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Quintana Roo

$120+ 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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
dic. 5 — dic. 121
vie. 12/5
vie. 12/12
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 noviembre 5, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$262
(Southwest)

One-way from

$120
(Southwest)

Popular in

March

Cheapest in

September

Average price

$446

Good round-trip deal

$281 or less

Good one-way deal

$124 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 ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in November 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 noviembre 5, 2025.

This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/153:40 pmMDW - CUN
Nonstop3h 45mSouthwest
sáb. 11/2211:20 amCUN - MDW
Nonstop3h 40mSouthwest
Deal found 11/3$277
This Southwest deal was found by Cheapflights users on 11/3. 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 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. 11/1511:20 amCUN - MDW
2 stops8h 45mSouthwest
Deal found 11/3$292
This Southwest deal was found by Cheapflights users on 11/3. 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 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
mié. 11/125:05 pmCUN - MDW
1 stop6h 30mSouthwest
Deal found 11/3$297
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/95:55 amMDW - CUN
1 stop6h 10mSouthwest
jue. 11/139:40 amCUN - MDW
1 stop11h 05mSouthwest
Deal found 11/3$307
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/59:20 amMDW - CUN
1 stop10h 05mSouthwest
mié. 12/101:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 11/3$310
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/85:35 amMDW - CUN
2 stops10h 25mSouthwest
jue. 12/111:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 11/3$314
This Southwest deal was found by Cheapflights users on 11/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/19:45 amMDW - CUN
2 stops9h 40mSouthwest
sáb. 12/204:25 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 11/2$315
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/185:25 amMDW - CUN
1 stop9h 00mSouthwest
sáb. 11/224:25 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 11/3$317
This Delta deal was found by Cheapflights users on 11/3. 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.
jue. 11/1310:47 amMDW - CUN
1 stop9h 33mDelta
vie. 11/211:32 pmCUN - MDW
1 stop11h 08mDelta
Deal found 11/3$318
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/108:50 amMDW - CUN
2 stops10h 35mSouthwest
sáb. 12/204:25 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 11/3$319
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/52:59 pmMDW - CZM
2 stops26h 17mMultiple Airlines
jue. 12/112:50 pmCZM - MDW
1 stop24h 30mMultiple Airlines
Deal found 11/4$533
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/52:59 pmMDW - CZM
2 stops26h 17mMultiple Airlines
sáb. 12/132:50 pmCZM - MDW
1 stop19h 15mMultiple Airlines
Deal found 11/4$566

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 noviembre 5, 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. 11/8

3:40 pm-8:25 pm

Nonstop3h 45m

Cancun

sáb. 11/15

11:20 am-6:35 pm

1 stop8h 15m

$292

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

dom. 1/11

6:45 am-9:11 pm

1 stop13h 26m

Cancun

jue. 1/15

1:40 pm-10:09 pm

1 stop9h 29m

$327

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

dom. 2/1

6:00 am-4:45 pm

1 stop9h 45m

Cancun

vie. 2/6

4:40 pm-10:26 pm

1 stop6h 46m

$327

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

sáb. 1/17

6:45 am-9:11 pm

1 stop13h 26m

Cancun

sáb. 1/24

8:00 am-3:40 pm

1 stop8h 40m

$327

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

lun. 1/5

6:45 am-2:03 pm

1 stop6h 18m

Cancun

jue. 1/15

4:40 pm-10:09 pm

1 stop6h 29m

$327

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

dom. 11/30

6:00 am-3:34 pm

1 stop8h 34m

Cancun

sáb. 12/6

8:00 am-3:44 pm

1 stop8h 44m

$327

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

mar. 2/3

9:34 am-9:11 pm

2 stops10h 37m

Cancun

vie. 2/6

12:05 pm-10:26 pm

2 stops11h 21m

$331

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

dom. 12/7

9:34 am-9:20 pm

2 stops10h 46m

Cancun

vie. 12/12

12:00 pm-11:47 pm

1 stop12h 47m

$331

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

sáb. 1/10

9:34 am-9:11 pm

2 stops10h 37m

Cancun

mié. 1/21

12:05 pm-10:26 pm

2 stops11h 21m

$331

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

lun. 11/17

9:34 am-9:20 pm

2 stops10h 46m

Cancun

vie. 11/21

8:00 am-6:14 pm

2 stops11h 14m

$351

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

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, 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 noviembre 5, 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 noviembre 5, 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
4,240 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
4,240 reviews
Southwest
8.0
Very good
4,240 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
8,004 reviews
Southwest
8.0
Very good
4,240 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
1,874 reviews
Southwest
8.0
Very good
4,240 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
1,672 reviews
Southwest
8.0
Very good
4,240 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
1,151 reviews
Southwest
8.0
Very good
4,240 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 $292, 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 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 $130. However, be on the lookout for offers from Delta and Aeromexico, 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 $324 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 $267.

  • 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 noviembre 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$490FlexibilityNo cancel feeOn-time69%
AeromexicoCheapest$312Average$510FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$345Average$572FlexibilityNo cancel feeOn-time63%
FrontierCheapest$362Average$567FlexibilityNo cancel feeOn-time62%
DeltaCheapest$380Average$618FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$486Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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