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Cheap flights from Quintana Roo to Chicago from $138

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 1/24. 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.
Frontier Logo
2:57 pm - 10:19 pm
CUN
-
MDW
8h 22m1 stop
Frontier Logo
6:20 am - 1:47 pm
MDW
-
CUN
6h 27m1 stop
$173Frontier
Thu, Jan 22 - Mon, Jan 26
Frontier Logo
2:57 pm - 10:19 pm
CUN
-
MDW
8h 22m1 stop
Frontier Logo
6:20 am - 1:47 pm
MDW
-
CUN
6h 27m1 stop
$233Frontier
Mon, Feb 2 - Mon, Feb 9
Frontier Logo
2:57 pm - 10:19 pm
CUN
-
MDW
8h 22m1 stop
Frontier Logo
5:01 pm - 10:32 am
MDW
-
CUN
16h 31m2 stops
$244Frontier
Thu, Jan 22 - Thu, Jan 29
Frontier Logo
2:57 pm - 10:19 pm
CUN
-
MDW
8h 22m1 stop
Frontier Logo
6:20 am - 1:47 pm
MDW
-
CUN
6h 27m1 stop
$249Frontier
Thu, Jan 29 - Thu, Feb 5
Frontier Logo
4:12 pm - 10:19 pm
CUN
-
MDW
7h 07m1 stop
Frontier Logo
6:10 am - 3:10 pm
MDW
-
CUN
8h 00m1 stop
$262Frontier
Thu, Jan 15 - Sun, Jan 18
Southwest Logo
1:45 pm - 4:30 pm
CUN
-
MDW
3h 45mnonstop
Southwest Logo
9:15 am - 1:55 pm
MDW
-
CUN
3h 40mnonstop
$272Southwest
Thu, Jan 22 - Mon, Jan 26
Delta Logo
12:05 pm - 10:22 pm
CUN
-
MDW
11h 17m2 stops
Delta Logo
10:46 am - 9:11 pm
MDW
-
CUN
9h 25m1 stop
$278Delta
Tue, Jan 27 - Mon, Feb 2
Aeromexico Logo
8:00 am - 5:29 pm
CUN
-
MDW
10h 29m1 stop
Aeromexico Logo
6:25 am - 4:35 pm
MDW
-
CUN
9h 10m1 stop
$279Aeromexico
Thu, Jan 22 - Sat, Jan 24
Aeromexico Logo
6:01 am - 10:22 pm
CUN
-
MDW
17h 21m2 stops
Aeromexico Logo
10:46 am - 9:20 pm
MDW
-
CUN
9h 34m1 stop
$280Aeromexico
Thu, Jan 22 - Sat, Jan 24
Delta Logo
12:35 pm - 9:45 pm
CUN
-
MDW
9h 10m1 stop
Delta Logo
1:05 pm - 8:03 pm
MDW
-
CUN
6h 58m1 stop
$320Delta
Thu, Apr 30 - Mon, May 4

Aeromexico flights from Quintana Roo to Chicago Midway Airport

Our best Aeromexico deals on Quintana Roo to Chicago Midway Airport flight tickets
Aeromexico
Jan 22
CUN8:00 amCancun
10h 29m
1 stop
MDW5:29 pmChicago Midway
Jan 24
MDW6:25 amChicago Midway
9h 10m
1 stop
CUN4:35 pmCancun
$279
Find similar
Aeromexico
Jan 22
CUN6:01 amCancun
17h 21m
2 stops
MDW10:22 pmChicago Midway
Jan 24
MDW10:46 amChicago Midway
9h 34m
1 stop
CUN9:20 pmCancun
$280
Find similar
Aeromexico
Feb 13
CUN6:01 amCancun
12h 44m
2 stops
MDW5:45 pmChicago Midway
Feb 16
MDW6:00 amChicago Midway
13h 02m
2 stops
CUN8:02 pmCancun
$391
Find similar

Delta flights from Quintana Roo to Chicago Midway Airport

Our best Delta deals on Quintana Roo to Chicago Midway Airport flight tickets
Delta
Jan 27
CUN12:05 pmCancun
11h 17m
2 stops
MDW10:22 pmChicago Midway
Feb 2
MDW10:46 amChicago Midway
9h 25m
1 stop
CUN9:11 pmCancun
$278
Find similar
Delta
Apr 30
CUN12:35 pmCancun
9h 10m
1 stop
MDW9:45 pmChicago Midway
May 4
MDW1:05 pmChicago Midway
6h 58m
1 stop
CUN8:03 pmCancun
$320
Find similar
Delta
Feb 11
CUN4:40 pmCancun
6h 42m
1 stop
MDW10:22 pmChicago Midway
Feb 15
MDW11:01 amChicago Midway
9h 10m
1 stop
CUN9:11 pmCancun
$330
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 December 15, 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

Thu 1/22

2:57 pm-10:19 pm

1 stop8h 22m

Chicago Midway

Mon 1/26

6:20 am-1:47 pm

1 stop6h 27m

$173

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Mon 2/2

2:57 pm-10:19 pm

1 stop8h 22m

Chicago Midway

Mon 2/9

6:20 am-1:47 pm

1 stop6h 27m

$233

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/22

2:57 pm-10:19 pm

1 stop8h 22m

Chicago Midway

Thu 1/29

5:01 pm-10:32 am

2 stops16h 31m

$244

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/29

2:57 pm-10:19 pm

1 stop8h 22m

Chicago Midway

Thu 2/5

6:20 am-1:47 pm

1 stop6h 27m

$249

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/15

4:12 pm-10:19 pm

1 stop7h 07m

Chicago Midway

Sun 1/18

6:10 am-3:10 pm

1 stop8h 00m

$262

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/22

1:45 pm-4:30 pm

Nonstop3h 45m

Chicago Midway

Mon 1/26

9:15 am-1:55 pm

Nonstop3h 40m

$272

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Tue 1/27

12:05 pm-10:22 pm

2 stops11h 17m

Chicago Midway

Mon 2/2

10:46 am-9:11 pm

1 stop9h 25m

$278

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/22

8:00 am-5:29 pm

1 stop10h 29m

Chicago Midway

Sat 1/24

6:25 am-4:35 pm

1 stop9h 10m

$279

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 1/22

6:01 am-10:22 pm

2 stops17h 21m

Chicago Midway

Sat 1/24

10:46 am-9:20 pm

1 stop9h 34m

$280

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 4/30

12:35 pm-9:45 pm

1 stop9h 10m

Chicago Midway

Mon 5/4

1:05 pm-8:03 pm

1 stop6h 58m

$320

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 afternoon because they tend to be around $538. 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.

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

Best Price Found

$190

Fastest flight time

3h 35m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Quintana Roo in the past 72 hours is $190. The best round-trip flight deal from Quintana Roo to Chicago Midway Airport found on momondo in the last 72 hours is $358.
The fastest flight from Quintana Roo to Chicago Midway Airport takes 3h 35m
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
Portage
Lansing
Valparaiso
Schererville
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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