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Quintana Roo

$119+ 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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
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 septiembre 11, 2025.

Round-trip from

$271
(Southwest)

One-way from

$119
(Southwest)

Popular in

March

Cheapest in

September

Average price

$354

Good round-trip deal

$326 or less

Good one-way deal

$124 or less
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. 6% potential increase in price ($28 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 September 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 septiembre 11, 2025.

This Southwest deal was found by Cheapflights users on 9/11. 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.
dom. 11/1610:40 amMDW - CUN
Nonstop3h 45mSouthwest
vie. 11/212:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 9/11$266
This Southwest deal was found by Cheapflights users on 9/10. 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.
sáb. 12/63:40 pmMDW - CUN
Nonstop3h 45mSouthwest
sáb. 12/133:10 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 9/10$271
This Southwest deal was found by Cheapflights users on 9/9. 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.
dom. 11/1610:40 amMDW - CUN
Nonstop3h 45mSouthwest
mié. 11/191:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 9/9$281
This Southwest deal was found by Cheapflights users on 9/11. 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.
sáb. 9/277:00 amMDW - CUN
1 stop7h 40mSouthwest
sáb. 10/412:00 pmCUN - MDW
Nonstop3h 35mSouthwest
Deal found 9/11$285
This Southwest deal was found by Cheapflights users on 9/10. 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.
mar. 9/169:55 amMDW - CUN
Nonstop3h 35mSouthwest
sáb. 9/202:25 pmCUN - MDW
Nonstop3h 40mSouthwest
Deal found 9/10$286
This Southwest deal was found by Cheapflights users on 9/9. 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.
sáb. 11/83:40 pmMDW - CUN
Nonstop3h 45mSouthwest
sáb. 11/158:40 amCUN - MDW
1 stop9h 05mSouthwest
Deal found 9/9$291
This Southwest deal was found by Cheapflights users on 9/11. 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.
mar. 10/289:40 amMDW - CUN
Nonstop3h 35mSouthwest
mar. 11/45:05 pmCUN - MDW
1 stop6h 30mSouthwest
Deal found 9/11$294
This Southwest deal was found by Cheapflights users on 9/11. 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.
sáb. 11/18:20 amMDW - CUN
2 stops11h 30mSouthwest
mar. 11/41:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 9/11$295
This Southwest deal was found by Cheapflights users on 9/10. 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.
sáb. 11/83:40 pmMDW - CUN
Nonstop3h 45mSouthwest
jue. 11/132:25 pmCUN - MDW
1 stop7h 05mSouthwest
Deal found 9/10$299
This Southwest deal was found by Cheapflights users on 9/11. 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.
lun. 9/159:55 amMDW - CUN
Nonstop3h 35mSouthwest
mié. 9/173:10 pmCUN - MDW
Nonstop3h 40mSouthwest
Deal found 9/11$301
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
sáb. 11/16:30 amMDW - CUN
1 stop27h 47mMultiple Airlines
vie. 11/710:37 amCUN - MDW
1 stop27h 00mMultiple Airlines
Deal found 9/10$302
This Delta deal was found by Cheapflights users on 9/9. 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.
dom. 12/286:00 pmMDW - CZM
2 stops20h 15mDelta
jue. 1/83:15 pmCZM - MDW
2 stops17h 35mDelta
Deal found 9/9$502

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 septiembre 11, 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

sáb. 12/6

3:40 pm-8:25 pm

Nonstop3h 45m

Cancun

sáb. 12/13

3:10 pm-5:55 pm

Nonstop3h 45m

$271

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

dom. 11/16

10:40 am-3:25 pm

Nonstop3h 45m

Cancun

mié. 11/19

1:45 pm-4:30 pm

Nonstop3h 45m

$281

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

sáb. 11/1

11:45 am-7:50 pm

1 stop8h 05m

Cancun

sáb. 11/8

3:10 pm-5:55 pm

Nonstop3h 45m

$285

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

mar. 9/23

9:55 am-1:30 pm

Nonstop3h 35m

Cancun

sáb. 9/27

10:45 am-5:20 pm

1 stop6h 35m

$306

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

sáb. 10/25

5:15 am-1:05 pm

1 stop7h 50m

Cancun

jue. 10/30

1:05 pm-12:25 am

1 stop11h 20m

$314

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

mié. 10/29

6:15 am-1:40 pm

1 stop7h 25m

Cancun

mié. 11/5

8:20 am-5:00 pm

1 stop9h 40m

$322

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

mar. 10/28

7:55 am-2:20 pm

1 stop6h 25m

Cancun

mar. 11/4

5:05 pm-10:35 pm

1 stop6h 30m

$322

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

mar. 11/11

5:35 am-4:25 pm

1 stop9h 50m

Cancun

mar. 11/18

5:05 pm-10:35 pm

1 stop6h 30m

$322

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

jue. 11/27

6:00 am-9:20 pm

1 stop14h 20m

Cancun

mié. 12/3

8:00 am-4:36 pm

1 stop9h 36m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

dom. 9/28

6:00 am-2:20 pm

1 stop8h 20m

Cancun

sáb. 10/4

8:00 am-9:10 pm

1 stop13h 10m

$326

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 40 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, 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 septiembre 11, 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 septiembre 11, 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
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

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
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

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
1,847 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

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
7.5
Good
1,701 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

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
6.6
Okay
1,155 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

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 $271, Southwest can have you in Quintana Roo from Chicago Midway Airport in 3h 45m. There are 1434 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 flights from Chicago Midway Airport to Quintana Roo?

    On average you can expect to pay $297 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 $313.

  • 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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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 septiembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$490FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$241Average$333FlexibilityNo cancel feeOn-time65%
AeromexicoCheapest$312Average$506FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$345Average$577FlexibilityNo cancel feeOn-time63%
FrontierCheapest$362Average$565FlexibilityNo cancel feeOn-time62%
DeltaCheapest$380Average$609FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$486Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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