are approximately 52% more expensive when compared to flights at the same time last year.

When to book flights from Cancún to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Cancún to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Cancún to Chicago (CUN to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Cancún to Chicago

Best Price Found	$148
Fastest flight time	3h 40m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Cancún in the past 72 hours is $148. The best round-trip flight deal from Cancún to Chicago found on momondo in the last 72 hours is $178.

The fastest flight from Cancún to Chicago takes 3h 40m

Direct flights go from Cancún to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

How far is Cancun to Chicago by plane?
A flight from Cancun to Chicago will travel around 1431.3 mi. 3h 45m is a normal flight duration for this route.
When did momondo last update prices for flights from Cancun Airport to Chicago?
Prices for flights from Cancun Airport to Chicago refresh daily.
How many operators does momondo search for flights from Cancun Airport to Chicago?
As of October 2025, there are 4 operators available to choose from for flights from Cancun Airport to Chicago.
How old do you have to be to fly from Cancun Airport to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Cancun Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Cancún to Chicago?
Based on momondo bookings for flights between Cancún and Chicago, the leading plane model is Boeing 737-900, making up 19.15% of the total bookings. Other popular models include Airbus A321-100/200 with 16.15%, Airbus A320neo with 15.14%, and Airbus A321neo with 11.02%.
What is the most popular airline from Cancún to Chicago?
Based on momondo bookings for flights between Cancún and Chicago, the leading airline is Southwest, making up 31% of the total bookings. Other popular airlines include Spirit Airlines with 31%, United Airlines with 25%, and Frontier with 13%.

Best airlines flying from Cancún to Chicago

Compare and see reviews for airlines that fly from Cancún to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $157	Free Cancellation	Rating 5.8 3,137 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $194	Free Cancellation	Rating 6.3 8,099 reviews	Search Spirit Airlines flights
United Airlines	PriceFrom $214	Free Cancellation	Rating 7.4 8,982 reviews	Search United Airlines flights
American Airlines	PriceFrom $272	Free Cancellation	Rating 7.2 11,040 reviews	Search American Airlines flights

United Airlines Flights From Cancún to Chicago
The lowest priced United Airlines flight from Cancún to Chicago from the last 72 hours was $214. Generally, United Airlines has 14 flights on this route every week with an average price of $325. United Airlines is rated 7.4/10 by our users.
American Airlines Flights From Cancún to Chicago
American Airlines is also a popular choice for this route. American Airlines flight deals for Cancún to Chicago start from as low as $272 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around $352. American Airlines operates 14 flights to Chicago from Cancún in an average week. Users have rated it 7.2/10 across 11,040 reviews.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Cancún to Chicago?

Finding the right flight to Chicago from Cancún is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Cancún to Chicago with flexible booking policies on momondo?

Flights from Cancún to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Cancún to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Cancún. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Cancún to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Cancún to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Sat 11/15

Sat 11/22

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Popular cities in the United States

Flights to New Yorkfrom $48

Flights to Los Angelesfrom $48

Flights to Miamifrom $53

Flights to Orlandofrom $54

Flights to Las Vegasfrom $38

Flights to San Franciscofrom $48

Flights to Washington, D.C.from $50

Flights to Bostonfrom $55

Flights to Atlantafrom $45

Flights to Dallasfrom $63

Flights to Seattlefrom $71

Flights to Denverfrom $54

Cheap flights from Cancún to Chicago from $139

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Cancún to Chicago departing on 11/26. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Cancún to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Frontier flights from Cancún to Chicago

Our best Frontier deals on Cancún to Chicago flight tickets

United Airlines flights from Cancún to Chicago

Our best United Airlines deals on Cancún to Chicago flight tickets

momondo Fare Finder

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

See travel insights to Chicago from

How to get the cheapest flight ticket from Cancún to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Cancún and Chicago?

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Cancún, with most prices found around $195. If you’re not able to fly to Chicago in January, then November is your next best option. Flight prices from Cancún to Chicago during November average around $238.

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Cancún to Chicago during this time can be as low as $215. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $268.

What is the cheapest Cancun to Chicago flight route?

Fly from Cancun to Chicago O'Hare Intl for the best Cancun - Chicago flight prices

How far in advance should I book a flight to Chicago?

What cabin class options are available on Cancun to Chicago flights?

There are 3 cabin classes available to choose from on Cancun to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Cancún to Chicago flights?

No. A direct flight is the cheapest option for a flight between Cancún to Chicago.

How have Cancún to Chicago flight prices changed over time?

As of October 2025, prices for Cancún to Chicago flights are approximately 52% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from Cancun to Chicago?

Southwest, Frontier, and Spirit Airlines are the most popular carriers operating from Cancun to Chicago

What airlines fly to Chicago?

How many flights depart from Cancún to Chicago on average per day?

As of October 2025, there are 8 flights per day flying from Cancún to Chicago. The most common time of day flights depart is 3:00PM, with 95% of flights taking off in the afternoon.

How many flights depart from Cancún to Chicago on average per week?

As of October 2025, there are 57 flights per week flying from Cancún to Chicago. The most common day of the week flights depart is Tue, with 16% of flights taking off on this day.

When to book flights from Cancún to Chicago

Cheap Cancún to Chicago (CUN to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Cancún to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is Cancun to Chicago by plane?

When did momondo last update prices for flights from Cancun Airport to Chicago?

How many operators does momondo search for flights from Cancun Airport to Chicago?

How old do you have to be to fly from Cancun Airport to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Cancún to Chicago?

What is the most popular airline from Cancún to Chicago?

Best airlines flying from Cancún to Chicago

Compare and see reviews for airlines that fly from Cancún to Chicago with momondo

United Airlines Flights From Cancún to Chicago

American Airlines Flights From Cancún to Chicago

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Cancún to Chicago?

Can I find flights from Cancún to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Cancún to Chicago?

I’m not ready to book a flight from Cancún to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago