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$149+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — MDW
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Delta deal was found by Cheapflights users on 1/28. 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 2/121:40 pm
CUN
-
MDW
1 stop9h 51m
Delta
Tue 2/1712:45 pm
MDW
-
CUN
1 stop7h 26m
Delta
Deal found 1/28$281
This Delta deal was found by Cheapflights users on 1/27. 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 1/304:40 pm
CUN
-
MDW
1 stop6h 42m
Delta
Mon 2/26:00 am
MDW
-
CUN
1 stop9h 35m
Delta
Deal found 1/27$282
This Aeromexico deal was found by Cheapflights users on 1/28. 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 2/68:00 am
CUN
-
MDW
1 stop10h 29m
Aeromexico
Mon 2/96:00 am
MDW
-
CUN
1 stop9h 35m
Aeromexico
Deal found 1/28$283
This Priceline deal was found by Cheapflights users on 1/26. 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 4/2311:30 am
CUN
-
MDW
1 stop10h 51m
Frontier
Mon 4/276:00 am
MDW
-
CUN
1 stop8h 56m
Frontier
Deal found 1/26$287
This Frontier deal was found by Cheapflights users on 1/27. 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 2/1911:48 am
CUN
-
MDW
1 stop10h 24m
Frontier
Mon 2/236:00 am
MDW
-
CUN
1 stop6h 37m
Frontier
Deal found 1/27$305
This Southwest deal was found by Cheapflights users on 1/27. 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 1/301:45 pm
CUN
-
MDW
Nonstop3h 45m
Southwest
Mon 2/29:15 am
MDW
-
CUN
Nonstop3h 40m
Southwest
Deal found 1/27$306
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/143:07 pm
CUN
-
MDW
Nonstop4h 06m
Multiple Airlines
Sat 3/217:54 pm
MDW
-
CUN
1 stop13h 54m
Multiple Airlines
Deal found 1/28$310
This Frontier deal was found by Cheapflights users on 1/27. 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 4/1610:34 am
CUN
-
MDW
2 stops21h 30m
Frontier
Tue 4/216:00 am
MDW
-
CUN
1 stop8h 56m
Frontier
Deal found 1/27$317
This Southwest deal was found by Cheapflights users on 1/28. 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 2/193:00 pm
CUN
-
MDW
Nonstop3h 45m
Southwest
Mon 2/2310:35 am
MDW
-
CUN
Nonstop3h 40m
Southwest
Deal found 1/28$332
This Southwest deal was found by Cheapflights users on 1/28. 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 2/133:40 pm
CUN
-
MDW
Nonstop3h 40m
Southwest
Mon 2/1610:45 am
MDW
-
CUN
Nonstop3h 40m
Southwest
Deal found 1/28$337
This Delta deal was found by Cheapflights users on 1/28. 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 4/168:00 am
CUN
-
MDW
1 stop8h 29m
Delta
Tue 4/219:27 am
MDW
-
CUN
2 stops10h 47m
Delta
Deal found 1/28$339

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$281
(Delta)

One-way from

$149
(Southwest)

Popular in

September

Cheapest in

February

Average price

$227

Good one-way deal

$348 or less
Provider with most accurate pricing for Cancun-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Cancun-Chicago (CHI) flights.
Search Deals
From Quintana Roo to Chicago Midway
Search Deals
One-way flight from Quintana Roo to Chicago Midway
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a one-way flight from Quintana Roo to Chicago Midway.
Search Deals

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 January 29, 2026.
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

11:00 am-5:45 pm

1 stop7h 45m

Chicago Midway

Mon 2/16

6:00 am-4:45 pm

1 stop9h 45m

$281

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 2/12

1:40 pm-10:31 pm

1 stop9h 51m

Chicago Midway

Tue 2/17

12:45 pm-9:11 pm

1 stop7h 26m

$281

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 4/23

11:30 am-10:21 pm

1 stop10h 51m

Chicago Midway

Mon 4/27

6:00 am-2:56 pm

1 stop8h 56m

$283

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 2/12

3:40 pm-6:20 pm

Nonstop3h 40m

Chicago Midway

Tue 2/17

10:35 am-3:15 pm

Nonstop3h 40m

$306

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 2/19

3:00 pm-5:45 pm

Nonstop3h 45m

Chicago Midway

Mon 2/23

10:35 am-3:15 pm

Nonstop3h 40m

$332

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 2/13

3:40 pm-6:20 pm

Nonstop3h 40m

Chicago Midway

Mon 2/16

10:45 am-3:25 pm

Nonstop3h 40m

$337

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 5/14

11:30 am-8:04 am

2 stops20h 34m

Chicago Midway

Tue 5/19

6:00 am-2:56 pm

1 stop8h 56m

$339

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 4/17

10:00 am-4:29 pm

1 stop6h 29m

Chicago Midway

Wed 4/22

10:43 am-8:14 pm

1 stop9h 31m

$341

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 4/23

8:05 am-10:28 pm

2 stops14h 23m

Chicago Midway

Mon 4/27

6:00 am-4:40 pm

2 stops10h 40m

$341

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 3/12

2:05 pm-5:50 pm

Nonstop3h 45m

$156

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 20 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 January 29, 2026.

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.

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 3h 40m. Fly via Delta, Frontier, or Southwest to get the fastest option. There are 1434 mi between Quintana Roo and Chicago Midway Airport. This flight may include one or multiple stops.

  • 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 $370, our data shows the cheapest flight currently is $253. When looking at the most popular route, (Cancun - Chicago Midway), you can expect to pay $282 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.

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
Merrillville
Hammond
Porter
Benton Harbor

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