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Cheap flights from Cancún to Chicago from $149

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

Southwest Logo
3:20 pm - 6:55 pmCUN-MDW
3h 35mnonstop
Southwest Logo
9:40 am - 1:15 pmMDW-CUN
3h 35mnonstop
$273Southwest
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Thu, Oct 16 - Mon, Oct 20
Delta Logo
8:10 am - 10:14 pmCUN-MDW
14h 04m2 stops
Delta Logo
11:10 am - 9:20 pmMDW-CUN
9h 10m2 stops
$276Delta
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Wed, Oct 22 - Sat, Nov 8
Delta Logo
8:00 am - 6:35 pmCUN-MDW
10h 35m2 stops
Delta Logo
6:00 am - 12:50 pmMDW-CUN
6h 50m1 stop
$286Delta
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Thu, Sep 25 - Tue, Sep 30
Frontier Logo
1:41 pm - 11:09 pmCUN-MDW
9h 28m1 stop
Frontier Logo
6:10 am - 12:26 pmMDW-CUN
6h 16m1 stop
$296Frontier
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Sat, Oct 18 - Sat, Oct 25
Frontier Logo
1:55 pm - 11:20 pmCUN-MDW
9h 25m1 stop
Frontier Logo
6:15 am - 12:40 pmMDW-CUN
6h 25m1 stop
$305Frontier
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Sun, Sep 21 - Sat, Sep 27
Southwest Logo
3:20 pm - 6:55 pmCUN-MDW
3h 35mnonstop
Southwest Logo
5:00 am - 12:40 pmMDW-CUN
7h 40m1 stop
$309Southwest
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Thu, Oct 16 - Mon, Oct 20
Frontier Logo
1:55 pm - 11:17 pmCUN-MDW
9h 22m1 stop
Frontier Logo
6:15 am - 12:40 pmMDW-CUN
6h 25m1 stop
$315Frontier
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Sat, Sep 13 - Sat, Sep 20
Frontier Logo
1:49 pm - 11:17 pmCUN-MDW
9h 28m1 stop
Frontier Logo
6:15 am - 12:24 pmMDW-CUN
6h 09m1 stop
$316Frontier
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Thu, Aug 14 - Thu, Aug 21
Aeromexico Logo
3:10 pm - 9:26 pmCUN-MDW
6h 16m1 stop
Aeromexico Logo
6:00 am - 11:30 amMDW-CUN
5h 30m1 stop
$340Aeromexico
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Fri, Sep 5 - Sun, Sep 7
Aeromexico Logo
2:00 pm - 9:26 pmCUN-MDW
7h 26m1 stop
Aeromexico Logo
12:43 pm - 8:15 pmMDW-CUN
7h 32m1 stop
$371Aeromexico
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Wed, Sep 10 - Thu, Sep 11

Southwest flights from Cancún to Chicago Midway Airport

Our best Southwest deals on Cancún to Chicago Midway Airport flight tickets
Southwest
Oct 16
CUN3:20 pmCancun
3h 35m
MDW6:55 pmChicago Midway
Oct 20
MDW9:40 amChicago Midway
3h 35m
CUN1:15 pmCancun
$273
Find similar
Southwest
Oct 16
CUN3:20 pmCancun
3h 35m
MDW6:55 pmChicago Midway
Oct 20
MDW5:00 amChicago Midway
7h 40m
1 stop
CUN12:40 pmCancun
$309
Find similar
Southwest
Aug 27
CUN12:50 pmCancun
6h 20m
1 stop
MDW7:10 pmChicago Midway
Sep 3
MDW9:55 amChicago Midway
3h 35m
CUN1:30 pmCancun
$320
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Delta flights from Cancún to Chicago Midway Airport

Our best Delta deals on Cancún to Chicago Midway Airport flight tickets
Delta
Oct 22
CUN8:10 amCancun
14h 04m
2 stops
MDW10:14 pmChicago Midway
Nov 8
MDW11:10 amChicago Midway
9h 10m
2 stops
CUN9:20 pmCancun
$276
Find similar
Delta
Sep 25
CUN8:00 amCancun
10h 35m
2 stops
MDW6:35 pmChicago Midway
Sep 30
MDW6:00 amChicago Midway
6h 50m
1 stop
CUN12:50 pmCancun
$286
Find similar
Delta
Sep 19
CUN8:00 amCancun
9h 35m
1 stop
MDW5:35 pmChicago Midway
Sep 26
MDW10:35 amChicago Midway
9h 40m
1 stop
CUN8:15 pmCancun
$317
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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 July 31, 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

Thu 10/16

3:20 pm-6:55 pm

Nonstop3h 35m

Chicago Midway

Mon 10/20

9:40 am-1:15 pm

Nonstop3h 35m

$273

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 10/22

8:10 am-10:14 pm

2 stops14h 04m

Chicago Midway

Sat 11/8

11:10 am-9:20 pm

2 stops9h 10m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 9/25

8:00 am-6:35 pm

2 stops10h 35m

Chicago Midway

Tue 9/30

6:00 am-12:50 pm

1 stop6h 50m

$286

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 10/18

1:41 pm-11:09 pm

1 stop9h 28m

Chicago Midway

Sat 10/25

6:10 am-12:26 pm

1 stop6h 16m

$296

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sun 9/21

1:55 pm-11:20 pm

1 stop9h 25m

Chicago Midway

Sat 9/27

6:15 am-12:40 pm

1 stop6h 25m

$305

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 10/16

3:20 pm-6:55 pm

Nonstop3h 35m

Chicago Midway

Mon 10/20

5:00 am-12:40 pm

1 stop7h 40m

$309

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 9/13

1:55 pm-11:17 pm

1 stop9h 22m

Chicago Midway

Sat 9/20

6:15 am-12:40 pm

1 stop6h 25m

$315

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 8/14

1:49 pm-11:17 pm

1 stop9h 28m

Chicago Midway

Thu 8/21

6:15 am-12:24 pm

1 stop6h 09m

$316

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 9/5

3:10 pm-9:26 pm

1 stop6h 16m

Chicago Midway

Sun 9/7

6:00 am-11:30 am

1 stop5h 30m

$340

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 9/10

2:00 pm-9:26 pm

1 stop7h 26m

Chicago Midway

Thu 9/11

12:43 pm-8:15 pm

1 stop7h 32m

$371

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 $337. 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, Wednesday 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 $461.

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 afternoon is the least expensive time of day to depart. momondo users have found prices as low as $321 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $451. 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 are 1 cabin classes 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 76% 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 July 2025, prices for Cancún to Chicago Midway Airport flights are approximately 28% 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

$149

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 $149. The best round-trip flight deal from Cancún to Chicago Midway Airport found on momondo in the last 72 hours is $273.
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
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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