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Playa del Carmen

$111+ 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 6/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
May 6 — May 131
Tue 5/6
Tue 5/13
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 April, booked 57 days in advance, depart on a Monday or Tuesday and return on a Monday

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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$299
(Southwest)

One-way from

$111
(Southwest)

Popular in

November

Cheapest in

September

Average price

$539
Provider with most accurate pricing for Chicago (CHI)-Cancun flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Cancun flights.
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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. 8% potential increase in price ($53 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Southwest deal was found by Cheapflights users on 4/30. 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.
Mon 5/196:20 amMDW - CUN
1 stop7h 45mSouthwest
Fri 5/239:00 amCUN - MDW
Nonstop3h 40mSouthwest
Deal found 4/30$299
This Trip.com deal was found by Cheapflights users on 4/30. 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.
Tue 6/1012:44 pmMDW - CUN
1 stop7h 36mAeromexico
Wed 6/112:00 pmCUN - MDW
1 stop7h 45mAeromexico
Deal found 4/30$309
This Delta deal was found by Cheapflights users on 5/1. 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 6/612:48 pmMDW - CUN
2 stops11h 34mDelta
Wed 6/1112:35 pmCUN - MDW
1 stop9h 10mDelta
Deal found 5/1$321
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 6/2812:44 pmMDW - CUN
1 stop7h 36mMultiple Airlines
Thu 7/33:05 pmCUN - MDW
1 stop20h 35mMultiple Airlines
Deal found 4/30$362
This Frontier deal was found by Cheapflights users on 4/29. 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.
Tue 6/36:40 amMDW - CUN
1 stop6h 20mFrontier
Sat 6/79:09 amCUN - MDW
1 stop10h 16mFrontier
Deal found 4/29$417

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 May 1, 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

Mon 5/19

5:10 am-1:20 pm

1 stop8h 10m

Cancun

Thu 5/22

9:00 am-12:40 pm

Nonstop3h 40m

$299

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 6/10

12:44 pm-8:20 pm

1 stop7h 36m

Cancun

Wed 6/11

2:00 pm-9:45 pm

1 stop7h 45m

$309

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 6/6

12:48 pm-8:20 pm

1 stop7h 32m

Cancun

Wed 6/11

12:35 pm-9:45 pm

1 stop9h 10m

$321

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 6/28

12:44 pm-8:20 pm

1 stop7h 36m

Cancun

Thu 7/3

3:05 pm-11:40 am

1 stop20h 35m

$362

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 6/3

6:40 am-1:00 pm

1 stop6h 20m

Cancun

Sat 6/7

9:09 am-7:25 pm

1 stop10h 16m

$417

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 6/10

4:30 pm-8:05 pm

Nonstop3h 35m

$111

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 6/30

9:12 pm-8:12 am

1 stop11h 00m

$143

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 6/26

10:26 am-8:20 pm

1 stop9h 54m

$144

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 5/6

6:04 am-2:01 pm

1 stop7h 57m

$146

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 5/30

8:55 pm-11:41 am

1 stop14h 46m

$152

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 12 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 April 25, 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 May 1, 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.

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 May 1, 2025.
See what other customers who have flown with Southwest, Delta and Aeromexico 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
8.0
Very good
4,294 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Aeromexico
7.5
Good
1,698 reviews
Southwest
8.0
Very good
4,294 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
WestJet
7.2
Good
2,826 reviews
Southwest
8.0
Very good
4,294 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Volaris
6.7
Okay
1,174 reviews
Southwest
8.0
Very good
4,294 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 $111. Aeromexico flights start at $144 while deals on Delta start at $146 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 $246 on average our data indicates $370 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

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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 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$419FlexibilityNo cancel feeOn-time69%
FrontierCheapest$198Average$445FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$241Average$333FlexibilityNo cancel feeOn-time65%
AeromexicoCheapest$320Average$526FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$380Average$536FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$429Average$686FlexibilityNo cancel feeOn-time63%
VolarisCheapest$486Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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