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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 2/28. 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
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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
11:00 am - 5:45 pm
CUN
-
MDW
7h 45m
1 stop
Delta Logo
10:45 am - 8:20 pm
MDW
-
CUN
9h 35m
1 stop
$277Delta
Thu, Mar 5 - Mon, Mar 9
Aeromexico Logo
8:00 am - 4:29 pm
CUN
-
MDW
8h 29m
1 stop
Aeromexico Logo
10:43 am - 8:14 pm
MDW
-
CUN
9h 31m
1 stop
$278Aeromexico
Thu, Apr 16 - Tue, Apr 21
Southwest Logo
2:55 pm - 5:40 pm
CUN
-
MDW
3h 45mnonstop
Southwest Logo
4:05 pm - 7:45 pm
MDW
-
CUN
3h 40mnonstop
$297Southwest
Thu, Mar 5 - Mon, Mar 9
Frontier Logo
11:48 am - 9:12 pm
CUN
-
MDW
10h 24m
1 stop
Frontier Logo
6:00 am - 1:37 pm
MDW
-
CUN
6h 37m
1 stop
$309Frontier
Thu, Feb 19 - Mon, Feb 23
Frontier Logo
11:48 am - 9:12 pm
CUN
-
MDW
10h 24m
1 stop
Frontier Logo
6:00 am - 1:37 pm
MDW
-
CUN
6h 37m
1 stop
$311Frontier
Thu, Feb 19 - Mon, Feb 23
Frontier Logo
9:01 am - 10:19 pm
CUN
-
MDW
13h 18m
1 stop
Frontier Logo
6:00 am - 2:59 pm
MDW
-
CUN
8h 59m
1 stop
$321Frontier
Fri, Mar 27 - Mon, Mar 30
Frontier Logo
12:15 pm - 8:53 pm
CUN
-
MDW
8h 38m
1 stop
Frontier Logo
6:05 am - 2:59 pm
MDW
-
CUN
8h 54m
1 stop
$328Frontier
Mon, Mar 9 - Thu, Mar 12
Frontier Logo
1:25 pm - 8:53 pm
CUN
-
MDW
8h 28m
1 stop
Frontier Logo
6:15 am - 2:33 pm
MDW
-
CUN
8h 18m
1 stop
$331Frontier
Fri, Mar 6 - Mon, Mar 9
Southwest Logo
2:55 pm - 5:40 pm
CUN
-
MDW
3h 45mnonstop
Southwest Logo
8:05 am - 11:50 am
MDW
-
CUN
3h 45mnonstop
$333Southwest
Thu, Mar 5 - Wed, Mar 11
Frontier Logo
10:01 am - 7:59 pm
CUN
-
MDW
10h 58m
1 stop
Frontier Logo
9:05 am - 4:32 pm
MDW
-
CUN
6h 27m
1 stop
$335Frontier
Sun, Feb 15 - Thu, Feb 19

Frontier flights from Cancún to Chicago Midway Airport

Our best Frontier deals on Cancún to Chicago Midway Airport flight tickets
Frontier
Feb 19
CUN11:48 amCancun
10h 24m
1 stop
MDW9:12 pmChicago Midway
Feb 23
MDW6:00 amChicago Midway
6h 37m
1 stop
CUN1:37 pmCancun
$309
Frontier
Feb 19
CUN11:48 amCancun
10h 24m
1 stop
MDW9:12 pmChicago Midway
Feb 23
MDW6:00 amChicago Midway
6h 37m
1 stop
CUN1:37 pmCancun
$311
Frontier
Mar 27
CUN9:01 amCancun
13h 18m
1 stop
MDW10:19 pmChicago Midway
Mar 30
MDW6:00 amChicago Midway
8h 59m
1 stop
CUN2:59 pmCancun
$321

Delta flights from Cancún to Chicago Midway Airport

Our best Delta deals on Cancún to Chicago Midway Airport flight tickets
Delta
Feb 6
CUN12:15 pmCancun
6h 14m
1 stop
MDW5:29 pmChicago Midway
Feb 9
MDW10:46 amChicago Midway
9h 25m
1 stop
CUN9:11 pmCancun
$277
Delta
Feb 6
CUN12:15 pmCancun
6h 14m
1 stop
MDW5:29 pmChicago Midway
Feb 10
MDW12:46 pmChicago Midway
7h 25m
1 stop
CUN9:11 pmCancun
$278
Delta
Feb 18
CUN8:00 amCancun
10h 45m
1 stop
MDW5:45 pmChicago Midway
Feb 22
MDW6:00 amChicago Midway
8h 35m
1 stop
CUN3:35 pmCancun
$348

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 February 3, 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

Thu 3/5

11:00 am-5:45 pm

1 stop7h 45m

Chicago Midway

Mon 3/9

10:45 am-8:20 pm

1 stop9h 35m

$277

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 4/16

8:00 am-4:29 pm

1 stop8h 29m

Chicago Midway

Tue 4/21

10:43 am-8:14 pm

1 stop9h 31m

$278

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 3/5

2:55 pm-5:40 pm

Nonstop3h 45m

Chicago Midway

Mon 3/9

4:05 pm-7:45 pm

Nonstop3h 40m

$297

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 2/19

11:48 am-9:12 pm

1 stop10h 24m

Chicago Midway

Mon 2/23

6:00 am-1:37 pm

1 stop6h 37m

$309

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 2/19

11:48 am-9:12 pm

1 stop10h 24m

Chicago Midway

Mon 2/23

6:00 am-1:37 pm

1 stop6h 37m

$311

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 3/27

9:01 am-10:19 pm

1 stop13h 18m

Chicago Midway

Mon 3/30

6:00 am-2:59 pm

1 stop8h 59m

$321

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Mon 3/9

12:15 pm-8:53 pm

1 stop8h 38m

Chicago Midway

Thu 3/12

6:05 am-2:59 pm

1 stop8h 54m

$328

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 3/6

1:25 pm-8:53 pm

1 stop8h 28m

Chicago Midway

Mon 3/9

6:15 am-2:33 pm

1 stop8h 18m

$331

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 3/5

2:55 pm-5:40 pm

Nonstop3h 45m

Chicago Midway

Wed 3/11

8:05 am-11:50 am

Nonstop3h 45m

$333

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sun 2/15

10:01 am-7:59 pm

1 stop10h 58m

Chicago Midway

Thu 2/19

9:05 am-4:32 pm

1 stop6h 27m

$335

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.

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

As of February 2026, prices for Cancún to Chicago Midway Airport flights are approximately 58% 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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