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Cheap flights from Chicago to Cancún from $92

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 12/8. 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

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Find the cheapest flights from Chicago to Cancún

Cheap round-trip flights

Spirit Airlines Logo
5:17 pm - 8:11 amORD-CUN
14h 54m1 stop
Spirit Airlines Logo
9:16 am - 9:58 pmCUN-ORD
12h 42m1 stop
$232Spirit Airlines
Find Deal
Sat, Sep 27 - Sat, Oct 4
Multiple Airlines Logo
5:05 am - 12:27 pmORD-CUN
6h 22m1 stop
Multiple Airlines Logo
11:38 am - 2:41 pmCUN-ORD
4h 03mnonstop
$233Multiple Airlines
Find Deal
Tue, Dec 9 - Fri, Dec 12
Frontier Logo
8:25 am - 12:18 pmORD-CUN
3h 53mnonstop
Frontier Logo
1:28 pm - 4:36 pmCUN-ORD
4h 08mnonstop
$241Frontier
Find Deal
Tue, Oct 28 - Thu, Nov 6
Frontier Logo
6:45 am - 11:46 amORD-CUN
4h 01mnonstop
Frontier Logo
11:38 am - 2:41 pmCUN-ORD
4h 03mnonstop
$258Frontier
Find Deal
Tue, Dec 9 - Sat, Dec 13
United Airlines Logo
8:43 am - 12:33 pmORD-CUN
3h 50mnonstop
United Airlines Logo
2:18 pm - 6:09 pmCUN-ORD
3h 51mnonstop
$261United Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
Southwest Logo
10:40 am - 3:25 pmMDW-CUN
3h 45mnonstop
Southwest Logo
1:45 pm - 4:30 pmCUN-MDW
3h 45mnonstop
$261Southwest
Find Deal
Sun, Nov 16 - Wed, Nov 19
United Airlines Logo
7:10 am - 2:40 pmORD-CUN
7h 30m1 stop
United Airlines Logo
3:38 pm - 7:36 pmCUN-ORD
3h 58mnonstop
$265United Airlines
Find Deal
Tue, Sep 30 - Fri, Oct 3
Southwest Logo
3:40 pm - 8:25 pmMDW-CUN
3h 45mnonstop
Southwest Logo
1:45 pm - 4:30 pmCUN-MDW
3h 45mnonstop
$266Southwest
Find Deal
Sat, Nov 15 - Wed, Nov 19
Delta Logo
10:35 am - 9:10 pmMDW-CUN
9h 35m1 stop
Delta Logo
4:25 pm - 9:46 pmCUN-MDW
6h 21m1 stop
$326Delta
Find Deal
Sat, Jan 17 - Sat, Jan 24
Delta Logo
10:35 am - 9:10 pmMDW-CUN
9h 35m1 stop
Delta Logo
12:05 pm - 9:46 pmCUN-MDW
10h 41m2 stops
$330Delta
Find Deal
Sat, Jan 17 - Sat, Jan 24

Frontier flights from Chicago to Cancún

Our best Frontier deals on Chicago to Cancún flight tickets
Frontier
Oct 28
ORD8:25 amChicago O'Hare Intl
3h 53m
CUN12:18 pmCancun
Nov 6
CUN1:28 pmCancun
4h 08m
ORD4:36 pmChicago O'Hare Intl
$241
Find similar
Frontier
Dec 9
ORD6:45 amChicago O'Hare Intl
4h 01m
CUN11:46 amCancun
Dec 13
CUN11:38 amCancun
4h 03m
ORD2:41 pmChicago O'Hare Intl
$258
Find similar
Frontier
Oct 28
ORD8:25 amChicago O'Hare Intl
3h 53m
CUN12:18 pmCancun
Nov 4
CUN1:28 pmCancun
4h 08m
ORD4:36 pmChicago O'Hare Intl
$267
Find similar

Southwest flights from Chicago to Cancún

Our best Southwest deals on Chicago to Cancún flight tickets
Southwest
Nov 16
MDW10:40 amChicago Midway
3h 45m
CUN3:25 pmCancun
Nov 19
CUN1:45 pmCancun
3h 45m
MDW4:30 pmChicago Midway
$261
Find similar
Southwest
Nov 15
MDW3:40 pmChicago Midway
3h 45m
CUN8:25 pmCancun
Nov 19
CUN1:45 pmCancun
3h 45m
MDW4:30 pmChicago Midway
$266
Find similar
Southwest
Nov 15
MDW3:40 pmChicago Midway
3h 45m
CUN8:25 pmCancun
Nov 20
CUN1:45 pmCancun
3h 45m
MDW4:30 pmChicago Midway
$271
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 September 17, 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

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 9/27

5:17 pm-8:11 am

1 stop14h 54m

Cancun

Sat 10/4

9:16 am-9:58 pm

1 stop12h 42m

$232

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 12/9

5:05 am-12:27 pm

1 stop6h 22m

Cancun

Fri 12/12

11:38 am-2:41 pm

Nonstop4h 03m

$233

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 10/28

8:25 am-12:18 pm

Nonstop3h 53m

Cancun

Thu 11/6

1:28 pm-4:36 pm

Nonstop4h 08m

$241

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 12/9

6:45 am-11:46 am

Nonstop4h 01m

Cancun

Sat 12/13

11:38 am-2:41 pm

Nonstop4h 03m

$258

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Mon 10/27

8:43 am-12:33 pm

Nonstop3h 50m

Cancun

Fri 10/31

2:18 pm-6:09 pm

Nonstop3h 51m

$261

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 11/16

10:40 am-3:25 pm

Nonstop3h 45m

Cancun

Wed 11/19

1:45 pm-4:30 pm

Nonstop3h 45m

$261

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 9/30

7:10 am-2:40 pm

1 stop7h 30m

Cancun

Fri 10/3

3:38 pm-7:36 pm

Nonstop3h 58m

$265

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/15

3:40 pm-8:25 pm

Nonstop3h 45m

Cancun

Wed 11/19

1:45 pm-4:30 pm

Nonstop3h 45m

$266

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 1/17

10:35 am-9:10 pm

1 stop9h 35m

Cancun

Sat 1/24

4:25 pm-9:46 pm

1 stop6h 21m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 1/17

10:35 am-9:10 pm

1 stop9h 35m

Cancun

Sat 1/24

12:05 pm-9:46 pm

2 stops10h 41m

$330

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 October to fly from Chicago, when ticket prices are also cheap, with an average price of $381.

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 $395. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $532. 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 $431 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 $370 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?

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

How have Chicago to Cancún flight prices changed over time?

As of September 2025, prices for Chicago to Cancún flights are approximately 16% cheaper 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 $352.
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
Spirit AirlinesPriceFrom $132Free CancellationRating
6.3
8,023 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $161Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
DeltaPriceFrom $168Free CancellationRating
7.9
7,961 reviews
Search Delta flights
FrontierPriceFrom $172Free CancellationRating
5.8
3,173 reviews
Search Frontier flights
VolarisPriceFrom $180Free CancellationRating
6.6
1,154 reviews
Search Volaris flights
AeromexicoPriceFrom $191Free CancellationRating
7.4
1,696 reviews
Search Aeromexico flights
Air CanadaPriceFrom $205Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
VivaPriceFrom $251Free CancellationRating
7.0
787 reviews
Search Viva flights
SouthwestPriceFrom $266Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
American AirlinesPriceFrom $338Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

  • Southwest Flights From Chicago to Cancún

    Southwest operates around 5 flights from Chicago to Cancún every week. The average price of these flights found in the last 72 hours has been $608, 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 4,242 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 8,926 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.

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