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Cheap flights from Quintana Roo to Chicago from $202

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 6/11. 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.
Delta Logo
8:00 am - 6:25 pm
CUN
-
MDW
10h 25m
2 stops
Delta Logo
12:41 pm - 8:15 pm
MDW
-
CUN
7h 34m
1 stop
$351Delta
Tue, Jul 28 - Fri, Jul 31
Delta Logo
8:00 am - 4:15 pm
CUN
-
MDW
8h 15m
1 stop
Delta Logo
6:58 pm - 11:35 am
MDW
-
CUN
16h 37m
1 stop
$352Delta
Tue, Jul 21 - Mon, Jul 27
Delta Logo
8:00 am - 4:15 pm
CUN
-
MDW
8h 15m
1 stop
Delta Logo
6:00 am - 1:00 pm
MDW
-
CUN
7h 00m
1 stop
$353Delta
Tue, Jul 28 - Fri, Jul 31
Volaris Logo
10:40 am - 7:34 pm
CUN
-
MDW
8h 54m
1 stop
Volaris Logo
8:23 pm - 9:55 am
MDW
-
CUN
13h 32m
1 stop
$397Volaris
Thu, Jul 16 - Mon, Jul 20
Delta Logo
8:00 am - 10:15 pm
CUN
-
MDW
14h 15m
1 stop
Delta Logo
6:00 am - 6:32 pm
MDW
-
CUN
12h 32m
2 stops
$399Delta
Wed, Jul 22 - Sun, Jul 26
Delta Logo
8:00 am - 8:02 pm
CUN
-
MDW
12h 02m
1 stop
Delta Logo
10:55 am - 8:15 pm
MDW
-
CUN
9h 20m
1 stop
$400Delta
Sat, Jul 4 - Sat, Jul 18
Delta Logo
8:00 am - 9:08 am
CUN
-
MDW
25h 08m
2 stops
Delta Logo
6:58 pm - 11:35 am
MDW
-
CUN
16h 37m
1 stop
$401Delta
Mon, Jul 20 - Sun, Jul 26
Delta Logo
8:00 am - 10:15 pm
CUN
-
MDW
14h 15m
1 stop
Delta Logo
6:00 am - 6:32 pm
MDW
-
CUN
12h 32m
2 stops
$402Delta
Wed, Jul 22 - Sun, Jul 26
Frontier Logo
3:01 pm - 10:08 pm
CUN
-
MDW
7h 07m
1 stop
Frontier Logo
6:00 am - 1:44 pm
MDW
-
CUN
7h 44m
1 stop
$411Frontier
Thu, Jul 9 - Mon, Jul 13
Frontier Logo
11:10 am - 8:32 pm
CUN
-
MDW
9h 22m
1 stop
Frontier Logo
6:05 am - 1:46 pm
MDW
-
CUN
7h 41m
1 stop
$412Frontier
Thu, Jul 9 - Mon, Jul 13

Volaris flights from Quintana Roo to Chicago Midway Airport

Our best Volaris deals on Quintana Roo to Chicago Midway Airport flight tickets
Volaris
Jul 16
CUN10:40 amCancun
8h 54m
1 stop
MDW7:34 pmChicago Midway
Jul 20
MDW8:23 pmChicago Midway
13h 32m
1 stop
CUN9:55 amCancun
$397
Volaris
Jun 18
CUN10:40 amCancun
8h 54m
1 stop
MDW7:34 pmChicago Midway
Jun 26
MDW8:23 pmChicago Midway
13h 32m
1 stop
CUN9:55 amCancun
$418
Volaris
Jun 18
CUN10:40 amCancun
8h 54m
1 stop
MDW7:34 pmChicago Midway
Jun 25
MDW8:49 pmChicago Midway
13h 06m
1 stop
CUN9:55 amCancun
$421

Southwest flights from Quintana Roo to Chicago Midway Airport

Our best Southwest deals on Quintana Roo to Chicago Midway Airport flight tickets
Southwest
Jun 18
CUN1:20 pmCancun
3h 35m
MDW4:55 pmChicago Midway
Jun 26
MDW9:55 amChicago Midway
3h 35m
CUN1:30 pmCancun
$433
Southwest
Jul 22
CUN3:05 pmCancun
3h 30m
MDW6:35 pmChicago Midway
Jul 28
MDW10:05 amChicago Midway
3h 35m
CUN1:40 pmCancun
$469
Southwest
Jul 9
CUN1:20 pmCancun
3h 35m
MDW4:55 pmChicago Midway
Jul 14
MDW7:25 amChicago Midway
6h 30m
1 stop
CUN1:55 pmCancun
$474

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 May 25, 2026.
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

Cheapest round-trip

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Tue 7/28

8:00 am-6:25 pm

2 stops10h 25m

Chicago Midway

Fri 7/31

12:41 pm-8:15 pm

1 stop7h 34m

$351

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Tue 7/21

8:00 am-4:15 pm

1 stop8h 15m

Chicago Midway

Mon 7/27

6:58 pm-11:35 am

1 stop16h 37m

$352

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Tue 7/28

8:00 am-4:15 pm

1 stop8h 15m

Chicago Midway

Fri 7/31

6:00 am-1:00 pm

1 stop7h 00m

$353

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 7/16

10:40 am-7:34 pm

1 stop8h 54m

Chicago Midway

Mon 7/20

8:23 pm-9:55 am

1 stop13h 32m

$397

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 7/22

8:00 am-10:15 pm

1 stop14h 15m

Chicago Midway

Sun 7/26

6:00 am-6:32 pm

2 stops12h 32m

$399

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 7/4

8:00 am-8:02 pm

1 stop12h 02m

Chicago Midway

Sat 7/18

10:55 am-8:15 pm

1 stop9h 20m

$400

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Mon 7/20

8:00 am-9:08 am

2 stops25h 08m

Chicago Midway

Sun 7/26

6:58 pm-11:35 am

1 stop16h 37m

$401

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 7/22

8:00 am-10:15 pm

1 stop14h 15m

Chicago Midway

Sun 7/26

6:00 am-6:32 pm

2 stops12h 32m

$402
Quickest round-trip

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 7/9

3:01 pm-10:08 pm

1 stop7h 07m

Chicago Midway

Mon 7/13

6:00 am-1:44 pm

1 stop7h 44m

$411

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 7/9

11:10 am-8:32 pm

1 stop9h 22m

Chicago Midway

Mon 7/13

6:05 am-1:46 pm

1 stop7h 41m

$412

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, Thursday is the cheapest day to fly to Chicago Midway Airport from Quintana Roo. The lowest ticket price found for a Thursday departure recently was $358. 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 at noon is the least expensive time of day to depart. momondo users have found prices as low as $358 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $471. 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 Airport flights?

There is only 1 cabin class available to choose from on Quintana Roo to Chicago Midway Airport 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 30m

Direct flights

Every day
The fastest flight from Quintana Roo to Chicago Midway Airport takes 3h 30m
Direct flights go from Quintana Roo to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Quintana Roo to Chicago Midway Airport

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

An easier way to manage your Chicago Midway Airport trip

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