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Quintana Roo

$107+ Cheap flights from Midway (MDW) to Quintana Roo

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Midway to Quintana Roo

Cheapest flights from Midway to Quintana Roo
Explore the most affordable flight options available from Midway to Quintana Roo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Super.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:25 am
MDW
-
CUN
1 stop7h 57m
Frontier
Sat 3/73:07 pm
CUN
-
MDW
Nonstop4h 06m
Frontier
Deal found 1/27$254
This Frontier deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/79:00 am
MDW
-
CUN
Nonstop4h 02m
Frontier
Sat 3/143:07 pm
CUN
-
MDW
Nonstop4h 06m
Frontier
Deal found 1/27$263
This Priceline deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/118:30 am
MDW
-
CUN
Nonstop3h 50m
Frontier
Sat 4/181:25 pm
CUN
-
MDW
1 stop8h 54m
Frontier
Deal found 1/27$271
This Frontier deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/118:30 am
MDW
-
CUN
Nonstop3h 50m
Frontier
Thu 4/1611:30 am
CUN
-
MDW
1 stop10h 51m
Frontier
Deal found 1/27$272
This WAYA deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/79:00 am
MDW
-
CUN
Nonstop4h 02m
Frontier
Tue 3/101:47 pm
CUN
-
MDW
1 stop7h 07m
Frontier
Deal found 1/27$276
This Mytrip deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:54 pm
MDW
-
CUN
1 stop13h 54m
Multiple Airlines
Sat 2/2810:16 am
CUN
-
MDW
1 stop12h 23m
Multiple Airlines
Deal found 1/28$283
This Trip.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:00 am
MDW
-
CUN
1 stop6h 37m
Frontier
Sat 3/73:07 pm
CUN
-
MDW
Nonstop4h 06m
Frontier
Deal found 1/27$285
This Gotogate deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:54 pm
MDW
-
CUN
1 stop13h 54m
Multiple Airlines
Sat 3/73:07 pm
CUN
-
MDW
Nonstop4h 06m
Multiple Airlines
Deal found 1/28$286
This Priceline deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/118:30 am
MDW
-
CUN
Nonstop3h 50m
Frontier
Tue 4/144:09 pm
CUN
-
MDW
1 stop27h 22m
Frontier
Deal found 1/27$289
This Delta deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/166:00 am
MDW
-
CZM
1 stop7h 55m
Delta
Wed 2/184:15 pm
CZM
-
MDW
1 stop16h 51m
Delta
Deal found 1/27$466
This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/96:00 am
MDW
-
CZM
1 stop7h 50m
Delta
Wed 2/114:15 pm
CZM
-
MDW
2 stops20h 31m
Delta
Deal found 1/26$471
This SmartFares deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
MDW
-
CZM
1 stop7h 55m
Aeromexico
Tue 3/102:00 pm
CZM
-
MDW
1 stop7h 31m
Aeromexico
Deal found 1/27$478

Find flight deals from Midway to Quintana Roo

Keep the following information in mind while searching for Midway to Quintana Roo flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$254
(Super.com)

One-way from

$107
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$388

Good round-trip deal

$441 or less

Good one-way deal

$144 or less
Provider with most accurate pricing for Chicago (CHI)-Cancun flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Cancun flights.
Search Deals
From Chicago Midway to Quintana Roo
Search Deals
One-way flight from Chicago Midway to Quintana Roo
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Quintana Roo.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Quintana Roo.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Quintana Roo 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, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Quintana Roo that are best for you.

Fly from

Midway

Fly to

Quintana Roo

Route

Depart

Return

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 3/9

8:05 am-11:50 am

Nonstop3h 45m

Cancun

Fri 3/13

8:30 am-12:10 pm

Nonstop3h 40m

$291

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 3/8

4:35 pm-8:15 pm

Nonstop3h 40m

Cancun

Thu 3/12

2:05 pm-5:50 pm

Nonstop3h 45m

$291

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 3/5

4:05 pm-8:45 pm

Nonstop3h 40m

Cancun

Mon 3/9

8:30 am-12:10 pm

Nonstop3h 40m

$301

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 2/16

6:00 am-4:45 pm

1 stop9h 45m

Cancun

Wed 2/25

12:15 pm-5:45 pm

1 stop6h 30m

$336

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 2/9

6:00 am-2:03 pm

1 stop7h 03m

Cancun

Fri 2/13

11:00 am-5:45 pm

1 stop7h 45m

$336

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 3/4

12:45 pm-9:11 pm

1 stop7h 26m

Cancun

Tue 3/17

10:50 am-5:54 pm

1 stop7h 04m

$336

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 2/7

9:33 am-9:20 pm

2 stops10h 47m

Cancun

Sat 2/14

12:05 pm-10:31 pm

2 stops11h 26m

$341

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 2/26

10:49 am-9:11 pm

1 stop9h 22m

Cancun

Thu 3/5

8:00 am-5:37 pm

2 stops10h 37m

$341

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 3/10

1:10 pm-8:20 pm

2 stops7h 10m

Cancun

Thu 3/12

10:50 am-5:54 pm

1 stop7h 04m

$341

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 3/7

4:13 pm-11:50 am

2 stops18h 37m

Cancun

Thu 3/12

8:00 am-5:54 pm

2 stops9h 54m

$341

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 40 results
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Best time to book a flight from Midway to Quintana Roo

Have a flexible travel schedule? Discover the best time to fly to Quintana Roo from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Quintana Roo

What is the cheapest month to book a flight from Chicago Midway Airport to Quintana Roo?

Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Quintana Roo (average of $260). Flying from Chicago Midway Airport to Quintana Roo in January is currently the most expensive (average of $391). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to QR?

Find hourly flight availability from Midway to Quintana Roo. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 29, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Quintana Roo as you normally would.

Reviews of airlines servicing Quintana Roo

Get insights into the airlines that provide service to Quintana Roo. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Quintana Roo. Reviews last updated January 29, 2026.
See what other customers who have flown with Southwest, Delta, and Aeromexico from Chicago Midway Airport to Quintana Roo have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,127 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Aeromexico
7.4
Good
1,586 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.7
Fair
3,056 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Midway to Quintana Roo. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to Quintana Roo?

    For as low as $291, Southwest can have you in Quintana Roo from Chicago Midway Airport in 3h 45m. There are 1434 mi between Chicago Midway Airport and Quintana Roo. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest flights from Chicago Midway Airport to Quintana Roo?

    On average you can expect to pay $398 for a flight from Chicago Midway Airport to Quintana Roo. The cheapest flight overall is $144 while the most popular route, (Chicago Midway - Cancun) is currently priced at $247.

  • Can I find deals for flights from Midway to Quintana Roo that include hotel bookings?

    Yes. In addition to deals on Midway to Quintana Roo flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Quintana Roo?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Quintana Roo.

  • Can I find deals for business class flights from Midway to Quintana Roo?

    Yes. Cheapflights offers flight deals from Midway to Quintana Roo by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Quintana Roo?

    Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Quintana Roo (average of $260). Flying from Chicago Midway Airport to Quintana Roo in January is currently the most expensive (average of $391). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Midway to Quintana Roo

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Midway to Quintana Roo

Discover the top 4 airlines that operate flights from Midway to Quintana Roo. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$295Average$524FlexibilityNo cancel feeOn-time63%
AeromexicoCheapest$309Average$398FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$358Average$3,633FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$362Average$476FlexibilityNo cancel feeOn-time62%

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