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Quintana Roo

$115+ 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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Nov 21 — Nov 281
Fri 11/21
Fri 11/28
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 October 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$252
(Southwest)

One-way from

$115
(Southwest)

Popular in

March

Cheapest in

September

Average price

$398

Good round-trip deal

$271 or less

Good one-way deal

$194 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. 5% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 22, 2025.

This Southwest deal was found by Cheapflights users on 10/21. 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 11/188:40 amMDW - CUN
Nonstop3h 45mSouthwest
Fri 11/212:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/21$252
This Southwest deal was found by Cheapflights users on 10/21. 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.
Mon 11/178:40 amMDW - CUN
Nonstop3h 45mSouthwest
Fri 11/212:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/21$257
This Southwest deal was found by Cheapflights users on 10/19. 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 11/210:40 amMDW - CUN
Nonstop3h 45mSouthwest
Thu 11/62:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/19$262
This Southwest deal was found by Cheapflights users on 10/21. 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.
Mon 11/178:40 amMDW - CUN
Nonstop3h 45mSouthwest
Sat 11/224:25 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/21$267
This Southwest deal was found by Cheapflights users on 10/21. 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.
Sat 10/259:40 amMDW - CUN
Nonstop3h 35mSouthwest
Sat 11/112:00 pmCUN - MDW
Nonstop3h 35mSouthwest
Deal found 10/21$272
This Southwest deal was found by Cheapflights users on 10/21. 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.
Sat 11/18:20 amMDW - CUN
1 stop11h 30mSouthwest
Wed 11/51:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/21$276
This Southwest deal was found by Cheapflights users on 10/19. 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 11/910:40 amMDW - CUN
Nonstop3h 45mSouthwest
Sat 11/151:00 pmCUN - MDW
1 stop6h 55mSouthwest
Deal found 10/19$277
This Southwest deal was found by Cheapflights users on 10/21. 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.
Sat 11/18:20 amMDW - CUN
1 stop11h 30mSouthwest
Sat 11/83:10 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/21$281
This Southwest deal was found by Cheapflights users on 10/19. 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.
Mon 10/279:40 amMDW - CUN
Nonstop3h 35mSouthwest
Sat 11/112:00 pmCUN - MDW
Nonstop3h 35mSouthwest
Deal found 10/19$282
This Southwest deal was found by Cheapflights users on 10/19. 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 11/910:40 amMDW - CUN
Nonstop3h 45mSouthwest
Wed 11/1212:55 pmCUN - MDW
1 stop9h 10mSouthwest
Deal found 10/19$287
This Southwest deal was found by Cheapflights users on 10/20. 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 10/285:35 amMDW - CUN
1 stop6h 30mSouthwest
Sat 11/12:00 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/20$291
This Delta deal was found by Cheapflights users on 10/20. 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 12/316:00 amMDW - CZM
1 stop8h 15mDelta
Thu 1/293:15 pmCZM - MDW
1 stop6h 31mDelta
Deal found 10/20$469

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 October 22, 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

Sat 11/1

8:20 am-7:50 pm

2 stops11h 30m

Cancun

Sat 11/8

3:10 pm-5:55 pm

Nonstop3h 45m

$281

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 11/16

5:10 am-2:55 pm

1 stop8h 45m

Cancun

Sat 11/22

11:20 am-2:00 pm

Nonstop3h 40m

$291

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 10/31

7:15 am-3:25 pm

1 stop8h 10m

Cancun

Tue 11/4

1:45 pm-4:30 pm

Nonstop3h 45m

$306

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 11/3

6:23 pm-9:20 pm

2 stops25h 57m

Cancun

Fri 11/14

11:50 am-8:52 am

2 stops22h 02m

$317

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 1/11

10:35 am-9:10 pm

1 stop9h 35m

Cancun

Fri 1/16

1:40 pm-9:46 pm

1 stop9h 06m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 1/19

1:05 pm-9:10 pm

1 stop7h 05m

Cancun

Thu 1/22

11:10 am-4:25 pm

1 stop6h 15m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 1/5

6:00 am-4:20 pm

1 stop9h 20m

Cancun

Thu 1/15

11:10 am-9:46 pm

1 stop11h 36m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 1/31

6:00 am-3:17 pm

1 stop8h 17m

Cancun

Sat 2/7

8:00 am-3:25 pm

1 stop8h 25m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 11/16

5:10 am-11:55 am

1 stop5h 45m

Cancun

Fri 11/21

12:55 pm-8:30 pm

2 stops8h 35m

$341

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 1/9

6:00 am-3:17 pm

1 stop8h 17m

Cancun

Mon 1/12

4:25 pm-9:46 pm

1 stop6h 21m

$346

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

Showing 1-10 of 45 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Quintana Roo (average of $245). 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 October 22, 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 October 22, 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
4,237 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,979 reviews
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
LATAM Airlines
7.5
Good
1,869 reviews
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Aeromexico
7.4
Good
1,681 reviews
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Volaris
6.7
Okay
1,152 reviews
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 $443, Southwest can have you in Quintana Roo from Chicago Midway Airport in 8h. There are 1469 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 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 $115. However, be on the lookout for offers from Aeromexico and Delta, 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 $374 for a flight from Chicago Midway Airport to Quintana Roo. The cheapest flight overall is $124 while the most popular route, (Chicago Midway - Cancun) is currently priced at $252.

  • 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Quintana Roo (average of $245). 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 7 airlines flying from Midway to Quintana Roo

Discover the top 7 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 October 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$490FlexibilityNo cancel feeOn-time69%
AeromexicoCheapest$312Average$500FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$345Average$574FlexibilityNo cancel feeOn-time63%
FrontierCheapest$362Average$567FlexibilityNo cancel feeOn-time62%
DeltaCheapest$380Average$616FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$486Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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