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Cheap flights from Quintana Roo to Chicago from $159

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 11/1. 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

Delta Logo
8:00 am - 3:26 pmCUN-MDW
7h 26m1 stop
Delta Logo
10:47 am - 9:20 pmMDW-CUN
9h 33m1 stop
$275Delta
Find Deal
Sat, Nov 1 - Wed, Nov 12
Delta Logo
8:00 am - 6:25 pmCUN-MDW
11h 25m2 stops
Delta Logo
11:10 am - 9:20 pmMDW-CUN
9h 10m2 stops
$276Delta
Find Deal
Wed, Nov 5 - Sat, Nov 8
Southwest Logo
3:15 pm - 6:50 pmCUN-MDW
3h 35mnonstop
Southwest Logo
10:40 am - 2:15 pmMDW-CUN
3h 35mnonstop
$295Southwest
Find Deal
Wed, Oct 15 - Sun, Oct 19
Southwest Logo
2:25 pm - 6:05 pmCUN-MDW
3h 40mnonstop
Southwest Logo
7:00 am - 2:40 pmMDW-CUN
7h 40m1 stop
$305Southwest
Find Deal
Sat, Sep 13 - Sat, Sep 20
Frontier Logo
1:55 pm - 11:20 pmCUN-MDW
9h 25m1 stop
Frontier Logo
6:20 am - 12:40 pmMDW-CUN
6h 20m1 stop
$345Frontier
Find Deal
Thu, Sep 18 - Thu, Sep 25
Frontier Logo
1:55 pm - 11:20 pmCUN-MDW
9h 25m1 stop
Frontier Logo
6:20 am - 12:40 pmMDW-CUN
6h 20m1 stop
$346Frontier
Find Deal
Sun, Sep 21 - Sun, Sep 28
Aeromexico Logo
8:00 am - 3:26 pmCUN-MDW
7h 26m1 stop
Aeromexico Logo
6:00 am - 8:15 pmMDW-CUN
14h 15m1 stop
$349Aeromexico
Find Deal
Sat, Sep 20 - Wed, Sep 24
Logo
9:09 am - 10:12 amCUN-MDW
25h 03m1 stop
Logo
3:27 pm - 9:10 amMDW-CUN
16h 43m1 stop
$351
Find Deal
Sat, Nov 1 - Fri, Nov 14
Aeromexico Logo
2:00 pm - 9:36 pmCUN-MDW
7h 36m1 stop
Aeromexico Logo
6:00 am - 8:15 pmMDW-CUN
14h 15m1 stop
$365Aeromexico
Find Deal
Thu, Sep 18 - Wed, Sep 24
Logo
11:47 am - 8:43 pmCUN-MDW
9h 56m1 stop
Logo
3:40 pm - 9:10 amMDW-CUN
16h 30m2 stops
$387
Find Deal
Thu, Nov 6 - Fri, Nov 14

Frontier flights from Quintana Roo to Chicago Midway Airport

Our best Frontier deals on Quintana Roo to Chicago Midway Airport flight tickets
Frontier
Sep 11
CUN1:55 pmCancun
9h 25m
1 stop
MDW11:20 pmChicago Midway
Sep 20
MDW6:15 amChicago Midway
6h 25m
1 stop
CUN12:40 pmCancun
$336
Find similar
Frontier
Sep 11
CUN1:55 pmCancun
9h 25m
1 stop
MDW11:20 pmChicago Midway
Sep 20
MDW6:15 amChicago Midway
6h 25m
1 stop
CUN12:40 pmCancun
$337
Find similar
Frontier
Sep 18
CUN1:55 pmCancun
9h 25m
1 stop
MDW11:20 pmChicago Midway
Sep 25
MDW6:20 amChicago Midway
6h 20m
1 stop
CUN12:40 pmCancun
$345
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
Nov 1
CUN8:00 amCancun
7h 26m
1 stop
MDW3:26 pmChicago Midway
Nov 12
MDW10:47 amChicago Midway
9h 33m
1 stop
CUN9:20 pmCancun
$275
Find similar
Delta
Nov 5
CUN8:00 amCancun
11h 25m
2 stops
MDW6:25 pmChicago Midway
Nov 8
MDW11:10 amChicago Midway
9h 10m
2 stops
CUN9:20 pmCancun
$276
Find similar
Delta
Dec 25
CUN4:30 pmCancun
6h 46m
1 stop
MDW10:16 pmChicago Midway
Jan 5
MDW6:00 amChicago Midway
8h 20m
1 stop
CUN3:20 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 September 3, 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 11/1

8:00 am-3:26 pm

1 stop7h 26m

Chicago Midway

Wed 11/12

10:47 am-9:20 pm

1 stop9h 33m

$275

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 11/5

8:00 am-6:25 pm

2 stops11h 25m

Chicago Midway

Sat 11/8

11:10 am-9:20 pm

2 stops9h 10m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 10/15

3:15 pm-6:50 pm

Nonstop3h 35m

Chicago Midway

Sun 10/19

10:40 am-2:15 pm

Nonstop3h 35m

$295

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 9/13

2:25 pm-6:05 pm

Nonstop3h 40m

Chicago Midway

Sat 9/20

7:00 am-2:40 pm

1 stop7h 40m

$305

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 9/18

1:55 pm-11:20 pm

1 stop9h 25m

Chicago Midway

Thu 9/25

6:20 am-12:40 pm

1 stop6h 20m

$345

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sun 9/21

1:55 pm-11:20 pm

1 stop9h 25m

Chicago Midway

Sun 9/28

6:20 am-12:40 pm

1 stop6h 20m

$346

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 9/20

8:00 am-3:26 pm

1 stop7h 26m

Chicago Midway

Wed 9/24

6:00 am-8:15 pm

1 stop14h 15m

$349

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 11/1

9:09 am-10:12 am

1 stop25h 03m

Chicago Midway

Fri 11/14

3:27 pm-9:10 am

1 stop16h 43m

$351

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 9/18

2:00 pm-9:36 pm

1 stop7h 36m

Chicago Midway

Wed 9/24

6:00 am-8:15 pm

1 stop14h 15m

$365

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 11/6

11:47 am-8:43 pm

1 stop9h 56m

Chicago Midway

Fri 11/14

3:40 pm-9:10 am

2 stops16h 30m

$387

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 $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, Monday 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 $539.

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 morning is the least expensive time of day to depart. momondo users have found prices as low as $451 when looking at flights departing in the morning. 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.

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

Best Price Found

$329

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 $329. The best round-trip flight deal from Quintana Roo to Chicago Midway Airport found on momondo in the last 72 hours is $445.
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
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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