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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 7/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
1 adult, Economy
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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 April 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$246
(Southwest)

One-way from

$111
(Southwest)

Popular in

March

Cheapest in

September

Average price

$404

Good round-trip deal

$426 or less

Good one-way deal

$220 or less
Provider with most accurate pricing for Chicago (CHI)-Cancun flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Cancun flights.
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From Chicago Midway to Quintana Roo
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One-way flight from Chicago Midway to Quintana Roo
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Highest demand for flights based on searches. 7% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Chicago Midway to Quintana Roo.
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Price to beat on a one-way flight from Chicago Midway to Quintana Roo.
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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 April 15, 2025.

This Southwest deal was found by Cheapflights users on 4/13. 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.
Wed 7/234:30 pmMDW - CUN
Nonstop3h 35mSouthwest
Wed 7/308:30 amCUN - MDW
Nonstop3h 35mSouthwest
Deal found 4/13$246
This Trip.com deal was found by Cheapflights users on 4/15. 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 5/56:04 amMDW - CUN
1 stop5h 21mAeromexico
Fri 5/99:55 amCUN - MDW
1 stop7h 48mAeromexico
Deal found 4/15$301
This Delta deal was found by Cheapflights users on 4/14. 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 6/1410:26 amMDW - CUN
1 stop9h 54mDelta
Thu 6/2612:35 pmCUN - MDW
1 stop9h 10mDelta
Deal found 4/14$321
This Trip.com deal was found by Cheapflights users on 4/14. 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 4/286:04 amMDW - CUN
1 stop5h 21mMultiple Airlines
Mon 5/52:31 pmCUN - MDW
1 stop9h 16mMultiple Airlines
Deal found 4/14$377
This Mytrip deal was found by Cheapflights users on 4/15. 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.
Thu 5/18:30 amMDW - CUN
1 stop27h 46mFrontier
Fri 5/911:13 amCUN - MDW
1 stop9h 20mFrontier
Deal found 4/15$408
This Aeromexico deal was found by Cheapflights users on 4/14. 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.
Wed 12/246:00 amMDW - CZM
1 stop8h 00mAeromexico
Thu 12/253:20 pmCZM - MDW
1 stop6h 45mAeromexico
Deal found 4/14$979
This Delta deal was found by Cheapflights users on 4/14. 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.
Wed 8/206:00 amMDW - CZM
2 stops32h 11mDelta
Thu 8/281:59 pmCZM - MDW
2 stops30h 48mDelta
Deal found 4/14$983

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 April 15, 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

Tue 7/8

4:30 pm-8:05 pm

Nonstop3h 35m

Cancun

Tue 7/15

8:30 am-12:05 pm

Nonstop3h 35m

$246

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 5/5

6:04 am-11:25 am

1 stop5h 21m

Cancun

Fri 5/9

9:55 am-5:43 pm

1 stop7h 48m

$301

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 6/14

10:26 am-8:20 pm

1 stop9h 54m

Cancun

Thu 6/26

12:35 pm-9:45 pm

1 stop9h 10m

$321

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 4/28

6:04 am-11:25 am

1 stop5h 21m

Cancun

Mon 5/5

2:31 pm-11:47 pm

1 stop9h 16m

$377

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 5/1

8:30 am-12:16 pm

1 stop27h 46m

Cancun

Fri 5/9

11:13 am-8:33 pm

1 stop9h 20m

$408

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Wed 8/20

6:00 am-1:11 pm

2 stops32h 11m

Cozumel

Thu 8/28

1:59 pm-9:47 pm

2 stops30h 48m

$983

ChicagoCozumel

MDW - CZM

MDWCZM

Chicago Midway

Mon 8/18

1:05 pm-1:11 pm

2 stops25h 06m

Cozumel

Thu 8/28

1:59 pm-9:47 pm

2 stops30h 48m

$1,013

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 7/9

4:30 pm-8:05 pm

Nonstop3h 35m

$111

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 5/30

10:25 am-12:30 am

2 stops14h 05m

$136

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 4/19

9:20 am-3:11 pm

1 stop5h 51m

$146

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

Showing 1-10 of 15 results
1
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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, 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 April 15, 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 April 15, 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
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Food

7.1

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
8.0
Very good
4,279 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Food

7.1

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
7,918 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Food

7.1

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
1,698 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Food

7.1

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
1,172 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Food

7.1

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.
Frontier
6.0
Okay
3,281 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Food

7.1

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 Aeromexico 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 $418 for a flight from Chicago Midway Airport to Quintana Roo. The cheapest flight overall is $120 while the most popular route, (Chicago Midway - Cancun) is currently priced at $309.

  • 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

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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 April 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$175Average$393FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$183Average$333FlexibilityNo cancel feeOn-time65%
FrontierCheapest$198Average$443FlexibilityNo cancel feeOn-time62%
AeromexicoCheapest$320Average$527FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$380Average$534FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$435Average$688FlexibilityNo cancel feeOn-time63%
VolarisCheapest$486Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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