Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Cancún from $100

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 1/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

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

Trusted and free

Trusted and free

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

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago to Cancún

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
9:00 am - 2:02 pm
MDW
-
CUN
4h 02mnonstop
Frontier Logo
2:07 pm - 6:14 pm
CUN
-
MDW
4h 07mnonstop
$213Frontier
Sat, Mar 7 - Sat, Mar 14
Multiple Airlines Logo
6:05 am - 10:54 am
ORD
-
CUN
3h 49mnonstop
Multiple Airlines Logo
11:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
$213Multiple Airlines
Thu, Jan 8 - Sat, Jan 31
Frontier Logo
9:00 am - 2:02 pm
MDW
-
CUN
4h 02mnonstop
Frontier Logo
2:07 pm - 6:14 pm
CUN
-
MDW
4h 07mnonstop
$214Frontier
Sat, Mar 7 - Sat, Mar 14
Frontier Logo
5:50 am - 3:05 pm
ORD
-
CUN
8h 15m1 stop
Frontier Logo
3:25 pm - 6:40 pm
CUN
-
ORD
4h 15mnonstop
$214Frontier
Sun, Jan 11 - Sat, Jan 17
Multiple Airlines Logo
5:15 am - 12:16 pm
ORD
-
CUN
6h 01m1 stop
Multiple Airlines Logo
11:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
$215Multiple Airlines
Sun, Jan 25 - Fri, Jan 30
Frontier Logo
10:37 am - 3:48 pm
ORD
-
CUN
4h 11mnonstop
Frontier Logo
11:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
$216Frontier
Sun, Jan 11 - Wed, Feb 4
Multiple Airlines Logo
5:15 am - 12:16 pm
ORD
-
CUN
6h 01m1 stop
Multiple Airlines Logo
11:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
$217Multiple Airlines
Tue, Jan 20 - Fri, Jan 23
Frontier Logo
10:37 am - 3:48 pm
ORD
-
CUN
4h 11mnonstop
Frontier Logo
3:24 pm - 10:39 pm
CUN
-
ORD
8h 15m1 stop
$218Frontier
Tue, Jan 6 - Mon, Jan 12
Frontier Logo
10:37 am - 3:48 pm
ORD
-
CUN
4h 11mnonstop
Frontier Logo
3:14 pm - 10:39 pm
CUN
-
ORD
8h 25m1 stop
$219Frontier
Mon, Jan 5 - Thu, Jan 8
Spirit Airlines Logo
8:36 pm - 12:00 pm
ORD
-
CUN
14h 24m1 stop
Spirit Airlines Logo
11:59 am - 2:53 pm
CUN
-
ORD
3h 54mnonstop
$222Spirit Airlines
Sat, Jan 17 - Thu, Jan 22

Frontier flights from Chicago to Cancún

Our best Frontier deals on Chicago to Cancún flight tickets
Frontier
Mar 7
MDW9:00 amChicago Midway
4h 02m
CUN2:02 pmCancun
Mar 14
CUN2:07 pmCancun
4h 07m
MDW6:14 pmChicago Midway
$213
Find similar
Frontier
Mar 7
MDW9:00 amChicago Midway
4h 02m
CUN2:02 pmCancun
Mar 14
CUN2:07 pmCancun
4h 07m
MDW6:14 pmChicago Midway
$214
Find similar
Frontier
Dec 15
ORD11:33 amChicago O'Hare Intl
4h 09m
CUN4:42 pmCancun
Dec 18
CUN6:22 pmCancun
4h 10m
ORD9:32 pmChicago O'Hare Intl
$215
Find similar

Spirit Airlines flights from Chicago to Cancún

Our best Spirit Airlines deals on Chicago to Cancún flight tickets
Spirit Airlines
Jan 17
ORD8:36 pmChicago O'Hare Intl
14h 24m
1 stop
CUN12:00 pmCancun
Jan 22
CUN11:59 amCancun
3h 54m
ORD2:53 pmChicago O'Hare Intl
$222
Find similar
Spirit Airlines
Feb 7
ORD8:36 pmChicago O'Hare Intl
14h 24m
1 stop
CUN12:00 pmCancun
Feb 14
CUN12:06 pmCancun
4h 01m
ORD3:07 pmChicago O'Hare Intl
$223
Find similar
Spirit Airlines
Feb 7
ORD6:05 amChicago O'Hare Intl
3h 49m
CUN10:54 amCancun
Feb 14
CUN12:06 pmCancun
4h 01m
ORD3:07 pmChicago O'Hare Intl
$226
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Cancún 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, momondo users made 832,500 searches. Data last updated December 10, 2025.
Use the filters below to find and compare flights from Chicago to Cancún that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 3/7

9:00 am-2:02 pm

Nonstop4h 02m

Cancun

Sat 3/14

2:07 pm-6:14 pm

Nonstop4h 07m

$213

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Thu 1/8

6:05 am-10:54 am

Nonstop3h 49m

Cancun

Sat 1/31

11:40 am-2:49 pm

Nonstop4h 09m

$213

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 3/7

9:00 am-2:02 pm

Nonstop4h 02m

Cancun

Sat 3/14

2:07 pm-6:14 pm

Nonstop4h 07m

$214

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 1/11

5:50 am-3:05 pm

1 stop8h 15m

Cancun

Sat 1/17

3:25 pm-6:40 pm

Nonstop4h 15m

$214

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 1/25

5:15 am-12:16 pm

1 stop6h 01m

Cancun

Fri 1/30

11:40 am-2:49 pm

Nonstop4h 09m

$215

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 1/11

10:37 am-3:48 pm

Nonstop4h 11m

Cancun

Wed 2/4

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

Fri 1/23

11:40 am-2:49 pm

Nonstop4h 09m

$217

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 1/6

10:37 am-3:48 pm

Nonstop4h 11m

Cancun

Mon 1/12

3:24 pm-10:39 pm

1 stop8h 15m

$218

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Mon 1/5

10:37 am-3:48 pm

Nonstop4h 11m

Cancun

Thu 1/8

3:14 pm-10:39 pm

1 stop8h 25m

$219

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 1/17

8:36 pm-12:00 pm

1 stop14h 24m

Cancun

Thu 1/22

11:59 am-2:53 pm

Nonstop3h 54m

$222

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $392.

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 $415. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $522. 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 $363 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 7% 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 December 2025, prices for Chicago to Cancún flights are approximately 47% 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

$127

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 $127. The best round-trip flight deal from Chicago to Cancún found on momondo in the last 72 hours is $322.
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 30m.

  • 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?

  • 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?

  • 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
Airline
Rating
Free Cancellation
Price
AeromexicoPriceFrom $145Free CancellationRating
7.4
1,642 reviews
Search Aeromexico flights
United AirlinesPriceFrom $161Free CancellationRating
7.4
9,095 reviews
Search United Airlines flights
Spirit AirlinesPriceFrom $164Free CancellationRating
6.3
8,175 reviews
Search Spirit Airlines flights
DeltaPriceFrom $168Free CancellationRating
7.9
8,009 reviews
Search Delta flights
VolarisPriceFrom $178Free CancellationRating
6.7
1,155 reviews
Search Volaris flights
FrontierPriceFrom $180Free CancellationRating
5.8
3,085 reviews
Search Frontier flights
VivaPriceFrom $255Free CancellationRating
7.0
794 reviews
Search Viva flights
JetBluePriceFrom $262Free CancellationRating
7.2
2,898 reviews
Search JetBlue flights
SouthwestPriceFrom $266Free CancellationRating
7.9
4,252 reviews
Search Southwest flights
American AirlinesPriceFrom $340Free CancellationRating
7.2
11,048 reviews
Search American Airlines flights

  • Southwest Flights From Chicago to Cancún

    Southwest operates around 4 flights from Chicago to Cancún every week. The average price of these flights found in the last 72 hours has been $578, but momondo users have found Southwest deals from Chicago to Cancún from as low as $266 round-trip. Southwest has been scored 7.9/10 in 4,252 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 $474, however, with flight time and availability significantly affecting the price. United Airlines (7.4/10 from 9,095 user reviews) flies into Cancún from Chicago 14 times in an average week so prices can vary.

Traveling to a place near Cancún?

Book flights to Cancún if you plan to visit one of these locations
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 1/9
Fri 1/16
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Mexico