HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Quintana Roo

$110+ 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Jul 7 — Jul 141
Mon 7/7
Mon 7/14
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Quintana Roo with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 July 2, 2025.

Round-trip from

$269
(Southwest)

One-way from

$110
(Priceline)

Popular in

March

Cheapest in

September

Average price

$387

Good round-trip deal

$346 or less

Good one-way deal

$121 or less
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. 6% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
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

Find 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 July 2, 2025.

This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/135:25 pmMDW - CUN
Nonstop3h 35mSouthwest
Thu 7/178:15 amCUN - MDW
Nonstop3h 35mSouthwest
Deal found 6/30$269
This Booking.com deal was found by Cheapflights users on 6/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/126:02 pmMDW - CUN
1 stop15h 35mFrontier
Fri 8/1510:37 amCUN - MDW
1 stop27h 13mFrontier
Deal found 6/30$295
This SmartFares deal was found by Cheapflights users on 7/1. 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.
Sat 8/3010:31 amMDW - CUN
1 stop9h 49mAeromexico
Sat 9/68:00 amCUN - MDW
1 stop13h 12mAeromexico
Deal found 7/1$304
This Delta deal was found by Cheapflights users on 6/30. 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.
Sat 9/2711:00 amMDW - CUN
1 stop9h 15mDelta
Sat 10/48:00 amCUN - MDW
1 stop7h 26mDelta
Deal found 6/30$323
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/156:40 pmMDW - CUN
1 stop19h 17mMultiple Airlines
Thu 8/219:54 amCUN - MDW
1 stop11h 57mMultiple Airlines
Deal found 7/1$345
This Delta deal was found by Cheapflights users on 6/30. 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 12/296:00 amMDW - CZM
1 stop8h 00mDelta
Tue 1/63:15 pmCZM - MDW
1 stop6h 31mDelta
Deal found 6/30$660
This Mytrip deal was found by Cheapflights users on 7/1. 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.
Wed 8/138:39 pmMDW - CZM
2 stops19h 29mMultiple Airlines
Wed 8/205:42 pmCZM - MDW
2 stops24h 34mMultiple Airlines
Deal found 7/1$716
This Aeromexico deal was found by Cheapflights users on 6/30. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:00 amMDW - CZM
1 stop8h 00mAeromexico
Tue 12/303:20 pmCZM - MDW
1 stop6h 45mAeromexico
Deal found 6/30$880

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 July 2, 2025.
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

Sun 7/13

5:25 pm-9:00 pm

Nonstop3h 35m

Cancun

Thu 7/17

8:15 am-11:50 am

Nonstop3h 35m

$269

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 8/12

6:02 pm-9:37 am

1 stop15h 35m

Cancun

Fri 8/15

10:37 am-1:50 pm

1 stop27h 13m

$295

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 8/30

10:31 am-8:20 pm

1 stop9h 49m

Cancun

Sat 9/6

8:00 am-9:12 pm

1 stop13h 12m

$304

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 9/27

11:00 am-8:15 pm

1 stop9h 15m

Cancun

Sat 10/4

8:00 am-3:26 pm

1 stop7h 26m

$323

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 8/18

6:00 am-8:59 am

1 stop26h 59m

Cancun

Thu 8/21

9:54 am-9:51 pm

1 stop11h 57m

$328

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Mon 12/29

6:00 am-2:00 pm

1 stop8h 00m

Cozumel

Tue 1/6

3:15 pm-9:46 pm

1 stop6h 31m

$660

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Wed 8/13

8:39 pm-3:08 pm

2 stops19h 29m

Cozumel

Wed 8/20

5:42 pm-7:16 pm

2 stops24h 34m

$716

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Mon 12/29

6:00 am-2:00 pm

1 stop8h 00m

Cozumel

Tue 12/30

3:20 pm-10:05 pm

1 stop6h 45m

$880

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 9/20

6:10 am-12:40 pm

1 stop6h 30m

$110

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 7/6

5:25 pm-9:00 pm

Nonstop3h 35m

$123

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 16 results
1
2

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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Quintana Roo (average of $360). Flying from Chicago Midway Airport to Quintana Roo in March is currently the most expensive (average of $492). 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 July 2, 2025.

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 July 2, 2025.
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
4,272 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,983 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Aeromexico
7.5
Good
1,718 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,290 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Quintana Roo one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $110. However, be on the lookout for offers from Southwest and Aeromexico, as they are both options that can get you from Chicago Midway Airport to Quintana Roo for a low price.

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

    On average you can expect to pay $279 for a flight from Chicago Midway Airport to Quintana Roo. The cheapest flight overall is $121 while the most popular route, (Chicago Midway - Cancun) is currently priced at $270.

  • 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Quintana Roo (average of $360). Flying from Chicago Midway Airport to Quintana Roo in March is currently the most expensive (average of $492). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Quintana Roo

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Cancún flights
O'Hare Intl to Mexico City flights
O'Hare Intl to Cozumel flights
Midway to Cancún flights
Midway to Mexico City flights
O'Hare Intl to Mexico City flights
O'Hare Intl to Guadalajara flights
O'Hare Intl to Puerto Vallarta flights
O'Hare Intl to San José del Cabo flights
Midway to Guadalajara flights
O'Hare Intl to Monterrey flights
Midway to Puerto Vallarta flights
O'Hare Intl to León flights
Midway to San José del Cabo flights
Midway to Morelia flights
O'Hare Intl to Morelia flights
O'Hare Intl to Durango flights
O'Hare Intl to Oaxaca flights
Midway to León flights
Midway to Cozumel flights
O'Hare Intl to Santiago de Querétaro flights
Midway to Aguascalientes flights
Midway to Durango flights
Midway to Monterrey flights
O'Hare Intl to San Luis Potosí flights
O'Hare Intl to Aguascalientes flights
O'Hare Intl to Zacatecas flights
O'Hare Intl to Ixtapa flights
O'Hare Intl to Mérida flights
Midway to Santiago de Querétaro flights
O'Hare Intl to Santa Maria Huatulco flights
O'Hare Intl to Mazatlán flights
O'Hare Intl to Puebla City flights
Midway to Oaxaca flights
O'Hare Intl to Tepic flights
Midway to Zacatecas flights
Midway to San Luis Potosí flights
Midway to Ixtapa flights
O'Hare Intl to Puerto Escondido flights
O'Hare Intl to Veracruz flights
O'Hare Intl to Acapulco flights
O'Hare Intl to Torreón flights
Midway to Mérida flights
Midway to Mazatlán flights
O'Hare Intl to Chihuahua flights
Midway to Puerto Escondido flights
Midway to Acapulco flights
Midway to Santa Maria Huatulco flights
O'Hare Intl to Hermosillo flights
Midway to Veracruz flights

Top 8 airlines flying from Midway to Quintana Roo

Discover the top 8 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 July 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$419FlexibilityNo cancel feeOn-time69%
FrontierCheapest$198Average$565FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$241Average$341FlexibilityNo cancel feeOn-time65%
AeromexicoCheapest$319Average$520FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$345Average$580FlexibilityNo cancel feeOn-time63%
DeltaCheapest$380Average$612FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$486Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.