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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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — MDW
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$273
(Southwest)

One-way from

$149
(Southwest)

Popular in

June

Cheapest in

January

Average price

$301

Good round-trip deal

$321 or less

Good one-way deal

$148 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. 13% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This Delta deal was found by Cheapflights users on 7/31. 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 10/248:00 amCUN - MDW
2 stops10h 25mDelta
Fri 10/3110:35 amMDW - CUN
1 stop9h 45mDelta
Deal found 7/31$276
This Aeromexico deal was found by Cheapflights users on 7/31. 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.
Thu 10/93:14 pmCUN - MDW
1 stop7h 00mAeromexico
Sun 10/126:00 amMDW - CUN
2 stops11h 45mAeromexico
Deal found 7/31$287
This Southwest deal was found by Cheapflights users on 7/31. 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 9/61:15 pmCUN - MDW
1 stop7h 30mSouthwest
Tue 9/99:55 amMDW - CUN
Nonstop3h 35mSouthwest
Deal found 7/31$289
This Frontier deal was found by Cheapflights users on 7/31. 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.
Sat 10/181:41 pmCUN - MDW
1 stop9h 28mFrontier
Sat 10/256:10 amMDW - CUN
1 stop6h 16mFrontier
Deal found 7/31$296
This Flightnetwork deal was found by Cheapflights users on 7/31. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/88:00 amCUN - MDW
1 stop11h 16mMultiple Airlines
Thu 10/97:23 pmMDW - CUN
1 stop17h 03mMultiple Airlines
Deal found 7/31$431

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 July 31, 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 10/24

8:00 am-6:25 pm

2 stops10h 25m

Chicago Midway

Fri 10/31

10:35 am-8:20 pm

1 stop9h 45m

$276

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Thu 10/9

3:14 pm-10:14 pm

1 stop7h 00m

Chicago Midway

Sun 10/12

6:00 am-5:45 pm

2 stops11h 45m

$287

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 9/6

1:15 pm-8:45 pm

1 stop7h 30m

Chicago Midway

Tue 9/9

9:55 am-1:30 pm

Nonstop3h 35m

$289

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 10/18

1:41 pm-11:09 pm

1 stop9h 28m

Chicago Midway

Sat 10/25

6:10 am-12:26 pm

1 stop6h 16m

$296

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 10/8

8:00 am-7:16 pm

1 stop11h 16m

Chicago Midway

Thu 10/9

7:23 pm-12:26 pm

1 stop17h 03m

$431

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 10/31

3:15 pm-6:50 pm

Nonstop3h 35m

$149

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Fri 9/5

8:00 am-9:26 pm

1 stop13h 26m

$175

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 10/4

7:05 am-9:10 pm

2 stops14h 05m

$185

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Sat 8/16

9:04 am-8:22 pm

1 stop11h 18m

$186

CancúnChicago

CUN - MDW

CUNMDW

Cancun

Wed 10/29

7:39 am-4:50 pm

1 stop9h 11m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 11 results
1
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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 July 31, 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.

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 July 31, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Aeromexico from Quintana Roo to Chicago Midway Airport to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Aeromexico
7.5
Good
1,721 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Volaris
6.6
Okay
1,164 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,239 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $149 on Southwest. Other airlines that offer cheap prices include Delta from $175 and Aeromexico from $179 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 $238, our data shows the cheapest flight currently is $148. When looking at the most popular route, (Cancun - Chicago Midway), you can expect to pay $273 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
Valparaiso
Chesterton

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