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Playa del Carmen

$119+ Cheap flights from Midway (MDW) to Playa del Carmen, Mexico

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 10/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Playa del Carmen are usually found in September or July, booked 57 days in advance, depart on a Monday or Tuesday and return on a Tuesday

Cheap flight deals from Midway to Playa del Carmen

Keep the following information in mind while searching for Midway to Playa del Carmen flight deals. Data was last updated September 16, 2025.

Round-trip from

$261
(Southwest)

One-way from

$119
(Southwest)

Popular in

December

Cheapest in

September

Average price

$430
From Chicago Midway to Playa del Carmen
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One-way flight from Chicago Midway to Playa del Carmen
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Highest demand for flights based on searches. 15% potential increase in price ($107 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midway to Playa del Carmen

Cheapest flights from Midway to Playa del Carmen
Explore the most affordable flight options available from Midway to Playa del Carmen. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1610:40 amMDW - CUN
Nonstop3h 45mSouthwest
Wed 11/191:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 9/15$261
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/153:40 pmMDW - CUN
Nonstop3h 45mSouthwest
Wed 11/191:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 9/15$266
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.
Sat 12/63:40 pmMDW - CUN
Nonstop3h 45mSouthwest
Fri 12/122:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 9/14$270
This Southwest deal was found by Cheapflights users on 9/16. 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.
Sat 12/63:40 pmMDW - CUN
Nonstop3h 45mSouthwest
Sat 12/1311:55 amCUN - MDW
Nonstop3h 50mSouthwest
Deal found 9/16$271
This Southwest deal was found by Cheapflights users on 9/16. 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.
Sun 9/2810:35 amMDW - CUN
Nonstop3h 35mSouthwest
Thu 10/23:20 pmCUN - MDW
Nonstop3h 35mSouthwest
Deal found 9/16$281
This Southwest deal was found by Cheapflights users on 9/16. 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.
Tue 9/309:55 amMDW - CUN
Nonstop3h 35mSouthwest
Sat 10/41:20 pmCUN - MDW
1 stop5h 45mSouthwest
Deal found 9/16$286
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/155:50 amMDW - CUN
2 stops9h 15mSouthwest
Thu 11/201:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 9/15$290
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/289:40 amMDW - CUN
Nonstop3h 35mSouthwest
Sat 11/111:55 amCUN - MDW
2 stops8h 25mSouthwest
Deal found 9/15$291

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Playa del Carmen 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 16, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Playa del Carmen that are best for you.

Fly from

Midway

Fly to

Playa del Carmen

Route

Depart

Return

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 12/6

3:40 pm-8:25 pm

Nonstop3h 45m

Cancun

Fri 12/12

2:15 pm-5:00 pm

Nonstop3h 45m

$270

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 9/28

10:35 am-2:10 pm

Nonstop3h 35m

Cancun

Thu 10/2

3:20 pm-6:55 pm

Nonstop3h 35m

$281

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/15

5:50 am-4:05 pm

2 stops9h 15m

Cancun

Wed 11/19

1:45 pm-4:30 pm

Nonstop3h 45m

$285

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 11/11

5:25 am-3:25 pm

1 stop9h 00m

Cancun

Sat 11/15

8:10 am-4:40 pm

1 stop9h 30m

$314

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 11/23

9:35 am-7:45 pm

1 stop9h 10m

Cancun

Wed 11/26

8:20 am-9:20 pm

2 stops14h 00m

$322

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 9/30

6:00 am-11:25 am

1 stop5h 25m

Cancun

Fri 10/3

8:00 am-9:36 pm

1 stop13h 36m

$326

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 10/18

10:35 am-11:25 am

2 stops24h 50m

Cancun

Wed 10/29

8:00 am-10:14 pm

1 stop14h 14m

$330

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 9/30

10:35 am-8:15 pm

1 stop9h 40m

Cancun

Tue 10/7

9:11 am-10:14 pm

2 stops13h 03m

$346

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 10/20

9:40 am-1:15 pm

Nonstop3h 35m

$119

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 9/29

9:55 am-1:30 pm

Nonstop3h 35m

$119

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 18 results
1
2

Best time to book a flight from Midway to Playa del Carmen

Have a flexible travel schedule? Discover the best time to fly to Playa del Carmen from Midway 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 Chicago Midway Airport to Playa del Carmen

How far ahead should I book a flight from Chicago Midway Airport to Playa del Carmen?

Use this chart to determine the optimal time to book a round-trip flight from Midway to Playa del Carmen. Price data was last updated on September 12, 2025.

The best time to book flights from Chicago Midway Airport to Playa del Carmen is 57 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago Midway Airport to Playa del Carmen?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Playa del Carmen (average of $360). Flying from Chicago Midway Airport to Playa del Carmen in March is currently the most expensive (average of $492). 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.

What is the cheapest time of day to fly from MDW to PL9?

Find hourly flight availability from Midway to Playa del Carmen. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Playa del Carmen as you normally would.

Weekly flight availability from Chicago Midway Airport to Playa del Carmen

Explore weekly flight availability from Midway to Playa del Carmen. 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 16, 2025.

The most flights from MDW to PL9 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).

Reviews of airlines servicing Playa del Carmen

Get insights into the airlines that provide service to Playa del Carmen. 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 Playa del Carmen. Reviews last updated September 16, 2025.
See what other customers who have flown with Southwest, Delta, and LATAM Airlines from Chicago Midway Airport to Playa del Carmen have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,957 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
LATAM Airlines
7.5
Good
1,847 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Aeromexico
7.5
Good
1,696 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Volaris
6.6
Okay
1,154 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midway to Playa del Carmen. 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 Chicago Midway Airport to Playa del Carmen?

    There are many flights that can get you from Chicago Midway Airport to Playa del Carmen in 3h 45m. Fly via Southwest to get the fastest option. There are 1434 mi between Chicago Midway Airport and Playa del Carmen. All flights are typically nonstop.

  • What are the cheapest flights from Chicago Midway Airport to Playa del Carmen?

    Looking at all options, your cheapest flight can be booked for $124. While the most popular route (Chicago Midway - Cancun) can be booked for $313 on average, our data indicates $312 when flying from Chicago Midway Airport to Playa del Carmen.

  • Can I find deals for flights from Midway to Playa del Carmen that include hotel bookings?

    Yes. In addition to deals on Midway to Playa del Carmen flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Playa del Carmen?

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

  • Can I find deals for business class flights from Midway to Playa del Carmen?

    Yes. Cheapflights offers flight deals from Midway to Playa del Carmen 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 Chicago Midway Airport to Playa del Carmen?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Playa del Carmen (average of $360). Flying from Chicago Midway Airport to Playa del Carmen in March is currently the most expensive (average of $492). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Midway to Playa del Carmen

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Cancún flights
Midway to Cancún flights
O'Hare Intl to Cozumel flights
Midway to Cozumel flights
O'Hare Intl to Chetumal flights

Top 7 airlines flying from Midway to Playa del Carmen

Discover the top 7 airlines that operate flights from Midway to Playa del Carmen. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$419FlexibilityNo cancel feeOn-time69%
AeromexicoCheapest$312Average$506FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$345Average$577FlexibilityNo cancel feeOn-time63%
FrontierCheapest$362Average$565FlexibilityNo cancel feeOn-time62%
DeltaCheapest$380Average$609FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$486Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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