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$137+ Cheap flights from Quintana Roo to Midway (MDW)

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 7/24. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — MDW
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
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Cheap flight deals from Quintana Roo to Midway

Keep the following information in mind while searching for Quintana Roo to Midway flight deals. Data was last updated April 17, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$249
(Southwest)

One-way from

$137
(Southwest)

Popular in

June

Cheapest in

January

Average price

$284

Good one-way deal

$267 or less
Provider with most accurate pricing for Cancun-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Cancun-Chicago (CHI) flights.
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From Quintana Roo to Chicago Midway
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One-way flight from Quintana Roo to Chicago Midway
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Highest demand for flights based on searches. 7% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 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 one-way flight from Quintana Roo to Chicago Midway.
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Find flight deals from Quintana Roo to Midway

Cheapest flights from Quintana Roo to Midway
Explore the most affordable flight options available from Quintana Roo to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2025.

This Southwest deal was found by Cheapflights users on 4/16. 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 4/309:00 amCUN - MDW
Nonstop3h 40mSouthwest
Mon 5/59:35 amMDW - CUN
Nonstop3h 35mSouthwest
Deal found 4/16$249
This Delta deal was found by Cheapflights users on 4/16. 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.
Thu 5/112:35 pmCUN - MDW
1 stop9h 47mDelta
Wed 5/710:25 amMDW - CUN
1 stop9h 55mDelta
Deal found 4/16$274
This Aeromexico deal was found by Cheapflights users on 4/16. 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 4/3012:35 pmCUN - MDW
1 stop9h 47mAeromexico
Mon 5/56:04 amMDW - CUN
1 stop5h 21mAeromexico
Deal found 4/16$319
This Booking.com deal was found by Cheapflights users on 4/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/13:15 pmCUN - MDW
1 stop27h 53mFrontier
Thu 5/156:30 pmMDW - CUN
1 stop18h 58mFrontier
Deal found 4/16$384
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Thu 5/12:00 pmCUN - MDW
1 stop8h 22mMultiple Airlines
Mon 5/52:45 pmMDW - CUN
2 stops9h 50mMultiple Airlines
Deal found 4/16$461
This eDestinos deal was found by Cheapflights users on 4/17. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/91:57 pmCUN - MDW
1 stop7h 25mVolaris
Sun 10/1210:41 pmMDW - CUN
1 stop14h 21mVolaris
Deal found 4/17$528
This WestJet deal was found by Cheapflights users on 4/17. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/2010:20 amCUN - MDW
2 stops23h 31mWestJet
Mon 7/211:05 pmMDW - CUN
2 stops20h 18mWestJet
Deal found 4/17$1,303
This Priceline deal was found by Cheapflights users on 4/17. 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.
Thu 6/51:20 amCUN - MDW
2 stops32h 20mLATAM Airlines
Sun 6/156:47 pmMDW - CUN
2 stops23h 48mLATAM Airlines
Deal found 4/17$2,291

Cheapflights Fare Finder

Customize your flight search to find flights from Quintana Roo to Midway 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 17, 2025.
Use the filters below to find and compare flights from Quintana Roo to Chicago Midway Airport that are best for you.

Fly from

Quintana Roo

Fly to

Midway

Route

Depart

Return

Price

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 4/30

9:00 am-12:40 pm

Nonstop3h 40m

Chicago Midway

Mon 5/5

9:35 am-1:10 pm

Nonstop3h 35m

$249

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 5/1

12:35 pm-10:22 pm

1 stop9h 47m

Chicago Midway

Wed 5/7

10:25 am-8:20 pm

1 stop9h 55m

$274

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 4/30

12:35 pm-10:22 pm

1 stop9h 47m

Chicago Midway

Mon 5/5

6:04 am-11:25 am

1 stop5h 21m

$319

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 5/1

3:15 pm-7:08 pm

1 stop27h 53m

Chicago Midway

Thu 5/15

6:30 pm-1:28 pm

1 stop18h 58m

$384

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 5/1

2:00 pm-10:22 pm

1 stop8h 22m

Chicago Midway

Mon 5/5

2:45 pm-12:35 am

2 stops9h 50m

$461

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 10/9

1:57 pm-9:22 pm

1 stop7h 25m

Chicago Midway

Sun 10/12

10:41 pm-1:02 pm

1 stop14h 21m

$528

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sun 7/20

10:20 am-9:51 am

2 stops23h 31m

Chicago Midway

Mon 7/21

1:05 pm-9:23 am

2 stops20h 18m

$1,303

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 6/5

1:20 am-9:40 am

2 stops32h 20m

Chicago Midway

Sun 6/15

6:47 pm-6:35 pm

2 stops23h 48m

$2,291

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 7/24

8:30 am-12:05 pm

Nonstop3h 35m

$137

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 5/14

9:55 am-6:45 pm

2 stops8h 50m

$174

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Showing 1-10 of 13 results
1
2

Best time to book a flight from Quintana Roo to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Quintana Roo 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 Quintana Roo to Chicago Midway Airport

What is the cheapest time of day to fly from QR to MDW?

Find hourly flight availability from Quintana Roo to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 17, 2025.

When flying from Quintana Roo to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated April 17, 2025.
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Crew

8.6

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
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Crew

8.6

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
7,917 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Crew

8.6

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.
LATAM Airlines
7.5
Good
1,761 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Crew

8.6

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
1,699 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Crew

8.6

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.
WestJet
7.2
Good
2,809 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Crew

8.6

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 Quintana Roo to Midway. 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 Quintana Roo to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $137 on Southwest. Other airlines that offer cheap prices include Delta from $174 and Frontier from $205 one-way.

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

    While on average a flight from Quintana Roo to Chicago Midway Airport is generally $338, our data shows the cheapest flight currently is $137. When looking at the most popular route, (Cancun - Chicago Midway), you can expect to pay $274 for that flight.

  • Can I find deals for flights from Quintana Roo to Midway that include hotel bookings?

    Yes. In addition to deals on Quintana Roo to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Quintana Roo to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Quintana Roo to Midway.

  • Can I find deals for business class flights from Quintana Roo to Midway?

    Yes. Cheapflights offers flight deals from Quintana Roo to Midway 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 Quintana Roo to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Quintana Roo to Chicago Midway Airport (average of $160). Flying from Quintana Roo to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Quintana Roo?

Book flights to Quintana Roo if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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