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

Seattle (SEA) has the shortest average layover time for this route: 1h 15m.

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.

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

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

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

As of August 2025, 5 flights take off from Chicago and land in Cancún each day. The most common flight departure time for this route is 10:00AM, with 100% 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 36% of people opting to fly with this airline when traveling to Cancún. Keep in mind that there are 11 different airlines that fly to Cancún on a routine basis, so you have a few additional options to choose from.

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

As of August 2025, 37 flights take off from Chicago and land in Cancún each week. The most common flight departure day for this route is Mon, with 22% of weekly flights taking off on this day.

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

Atlanta (ATL) was the most common stop: 32% 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 Monterrey (MTY) offer the lowest average round-trip price of $305.

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 11 operators available for flights from Chicago to Cancun Airport as of August 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.

$99 Cheap Flights from Chicago to Cancún (CHI-CUN) in 2025

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Find the cheapest flights from Chicago to Cancún (CHI-CUN)

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

5:05 am - 12:59 pmORD-CUN

7h 54m1 stop

10:20 am - 7:50 pmCUN-ORD

9h 30m1 stop

$241Spirit Airlines

Find Deal

Tue, Sep 16 - Fri, Sep 26

5:05 am - 12:37 pmORD-CUN

7h 32m1 stop

2:07 pm - 10:48 pmCUN-ORD

8h 41m1 stop

$242Spirit Airlines

Find Deal

Sun, Aug 31 - Sat, Sep 6

5:05 am - 12:59 pmORD-CUN

7h 54m1 stop

9:16 am - 9:58 pmCUN-ORD

12h 42m1 stop

$243Spirit Airlines

Find Deal

Tue, Sep 16 - Thu, Sep 18

8:15 am - 12:08 pmORD-CUN

3h 53mnonstop

1:28 pm - 4:36 pmCUN-ORD

4h 08mnonstop

$253Frontier

Find Deal

Thu, Oct 30 - Sun, Nov 2

8:05 am - 11:56 amORD-CUN

3h 51mnonstop

1:06 pm - 5:14 pmCUN-ORD

4h 08mnonstop

$254Frontier

Find Deal

Sat, Oct 18 - Sat, Oct 25

3:40 pm - 8:25 pmMDW-CUN

3h 45mnonstop

11:20 am - 2:00 pmCUN-MDW

3h 40mnonstop

$271Southwest

Find Deal

Sat, Nov 8 - Sat, Nov 22

10:02 am - 1:50 pmORD-CUN

3h 48mnonstop

2:50 pm - 6:50 pmCUN-ORD

4h 00mnonstop

$281American Airlines

Find Deal

Mon, Sep 29 - Fri, Oct 3

10:35 am - 2:10 pmMDW-CUN

3h 35mnonstop

3:10 pm - 6:50 pmCUN-MDW

3h 40mnonstop

$281Southwest

Find Deal

Sun, Sep 14 - Thu, Sep 18

10:35 am - 8:20 pmMDW-CUN

9h 45m1 stop

1:58 pm - 10:14 pmCUN-MDW

8h 16m1 stop

$326Delta

Find Deal

Sat, Oct 25 - Wed, Oct 29

6:00 am - 12:50 pmMDW-CUN

6h 50m1 stop

1:30 pm - 8:40 amCUN-MDW

19h 10m2 stops

$330Delta

Find Deal

Sat, Sep 13 - Sat, Sep 27

Spirit Airlines flights from Chicago to Cancún

Our best Spirit Airlines deals on Chicago to Cancún flight tickets

Spirit Airlines

Sep 16

ORD5:05 amChicago O'Hare Intl

7h 54m

1 stop

CUN12:59 pmCancun

Sep 26

CUN10:20 amCancun

9h 30m

1 stop

ORD7:50 pmChicago O'Hare Intl

$241

Find similar

Spirit Airlines

Aug 31

ORD5:05 amChicago O'Hare Intl

7h 32m

1 stop

CUN12:37 pmCancun

Sep 6

CUN2:07 pmCancun

8h 41m

1 stop

ORD10:48 pmChicago O'Hare Intl

$242

Find similar

Spirit Airlines

Sep 16

ORD5:05 amChicago O'Hare Intl

7h 54m

1 stop

CUN12:59 pmCancun

Sep 18

CUN9:16 amCancun

12h 42m

1 stop

ORD9:58 pmChicago O'Hare Intl

$243

Find similar

Frontier flights from Chicago to Cancún

Our best Frontier deals on Chicago to Cancún flight tickets

Frontier

Aug 23

ORD6:45 amChicago O'Hare Intl

3h 51m

CUN10:36 amCancun

Aug 28

CUN11:51 amCancun

4h 01m

ORD3:52 pmChicago O'Hare Intl

$244

Find similar

Frontier

Aug 24

ORD6:45 amChicago O'Hare Intl

3h 51m

CUN10:36 amCancun

Aug 28

CUN11:51 amCancun

4h 01m

ORD3:52 pmChicago O'Hare Intl

$245

Find similar

Frontier

Aug 24

ORD6:45 amChicago O'Hare Intl

3h 51m

CUN10:36 amCancun

Aug 28

CUN11:51 amCancun

4h 01m

ORD3:52 pmChicago O'Hare Intl

$246

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 9/16

5:05 am-12:59 pm

1 stop7h 54m

Cancun

Fri 9/26

10:20 am-7:50 pm

1 stop9h 30m

$241

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 8/31

5:05 am-12:37 pm

1 stop7h 32m

Cancun

Sat 9/6

2:07 pm-10:48 pm

1 stop8h 41m

$242

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 9/16

5:05 am-12:59 pm

1 stop7h 54m

Cancun

Thu 9/18

9:16 am-9:58 pm

1 stop12h 42m

$243

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Thu 10/30

8:15 am-12:08 pm

Nonstop3h 53m

Cancun

Sun 11/2

1:28 pm-4:36 pm

Nonstop4h 08m

$253

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 10/18

8:05 am-11:56 am

Nonstop3h 51m

Cancun

Sat 10/25

1:06 pm-5:14 pm

Nonstop4h 08m

$254

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/8

3:40 pm-8:25 pm

Nonstop3h 45m

Cancun

Sat 11/22

11:20 am-2:00 pm

Nonstop3h 40m

$271

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Mon 9/29

10:02 am-1:50 pm

Nonstop3h 48m

Cancun

Fri 10/3

2:50 pm-6:50 pm

Nonstop4h 00m

$281

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 9/14

10:35 am-2:10 pm

Nonstop3h 35m

Cancun

Thu 9/18

3:10 pm-6:50 pm

Nonstop3h 40m

$281

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 10/25

10:35 am-8:20 pm

1 stop9h 45m

Cancun

Wed 10/29

1:58 pm-10:14 pm

1 stop8h 16m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 9/13

6:00 am-12:50 pm

1 stop6h 50m

Cancun

Sat 9/27

1:30 pm-8:40 am

2 stops19h 10m

$330

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

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 October to fly from Chicago, when ticket prices are also cheap, with an average price of $367.

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 $386. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $534. 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 evening. Flights from Chicago to Cancún during this time can be as low as $405. Flights to Cancún are more costly at noon, with an average ticket price of $713. 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 $427 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 $365 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.

How have Chicago to Cancún flight prices changed over time?

As of August 2025, prices for Chicago to Cancún flights are approximately 12% 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	$99
Fastest flight time	3h 29m
Direct flights	Every day
Airports in Cancún	1 airport

The best one-way flight to Cancún from Chicago in the past 72 hours is $99. The best round-trip flight deal from Chicago to Cancún found on momondo in the last 72 hours is $241.

The fastest flight from Chicago to Cancún takes 3h 29m

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 29m.
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 11 operators available for flights from Chicago to Cancun Airport as of August 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 Boeing 737-900, making up 21.37% of the total bookings. Other popular models include Airbus A320neo with 19.64%, Airbus A321-100/200 with 16.30%, and Boeing 737-800 with 15.91%.
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 31% of all bookings. The subsequent popular airlines are American Airlines at 20%, Spirit Airlines at 19%, and Frontier at 15%.

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
Spirit Airlines	PriceFrom $124	Free Cancellation	Rating 6.3 8,038 reviews	Search Spirit Airlines flights
United Airlines	PriceFrom $161	Free Cancellation	Rating 7.4 8,925 reviews	Search United Airlines flights
Delta	PriceFrom $168	Free Cancellation	Rating 8.0 7,981 reviews	Search Delta flights
Frontier	PriceFrom $170	Free Cancellation	Rating 5.8 3,212 reviews	Search Frontier flights
Volaris	PriceFrom $179	Free Cancellation	Rating 6.6 1,162 reviews	Search Volaris flights
Aeromexico	PriceFrom $191	Free Cancellation	Rating 7.5 1,720 reviews	Search Aeromexico flights
Viva	PriceFrom $251	Free Cancellation	Rating 7.0 789 reviews	Search Viva flights
Southwest	PriceFrom $266	Free Cancellation	Rating 8.0 4,246 reviews	Search Southwest flights
American Airlines	PriceFrom $332	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Avianca	PriceFrom $552	Free Cancellation	Rating 6.7 2,407 reviews	Search Avianca flights

Southwest Flights From Chicago to Cancún
Southwest operates around 7 flights from Chicago to Cancún every week. The average price of these flights found in the last 72 hours has been $622, 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 4,246 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 $484, however, with flight time and availability significantly affecting the price. United Airlines (7.4/10 from 8,925 user reviews) flies into Cancún from Chicago 8 times in an average week so prices can vary.

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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.

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Cheap flights from Chicago to Cancún from $99

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 10/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

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Find the cheapest flights from Chicago to Cancún (CHI-CUN)

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Spirit Airlines flights from Chicago to Cancún

Our best Spirit Airlines deals on Chicago to Cancún flight tickets

Frontier flights from Chicago to Cancún

Our best Frontier deals on Chicago to Cancún flight tickets

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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 October to fly from Chicago, when ticket prices are also cheap, with an average price of $367.

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.

How have Chicago to Cancún flight prices changed over time?

As of August 2025, prices for Chicago to Cancún flights are approximately 12% more expensive when compared to flights at the same time last year.

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

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

What airlines fly to Cancún?

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

Atlanta (ATL) was the most common stop: 32% 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 Monterrey (MTY) offer the lowest average round-trip price of $305.

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?

Seattle (SEA) has the shortest average layover time for this route: 1h 15m.

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

As of August 2025, 5 flights take off from Chicago and land in Cancún each day. The most common flight departure time for this route is 10:00AM, with 100% of daily flights taking off at noon.

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

As of August 2025, 37 flights take off from Chicago and land in Cancún each week. The most common flight departure day for this route is Mon, with 22% 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?

Why use momondo?

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

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

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

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

Get notified when prices go down

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

Find better results for your trip to Mexico