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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 8/27. 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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Cheap round-trip flights

Delta Logo
8:07 am - 9:44 pmCUN-MDW
13h 37m2 stops
Delta Logo
10:31 am - 8:20 pmMDW-CUN
9h 49m1 stop
$276Delta
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Wed, Aug 13 - Wed, Aug 20
Southwest Logo
3:10 pm - 6:50 pmCUN-MDW
3h 40mnonstop
Southwest Logo
9:55 am - 1:30 pmMDW-CUN
3h 35mnonstop
$284Southwest
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Fri, Sep 19 - Mon, Sep 22
Delta Logo
8:00 am - 9:36 pmCUN-MDW
13h 36m1 stop
Delta Logo
6:00 am - 12:50 pmMDW-CUN
6h 50m1 stop
$302Delta
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Sun, Sep 21 - Sun, Sep 28
Southwest Logo
2:15 pm - 5:00 pmCUN-MDW
3h 45mnonstop
Southwest Logo
11:25 am - 7:45 pmMDW-CUN
7h 20m1 stop
$309Southwest
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Thu, Nov 13 - Mon, Nov 17
Southwest Logo
3:10 pm - 6:50 pmCUN-MDW
3h 40mnonstop
Southwest Logo
6:30 am - 12:40 pmMDW-CUN
6h 10m1 stop
$314Southwest
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Fri, Sep 19 - Mon, Sep 22
Frontier Logo
3:25 pm - 11:41 amCUN-MDW
20h 16m1 stop
Frontier Logo
10:58 am - 12:39 pmMDW-CUN
25h 41m1 stop
$319Frontier
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Thu, Aug 14 - Fri, Aug 22
Southwest Logo
8:15 am - 11:50 amCUN-MDW
3h 35mnonstop
Southwest Logo
4:35 pm - 8:10 pmMDW-CUN
3h 35mnonstop
$320Southwest
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Thu, Jul 24 - Thu, Jul 31
Frontier Logo
1:49 pm - 11:17 pmCUN-MDW
9h 28m1 stop
Frontier Logo
12:35 pm - 4:20 pmMDW-CUN
27h 45m1 stop
$333Frontier
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Fri, Aug 1 - Fri, Aug 8
Logo
1:54 pm - 11:08 pmCUN-MDW
9h 14m1 stop
Logo
6:00 am - 12:50 pmMDW-CUN
6h 50m1 stop
$352
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Sat, Aug 23 - Wed, Aug 27
Aeromexico Logo
1:35 pm - 9:44 pmCUN-MDW
9h 09m1 stop
Aeromexico Logo
6:00 am - 12:25 pmMDW-CUN
5h 25m1 stop
$495Aeromexico
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Thu, Nov 27 - Mon, Dec 1

Delta flights from Cancún to Chicago Midway Airport

Our best Delta deals on Cancún to Chicago Midway Airport flight tickets
Delta
Aug 13
CUN8:07 amCancun
13h 37m
2 stops
MDW9:44 pmChicago Midway
Aug 20
MDW10:31 amChicago Midway
9h 49m
1 stop
CUN8:20 pmCancun
$276
Find similar
Delta
Sep 21
CUN8:00 amCancun
13h 36m
1 stop
MDW9:36 pmChicago Midway
Sep 28
MDW6:00 amChicago Midway
6h 50m
1 stop
CUN12:50 pmCancun
$302
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Delta
Nov 27
CUN6:00 amCancun
10h 30m
2 stops
MDW3:30 pmChicago Midway
Dec 1
MDW10:35 amChicago Midway
9h 27m
1 stop
CUN9:02 pmCancun
$348
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Southwest flights from Cancún to Chicago Midway Airport

Our best Southwest deals on Cancún to Chicago Midway Airport flight tickets
Southwest
Sep 19
CUN3:10 pmCancun
3h 40m
MDW6:50 pmChicago Midway
Sep 22
MDW9:55 amChicago Midway
3h 35m
CUN1:30 pmCancun
$284
Find similar
Southwest
Nov 13
CUN2:15 pmCancun
3h 45m
MDW5:00 pmChicago Midway
Nov 17
MDW11:25 amChicago Midway
7h 20m
1 stop
CUN7:45 pmCancun
$309
Find similar
Southwest
Sep 19
CUN3:10 pmCancun
3h 40m
MDW6:50 pmChicago Midway
Sep 22
MDW6:30 amChicago Midway
6h 10m
1 stop
CUN12:40 pmCancun
$314
Find similar

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, 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 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 $276.
The fastest flight from Cancún to Chicago Midway Airport takes 3h 35m
Direct flights go from Cancún to Chicago Midway Airport every day.
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  • 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
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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