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Quintana Roo

$128+ 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
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 December 4, 2025.

This SmartFares deal was found by Cheapflights users on 12/3. 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.
Mon 12/812:50 pmMDW - CUN
1 stop7h 30mAeromexico
Fri 12/121:33 pmCUN - MDW
1 stop11h 14mAeromexico
Deal found 12/3$302
This Aeromexico deal was found by Cheapflights users on 12/3. 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.
Sat 12/66:00 amMDW - CUN
1 stop5h 23mAeromexico
Wed 12/108:00 amCUN - MDW
1 stop9h 34mAeromexico
Deal found 12/3$318
This Aeromexico deal was found by Cheapflights users on 12/4. 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.
Sun 12/76:00 amMDW - CUN
1 stop7h 05mAeromexico
Tue 12/1612:00 pmCUN - MDW
1 stop12h 47mAeromexico
Deal found 12/4$320
This Delta deal was found by Cheapflights users on 12/2. 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.
Sun 12/76:00 amMDW - CUN
1 stop7h 05mDelta
Sun 12/2111:25 amCUN - MDW
1 stop11h 57mDelta
Deal found 12/2$327
This Frontier deal was found by Cheapflights users on 12/2. 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.
Wed 12/316:12 amMDW - CUN
1 stop6h 28mFrontier
Wed 1/73:14 pmCUN - MDW
1 stop8h 03mFrontier
Deal found 12/2$328
This Delta deal was found by Cheapflights users on 12/3. 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 12/69:29 amMDW - CUN
2 stops10h 51mDelta
Fri 12/128:00 amCUN - MDW
1 stop9h 18mDelta
Deal found 12/3$331
This Aeromexico deal was found by Cheapflights users on 12/3. 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.
Sat 12/66:00 amMDW - CUN
1 stop7h 05mAeromexico
Mon 12/158:00 amCUN - MDW
1 stop9h 34mAeromexico
Deal found 12/3$339
This Frontier deal was found by Cheapflights users on 12/3. 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.
Sun 12/146:15 amMDW - CUN
1 stop6h 43mFrontier
Tue 12/232:50 pmCUN - MDW
1 stop8h 22mFrontier
Deal found 12/3$344
This Delta deal was found by Cheapflights users on 12/2. 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 12/1012:50 pmMDW - CUN
1 stop7h 30mDelta
Sat 12/133:15 pmCUN - MDW
1 stop9h 32mDelta
Deal found 12/2$347
This Frontier deal was found by Cheapflights users on 12/3. 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 12/136:00 amMDW - CUN
1 stop6h 38mFrontier
Sat 12/202:50 pmCUN - MDW
1 stop8h 22mFrontier
Deal found 12/3$349
This Priceline deal was found by Cheapflights users on 12/4. 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 12/136:00 amMDW - CUN
1 stop6h 38mMultiple Airlines
Tue 12/1612:00 pmCUN - MDW
1 stop12h 47mMultiple Airlines
Deal found 12/4$350
This Delta deal was found by Cheapflights users on 12/3. 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.
Sun 12/149:34 amMDW - CUN
2 stops10h 46mDelta
Tue 12/2311:25 amCUN - MDW
1 stop11h 57mDelta
Deal found 12/3$351

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 December 4, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$291
(Kiwi.com)

One-way from

$128
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$502

Good round-trip deal

$357 or less

Good one-way deal

$124 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. 5% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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

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 December 4, 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 12/7

6:00 am-12:23 pm

1 stop5h 23m

Cancun

Wed 12/10

8:00 am-4:34 pm

1 stop9h 34m

$318

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 12/8

6:00 am-12:23 pm

1 stop5h 23m

Cancun

Fri 12/12

4:34 pm-11:47 pm

1 stop8h 13m

$327

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 12/7

6:00 am-2:05 pm

1 stop7h 05m

Cancun

Sat 12/13

8:00 am-6:06 pm

2 stops11h 06m

$331

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 1/17

6:45 am-9:11 pm

1 stop13h 26m

Cancun

Sat 1/24

8:00 am-3:38 pm

1 stop8h 38m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 2/2

12:48 pm-9:11 pm

1 stop7h 23m

Cancun

Mon 2/9

4:40 pm-10:22 pm

1 stop6h 42m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 2/6

6:00 am-4:35 pm

1 stop9h 35m

Cancun

Tue 2/10

4:40 pm-10:22 pm

1 stop6h 42m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 2/7

10:53 am-9:20 pm

1 stop9h 27m

Cancun

Tue 2/10

3:13 pm-10:22 pm

1 stop8h 09m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 1/23

6:00 am-4:35 pm

1 stop9h 35m

Cancun

Wed 1/28

4:40 pm-10:22 pm

1 stop6h 42m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 1/13

6:45 am-4:35 pm

1 stop8h 50m

Cancun

Thu 1/15

12:15 pm-10:07 pm

1 stop10h 52m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 1/31

6:25 am-3:30 pm

1 stop8h 05m

Cancun

Wed 2/4

12:15 pm-5:29 pm

1 stop6h 14m

$333

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

Showing 1-10 of 39 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 $255). Flying from Chicago Midway Airport to Quintana Roo in January is currently the most expensive (average of $430). 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 December 4, 2025.

One of the essential ways to save on airfare from Chicago Midway Airport to Quintana Roo is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 25% on airfare.

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 December 4, 2025.
See what other customers who have flown with Southwest, Delta, and LATAM Airlines 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
4,251 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

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
4,251 reviews
Southwest
8.0
Very good
4,251 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

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
8,011 reviews
Southwest
8.0
Very good
4,251 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

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
LATAM Airlines
7.5
Good
1,890 reviews
Southwest
8.0
Very good
4,251 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

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
7.5
Good
1,650 reviews
Southwest
8.0
Very good
4,251 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

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
Volaris
6.7
Okay
1,155 reviews
Southwest
8.0
Very good
4,251 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

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 $318, Delta can have you in Quintana Roo from Chicago Midway Airport in 5h 23m. There are 1434 mi between Chicago Midway Airport and Quintana Roo.

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

    On average you can expect to pay $379 for a flight from Chicago Midway Airport to Quintana Roo. The cheapest flight overall is $114 while the most popular route, (Chicago Midway - Cancun) is currently priced at $321.

  • 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 $255). Flying from Chicago Midway Airport to Quintana Roo in January is currently the most expensive (average of $430). 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 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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$490FlexibilityNo cancel feeOn-time69%
AeromexicoCheapest$312Average$515FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$345Average$569FlexibilityNo cancel feeOn-time63%
FrontierCheapest$362Average$567FlexibilityNo cancel feeOn-time62%
DeltaCheapest$380Average$615FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$506Average$667FlexibilityNo cancel feeOn-time71%
VolarisCheapest$518Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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