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Cheap flights from Cancún to Chicago from $144

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 1/22. 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
8:00 am - 5:55 pm
CUN
-
MDW
10h 55m2 stops
Delta Logo
9:32 am - 9:11 pm
MDW
-
CUN
10h 39m2 stops
$278Delta
Wed, Jan 28 - Wed, Feb 4
Delta Logo
11:05 am - 10:07 pm
CUN
-
MDW
12h 02m1 stop
Delta Logo
9:32 am - 9:11 pm
MDW
-
CUN
10h 39m2 stops
$279Delta
Thu, Jan 15 - Sun, Jan 18
Frontier Logo
3:14 pm - 10:17 pm
CUN
-
MDW
8h 03m1 stop
Frontier Logo
6:10 am - 2:04 pm
MDW
-
CUN
6h 54m1 stop
$301Frontier
Thu, Jan 8 - Mon, Jan 12
Frontier Logo
3:14 pm - 10:17 pm
CUN
-
MDW
8h 03m1 stop
Frontier Logo
4:31 pm - 12:38 pm
MDW
-
CUN
19h 07m2 stops
$308Frontier
Thu, Jan 8 - Mon, Jan 12
Delta Logo
8:15 am - 10:29 pm
CUN
-
MDW
14h 14m1 stop
Delta Logo
6:30 am - 1:59 pm
MDW
-
CUN
7h 29m1 stop
$320Delta
Thu, Apr 30 - Mon, May 4
Frontier Logo
3:14 pm - 10:17 pm
CUN
-
MDW
8h 03m1 stop
Frontier Logo
11:27 am - 10:32 am
MDW
-
CUN
22h 05m2 stops
$327Frontier
Thu, Jan 8 - Thu, Jan 15
Delta Logo
12:05 pm - 10:07 pm
CUN
-
MDW
11h 02m2 stops
Delta Logo
12:48 pm - 9:11 pm
MDW
-
CUN
7h 23m1 stop
$330Delta
Fri, Jan 16 - Mon, Jan 19
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
$331Delta
Wed, Feb 11 - Sun, Feb 15
Frontier Logo
2:57 pm - 10:19 pm
CUN
-
MDW
8h 22m1 stop
Frontier Logo
6:20 am - 1:47 pm
MDW
-
CUN
6h 27m1 stop
$332Frontier
Thu, Jan 29 - Thu, Feb 5
Frontier Logo
3:14 pm - 10:17 pm
CUN
-
MDW
8h 03m1 stop
Frontier Logo
6:10 am - 2:04 pm
MDW
-
CUN
6h 54m1 stop
$337Frontier
Thu, Jan 8 - Mon, Jan 12

Delta flights from Cancún to Chicago Midway Airport

Our best Delta deals on Cancún to Chicago Midway Airport flight tickets
Delta
Jan 28
CUN12:15 pmCancun
6h 14m
1 stop
MDW5:29 pmChicago Midway
Feb 4
MDW12:46 pmChicago Midway
7h 25m
1 stop
CUN9:11 pmCancun
$278
Find similar
Delta
Jan 15
CUN8:00 amCancun
10h 34m
2 stops
MDW5:34 pmChicago Midway
Jan 18
MDW9:32 amChicago Midway
10h 39m
2 stops
CUN9:11 pmCancun
$279
Find similar
Delta
Apr 30
CUN8:15 amCancun
14h 14m
1 stop
MDW10:29 pmChicago Midway
May 4
MDW6:30 amChicago Midway
7h 29m
1 stop
CUN1:59 pmCancun
$320
Find similar

Aeromexico flights from Cancún to Chicago Midway Airport

Our best Aeromexico deals on Cancún to Chicago Midway Airport flight tickets
Aeromexico
Dec 29
CUN12:25 pmCancun
10h 57m
1 stop
MDW10:22 pmChicago Midway
Jan 3
MDW9:50 amChicago Midway
5h 40m
1 stop
CUN4:30 pmCancun
$279
Find similar
Aeromexico
Feb 6
CUN1:40 pmCancun
9h 42m
1 stop
MDW10:22 pmChicago Midway
Feb 9
MDW10:46 amChicago Midway
9h 25m
1 stop
CUN9:11 pmCancun
$455
Find similar
Aeromexico
Feb 6
CUN5:45 pmCancun
29h 37m
2 stops
MDW10:22 pmChicago Midway
Feb 9
MDW6:00 amChicago Midway
15h 28m
2 stops
CUN10:28 pmCancun
$486
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 December 27, 2025.
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

8:00 am-5:55 pm

2 stops10h 55m

Chicago Midway

Wed 2/4

9:32 am-9:11 pm

2 stops10h 39m

$278

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/15

11:05 am-10:07 pm

1 stop12h 02m

Chicago Midway

Sun 1/18

9:32 am-9:11 pm

2 stops10h 39m

$279

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/8

3:14 pm-10:17 pm

1 stop8h 03m

Chicago Midway

Mon 1/12

6:10 am-2:04 pm

1 stop6h 54m

$301

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/8

3:14 pm-10:17 pm

1 stop8h 03m

Chicago Midway

Mon 1/12

4:31 pm-12:38 pm

2 stops19h 07m

$308

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 4/30

8:15 am-10:29 pm

1 stop14h 14m

Chicago Midway

Mon 5/4

6:30 am-1:59 pm

1 stop7h 29m

$320

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/8

3:14 pm-10:17 pm

1 stop8h 03m

Chicago Midway

Thu 1/15

11:27 am-10:32 am

2 stops22h 05m

$327

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 1/16

12:05 pm-10:07 pm

2 stops11h 02m

Chicago Midway

Mon 1/19

12:48 pm-9:11 pm

1 stop7h 23m

$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

$331

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/29

2:57 pm-10:19 pm

1 stop8h 22m

Chicago Midway

Thu 2/5

6:20 am-1:47 pm

1 stop6h 27m

$332

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/8

3:14 pm-10:17 pm

1 stop8h 03m

Chicago Midway

Mon 1/12

6:10 am-2:04 pm

1 stop6h 54m

$337

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 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?

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

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

As of December 2025, prices for Cancún to Chicago Midway Airport flights are approximately 59% 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

$190

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 $190. 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
Valparaiso
Schererville
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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