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Cheap flights from Cancún to Chicago Midway Airport from $137

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 Midway Airport departing on 5/8. 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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0 bags
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Find the cheapest flights from Cancún to Chicago

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Cancún to Chicago.
3:11 pm - 10:22 pmCUN-MDW
7h 11m1 stop
6:04 am - 2:01 pmMDW-CUN
7h 57m1 stop
$267Aeromexico
Find Deal
Thu, May 1 - Mon, May 5
3:11 pm - 10:22 pmCUN-MDW
7h 11m1 stop
6:04 am - 12:50 pmMDW-CUN
6h 46m1 stop
$275Delta
Find Deal
Thu, May 1 - Tue, May 6
10:00 am - 9:45 pmCUN-MDW
11h 45m1 stop
9:35 am - 1:10 pmMDW-CUN
3h 35mnonstop
$372Southwest
Find Deal
Sat, Apr 19 - Mon, Apr 28
1:31 pm - 10:05 amCUN-MDW
20h 34m1 stop
6:30 pm - 12:16 pmMDW-CUN
17h 46m1 stop
$384Frontier
Find Deal
Thu, Apr 24 - Thu, May 1
2:05 pm - 11:21 pmCUN-MDW
9h 16m1 stop
9:12 pm - 8:05 amMDW-CUN
10h 53m1 stop
$390Frontier
Find Deal
Thu, May 29 - Fri, May 30
9:20 am - 8:17 pmCUN-MDW
10h 57m1 stop
12:48 pm - 8:20 pmMDW-CUN
7h 32m1 stop
Sat, May 31 - Fri, Jun 6
10:00 am - 6:50 pmCUN-MDW
8h 50m1 stop
5:35 am - 12:50 pmMDW-CUN
7h 15m1 stop
$449Southwest
Find Deal
Sat, Apr 19 - Mon, Apr 28
9:49 am - 8:41 pmCUN-MDW
10h 52m1 stop
9:59 pm - 11:47 amMDW-CUN
13h 48m1 stop
$589Volaris
Find Deal
Sat, May 31 - Wed, Jun 4
10:07 am - 8:44 pmCUN-MDW
10h 37m1 stop
10:41 pm - 1:02 pmMDW-CUN
14h 21m1 stop
$614Volaris
Find Deal
Sun, Sep 14 - Wed, Sep 17
8:00 am - 7:06 pmCUN-MDW
11h 06m1 stop
9:59 pm - 11:55 amMDW-CUN
13h 56m2 stops
Fri, Apr 25 - Fri, Apr 25

Frontier flights from Cancún to Chicago Midway Airport

Our best Frontier deals on Cancún to Chicago Midway Airport flight tickets
Frontier
Apr 24
CUN1:31 pmCancun
20h 34m
1 stop
MDW10:05 amChicago Midway
May 1
MDW6:30 pmChicago Midway
17h 46m
1 stop
CUN12:16 pmCancun
Frontier
Apr 4
CUN10:50 amCancun
11h 42m
1 stop
MDW10:32 pmChicago Midway
Apr 8
MDW2:36 pmChicago Midway
18h 49m
1 stop
CUN9:25 amCancun
Frontier
May 29
CUN2:05 pmCancun
9h 16m
1 stop
MDW11:21 pmChicago Midway
May 30
MDW9:12 pmChicago Midway
10h 53m
1 stop
CUN8:05 amCancun

Southwest flights from Cancún to Chicago Midway Airport

Our best Southwest deals on Cancún to Chicago Midway Airport flight tickets
Southwest
Apr 19
CUN10:00 amCancun
11h 45m
1 stop
MDW9:45 pmChicago Midway
Apr 28
MDW9:35 amChicago Midway
3h 35m
CUN1:10 pmCancun
Southwest
Apr 4
CUN8:10 amCancun
6h 45m
1 stop
MDW2:55 pmChicago Midway
Apr 7
MDW4:30 pmChicago Midway
3h 55m
CUN8:25 pmCancun
Southwest
Apr 19
CUN10:00 amCancun
8h 50m
1 stop
MDW6:50 pmChicago Midway
Apr 28
MDW5:35 amChicago Midway
7h 15m
1 stop
CUN12:50 pmCancun

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 $443. 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, Thursday 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 $443.

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 $443 when looking at flights departing in the morning. Try not to purchase tickets in the morning because they tend to be around $443. 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.

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

As of March 2025, prices for Cancún to Chicago Midway Airport flights are approximately 60% cheaper 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

$137

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 $137. The best round-trip flight deal from Cancún to Chicago Midway Airport found on momondo in the last 72 hours is $267.
The fastest flight from Cancún to Chicago Midway Airport takes 3h 35m
Direct flights go from Cancún to Chicago Midway Airport every day.

  • 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Crown Point
Munster
Monticello
Chesterton
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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