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Cheap flights from Cancún to Chicago from $153

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Cancún to Chicago departing on 2/21. 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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Find the cheapest flights from Cancún to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
12:15 pm - 5:29 pm
CUN
-
MDW
6h 14m1 stop
Delta Logo
12:46 pm - 9:11 pm
MDW
-
CUN
7h 25m1 stop
$278Delta
Wed, Jan 28 - Wed, Feb 4
Aeromexico Logo
1:40 pm - 10:22 pm
CUN
-
MDW
9h 42m1 stop
Aeromexico Logo
6:00 am - 1:28 am
MDW
-
CUN
18h 28m2 stops
$279Aeromexico
Fri, Feb 6 - Mon, Feb 9
Delta Logo
3:13 pm - 10:22 pm
CUN
-
MDW
8h 09m1 stop
Delta Logo
6:00 am - 4:35 pm
MDW
-
CUN
9h 35m1 stop
$280Delta
Thu, Jan 29 - Mon, Feb 2
Delta Logo
11:10 am - 6:40 pm
CUN
-
MDW
7h 30m1 stop
Delta Logo
6:30 am - 1:59 pm
MDW
-
CUN
7h 29m1 stop
$311Delta
Thu, Apr 9 - Sat, Apr 18
Frontier Logo
1:31 pm - 11:42 pm
CUN
-
MDW
10h 11m1 stop
Frontier Logo
9:00 am - 1:02 pm
MDW
-
CUN
4h 02mnonstop
$317Frontier
Mon, Apr 6 - Sat, Apr 11
Delta Logo
1:40 pm - 10:22 pm
CUN
-
MDW
9h 42m1 stop
Delta Logo
6:00 am - 6:47 pm
MDW
-
CUN
11h 47m2 stops
$330Delta
Wed, Feb 11 - Sun, Feb 15
Delta Logo
12:05 pm - 10:22 pm
CUN
-
MDW
11h 17m2 stops
Delta Logo
6:00 am - 6:47 pm
MDW
-
CUN
11h 47m2 stops
$332Delta
Wed, Feb 11 - Sun, Feb 15
Aeromexico Logo
8:00 am - 10:31 pm
CUN
-
MDW
15h 31m1 stop
Aeromexico Logo
6:00 am - 9:11 pm
MDW
-
CUN
14h 11m1 stop
$339Aeromexico
Thu, Feb 19 - Thu, Feb 26
Delta Logo
8:00 am - 5:37 pm
CUN
-
MDW
10h 37m2 stops
Delta Logo
9:34 am - 9:11 pm
MDW
-
CUN
10h 37m2 stops
$348Delta
Thu, Feb 12 - Sat, Feb 21
Delta Logo
9:55 am - 4:36 pm
CUN
-
MDW
6h 41m1 stop
Delta Logo
6:30 am - 1:59 pm
MDW
-
CUN
7h 29m1 stop
$351Delta
Tue, Apr 14 - Fri, Apr 24

Frontier flights from Cancún to Chicago Midway Airport

Our best Frontier deals on Cancún to Chicago Midway Airport flight tickets
Frontier
Apr 6
CUN1:31 pmCancun
10h 11m
1 stop
MDW11:42 pmChicago Midway
Apr 11
MDW9:00 amChicago Midway
4h 02m
CUN1:02 pmCancun
$317
Find similar
Frontier
Jan 12
CUN3:24 pmCancun
7h 53m
1 stop
MDW10:17 pmChicago Midway
Jan 18
MDW6:10 amChicago Midway
8h 00m
1 stop
CUN3:10 pmCancun
$339
Find similar
Frontier
Apr 6
CUN10:39 amCancun
10h 06m
1 stop
MDW8:45 pmChicago Midway
Apr 11
MDW12:33 pmChicago Midway
20h 55m
2 stops
CUN9:28 amCancun
$397
Find similar

Southwest flights from Cancún to Chicago Midway Airport

Our best Southwest deals on Cancún to Chicago Midway Airport flight tickets
Southwest
Jan 23
CUN1:45 pmCancun
3h 45m
MDW4:30 pmChicago Midway
Jan 26
MDW9:15 amChicago Midway
3h 40m
CUN1:55 pmCancun
$363
Find similar
Southwest
Jan 29
CUN1:45 pmCancun
3h 45m
MDW4:30 pmChicago Midway
Feb 2
MDW9:15 amChicago Midway
3h 40m
CUN1:55 pmCancun
$368
Find similar
Southwest
Jan 23
CUN1:45 pmCancun
3h 45m
MDW4:30 pmChicago Midway
Jan 26
MDW6:15 amChicago Midway
12h 30m
1 stop
CUN7:45 pmCancun
$373
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Cancún to Chicago Midway Airport 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 January 6, 2026.
Use the filters below to find and compare flights from Cancún to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 1/28

12:15 pm-5:29 pm

1 stop6h 14m

Chicago Midway

Wed 2/4

12:46 pm-9:11 pm

1 stop7h 25m

$278

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 2/6

1:40 pm-10:22 pm

1 stop9h 42m

Chicago Midway

Mon 2/9

6:00 am-1:28 am

2 stops18h 28m

$279

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/29

3:13 pm-10:22 pm

1 stop8h 09m

Chicago Midway

Mon 2/2

6:00 am-4:35 pm

1 stop9h 35m

$280

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 4/9

11:10 am-6:40 pm

1 stop7h 30m

Chicago Midway

Sat 4/18

6:30 am-1:59 pm

1 stop7h 29m

$311

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Mon 4/6

1:31 pm-11:42 pm

1 stop10h 11m

Chicago Midway

Sat 4/11

9:00 am-1:02 pm

Nonstop4h 02m

$317

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 2/11

1:40 pm-10:22 pm

1 stop9h 42m

Chicago Midway

Sun 2/15

6:00 am-6:47 pm

2 stops11h 47m

$330

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 2/11

12:05 pm-10:22 pm

2 stops11h 17m

Chicago Midway

Sun 2/15

6:00 am-6:47 pm

2 stops11h 47m

$332

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 2/19

8:00 am-10:31 pm

1 stop15h 31m

Chicago Midway

Thu 2/26

6:00 am-9:11 pm

1 stop14h 11m

$339

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 2/12

8:00 am-5:37 pm

2 stops10h 37m

Chicago Midway

Sat 2/21

9:34 am-9:11 pm

2 stops10h 37m

$348

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Tue 4/14

9:55 am-4:36 pm

1 stop6h 41m

Chicago Midway

Fri 4/24

6:30 am-1:59 pm

1 stop7h 29m

$351

Flights are sorted by cheapest round-trip flights first.

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See travel insights to Chicago from

How to get the cheapest flight ticket from Cancún to Chicago Midway Airport

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 day to depart on your flight to Chicago Midway Airport?

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Cancún. The lowest ticket price found for a Thursday departure recently was $358. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Tuesday is the most expensive day to depart from Cancún because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $552.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Cancún at noon is the least expensive time of day to depart. momondo users have found prices as low as $358 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $538. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Cancun to Chicago Midway flight route?

Fly from Cancun to Chicago Midway for the best Cancun - Chicago Midway flight prices

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

There is only 1 cabin class available to choose from on Cancun to Chicago Midway 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 Cancún to Chicago Midway Airport flights?

You could potentially save up to 12% on your flight if you consider stops on a Cancún to Chicago Midway Airport flight.

How have Cancún to Chicago Midway Airport flight prices changed over time?

As of January 2026, prices for Cancún to Chicago Midway Airport flights are approximately 54% more expensive when compared to flights at the same time last year.

When to book flights from Cancún to Chicago Midway Airport

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

Cheap Cancún to Chicago Midway Airport (CUN to MDW) flight deals and tips

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

Best Price Found

$328

Fastest flight time

3h 40m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Cancún in the past 72 hours is $328. The best round-trip flight deal from Cancún to Chicago Midway Airport found on momondo in the last 72 hours is $358.
The fastest flight from Cancún to Chicago Midway Airport takes 3h 40m
Direct flights go from Cancún to Chicago Midway Airport every day.
Search flight deals

  • How far is Cancun to Chicago Midway by plane?

    Chicago Midway is 1425.4 mi away from Cancun. Flights usually cover this in 3h 40m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Cancun Airport to Chicago Midway Airport refresh daily.

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Cancun Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway 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 Cancún to Chicago Midway Airport?

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Cancún to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

momondo does allow users to show only those flights to Chicago from Cancún which offer a flexible booking policy as well as other useful filters and features.

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

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

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

Yes. momondo can track prices for Cancún to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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