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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 10/31. 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

Frontier Logo
11:16 am - 11:20 pmCUN-MDW
12h 04m1 stop
Frontier Logo
6:20 am - 12:19 pmMDW-CUN
5h 59m1 stop
$270Frontier
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Fri, Oct 24 - Fri, Oct 31
Southwest Logo
2:30 pm - 5:15 pmCUN-MDW
3h 45mnonstop
Southwest Logo
5:55 am - 10:40 amMDW-CUN
3h 45mnonstop
$275Southwest
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Fri, Dec 26 - Sat, Jan 3
Delta Logo
8:00 am - 4:36 pmCUN-MDW
9h 36m1 stop
Delta Logo
9:34 am - 9:20 pmMDW-CUN
10h 46m2 stops
$276Delta
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Fri, Dec 5 - Tue, Dec 9
Frontier Logo
11:16 am - 11:20 pmCUN-MDW
12h 04m1 stop
Frontier Logo
6:20 am - 12:19 pmMDW-CUN
5h 59m1 stop
$284Frontier
Find Deal
Fri, Oct 24 - Fri, Oct 31
Southwest Logo
4:00 pm - 11:30 pmCUN-MDW
8h 30m1 stop
Southwest Logo
8:40 am - 1:25 pmMDW-CUN
3h 45mnonstop
$298Southwest
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Thu, Nov 13 - Tue, Nov 18
Frontier Logo
1:30 pm - 9:45 pmCUN-MDW
8h 15m1 stop
Frontier Logo
8:55 am - 10:42 amMDW-CUN
24h 47m1 stop
$323Frontier
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Fri, Oct 31 - Fri, Nov 7
Southwest Logo
12:55 pm - 7:40 pmCUN-MDW
7h 45m1 stop
Southwest Logo
5:55 am - 10:40 amMDW-CUN
3h 45mnonstop
$326Southwest
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Fri, Dec 26 - Sat, Jan 3
Delta Logo
5:30 pm - 12:35 pmCUN-MDW
20h 05m2 stops
Delta Logo
5:59 pm - 10:00 amMDW-CUN
15h 01m2 stops
$330Delta
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Fri, Feb 13 - Tue, Feb 17
Aeromexico Logo
6:00 am - 4:38 pmCUN-MDW
11h 38m2 stops
Aeromexico Logo
6:00 am - 9:20 pmMDW-CUN
14h 20m1 stop
$549Aeromexico
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Thu, Nov 20 - Sat, Nov 22
Aeromexico Logo
8:00 am - 4:09 pmCUN-MDW
8h 09m1 stop
Aeromexico Logo
10:35 am - 8:20 pmMDW-CUN
9h 45m1 stop
$597Aeromexico
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Wed, Oct 8 - Mon, Oct 13

Delta flights from Cancún to Chicago Midway Airport

Our best Delta deals on Cancún to Chicago Midway Airport flight tickets
Delta
Dec 5
CUN8:00 amCancun
9h 36m
1 stop
MDW4:36 pmChicago Midway
Dec 9
MDW9:34 amChicago Midway
10h 46m
2 stops
CUN9:20 pmCancun
$276
Find similar
Delta
Feb 13
CUN5:30 pmCancun
20h 05m
2 stops
MDW12:35 pmChicago Midway
Feb 17
MDW5:59 pmChicago Midway
15h 01m
2 stops
CUN10:00 amCancun
$330
Find similar
Delta
Feb 13
CUN1:40 pmCancun
9h 06m
1 stop
MDW9:46 pmChicago Midway
Feb 17
MDW1:05 pmChicago Midway
7h 05m
1 stop
CUN9:10 pmCancun
$331
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Aeromexico flights from Cancún to Chicago Midway Airport

Our best Aeromexico deals on Cancún to Chicago Midway Airport flight tickets
Aeromexico
Nov 20
CUN6:00 amCancun
11h 38m
2 stops
MDW4:38 pmChicago Midway
Nov 22
MDW6:00 amChicago Midway
14h 20m
1 stop
CUN9:20 pmCancun
$549
Find similar
Aeromexico
Oct 8
CUN8:00 amCancun
8h 09m
1 stop
MDW4:09 pmChicago Midway
Oct 13
MDW10:35 amChicago Midway
9h 45m
1 stop
CUN8:20 pmCancun
$597
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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 September 16, 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

Fri 10/24

11:16 am-11:20 pm

1 stop12h 04m

Chicago Midway

Fri 10/31

6:20 am-12:19 pm

1 stop5h 59m

$270

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 12/26

2:30 pm-5:15 pm

Nonstop3h 45m

Chicago Midway

Sat 1/3

5:55 am-10:40 am

Nonstop3h 45m

$275

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 12/5

8:00 am-4:36 pm

1 stop9h 36m

Chicago Midway

Tue 12/9

9:34 am-9:20 pm

2 stops10h 46m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 10/24

11:16 am-11:20 pm

1 stop12h 04m

Chicago Midway

Fri 10/31

6:20 am-12:19 pm

1 stop5h 59m

$284

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 11/13

4:00 pm-11:30 pm

1 stop8h 30m

Chicago Midway

Tue 11/18

8:40 am-1:25 pm

Nonstop3h 45m

$298

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 10/31

1:30 pm-9:45 pm

1 stop8h 15m

Chicago Midway

Fri 11/7

8:55 am-10:42 am

1 stop24h 47m

$323

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 12/26

12:55 pm-7:40 pm

1 stop7h 45m

Chicago Midway

Sat 1/3

5:55 am-10:40 am

Nonstop3h 45m

$326

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 2/13

5:30 pm-12:35 pm

2 stops20h 05m

Chicago Midway

Tue 2/17

5:59 pm-10:00 am

2 stops15h 01m

$330

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 11/20

6:00 am-4:38 pm

2 stops11h 38m

Chicago Midway

Sat 11/22

6:00 am-9:20 pm

1 stop14h 20m

$549

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 10/8

8:00 am-4:09 pm

1 stop8h 09m

Chicago Midway

Mon 10/13

10:35 am-8:20 pm

1 stop9h 45m

$597

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, Tuesday is the cheapest day to fly to Chicago Midway Airport from Cancún. The lowest ticket price found for a Tuesday departure recently was $406. 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, Monday 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 $539.

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

Flying to Chicago Midway Airport from Cancún in the morning is the least expensive time of day to depart. momondo users have found prices as low as $461 when looking at flights departing in the morning. 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 September 2025, prices for Cancún to Chicago Midway Airport flights are approximately 98% 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

$313

Fastest flight time

3h 35m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Cancún in the past 72 hours is $313. The best round-trip flight deal from Cancún to Chicago Midway Airport found on momondo in the last 72 hours is $445.
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
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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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