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Playa del Carmen

$108+ 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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Mar 19 — Mar 261
Thu 3/19
Thu 3/26
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 February, booked 40 days in advance, depart on a Monday or Tuesday 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 February 17, 2026.

This Super.com deal was found by Cheapflights users on 2/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/79:00 am
MDW
-
CUN
Nonstop4h 02m
Frontier
Sat 3/143:07 pm
CUN
-
MDW
Nonstop4h 06m
Frontier
Deal found 2/16$252
This Gotogate deal was found by Cheapflights users on 2/15. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:54 pm
MDW
-
CUN
1 stop13h 54m
Multiple Airlines
Sat 3/73:07 pm
CUN
-
MDW
Nonstop4h 06m
Multiple Airlines
Deal found 2/15$265
This Trip.com deal was found by Cheapflights users on 2/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:54 pm
MDW
-
CUN
1 stop13h 54m
Multiple Airlines
Sat 3/143:07 pm
CUN
-
MDW
Nonstop4h 06m
Multiple Airlines
Deal found 2/16$285
This FlightHub deal was found by Cheapflights users on 2/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:54 pm
MDW
-
CUN
1 stop13h 54m
Volaris
Thu 3/1210:39 am
CUN
-
MDW
1 stop7h 55m
Volaris
Deal found 2/14$290
This FlightHub deal was found by Cheapflights users on 2/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:54 pm
MDW
-
CUN
1 stop13h 54m
Volaris
Fri 3/1310:39 am
CUN
-
MDW
1 stop7h 55m
Volaris
Deal found 2/13$291
This Southwest deal was found by Cheapflights users on 2/13. 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 3/84:35 pm
MDW
-
CUN
Nonstop3h 40m
Southwest
Thu 3/122:05 pm
CUN
-
MDW
Nonstop3h 45m
Southwest
Deal found 2/13$293
This Southwest deal was found by Cheapflights users on 2/16. 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.
Fri 3/64:05 pm
MDW
-
CUN
Nonstop3h 40m
Southwest
Fri 3/138:30 am
CUN
-
MDW
Nonstop3h 40m
Southwest
Deal found 2/16$298
This Mytrip deal was found by Cheapflights users on 2/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:54 pm
MDW
-
CUN
1 stop13h 54m
Volaris
Thu 3/1210:39 am
CUN
-
MDW
1 stop7h 55m
Volaris
Deal found 2/15$301

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 February 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$252
(Super.com)

One-way from

$108
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$402
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. 5% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 17, 2026.
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 3/8

4:35 pm-8:15 pm

Nonstop3h 40m

Cancun

Wed 3/11

8:30 am-12:10 pm

Nonstop3h 40m

$293

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 3/8

4:35 pm-8:15 pm

Nonstop3h 40m

Cancun

Fri 3/13

8:30 am-12:10 pm

Nonstop3h 40m

$298

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 3/6

4:05 pm-8:45 pm

Nonstop3h 40m

Cancun

Mon 3/9

8:30 am-12:10 pm

Nonstop3h 40m

$303

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 3/22

6:34 pm-9:50 am

1 stop15h 16m

Cancun

Wed 3/25

10:50 am-5:54 pm

1 stop7h 04m

$338

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 3/24

6:00 am-11:34 am

1 stop5h 34m

Cancun

Wed 3/25

3:25 pm-10:31 pm

1 stop7h 06m

$338

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 3/22

6:34 pm-9:50 am

1 stop15h 16m

Cancun

Thu 3/26

8:00 am-10:31 pm

1 stop14h 31m

$338

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 2/27

6:00 am-4:45 pm

1 stop9h 45m

Cancun

Thu 3/5

8:00 am-5:45 pm

1 stop10h 45m

$338

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 3/17

10:45 am-8:20 pm

1 stop9h 35m

Cancun

Thu 3/26

3:25 pm-10:31 pm

1 stop7h 06m

$338

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 2/27

6:00 am-4:45 pm

1 stop9h 45m

Cancun

Wed 3/4

8:00 am-10:31 pm

1 stop15h 31m

$338

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 2/26

10:49 am-9:11 pm

1 stop9h 22m

Cancun

Tue 3/3

3:13 pm-10:33 pm

1 stop8h 20m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/16

Showing 1-10 of 20 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 February 13, 2026.

The best time to book flights from Chicago Midway Airport to Playa del Carmen is 40 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, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Playa del Carmen (average of $198). Flying from Chicago Midway Airport to Playa del Carmen in August is currently the most expensive (average of $376). 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 February 17, 2026.

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 February 17, 2026.
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
4,290 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

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
4,290 reviews
Southwest
8.0
Very good
4,290 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

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
8,206 reviews
Southwest
8.0
Very good
4,290 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

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
1,575 reviews
Southwest
8.0
Very good
4,290 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

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
5.7
Fair
3,047 reviews
Southwest
8.0
Very good
4,290 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

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

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

    Looking at all options, your cheapest flight can be booked for $168. While the most popular route (Chicago Midway - Cancun) can be booked for $249 on average, our data indicates $438 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, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Playa del Carmen (average of $198). Flying from Chicago Midway Airport to Playa del Carmen in August is currently the most expensive (average of $376). 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

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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 4 airlines flying from Midway to Playa del Carmen

Discover the top 4 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 February 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$198Average$445FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$293Average$520FlexibilityNo cancel feeOn-time63%
AeromexicoCheapest$309Average$398FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$358Average$3,633FlexibilityNo cancel feeOn-timeN/A

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