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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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — MDW
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$265
(Southwest)

One-way from

$144
(Southwest)

Popular in

September

Cheapest in

January

Average price

$239
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. 15% potential increase in price ($51 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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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 November 6, 2025.

This Delta deal was found by Cheapflights users on 11/5. 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.
Fri 12/54:34 pmCUN - MDW
1 stop8h 13mDelta
Tue 12/912:50 pmMDW - CUN
1 stop7h 30mDelta
Deal found 11/5$275
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.
Wed 11/268:00 amCUN - MDW
2 stops11h 08mDelta
Mon 12/16:00 amMDW - CUN
1 stop8h 34mDelta
Deal found 11/3$276
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1411:50 amCUN - MDW
1 stop12h 50mDelta
Mon 11/179:34 amMDW - CUN
2 stops10h 46mDelta
Deal found 11/4$277
This Delta deal was found by Cheapflights users on 11/5. 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.
Fri 12/58:00 amCUN - MDW
2 stops11h 00mDelta
Fri 12/129:34 amMDW - CUN
2 stops10h 46mDelta
Deal found 11/5$326
This Delta deal was found by Cheapflights users on 11/6. 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.
Fri 12/2611:25 amCUN - MDW
1 stop11h 57mDelta
Mon 1/59:34 amMDW - CUN
2 stops10h 37mDelta
Deal found 11/6$327
This Delta deal was found by Cheapflights users on 11/5. 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.
Fri 11/74:17 pmCUN - MDW
1 stop6h 57mDelta
Mon 11/106:00 amMDW - CUN
1 stop5h 22mDelta
Deal found 11/5$332
This Southwest deal was found by Cheapflights users on 11/6. 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.
Thu 11/132:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Mon 11/178:40 amMDW - CUN
Nonstop3h 45mSouthwest
Deal found 11/6$338
This Priceline deal was found by Cheapflights users on 11/5. 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.
Fri 12/122:33 pmCUN - MDW
1 stop8h 39mFrontier
Mon 12/156:15 amMDW - CUN
1 stop6h 33mFrontier
Deal found 11/5$358
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.
Wed 11/262:30 pmCUN - MDW
Nonstop3h 45mSouthwest
Mon 12/19:45 amMDW - CUN
1 stop9h 40mSouthwest
Deal found 11/3$359

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 November 6, 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 2/13

8:00 am-10:44 pm

1 stop15h 44m

Chicago Midway

Tue 2/17

9:34 am-9:10 pm

2 stops10h 36m

$274

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 1/23

4:40 pm-10:26 pm

1 stop6h 46m

Chicago Midway

Mon 1/26

6:00 am-4:45 pm

1 stop9h 45m

$275

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 12/5

8:00 am-4:18 pm

1 stop9h 18m

Chicago Midway

Tue 12/9

9:34 am-9:20 pm

2 stops10h 46m

$275

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 1/14

12:05 pm-10:09 pm

2 stops11h 04m

Chicago Midway

Sat 1/17

6:45 am-9:11 pm

1 stop13h 26m

$275

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 11/26

8:00 am-6:08 pm

2 stops11h 08m

Chicago Midway

Mon 12/1

6:00 am-3:34 pm

1 stop8h 34m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 2/12

3:40 pm-6:20 pm

Nonstop3h 40m

$144

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 2/14

11:00 am-1:35 pm

Nonstop3h 35m

$149

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 11/22

11:00 am-11:40 pm

1 stop13h 40m

$174

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 2/6

12:05 pm-10:26 pm

2 stops11h 21m

$175

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Tue 2/3

1:40 pm-10:26 pm

1 stop9h 46m

$175

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 17 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 November 6, 2025.

One of the essential ways to save on airfare from Quintana Roo to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 75% on airfare.

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 15h 44m. Fly via Delta to get the fastest option. There are 1434 mi between Quintana Roo and Chicago Midway Airport.

  • 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.

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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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