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$144+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — MDW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$270
(Frontier)

One-way from

$144
(Southwest)

Popular in

June

Cheapest in

January

Average price

$337

Good round-trip deal

$445 or less

Good one-way deal

$313 or less
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. 10% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 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 Quintana Roo to Chicago Midway.
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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 September 15, 2025.

This Frontier deal was found by Cheapflights users on 9/14. 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.
Fri 10/2411:16 amCUN - MDW
1 stop12h 04mFrontier
Fri 10/316:20 amMDW - CUN
1 stop5h 59mFrontier
Deal found 9/14$270
This Southwest deal was found by Cheapflights users on 9/14. 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.
Fri 12/262:30 pmCUN - MDW
Nonstop3h 45mSouthwest
Sat 1/35:55 amMDW - CUN
Nonstop3h 45mSouthwest
Deal found 9/14$275
This Delta deal was found by Cheapflights users on 9/15. 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 9/1812:35 pmCUN - MDW
1 stop9h 01mDelta
Mon 9/2212:43 pmMDW - CUN
1 stop7h 32mDelta
Deal found 9/15$276
This Southwest deal was found by Cheapflights users on 9/12. 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 11/151:50 pmCUN - MDW
1 stop6h 15mSouthwest
Tue 11/188:40 amMDW - CUN
Nonstop3h 45mSouthwest
Deal found 9/12$290
This Delta deal was found by Cheapflights users on 9/13. 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 10/238:00 amCUN - MDW
2 stops10h 25mDelta
Sun 10/2612:48 pmMDW - CUN
1 stop7h 32mDelta
Deal found 9/13$328
This Aeromexico deal was found by Cheapflights users on 9/15. 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.
Fri 12/53:07 pmCUN - MDW
1 stop9h 25mAeromexico
Tue 12/912:50 pmMDW - CUN
1 stop7h 30mAeromexico
Deal found 9/15$330
This Frontier deal was found by Cheapflights users on 9/14. 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.
Thu 10/301:30 pmCUN - MDW
1 stop8h 33mFrontier
Sun 11/25:20 amMDW - CUN
1 stop6h 00mFrontier
Deal found 9/14$331
This Priceline deal was found by Cheapflights users on 9/14. 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 12/65:13 pmCUN - MDW
1 stop6h 52mFrontier
Mon 12/86:00 amMDW - CUN
1 stop8h 58mFrontier
Deal found 9/14$335

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 September 15, 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

Fri 12/5

8:00 am-6:00 pm

2 stops11h 00m

Chicago Midway

Tue 12/9

12:50 pm-9:20 pm

1 stop7h 30m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 9/18

8:00 am-9:36 pm

1 stop13h 36m

Chicago Midway

Mon 9/22

10:35 am-8:15 pm

1 stop9h 40m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 11/15

1:50 pm-7:05 pm

1 stop6h 15m

Chicago Midway

Tue 11/18

8:40 am-1:25 pm

Nonstop3h 45m

$290

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 10/23

8:00 am-10:14 pm

1 stop14h 14m

Chicago Midway

Sun 10/26

12:48 pm-8:20 pm

1 stop7h 32m

$328

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 12/6

5:13 pm-11:05 pm

1 stop6h 52m

Chicago Midway

Mon 12/8

6:00 am-3:58 pm

1 stop8h 58m

$335

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 10/9

3:20 pm-6:55 pm

Nonstop3h 35m

$144

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 12/10

1:45 pm-4:30 pm

Nonstop3h 45m

$148

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 12/12

2:15 pm-5:00 pm

Nonstop3h 45m

$148

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 12/13

11:55 am-2:45 pm

Nonstop3h 50m

$149

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 9/25

3:10 pm-6:50 pm

Nonstop3h 40m

$164

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 14 results
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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 September 15, 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.

Weekly flight availability from Quintana Roo to Chicago Midway Airport

Explore weekly flight availability from Quintana Roo to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 15, 2025.

The most flights from MXQR to MDW are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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.

  • How long is the flight from Quintana Roo to Chicago Midway Airport?

    There are many flights that can get you from Quintana Roo to Chicago Midway Airport in 11h. Fly via Delta to get the fastest option. There are 1434 mi between Quintana Roo and Chicago Midway Airport.

  • 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 $466, our data shows the cheapest flight currently is $209. When looking at the most popular route, (Cancun - Chicago Midway), you can expect to pay $275 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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