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Playa del Carmen

$106+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Feb 26 — Mar 51
Wed 2/26
Wed 3/5
1 adult, Economy
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The best prices from Chicago Midway to Playa del Carmen are usually found in February or April, booked 57 days in advance, depart on a Monday or Thursday 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 February 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$247
(Kiwi.com)

One-way from

$106
(Travelocity)

Popular in

December

Cheapest in

February

Average price

$388
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. 18% potential increase in price ($127 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 February 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 February 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Tue 4/12:45 pmMDW - CUN
1 stop21h 20mFrontier
Tue 4/810:40 amCUN - MDW
1 stop9h 11mFrontier
Deal found 2/19$247
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Tue 4/14:40 pmMDW - CUN
1 stop15h 33mMultiple Airlines
Thu 4/1010:30 amCUN - MDW
1 stop11h 57mMultiple Airlines
Deal found 2/19$266
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/78:45 amMDW - CUN
1 stop6h 05mSouthwest
Wed 5/149:00 amCUN - MDW
Nonstop3h 40mSouthwest
Deal found 2/20$307
This Trip.com deal was found by Cheapflights users on 2/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/216:04 amMDW - CUN
1 stop7h 57mAeromexico
Thu 4/2411:03 amCUN - MDW
1 stop6h 56mAeromexico
Deal found 2/20$373
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/29:33 amMDW - CUN
2 stops10h 32mDelta
Sat 3/88:00 amCUN - MDW
1 stop7h 53mDelta
Deal found 2/20$395
This CheapOair deal was found by Cheapflights users on 2/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/298:39 pmMDW - CUN
1 stop12h 25mVolaris
Sat 4/58:00 amCUN - MDW
1 stop11h 06mVolaris
Deal found 2/19$417

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 February 21, 2025.

Fly from

Midway

Fly to

Playa del Carmen

Route

Depart

Return

Price

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 4/1

2:45 pm-12:05 pm

1 stop21h 20m

Cancun

Tue 4/8

10:40 am-7:51 pm

1 stop9h 11m

$247

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 4/1

4:40 pm-8:13 am

1 stop15h 33m

Cancun

Thu 4/10

10:30 am-10:27 pm

1 stop11h 57m

$266

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 5/7

8:45 am-2:50 pm

1 stop6h 05m

Cancun

Wed 5/14

9:00 am-12:40 pm

Nonstop3h 40m

$307

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 4/21

6:04 am-2:01 pm

1 stop7h 57m

Cancun

Thu 4/24

11:03 am-5:59 pm

1 stop6h 56m

$373

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 3/2

9:33 am-9:05 pm

2 stops10h 32m

Cancun

Sat 3/8

8:00 am-2:53 pm

1 stop7h 53m

$395

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 3/7

7:55 pm-9:04 am

1 stop12h 09m

Cancun

Sun 3/9

8:00 am-7:10 pm

1 stop11h 10m

$416

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 5/5

8:03 pm-2:10 pm

1 stop18h 07m

$106

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sun 4/6

4:30 pm-8:25 pm

Nonstop3h 55m

$110

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 4/1

4:40 pm-8:13 am

1 stop15h 33m

$133

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 2/24

7:55 pm-9:49 pm

1 stop24h 54m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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 February 14, 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 February 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 February 16, 2025.

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. Sunday 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 February 21, 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
8.1
Very good
4,401 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,401 reviews
Southwest
8.1
Very good
4,401 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,401 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Aeromexico
7.5
Good
1,771 reviews
Southwest
8.1
Very good
4,401 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Volaris
6.7
Okay
1,208 reviews
Southwest
8.1
Very good
4,401 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Frontier
6.0
Okay
3,354 reviews
Southwest
8.1
Very good
4,401 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Frontier, which is currently one of the cheapest options available, starting at $106. Southwest flights start at $110 while deals on Volaris 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 $332 on average our data indicates $473 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 February 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$175Average$393FlexibilityNo cancel feeOn-time69%
FrontierCheapest$177Average$338FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$183Average$409FlexibilityNo cancel feeOn-time65%
DeltaCheapest$380Average$537FlexibilityNo cancel feeOn-timeN/A
AeromexicoCheapest$382Average$567FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$460Average$704FlexibilityNo cancel feeOn-time63%
VolarisCheapest$486Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%
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