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Cheap flights from Cancún to Chicago from $146

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 2/27. 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 14m
1 stop
Delta Logo
9:33 am - 9:11 pm
MDW
-
CUN
10h 38m
2 stops
$281Delta
Fri, Jan 30 - Mon, Feb 2
Volaris Logo
10:39 am - 6:34 pm
CUN
-
MDW
7h 55m
1 stop
Volaris Logo
7:54 pm - 9:48 am
MDW
-
CUN
13h 54m
1 stop
$319Volaris
Fri, Mar 20 - Sat, Mar 21
Multiple Airlines Logo
9:01 am - 10:19 pm
CUN
-
MDW
13h 18m
1 stop
Multiple Airlines Logo
7:54 pm - 9:48 am
MDW
-
CUN
13h 54m
1 stop
$320Multiple Airlines
Thu, Mar 12 - Tue, Mar 17
Frontier Logo
1:31 pm - 10:19 pm
CUN
-
MDW
8h 48m
1 stop
Frontier Logo
6:00 am - 2:56 pm
MDW
-
CUN
8h 56m
1 stop
$323Frontier
Tue, Apr 7 - Sun, Apr 12
Frontier Logo
2:49 pm - 10:29 pm
CUN
-
MDW
8h 40m
1 stop
Frontier Logo
6:00 am - 2:59 pm
MDW
-
CUN
8h 59m
1 stop
$331Frontier
Thu, Mar 5 - Thu, Mar 12
Southwest Logo
9:30 am - 12:10 pm
CUN
-
MDW
3h 40mnonstop
Southwest Logo
4:05 pm - 7:45 pm
MDW
-
CUN
3h 40mnonstop
$332Southwest
Fri, Mar 6 - Mon, Mar 9
Southwest Logo
11:25 am - 8:55 pm
CUN
-
MDW
10h 30m
2 stops
Southwest Logo
10:35 am - 3:15 pm
MDW
-
CUN
3h 40mnonstop
$335Southwest
Thu, Feb 12 - Tue, Feb 17
Delta Logo
12:05 pm - 10:31 pm
CUN
-
MDW
11h 26m
2 stops
Delta Logo
12:45 pm - 9:11 pm
MDW
-
CUN
7h 26m
1 stop
$337Delta
Wed, Feb 18 - Wed, Feb 25
Frontier Logo
2:49 pm - 10:29 pm
CUN
-
MDW
8h 40m
1 stop
Frontier Logo
6:00 am - 2:59 pm
MDW
-
CUN
8h 59m
1 stop
$338Frontier
Thu, Mar 5 - Thu, Mar 12
Southwest Logo
11:25 am - 8:55 pm
CUN
-
MDW
10h 30m
2 stops
Southwest Logo
5:55 am - 4:00 pm
MDW
-
CUN
9h 05m
1 stop
$339Southwest
Thu, Feb 12 - Tue, Feb 17

Delta flights from Cancún to Chicago Midway Airport

Our best Delta deals on Cancún to Chicago Midway Airport flight tickets
Delta
Jan 30
CUN4:40 pmCancun
6h 42m
1 stop
MDW10:22 pmChicago Midway
Feb 2
MDW9:33 amChicago Midway
10h 38m
2 stops
CUN9:11 pmCancun
$281
Delta
Feb 18
CUN12:05 pmCancun
11h 26m
2 stops
MDW10:31 pmChicago Midway
Feb 25
MDW12:45 pmChicago Midway
7h 26m
1 stop
CUN9:11 pmCancun
$337
Delta
Apr 30
CUN9:55 amCancun
12h 34m
1 stop
MDW10:29 pmChicago Midway
May 5
MDW6:30 amChicago Midway
6h 15m
1 stop
CUN12:45 pmCancun
$341

Southwest flights from Cancún to Chicago Midway Airport

Our best Southwest deals on Cancún to Chicago Midway Airport flight tickets
Southwest
Mar 6
CUN9:30 amCancun
3h 40m
MDW12:10 pmChicago Midway
Mar 9
MDW4:05 pmChicago Midway
3h 40m
CUN7:45 pmCancun
$332
Southwest
Feb 12
CUN5:25 pmCancun
7h 55m
1 stop
MDW12:20 amChicago Midway
Feb 17
MDW10:35 amChicago Midway
3h 40m
CUN3:15 pmCancun
$335
Southwest
Feb 12
CUN11:25 amCancun
10h 30m
2 stops
MDW8:55 pmChicago Midway
Feb 17
MDW5:55 amChicago Midway
9h 05m
1 stop
CUN4:00 pmCancun
$339

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 20, 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

Fri 1/30

12:15 pm-5:29 pm

1 stop6h 14m

Chicago Midway

Mon 2/2

9:33 am-9:11 pm

2 stops10h 38m

$281

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 3/20

10:39 am-6:34 pm

1 stop7h 55m

Chicago Midway

Sat 3/21

7:54 pm-9:48 am

1 stop13h 54m

$319

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 3/12

9:01 am-10:19 pm

1 stop13h 18m

Chicago Midway

Tue 3/17

7:54 pm-9:48 am

1 stop13h 54m

$320

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Tue 4/7

1:31 pm-10:19 pm

1 stop8h 48m

Chicago Midway

Sun 4/12

6:00 am-2:56 pm

1 stop8h 56m

$323

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 3/5

2:49 pm-10:29 pm

1 stop8h 40m

Chicago Midway

Thu 3/12

6:00 am-2:59 pm

1 stop8h 59m

$331

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 3/6

9:30 am-12:10 pm

Nonstop3h 40m

Chicago Midway

Mon 3/9

4:05 pm-7:45 pm

Nonstop3h 40m

$332

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 2/12

11:25 am-8:55 pm

2 stops10h 30m

Chicago Midway

Tue 2/17

10:35 am-3:15 pm

Nonstop3h 40m

$335

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 2/18

12:05 pm-10:31 pm

2 stops11h 26m

Chicago Midway

Wed 2/25

12:45 pm-9:11 pm

1 stop7h 26m

$337

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 3/5

2:49 pm-10:29 pm

1 stop8h 40m

Chicago Midway

Thu 3/12

6:00 am-2:59 pm

1 stop8h 59m

$338

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 2/12

11:25 am-8:55 pm

2 stops10h 30m

Chicago Midway

Tue 2/17

5:55 am-4:00 pm

1 stop9h 05m

$339

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 January 2026, prices for Cancún to Chicago Midway Airport flights are approximately 77% 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

Fastest flight time

3h 35m

Direct flights

Every day
The fastest flight from Cancún to Chicago Midway Airport takes 3h 35m
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 35m, 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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