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Cheap flights from Quintana Roo to Chicago from $139

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Quintana Roo to Chicago departing on 1/22. 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 Quintana Roo to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
4:25 pm - 7:10 pmCUN-MDW
3h 45mnonstop
Southwest Logo
5:55 am - 10:40 amMDW-CUN
3h 45mnonstop
$275Southwest
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Sat, Nov 22 - Sat, Nov 29
Delta Logo
3:15 pm - 11:47 pmCUN-MDW
9h 32m1 stop
Delta Logo
12:50 pm - 9:20 pmMDW-CUN
7h 30m1 stop
$276Delta
Find Deal
Fri, Dec 5 - Tue, Dec 9
Delta Logo
8:00 am - 4:38 pmCUN-MDW
9h 38m1 stop
Delta Logo
10:47 am - 9:20 pmMDW-CUN
9h 33m1 stop
$277Delta
Find Deal
Fri, Nov 21 - Sun, Nov 30
Delta Logo
8:00 am - 4:38 pmCUN-MDW
9h 38m1 stop
Delta Logo
12:50 pm - 9:20 pmMDW-CUN
7h 30m1 stop
$297Delta
Find Deal
Fri, Nov 14 - Tue, Dec 2
Aeromexico Logo
8:00 am - 4:39 pmCUN-MDW
9h 39m1 stop
Aeromexico Logo
6:00 am - 9:20 pmMDW-CUN
14h 20m1 stop
$332Aeromexico
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Wed, Nov 12 - Fri, Nov 14
Multiple Airlines Logo
10:55 pm - 9:28 pmCUN-MDW
23h 33m2 stops
Multiple Airlines Logo
12:50 pm - 9:20 pmMDW-CUN
7h 30m1 stop
$378Multiple Airlines
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Thu, Dec 4 - Mon, Dec 8
Frontier Logo
2:51 pm - 11:25 pmCUN-MDW
9h 34m1 stop
Frontier Logo
6:00 am - 1:36 pmMDW-CUN
6h 36m1 stop
$380Frontier
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Thu, Feb 19 - Mon, Feb 23
Aeromexico Logo
8:00 am - 10:22 pmCUN-MDW
15h 22m1 stop
Aeromexico Logo
6:00 am - 4:30 pmMDW-CUN
9h 30m1 stop
$406Aeromexico
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Sat, Dec 27 - Wed, Dec 31
Multiple Airlines Logo
11:14 am - 10:43 pmCUN-MDW
12h 29m1 stop
Multiple Airlines Logo
5:30 pm - 1:35 pmMDW-CUN
19h 05m2 stops
$457Multiple Airlines
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Wed, Nov 26 - Thu, Nov 27
Frontier Logo
12:34 pm - 3:28 pmCUN-MDW
27h 54m1 stop
Frontier Logo
9:15 am - 11:24 amMDW-CUN
25h 09m1 stop
$460Frontier
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Fri, Dec 19 - Sat, Dec 27

Southwest flights from Quintana Roo to Chicago Midway Airport

Our best Southwest deals on Quintana Roo to Chicago Midway Airport flight tickets
Southwest
Nov 22
CUN4:25 pmCancun
3h 45m
MDW7:10 pmChicago Midway
Nov 29
MDW5:55 amChicago Midway
3h 45m
CUN10:40 amCancun
$275
Find similar
Southwest
Nov 2
CUN2:15 pmCancun
3h 45m
MDW5:00 pmChicago Midway
Nov 9
MDW10:40 amChicago Midway
3h 45m
CUN3:25 pmCancun
$296
Find similar
Southwest
Nov 2
CUN2:15 pmCancun
3h 45m
MDW5:00 pmChicago Midway
Nov 9
MDW5:55 amChicago Midway
6h 10m
1 stop
CUN1:05 pmCancun
$306
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Delta flights from Quintana Roo to Chicago Midway Airport

Our best Delta deals on Quintana Roo to Chicago Midway Airport flight tickets
Delta
Dec 5
CUN3:15 pmCancun
9h 32m
1 stop
MDW11:47 pmChicago Midway
Dec 9
MDW12:50 pmChicago Midway
7h 30m
1 stop
CUN9:20 pmCancun
$276
Find similar
Delta
Nov 21
CUN8:00 amCancun
9h 38m
1 stop
MDW4:38 pmChicago Midway
Nov 30
MDW10:47 amChicago Midway
9h 33m
1 stop
CUN9:20 pmCancun
$277
Find similar
Delta
Nov 14
CUN8:00 amCancun
9h 38m
1 stop
MDW4:38 pmChicago Midway
Dec 2
MDW12:50 pmChicago Midway
7h 30m
1 stop
CUN9:20 pmCancun
$297
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Quintana Roo 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 October 27, 2025.
Use the filters below to find and compare flights from Quintana Roo to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 11/22

4:25 pm-7:10 pm

Nonstop3h 45m

Chicago Midway

Sat 11/29

5:55 am-10:40 am

Nonstop3h 45m

$275

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 12/5

3:15 pm-11:47 pm

1 stop9h 32m

Chicago Midway

Tue 12/9

12:50 pm-9:20 pm

1 stop7h 30m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 11/21

8:00 am-4:38 pm

1 stop9h 38m

Chicago Midway

Sun 11/30

10:47 am-9:20 pm

1 stop9h 33m

$277

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 11/14

8:00 am-4:38 pm

1 stop9h 38m

Chicago Midway

Tue 12/2

12:50 pm-9:20 pm

1 stop7h 30m

$297

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 11/12

8:00 am-4:39 pm

1 stop9h 39m

Chicago Midway

Fri 11/14

6:00 am-9:20 pm

1 stop14h 20m

$332

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 12/4

10:55 pm-9:28 pm

2 stops23h 33m

Chicago Midway

Mon 12/8

12:50 pm-9:20 pm

1 stop7h 30m

$378

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 2/19

2:51 pm-11:25 pm

1 stop9h 34m

Chicago Midway

Mon 2/23

6:00 am-1:36 pm

1 stop6h 36m

$380

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 12/27

8:00 am-10:22 pm

1 stop15h 22m

Chicago Midway

Wed 12/31

6:00 am-4:30 pm

1 stop9h 30m

$406

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 11/26

11:14 am-10:43 pm

1 stop12h 29m

Chicago Midway

Thu 11/27

5:30 pm-1:35 pm

2 stops19h 05m

$457

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 12/19

12:34 pm-3:28 pm

1 stop27h 54m

Chicago Midway

Sat 12/27

9:15 am-11:24 am

1 stop25h 09m

$460

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 Quintana Roo 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, Wednesday is the cheapest day to fly to Chicago Midway Airport from Quintana Roo. The lowest ticket price found for a Wednesday departure recently was $461. 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 Quintana Roo 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 Quintana Roo in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $455 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $461. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Quintana Roo to Chicago Midway flight route?

Fly from Cancun to Chicago Midway for the best Quintana Roo - Chicago Midway flight prices

What cabin class options are available on Quintana Roo to Chicago Midway flights?

There is only 1 cabin class available to choose from on Quintana Roo 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 Quintana Roo to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Quintana Roo to Chicago Midway Airport.

Cheap Quintana Roo to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Quintana Roo to Chicago Midway Airport

Fastest flight time

3h 40m

Direct flights

Every day
The fastest flight from Quintana Roo to Chicago Midway Airport takes 3h 40m
Direct flights go from Quintana Roo to Chicago Midway Airport every day.
Search flight deals

  • When did momondo last update prices for flights from Quintana Roo to Chicago Midway Airport?

    Prices for flights from Quintana Roo to Chicago Midway Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Quintana Roo to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Quintana Roo to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Quintana Roo 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 Quintana Roo to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Quintana Roo.

Can I find flights from Quintana Roo to Chicago with flexible booking policies on momondo?

Flights from Quintana Roo to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Quintana Roo to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Quintana Roo.

I’m not ready to book a flight from Quintana Roo to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Quintana Roo and alert you when they change.

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