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Playa del Carmen

$116+ 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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1. Tell us where you want to go

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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 Thursday and return on a Thursday

Cheap 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 December 28, 2025.

This Delta deal was found by Cheapflights users on 12/27. 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.
Tue 12/305:59 pmMDW - CUN
1 stop17h 11mDelta
Wed 1/143:13 pmCUN - MDW
1 stop7h 54mDelta
Deal found 12/27$327
This Delta deal was found by Cheapflights users on 12/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/299:29 amMDW - CUN
2 stops23h 46mDelta
Wed 12/315:30 pmCUN - MDW
2 stops16h 19mDelta
Deal found 12/26$331
This Delta deal was found by Cheapflights users on 12/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:08 pmMDW - CUN
1 stop16h 07mDelta
Tue 1/65:25 pmCUN - MDW
1 stop16h 43mDelta
Deal found 12/26$420
This Aeromexico deal was found by Cheapflights users on 12/27. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3012:45 pmMDW - CUN
1 stop7h 35mAeromexico
Wed 12/311:40 pmCUN - MDW
1 stop9h 42mAeromexico
Deal found 12/27$461
This Delta deal was found by Cheapflights users on 12/25. 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 12/319:50 amMDW - CUN
1 stop5h 40mDelta
Wed 1/71:40 pmCUN - MDW
1 stop9h 27mDelta
Deal found 12/25$467
This Delta deal was found by Cheapflights users on 12/25. 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 12/313:29 pmMDW - CUN
2 stops19h 34mDelta
Mon 1/55:45 pmCUN - MDW
2 stops16h 07mDelta
Deal found 12/25$478
This Delta deal was found by Cheapflights users on 12/27. 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.
Tue 12/305:59 pmMDW - CUN
1 stop17h 11mDelta
Thu 1/15:30 pmCUN - MDW
1 stop16h 35mDelta
Deal found 12/27$479

Find 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 December 28, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$291
(CheapOair)

One-way from

$116
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$710
Provider with most accurate pricing for Chicago (CHI)-Cancun flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Cancun flights.
Search Deals
From Chicago Midway to Playa del Carmen
Search Deals
One-way flight from Chicago Midway to Playa del Carmen
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($77 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 28, 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

Sun 1/25

6:00 am-2:03 pm

1 stop7h 03m

Cancun

Fri 1/30

1:40 pm-10:22 pm

1 stop9h 42m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 1/7

11:21 am-9:11 pm

1 stop8h 50m

Cancun

Tue 1/13

8:00 am-4:29 pm

1 stop9h 29m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 2/7

6:25 am-8:02 pm

2 stops12h 37m

Cancun

Sat 2/14

8:00 am-3:21 pm

1 stop8h 21m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 2/15

6:00 am-6:47 pm

2 stops11h 47m

Cancun

Mon 2/23

8:00 am-5:45 pm

1 stop10h 45m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 1/1

6:00 am-1:46 pm

1 stop6h 46m

Cancun

Sat 1/10

5:10 pm-8:52 am

1 stop16h 42m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 1/23

6:00 am-4:35 pm

1 stop9h 35m

Cancun

Tue 1/27

4:40 pm-10:22 pm

1 stop6h 42m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 2/28

11:06 am-9:11 pm

1 stop9h 05m

Cancun

Sun 3/8

3:25 pm-10:31 pm

1 stop7h 06m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 2/28

11:06 am-9:11 pm

1 stop9h 05m

Cancun

Tue 3/3

8:00 am-5:45 pm

1 stop10h 45m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 2/28

11:06 am-9:11 pm

1 stop9h 05m

Cancun

Sat 3/7

12:15 pm-10:31 pm

1 stop11h 16m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 2/27

6:00 am-3:35 pm

1 stop8h 35m

Cancun

Mon 3/2

11:00 am-5:45 pm

1 stop7h 45m

$333

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

Showing 1-10 of 21 results
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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 December 26, 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, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Playa del Carmen (average of $254). Flying from Chicago Midway Airport to Playa del Carmen in January is currently the most expensive (average of $430). 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 December 28, 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.

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 December 28, 2025.
See what other customers who have flown with Southwest, Delta, and Aeromexico 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
4,256 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,256 reviews
Southwest
8.0
Very good
4,256 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,018 reviews
Southwest
8.0
Very good
4,256 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Aeromexico
7.4
Good
1,622 reviews
Southwest
8.0
Very good
4,256 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,113 reviews
Southwest
8.0
Very good
4,256 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,064 reviews
Southwest
8.0
Very good
4,256 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 7h 03m. Fly via Delta to get the fastest option. There are 1434 mi between Chicago Midway Airport and Playa del Carmen.

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

    Looking at all options, your cheapest flight can be booked for $97. While the most popular route (Chicago Midway - Cancun) can be booked for $286 on average, our data indicates $350 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, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Playa del Carmen (average of $254). Flying from Chicago Midway Airport to Playa del Carmen in January is currently the most expensive (average of $430). 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 6 airlines flying from Midway to Playa del Carmen

Discover the top 6 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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$419FlexibilityNo cancel feeOn-time69%
AeromexicoCheapest$309Average$398FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$312Average$546FlexibilityNo cancel feeOn-time63%
FrontierCheapest$362Average$528FlexibilityNo cancel feeOn-time62%
DeltaCheapest$375Average$3,628FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$506Average$667FlexibilityNo cancel feeOn-time71%

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