HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Playa del Carmen with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Midway to Playa del Carmen

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Playa del Carmen (PL9). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$300
(Kiwi.com)

One-way from

$116
(Southwest)

Popular in

June

Cheapest in

February

Average price

$692
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. 7% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2025
Search Deals

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 January 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 1/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/225:10 amMDW - CUN
1 stop27h 46mFrontier
Wed 2/263:49 pmCUN - MDW
1 stop9h 28mFrontier
Deal found 1/21$300
This Southwest deal was found by Cheapflights users on 1/21. 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 4/276:55 amMDW - CUN
1 stop7h 55mSouthwest
Thu 5/19:00 amCUN - MDW
Nonstop3h 40mSouthwest
Deal found 1/21$313
This Expedia deal was found by Cheapflights users on 1/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/510:57 amMDW - CUN
1 stop9h 08mMultiple Airlines
Wed 2/123:49 pmCUN - MDW
1 stop9h 28mMultiple Airlines
Deal found 1/20$318
This Delta deal was found by Cheapflights users on 1/21. 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 4/146:00 amMDW - CUN
1 stop5h 30mDelta
Thu 5/111:10 amCUN - MDW
1 stop6h 50mDelta
Deal found 1/21$386
This Aeromexico deal was found by Cheapflights users on 1/21. 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.
Wed 3/512:44 pmMDW - CUN
2 stops11h 14mAeromexico
Tue 3/112:05 pmCUN - MDW
1 stop8h 18mAeromexico
Deal found 1/21$391
This Gotogate deal was found by Cheapflights users on 1/21. 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.
Tue 3/188:39 pmMDW - CUN
1 stop14h 24mVolaris
Sat 3/228:00 amCUN - MDW
1 stop11h 10mVolaris
Deal found 1/21$452

Find flights from Midway to Playa del Carmen within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 4/26

8:21 am-12:25 pm

1 stop28h 04m

Cancun

Thu 5/1

3:15 pm-7:08 pm

1 stop27h 53m

$312

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 2/10

7:55 pm-3:49 pm

1 stop18h 54m

Cancun

Wed 2/12

3:49 pm-12:17 am

1 stop9h 28m

$313

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 3/7

4:30 pm-9:25 pm

Nonstop3h 55m

Cancun

Tue 3/11

12:55 pm-10:45 pm

1 stop9h 50m

$329

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 3/5

12:44 pm-9:05 pm

1 stop7h 21m

Cancun

Tue 3/11

10:00 am-4:14 pm

1 stop6h 14m

$367

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 2/11

12:44 pm-9:05 pm

1 stop7h 21m

Cancun

Wed 2/12

8:00 am-4:20 pm

1 stop9h 20m

$382

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 3/6

7:55 pm-9:04 am

1 stop12h 09m

Cancun

Thu 3/13

1:57 pm-9:18 pm

1 stop7h 21m

$407

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 3/10

4:30 pm-8:25 pm

Nonstop3h 55m

$116

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 5/5

8:03 pm-2:10 pm

1 stop18h 07m

$121

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 4/1

2:36 pm-10:19 am

1 stop19h 43m

$133

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 2/22

9:33 am-9:05 pm

2 stops10h 32m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 12 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.

Travel insights for flights from Midway to Playa del Carmen

Get recent, data-driven insights about flights from Midway to Playa del Carmen including ideal travel times, pricing trends, and more.

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 January 17, 2025.

The best time to book flights from Chicago Midway Airport to Playa del Carmen is 39 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 January 21, 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.

What is the cheapest day to fly from Chicago Midway Airport to Playa del Carmen?

Use this chart to determine the cheapest time to fly round-trip from Midway to Playa del Carmen. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago Midway Airport to Playa del Carmen flight should consider departing on Friday at noon when fares are most often at their lowest. Saturday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Playa del Carmen by month

Plan your trip to Playa del Carmen by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Playa del Carmen ranges from 1.1 - 11.1 inches per month. October is typically the wettest month, when rainfall can reach 11.1 in. April is typically the driest time to visit Playa del Carmen when rainfall is around 1.1 in.

Temperature in Playa del Carmen by month

Plan your trip to Playa del Carmen by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Playa del Carmen, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 86.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 75.2 F).

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 January 21, 2025.
See what other customers who have flown with Frontier, Southwest and Volaris from Chicago to Playa del Carmen have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Aeromexico
7.5
Good
1,849 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Volaris
6.7
Okay
1,248 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,443 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Playa del Carmen one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $116. Frontier flights start at $121 while deals on Delta start at $176 one-way.

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

    Looking at all options, your cheapest flight can be booked for $111. While the most popular route (Chicago Midway - Cancun) can be booked for $326 on average our data indicates $531 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 8 airlines flying from Midway to Playa del Carmen

Discover the top 8 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$171Average$275FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$177Average$409FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$311Average$393FlexibilityNo cancel feeOn-time69%
DeltaCheapest$380Average$539FlexibilityNo cancel feeOn-timeN/A
AeromexicoCheapest$382Average$562FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$467Average$705FlexibilityNo cancel feeOn-time63%
VolarisCheapest$477Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.