HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Quintana Roo

$111+ 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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Mar 17 — Mar 241
Mon 3/17
Mon 3/24
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 March 12, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$302
(Kiwi.com)

One-way from

$111
(Southwest)

Popular in

March

Cheapest in

September

Average price

$521

Good round-trip deal

$455 or less

Good one-way deal

$340 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. 6% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Tue 4/82:45 pmMDW - CUN
1 stop21h 20mFrontier
Tue 4/1512:40 pmCUN - MDW
1 stop7h 05mFrontier
Deal found 3/11$302
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Tue 3/254:58 pmMDW - CUN
2 stops15h 15mMultiple Airlines
Tue 4/111:14 amCUN - MDW
1 stop8h 37mMultiple Airlines
Deal found 3/11$303
This iWofly deal was found by Cheapflights users on 3/11. 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/29:54 amMDW - CUN
1 stop10h 06mAeromexico
Wed 4/98:00 amCUN - MDW
1 stop8h 12mAeromexico
Deal found 3/11$316
This Southwest deal was found by Cheapflights users on 3/11. 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.
Tue 4/85:35 amMDW - CUN
1 stop8h 35mSouthwest
Tue 4/159:00 amCUN - MDW
Nonstop3h 40mSouthwest
Deal found 3/11$320
This Delta deal was found by Cheapflights users on 3/11. 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 3/159:25 amMDW - CUN
1 stop5h 52mDelta
Wed 3/1911:05 amCUN - MDW
1 stop6h 57mDelta
Deal found 3/11$321
This Gotogate deal was found by Cheapflights users on 3/11. 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.
Sat 5/1010:41 pmMDW - CUN
1 stop14h 21mVolaris
Sat 5/248:00 amCUN - MDW
1 stop11h 06mVolaris
Deal found 3/11$343
This Aeromexico deal was found by Cheapflights users on 3/11. 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.
Tue 4/86:00 amMDW - CZM
1 stop8h 00mAeromexico
Sun 4/132:20 pmCZM - MDW
1 stop6h 57mAeromexico
Deal found 3/11$518
This Mytrip deal was found by Cheapflights users on 3/11. 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.
Tue 7/18:39 pmMDW - CZM
2 stops21h 13mVolaris
Mon 7/75:42 pmCZM - MDW
2 stops24h 34mVolaris
Deal found 3/11$593
This Mytrip deal was found by Cheapflights users on 3/11. 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 4/2310:41 pmMDW - CZM
2 stops19h 14mMultiple Airlines
Wed 4/305:42 pmCZM - MDW
2 stops24h 24mMultiple Airlines
Deal found 3/11$660
This Delta deal was found by Cheapflights users on 3/11. 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.
Fri 3/286:00 amMDW - CZM
1 stop8h 00mDelta
Thu 4/32:20 pmCZM - MDW
1 stop7h 01mDelta
Deal found 3/11$753

Find flights from Midway to Quintana Roo within your budget

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 March 12, 2025.

Fly from

Midway

Fly to

Quintana Roo

Route

Depart

Return

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 4/8

2:45 pm-12:05 pm

1 stop21h 20m

Cancun

Tue 4/15

12:40 pm-7:45 pm

1 stop7h 05m

$302

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 3/25

4:58 pm-8:13 am

2 stops15h 15m

Cancun

Tue 4/1

11:14 am-7:51 pm

1 stop8h 37m

$303

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 4/2

9:54 am-8:00 pm

1 stop10h 06m

Cancun

Wed 4/9

8:00 am-4:12 pm

1 stop8h 12m

$316

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 4/8

5:35 am-2:10 pm

1 stop8h 35m

Cancun

Tue 4/15

9:00 am-12:40 pm

Nonstop3h 40m

$320

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 4/9

9:52 am-8:00 pm

1 stop10h 08m

Cancun

Tue 4/15

12:35 pm-10:22 pm

1 stop9h 47m

$321

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 5/10

10:41 pm-1:02 pm

1 stop14h 21m

Cancun

Sat 5/24

8:00 am-7:06 pm

1 stop11h 06m

$343

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Tue 4/8

6:00 am-1:00 pm

1 stop8h 00m

Cozumel

Sun 4/13

2:20 pm-10:17 pm

1 stop6h 57m

$518

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Tue 7/1

8:39 pm-4:52 pm

2 stops21h 13m

Cozumel

Mon 7/7

5:42 pm-7:16 pm

2 stops24h 34m

$593

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Wed 4/23

10:41 pm-4:55 pm

2 stops19h 14m

Cozumel

Wed 4/30

5:42 pm-7:06 pm

2 stops24h 24m

$660

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Fri 3/28

6:00 am-1:00 pm

1 stop8h 00m

Cozumel

Thu 4/3

2:20 pm-10:21 pm

1 stop7h 01m

$753

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/11

Showing 1-10 of 20 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.

Travel insights for flights from Midway to Quintana Roo

Get recent, data-driven insights about flights from Midway to Quintana Roo including ideal travel times, pricing trends, and more.

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 March 12, 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.

Rainfall in Quintana Roo by month

Plan your trip to Quintana Roo by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Quintana Roo ranges from 1.1 - 11.1 inches per month. October is typically the wettest month, when rainfall can reach 11.1 in. April is typically the driest time to visit Quintana Roo when rainfall is around 1.1 in.

Temperature in Quintana Roo by month

Plan your trip to Quintana Roo by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Quintana Roo, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 86.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 75.2 F).

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 March 12, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Aeromexico from Chicago to Quintana Roo to help guide your decision. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,297 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Southwest
8.1
Very good
4,297 reviews
Southwest
8.1
Very good
4,297 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Delta
8.0
Very good
7,966 reviews
Southwest
8.1
Very good
4,297 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Aeromexico
7.5
Good
1,725 reviews
Southwest
8.1
Very good
4,297 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

WestJet
7.2
Good
2,776 reviews
Southwest
8.1
Very good
4,297 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Volaris
6.7
Okay
1,190 reviews
Southwest
8.1
Very good
4,297 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 Southwest, with whom users have recently found tickets for as low as $111. However, be on the lookout for offers from Volaris and Frontier, 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 $495 for a flight from Chicago Midway Airport to Quintana Roo. The cheapest flight overall is $110 while the most popular route, (Chicago Midway - Cancun) is currently priced at $308.

  • 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
Midway to Cancún flights
O'Hare Intl to Cozumel flights
Midway to Mexico City flights
O'Hare Intl to Guadalajara flights
O'Hare Intl to Mexico City flights
O'Hare Intl to San José del Cabo flights
Midway to Guadalajara flights
O'Hare Intl to Puerto Vallarta flights
Midway to Cozumel flights
Midway to San José del Cabo flights
O'Hare Intl to Morelia flights
Midway to Puerto Vallarta flights
O'Hare Intl to León flights
Midway to Morelia flights
Midway to León flights
O'Hare Intl to Oaxaca flights
O'Hare Intl to Monterrey flights
O'Hare Intl to San Luis Potosí flights
O'Hare Intl to Aguascalientes flights
Midway to Aguascalientes flights
O'Hare Intl to Santiago de Querétaro flights
O'Hare Intl to Ixtapa flights
O'Hare Intl to Mérida flights
O'Hare Intl to Durango flights
Midway to Durango flights
Midway to Oaxaca flights
Midway to Monterrey flights
O'Hare Intl to Zacatecas flights
O'Hare Intl to Mazatlán flights
O'Hare Intl to Veracruz flights
Midway to Zacatecas flights
Midway to San Luis Potosí flights
O'Hare Intl to Puerto Escondido flights
O'Hare Intl to Puebla City flights
Midway to Santiago de Querétaro flights
Midway to Mérida flights
Midway to Mazatlán flights
O'Hare Intl to Tampico flights
O'Hare Intl to Hermosillo flights
O'Hare Intl to La Paz flights
O'Hare Intl to Acapulco flights
O'Hare Intl to Santa Maria Huatulco flights
Midway to Ixtapa flights
O'Hare Intl to Chihuahua flights
O'Hare Intl to Tijuana flights
Midway to Veracruz flights
O'Hare Intl to Tepic flights
O'Hare Intl to Manzanillo 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 March 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$175Average$393FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$183Average$409FlexibilityNo cancel feeOn-time65%
FrontierCheapest$198Average$443FlexibilityNo cancel feeOn-time62%
AeromexicoCheapest$378Average$552FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$380Average$540FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$438Average$700FlexibilityNo cancel feeOn-time63%
VolarisCheapest$477Average$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.