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

Generally, flights departing at night tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

Which layover airport offers the lowest fares from Chicago to Cancún?

Flights via Mexico City (MEX) offer the lowest average round-trip price of $299.

How often are flights from Chicago to Cancún delayed?

Historically, on average around 13% of flights between Chicago and Cancún have experienced a delay on any given week. The average delay length over the past 12 months has been 143 minutes.

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

As of November 2025, 65 flights take off from Chicago and land in Cancún each week. The most common flight departure day for this route is Mon, with 18% of weekly flights taking off on this day.

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

As of November 2025, 9 flights take off from Chicago and land in Cancún each day. The most common flight departure time for this route is 8:00AM, with 97% of daily flights taking off at noon.

What airlines fly to Cancún?

United Airlines, American Airlines and Spirit Airlines are the top three most popular airlines that fly to Cancún from Chicago according to our data. United Airlines is the first choice among our users, with 34% of people opting to fly with this airline when traveling to Cancún. Keep in mind that there are 12 different airlines that fly to Cancún on a routine basis, so you have a few additional options to choose from.

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

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Saturday has historically seen more delays on average compared to the rest of the week.

Which layover airport has the shortest connection time from Chicago to Cancún?

Detroit (DTW) has the shortest average layover time for this route: 1h 23m.

Which airport is the most popular layover for flights between Chicago and Cancún?

Atlanta (ATL) was the most common stop: 44% of momondo users choosing 1-stop flights on this route connected there.

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

United Airlines, JetBlue, and Southwest are the most popular carriers operating from Chicago to Cancun

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

According to our data, TUI fly have had the least number of delays on this route over the last 12 months; with no flights being classified as delayed.

Which layover airport has the shortest travel time from Chicago to Cancún?

Flights connecting via St. Louis (STL) have the shortest average one-way travel time: 5h 10m.

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

Prices for flights from Chicago to Cancun Airport are updated daily.

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

There are 12 operators available for flights from Chicago to Cancun Airport as of November 2025.

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

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Cancun Airport.

What documentation or ID do you need to fly to Cancun Airport?

The necessary travel and health documents for your Cancun Airport 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.

$105 Cheap Flights from Chicago to Cancún in 2025/26

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

Prices are currently low for flights on this route. Typical prices usually range from $354 to $740. The lowest price recently found on this route was $216.

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Chicago to Cancún

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

1:20 am - 6:45 pmORD-CUN

16h 25m1 stop

11:40 am - 2:49 pmCUN-ORD

4h 09mnonstop

$216Multiple Airlines

Find Deal

Sun, Jan 18 - Fri, Jan 23

5:15 am - 12:16 pmORD-CUN

6h 01m1 stop

11:40 am - 2:49 pmCUN-ORD

4h 09mnonstop

$217Multiple Airlines

Find Deal

Tue, Jan 20 - Thu, Jan 22

1:20 am - 6:45 pmORD-CUN

16h 25m1 stop

11:40 am - 2:49 pmCUN-ORD

4h 09mnonstop

$218Multiple Airlines

Find Deal

Sun, Jan 18 - Thu, Jan 22

6:15 am - 11:19 amORD-CUN

4h 04mnonstop

11:40 am - 2:49 pmCUN-ORD

4h 09mnonstop

$221Frontier

Find Deal

Tue, Jan 20 - Sun, Jan 25

6:45 am - 11:49 amORD-CUN

4h 04mnonstop

11:40 am - 2:49 pmCUN-ORD

4h 09mnonstop

$222Frontier

Find Deal

Mon, Jan 19 - Sat, Jan 24

5:15 am - 12:16 pmORD-CUN

6h 01m1 stop

11:59 am - 2:53 pmCUN-ORD

3h 54mnonstop

$223Spirit Airlines

Find Deal

Sun, Jan 18 - Fri, Jan 23

5:15 am - 12:16 pmORD-CUN

6h 01m1 stop

11:59 am - 2:53 pmCUN-ORD

3h 54mnonstop

$224Spirit Airlines

Find Deal

Wed, Jan 21 - Thu, Jan 22

9:15 am - 1:55 pmMDW-CUN

3h 40mnonstop

3:00 pm - 5:45 pmCUN-MDW

3h 45mnonstop

$269Southwest

Find Deal

Mon, Feb 2 - Fri, Feb 6

11:21 am - 9:11 pmMDW-CUN

8h 50m1 stop

4:40 pm - 10:07 pmCUN-MDW

6h 27m1 stop

$303Aeromexico

Find Deal

Thu, Jan 8 - Thu, Jan 15

9:15 am - 1:55 pmMDW-CUN

3h 40mnonstop

1:45 pm - 4:30 pmCUN-MDW

3h 45mnonstop

$314Southwest

Find Deal

Tue, Jan 20 - Tue, Feb 3

Spirit Airlines flights from Chicago to Cancún

Our best Spirit Airlines deals on Chicago to Cancún flight tickets

Spirit Airlines

Dec 3

ORD9:22 pmChicago O'Hare Intl

14h 47m

1 stop

CUN1:09 pmCancun

Dec 6

CUN11:50 amCancun

4h 03m

ORD2:53 pmChicago O'Hare Intl

$223

Find similar

Spirit Airlines

Jan 21

ORD5:15 amChicago O'Hare Intl

6h 01m

1 stop

CUN12:16 pmCancun

Jan 22

CUN11:59 amCancun

3h 54m

ORD2:53 pmChicago O'Hare Intl

$224

Find similar

Spirit Airlines

Jan 17

ORD6:05 amChicago O'Hare Intl

3h 49m

CUN10:54 amCancun

Jan 22

CUN11:59 amCancun

3h 54m

ORD2:53 pmChicago O'Hare Intl

$225

Find similar

Southwest flights from Chicago to Cancún

Our best Southwest deals on Chicago to Cancún flight tickets

Southwest

Feb 2

MDW9:15 amChicago Midway

3h 40m

CUN1:55 pmCancun

Feb 6

CUN3:00 pmCancun

3h 45m

MDW5:45 pmChicago Midway

$269

Find similar

Southwest

Jan 20

MDW9:15 amChicago Midway

3h 40m

CUN1:55 pmCancun

Feb 3

CUN1:45 pmCancun

3h 45m

MDW4:30 pmChicago Midway

$314

Find similar

Southwest

Feb 2

MDW6:50 amChicago Midway

7h 35m

1 stop

CUN3:25 pmCancun

Feb 6

CUN3:00 pmCancun

3h 45m

MDW5:45 pmChicago Midway

$318

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 1/18

1:20 am-6:45 pm

1 stop16h 25m

Cancun

Fri 1/23

11:40 am-2:49 pm

Nonstop4h 09m

$216

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 1/20

5:15 am-12:16 pm

1 stop6h 01m

Cancun

Thu 1/22

11:40 am-2:49 pm

Nonstop4h 09m

$217

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 1/18

1:20 am-6:45 pm

1 stop16h 25m

Cancun

Thu 1/22

11:40 am-2:49 pm

Nonstop4h 09m

$218

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 1/20

6:15 am-11:19 am

Nonstop4h 04m

Cancun

Sun 1/25

11:40 am-2:49 pm

Nonstop4h 09m

$221

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Mon 1/19

6:45 am-11:49 am

Nonstop4h 04m

Cancun

Sat 1/24

11:40 am-2:49 pm

Nonstop4h 09m

$222

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 1/18

5:15 am-12:16 pm

1 stop6h 01m

Cancun

Fri 1/23

11:59 am-2:53 pm

Nonstop3h 54m

$223

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Wed 1/21

5:15 am-12:16 pm

1 stop6h 01m

Cancun

Thu 1/22

11:59 am-2:53 pm

Nonstop3h 54m

$224

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 2/2

9:15 am-1:55 pm

Nonstop3h 40m

Cancun

Fri 2/6

3:00 pm-5:45 pm

Nonstop3h 45m

$269

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 1/8

11:21 am-9:11 pm

1 stop8h 50m

Cancun

Thu 1/15

4:40 pm-10:07 pm

1 stop6h 27m

$303

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 1/20

9:15 am-1:55 pm

Nonstop3h 40m

Cancun

Tue 2/3

1:45 pm-4:30 pm

Nonstop3h 45m

$314

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 Chicago to Cancún

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

Delays

Layovers

Other information

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

What is the cheapest month to fly to Cancún?

If you don’t want to visit Cancún in September, then you should wait until July to fly from Chicago, when ticket prices are also cheap, with an average price of $394.

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

The cheapest day to depart from Chicago to Cancún is on a Monday when prices can be found for as low as $414. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $525. These prices are subject to change though, so be sure to set up a Price Alert for flights to Cancún.

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

Our most recent data shows that the best time of day to fly to Cancún is in the morning. Flights from Chicago to Cancún during this time can be as low as $466. Flights to Cancún are more costly at noon, with an average ticket price of $653. Departure times at noon fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago to Cancun flight route?

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

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

You are more likely to see cheaper flights to Cancún from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Cancún for around $440 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Cancún from Chicago for as low as $367 on momondo.

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

There are 4 cabin classes available to choose from on Chicago to Cancun 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 Chicago to Cancún flights?

You could potentially save up to 5% on your flight if you consider stops on a Chicago to Cancún flight.

How have Chicago to Cancún flight prices changed over time?

As of November 2025, prices for Chicago to Cancún flights are approximately 4% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Cancún

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

Estimated round-trip price

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

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

Best Price Found	$124
Fastest flight time	3h 30m
Direct flights	Every day
Airports in Cancún	1 airport

The best one-way flight to Cancún from Chicago in the past 72 hours is $124. The best round-trip flight deal from Chicago to Cancún found on momondo in the last 72 hours is $301.

The fastest flight from Chicago to Cancún takes 3h 30m

Direct flights go from Chicago to Cancún every day.

There is 1 airport near Cancún: Cancun (CUN)

Search flight deals

How far is Chicago to Cancun by plane?
Cancun is 1431.3 mi away from Chicago. By plane, this route typically takes 3h 35m.
When did momondo last update prices for flights from Chicago to Cancun Airport?
Prices for flights from Chicago to Cancun Airport are updated daily.
How many operators does momondo search for flights from Chicago to Cancun Airport?
There are 12 operators available for flights from Chicago to Cancun Airport as of November 2025.
How old do you have to be to fly from Chicago to Cancun Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Cancun Airport.
What documentation or ID do you need to fly to Cancun Airport?
The necessary travel and health documents for your Cancun Airport 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 Chicago to Cancún?
Based on momondo bookings for flights between Chicago and Cancún, the leading plane model is Airbus A321neo, making up 18.98% of the total bookings. Other popular models include Boeing 737-800 with 16.40%, Boeing 777 with 15.34%, and Boeing 737 MAX 9 with 11.25%.
What is the most popular airline from Chicago to Cancún?
momondo data reveals that the most frequently booked airline on the route from Chicago to Cancún is United Airlines, representing 28% of all bookings. The subsequent popular airlines are American Airlines at 22%, Spirit Airlines at 19%, and Frontier at 16%.

Best airlines flying from Chicago to Cancún

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

Airline	Rating	Free Cancellation	Price
Aeromexico	PriceFrom $145	Free Cancellation	Rating 7.4 1,658 reviews	Search Aeromexico flights
United Airlines	PriceFrom $161	Free Cancellation	Rating 7.4 9,046 reviews	Search United Airlines flights
Spirit Airlines	PriceFrom $161	Free Cancellation	Rating 6.3 8,158 reviews	Search Spirit Airlines flights
Delta	PriceFrom $168	Free Cancellation	Rating 7.9 7,998 reviews	Search Delta flights
Frontier	PriceFrom $177	Free Cancellation	Rating 5.8 3,099 reviews	Search Frontier flights
Volaris	PriceFrom $180	Free Cancellation	Rating 6.7 1,153 reviews	Search Volaris flights
Viva	PriceFrom $251	Free Cancellation	Rating 7.0 788 reviews	Search Viva flights
Southwest	PriceFrom $266	Free Cancellation	Rating 8.0 4,254 reviews	Search Southwest flights
Air Canada	PriceFrom $279	Free Cancellation	Rating 7.1 10,476 reviews	Search Air Canada flights
American Airlines	PriceFrom $340	Free Cancellation	Rating 7.2 11,038 reviews	Search American Airlines flights

Southwest Flights From Chicago to Cancún
Southwest operates around 9 flights from Chicago to Cancún every week. The average price of these flights found in the last 72 hours has been $580, but momondo users have found Southwest deals from Chicago to Cancún from as low as $266 round-trip. Southwest has been scored 8.0/10 in 4,254 reviews.
United Airlines Flights From Chicago to Cancún
$161 is the best United Airlines flight deal from Chicago to Cancún found on momondo over the last 72 hours. The average United Airlines ticket price found was closer to $511, however, with flight time and availability significantly affecting the price. United Airlines (7.4/10 from 9,046 user reviews) flies into Cancún from Chicago 14 times in an average week so prices can vary.

Playa del Carmen

Isla Mujeres

Holbox

Puerto Morelos

Akumal

Puerto Aventuras

Valladolid

Punta Sam

Why use momondo?

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

Finding the right flight to Cancún from Chicago 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 Cancún quick and easy, saving you time and money.

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

Yes. momondo enables you to select and highlight flights to Cancún from Chicago with this policy.

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

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

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

Yes momondo offers price alerts on flights to Cancún from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Cancún 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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Fri 12/26

Fri 1/2

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Mexico

Cheap flights from Chicago to Cancún from $105

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Cancún departing on 1/4. 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 Chicago to Cancún

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Spirit Airlines flights from Chicago to Cancún

Our best Spirit Airlines deals on Chicago to Cancún flight tickets

Southwest flights from Chicago to Cancún

Our best Southwest deals on Chicago to Cancún flight tickets

momondo Fare Finder

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

See travel insights to Cancún from

How to get the cheapest flight ticket from Chicago to Cancún

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 Chicago and Cancún?

What is the cheapest month to fly to Cancún?

If you don’t want to visit Cancún in September, then you should wait until July to fly from Chicago, when ticket prices are also cheap, with an average price of $394.

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

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

What is the cheapest Chicago to Cancun flight route?

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

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

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

There are 4 cabin classes available to choose from on Chicago to Cancun 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 Chicago to Cancún flights?

You could potentially save up to 5% on your flight if you consider stops on a Chicago to Cancún flight.

How have Chicago to Cancún flight prices changed over time?

As of November 2025, prices for Chicago to Cancún flights are approximately 4% more expensive when compared to flights at the same time last year.

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

United Airlines, JetBlue, and Southwest are the most popular carriers operating from Chicago to Cancun

What airlines fly to Cancún?

How often are flights from Chicago to Cancún delayed?

Historically, on average around 13% of flights between Chicago and Cancún have experienced a delay on any given week. The average delay length over the past 12 months has been 143 minutes.

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

Generally, flights departing at night tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

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

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Saturday has historically seen more delays on average compared to the rest of the week.

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

According to our data, TUI fly have had the least number of delays on this route over the last 12 months; with no flights being classified as delayed.

Which airport is the most popular layover for flights between Chicago and Cancún?

Atlanta (ATL) was the most common stop: 44% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Chicago to Cancún?

Flights via Mexico City (MEX) offer the lowest average round-trip price of $299.

Which layover airport has the shortest travel time from Chicago to Cancún?

Flights connecting via St. Louis (STL) have the shortest average one-way travel time: 5h 10m.

Which layover airport has the shortest connection time from Chicago to Cancún?

Detroit (DTW) has the shortest average layover time for this route: 1h 23m.

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

As of November 2025, 9 flights take off from Chicago and land in Cancún each day. The most common flight departure time for this route is 8:00AM, with 97% of daily flights taking off at noon.

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

As of November 2025, 65 flights take off from Chicago and land in Cancún each week. The most common flight departure day for this route is Mon, with 18% of weekly flights taking off on this day.

When to book flights from Chicago to Cancún

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

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

Best Price Found

Fastest flight time

Direct flights

Airports in Cancún

How far is Chicago to Cancun by plane?

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

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

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

What documentation or ID do you need to fly to Cancun Airport?

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

What is the most popular airline from Chicago to Cancún?

Best airlines flying from Chicago to Cancún

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

Southwest Flights From Chicago to Cancún

United Airlines Flights From Chicago to Cancún

Traveling to a place near Cancún?