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, 8 flights take off from Chicago and land in Cancún each day. The most common flight departure time for this route is 8:00AM, with 100% of daily flights taking off at noon.

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

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

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

As of November 2025, 56 flights take off from Chicago and land in Cancún each week. The most common flight departure day for this route is Thu, with 16% of weekly flights taking off on this day.

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

Atlanta (ATL) was the most common stop: 40% of momondo users choosing 1-stop flights on this route connected there.

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.

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.

$115 Cheap Flights from Chicago to Cancún in 2025/26

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Find the cheapest flights from Chicago to Cancún

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Cheap round-trip flights

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11:43 am - 4:52 pmORD-CUN

4h 09mnonstop

6:22 pm - 9:32 pmCUN-ORD

4h 10mnonstop

$224Frontier

Find Deal

Tue, Dec 16 - Wed, Dec 24

6:15 am - 11:19 amORD-CUN

4h 04mnonstop

11:40 am - 2:49 pmCUN-ORD

4h 09mnonstop

$225Frontier

Find Deal

Thu, Jan 22 - Sun, Jan 25

6:05 am - 10:54 amORD-CUN

3h 49mnonstop

11:59 am - 2:53 pmCUN-ORD

3h 54mnonstop

$227Spirit Airlines

Find Deal

Thu, Jan 8 - Mon, Jan 12

6:05 am - 10:54 amORD-CUN

3h 49mnonstop

1:21 pm - 7:17 pmCUN-ORD

6h 56m1 stop

$228Spirit Airlines

Find Deal

Sun, Jan 18 - Sun, Jan 25

9:15 am - 1:55 pmMDW-CUN

3h 40mnonstop

1:45 pm - 4:30 pmCUN-MDW

3h 45mnonstop

$269Southwest

Find Deal

Mon, Jan 26 - Thu, Jan 29

12:47 pm - 9:20 pmMDW-CUN

7h 33m1 stop

4:30 pm - 10:22 pmCUN-MDW

6h 52m1 stop

$296Aeromexico

Find Deal

Mon, Dec 1 - Sat, Dec 20

12:50 pm - 9:20 pmMDW-CUN

7h 30m1 stop

11:09 am - 4:31 pmCUN-MDW

6h 22m1 stop

$304Aeromexico

Find Deal

Tue, Dec 2 - Thu, Dec 18

6:54 pm - 9:48 amMDW-CUN

13h 54m1 stop

10:39 am - 5:34 pmCUN-MDW

7h 55m1 stop

$309Volaris

Find Deal

Wed, Feb 4 - Wed, Feb 11

6:54 pm - 9:48 amMDW-CUN

13h 54m1 stop

10:39 am - 5:34 pmCUN-MDW

7h 55m1 stop

$310Volaris

Find Deal

Mon, Feb 2 - Wed, Feb 4

9:15 am - 1:55 pmMDW-CUN

3h 40mnonstop

1:45 pm - 4:30 pmCUN-MDW

3h 45mnonstop

$314Southwest

Find Deal

Mon, Feb 2 - Wed, Feb 4

Southwest flights from Chicago to Cancún

Our best Southwest deals on Chicago to Cancún flight tickets

Southwest

Jan 26

MDW9:15 amChicago Midway

3h 40m

CUN1:55 pmCancun

Jan 29

CUN1:45 pmCancun

3h 45m

MDW4:30 pmChicago Midway

$269

Find similar

Southwest

Feb 1

MDW10:45 amChicago Midway

8h 00m

1 stop

CUN7:45 pmCancun

Feb 6

CUN3:00 pmCancun

3h 45m

MDW5:45 pmChicago Midway

$318

Find similar

Southwest

Jan 6

MDW9:15 amChicago Midway

3h 40m

CUN1:55 pmCancun

Jan 13

CUN2:45 pmCancun

7h 15m

1 stop

MDW9:00 pmChicago Midway

$324

Find similar

Aeromexico flights from Chicago to Cancún

Our best Aeromexico deals on Chicago to Cancún flight tickets

Aeromexico

Dec 1

MDW12:47 pmChicago Midway

7h 33m

1 stop

CUN9:20 pmCancun

Dec 20

CUN4:30 pmCancun

6h 52m

1 stop

MDW10:22 pmChicago Midway

$296

Find similar

Aeromexico

Dec 2

MDW12:50 pmChicago Midway

7h 30m

1 stop

CUN9:20 pmCancun

Dec 18

CUN11:09 amCancun

6h 22m

1 stop

MDW4:31 pmChicago Midway

$304

Find similar

Aeromexico

Dec 1

MDW10:47 amChicago Midway

9h 33m

1 stop

CUN9:20 pmCancun

Dec 10

CUN8:00 amCancun

9h 34m

1 stop

MDW4:34 pmChicago Midway

$319

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 12/16

11:43 am-4:52 pm

Nonstop4h 09m

Cancun

Wed 12/24

6:22 pm-9:32 pm

Nonstop4h 10m

$224

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Thu 1/22

6:15 am-11:19 am

Nonstop4h 04m

Cancun

Sun 1/25

11:40 am-2:49 pm

Nonstop4h 09m

$225

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Thu 1/8

6:05 am-10:54 am

Nonstop3h 49m

Cancun

Mon 1/12

11:59 am-2:53 pm

Nonstop3h 54m

$227

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 1/18

6:05 am-10:54 am

Nonstop3h 49m

Cancun

Sun 1/25

1:21 pm-7:17 pm

1 stop6h 56m

$228

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 1/26

9:15 am-1:55 pm

Nonstop3h 40m

Cancun

Thu 1/29

1:45 pm-4:30 pm

Nonstop3h 45m

$269

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 12/1

12:47 pm-9:20 pm

1 stop7h 33m

Cancun

Sat 12/20

4:30 pm-10:22 pm

1 stop6h 52m

$296

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 12/2

12:50 pm-9:20 pm

1 stop7h 30m

Cancun

Thu 12/18

11:09 am-4:31 pm

1 stop6h 22m

$304

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 2/4

6:54 pm-9:48 am

1 stop13h 54m

Cancun

Wed 2/11

10:39 am-5:34 pm

1 stop7h 55m

$309

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 2/2

6:54 pm-9:48 am

1 stop13h 54m

Cancun

Wed 2/4

10:39 am-5:34 pm

1 stop7h 55m

$310

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 2/2

9:15 am-1:55 pm

Nonstop3h 40m

Cancun

Wed 2/4

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

Layovers

Other information

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 $396.

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 $405. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $527. 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 $441 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 $281.

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 21%, 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 1,672 reviews	Search Aeromexico flights
Spirit Airlines	PriceFrom $152	Free Cancellation	Rating 6.3 8,140 reviews	Search Spirit Airlines flights
United Airlines	PriceFrom $161	Free Cancellation	Rating 7.4 9,015 reviews	Search United Airlines flights
Delta	PriceFrom $168	Free Cancellation	Rating 7.9 8,007 reviews	Search Delta flights
Frontier	PriceFrom $176	Free Cancellation	Rating 5.8 3,114 reviews	Search Frontier flights
Volaris	PriceFrom $178	Free Cancellation	Rating 6.7 1,148 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 4,235 reviews	Search Southwest flights
Air Canada	PriceFrom $279	Free Cancellation	Rating 7.1 10,444 reviews	Search Air Canada flights
American Airlines	PriceFrom $340	Free Cancellation	Rating 7.2 11,050 reviews	Search American Airlines flights

Southwest Flights From Chicago to Cancún
Southwest operates around 6 flights from Chicago to Cancún every week. The average price of these flights found in the last 72 hours has been $585, 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 4,235 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 $516, however, with flight time and availability significantly affecting the price. United Airlines (7.4/10 from 9,015 user reviews) flies into Cancún from Chicago 14 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 $115

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 1/9. 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

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Find the cheapest flights from Chicago to Cancún

Cheap round-trip flights

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Cheap last minute flights

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Southwest flights from Chicago to Cancún

Our best Southwest deals on Chicago to Cancún flight tickets

Aeromexico flights from Chicago to Cancún

Our best Aeromexico deals on Chicago to Cancún flight tickets

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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 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 $396.

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?

Viva, Spirit Airlines, and Volaris 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: 40% 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, 8 flights take off from Chicago and land in Cancún each day. The most common flight departure time for this route is 8:00AM, with 100% of daily flights taking off at noon.

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

As of November 2025, 56 flights take off from Chicago and land in Cancún each week. The most common flight departure day for this route is Thu, with 16% 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.