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Playa del Carmen

$101+ 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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Jan 13 — Jan 201
Tue 1/13
Tue 1/20
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 July, booked 57 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 December 14, 2025.

This Frontier deal was found by Cheapflights users on 12/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:12 amMDW - CUN
1 stop6h 28mFrontier
Thu 1/154:12 pmCUN - MDW
1 stop7h 07mFrontier
Deal found 12/13$269
This Frontier deal was found by Cheapflights users on 12/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:12 amMDW - CUN
1 stop6h 28mFrontier
Thu 1/83:14 pmCUN - MDW
1 stop8h 03mFrontier
Deal found 12/13$277
This Frontier deal was found by Cheapflights users on 12/11. 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.
Wed 12/313:10 pmMDW - CUN
2 stops18h 33mFrontier
Thu 1/222:57 pmCUN - MDW
1 stop8h 22mFrontier
Deal found 12/11$323
This Delta deal was found by Cheapflights users on 12/12. 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 12/156:00 amMDW - CUN
1 stop7h 05mDelta
Sun 12/2112:25 pmCUN - MDW
1 stop10h 57mDelta
Deal found 12/12$327
This Delta deal was found by Cheapflights users on 12/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/179:34 amMDW - CUN
2 stops10h 46mDelta
Sun 12/218:00 amCUN - MDW
1 stop9h 20mDelta
Deal found 12/13$331
This Frontier deal was found by Cheapflights users on 12/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:14 amMDW - CUN
1 stop6h 25mFrontier
Thu 1/83:14 pmCUN - MDW
1 stop8h 03mFrontier
Deal found 12/13$347
This Delta deal was found by Cheapflights users on 12/12. 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 12/149:34 amMDW - CUN
2 stops10h 46mDelta
Tue 12/168:00 amCUN - MDW
2 stops11h 00mDelta
Deal found 12/12$351
This Southwest deal was found by Cheapflights users on 12/12. 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 12/1410:40 amMDW - CUN
Nonstop3h 45mSouthwest
Tue 12/161:45 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 12/12$352
This Delta deal was found by Cheapflights users on 12/12. 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 12/146:00 amMDW - CUN
1 stop7h 05mDelta
Thu 12/1811:09 amCUN - MDW
1 stop6h 22mDelta
Deal found 12/12$354
This Southwest deal was found by Cheapflights users on 12/12. 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 12/1410:40 amMDW - CUN
Nonstop3h 45mSouthwest
Thu 12/182:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 12/12$359

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 14, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$224
(Frontier)

One-way from

$101
(Frontier)

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 14, 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

Wed 12/17

9:34 am-9:20 pm

2 stops10h 46m

Cancun

Fri 12/19

12:15 pm-6:00 pm

1 stop6h 45m

$331

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 2/7

6:25 am-8:02 pm

2 stops12h 37m

Cancun

Tue 2/10

4:40 pm-10:22 pm

1 stop6h 42m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 1/28

6:00 am-6:47 pm

2 stops11h 47m

Cancun

Wed 2/4

11:18 am-10:22 pm

2 stops12h 04m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 1/24

6:25 am-8:02 pm

2 stops12h 37m

Cancun

Tue 1/27

3:13 pm-10:22 pm

1 stop8h 09m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 1/13

6:45 am-3:30 pm

1 stop7h 45m

Cancun

Thu 1/15

3:13 pm-10:07 pm

1 stop7h 54m

$333

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 2/4

9:32 am-9:11 pm

2 stops10h 39m

Cancun

Sat 2/7

1:40 pm-10:22 pm

1 stop9h 42m

$338

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 1/23

9:32 am-9:11 pm

2 stops10h 39m

Cancun

Tue 1/27

1:40 pm-10:22 pm

1 stop9h 42m

$338

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 3/5

9:34 am-9:11 pm

2 stops10h 37m

Cancun

Mon 3/9

8:00 am-10:29 pm

1 stop14h 29m

$338

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 2/19

10:53 am-9:11 pm

1 stop9h 18m

Cancun

Tue 2/24

12:05 pm-10:44 pm

2 stops11h 39m

$338

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 3/6

10:53 am-9:11 pm

1 stop9h 18m

Cancun

Wed 3/11

11:05 am-10:29 pm

2 stops11h 24m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 22 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 12, 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 14, 2025.

When flying from Chicago Midway Airport to Playa del Carmen, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 25% versus a flight at noon.

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 14, 2025.
See what other customers who have flown with Southwest, Delta, and LATAM Airlines 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
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

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
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

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
8,007 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

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
LATAM Airlines
7.5
Good
1,891 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

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
1,638 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

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
Volaris
6.7
Okay
1,153 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

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 10h 46m. 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 $226 on average, our data indicates $349 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

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 December 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$161Average$419FlexibilityNo cancel feeOn-time69%
AeromexicoCheapest$312Average$519FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$345Average$569FlexibilityNo cancel feeOn-time63%
FrontierCheapest$362Average$565FlexibilityNo cancel feeOn-time62%
DeltaCheapest$380Average$607FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$506Average$667FlexibilityNo cancel feeOn-time71%
VolarisCheapest$848Average$872FlexibilityNo cancel feeOn-time79%
LATAM AirlinesCheapest$3,369Average$3,369FlexibilityNo cancel feeOn-time81%

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