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Playa del Carmen

$132+ 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 6/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Jun 13 — Jun 201
Sat 6/13
Sat 6/20
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Playa del Carmen are usually found in October or February, booked 11 days in advance, depart on a Tuesday or Monday 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 May 14, 2026.

This FlightHub deal was found by Cheapflights users on 5/13. 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.
Sun 6/148:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Wed 6/1710:40 am
CUN
-
MDW
1 stop8h 24m
Volaris
Deal found 5/13$341
This FlightHub deal was found by Cheapflights users on 5/13. 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.
Mon 6/158:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Thu 6/1810:40 am
CUN
-
MDW
1 stop8h 54m
Volaris
Deal found 5/13$348
This FlightHub deal was found by Cheapflights users on 5/13. 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.
Sun 7/58:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Wed 7/810:40 am
CUN
-
MDW
1 stop8h 24m
Volaris
Deal found 5/13$349
This FlightHub deal was found by Cheapflights users on 5/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/118:49 pm
MDW
-
CUN
1 stop13h 06m
Volaris
Thu 6/1810:40 am
CUN
-
MDW
1 stop8h 54m
Volaris
Deal found 5/12$352
This Kissandfly.com deal was found by Cheapflights users on 5/13. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/88:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Wed 6/1710:40 am
CUN
-
MDW
1 stop8h 24m
Volaris
Deal found 5/13$353
This FlightHub deal was found by Cheapflights users on 5/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/128:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Wed 6/1710:40 am
CUN
-
MDW
1 stop8h 24m
Volaris
Deal found 5/12$354
This FlightHub deal was found by Cheapflights users on 5/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/68:23 pm
MDW
-
CUN
1 stop13h 32m
Multiple Airlines
Fri 7/103:01 pm
CUN
-
MDW
1 stop7h 07m
Multiple Airlines
Deal found 5/12$356
This FlightHub deal was found by Cheapflights users on 5/13. 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.
Mon 6/18:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Fri 6/510:40 am
CUN
-
MDW
1 stop8h 24m
Volaris
Deal found 5/13$360
This FlightHub deal was found by Cheapflights users on 5/13. 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.
Sun 6/218:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Sun 6/2810:40 am
CUN
-
MDW
1 stop8h 24m
Volaris
Deal found 5/13$361
This FlightHub deal was found by Cheapflights users on 5/13. 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 7/38:23 pm
MDW
-
CUN
1 stop13h 32m
Multiple Airlines
Wed 7/83:01 pm
CUN
-
MDW
1 stop7h 07m
Multiple Airlines
Deal found 5/13$362
This FlightHub deal was found by Cheapflights users on 5/13. 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.
Mon 6/158:23 pm
MDW
-
CUN
1 stop13h 32m
Volaris
Sun 6/2110:40 am
CUN
-
MDW
1 stop8h 24m
Volaris
Deal found 5/13$365

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 May 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$341
(FlightHub)

One-way from

$132
(FlightHub)

Popular in

May

Cheapest in

October

Average price

$618
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. 11% potential increase in price ($61 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 14, 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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 5/29

10:59 am-8:16 pm

1 stop9h 17m

Cancun

Wed 6/3

8:09 am-9:09 pm

2 stops13h 00m

$428

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 7/23

11:05 am-8:15 pm

1 stop9h 10m

Cancun

Tue 7/28

8:00 am-6:25 pm

2 stops10h 25m

$451

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 8/20

12:46 pm-12:22 am

2 stops11h 36m

Cancun

Mon 8/24

3:32 pm-10:36 pm

1 stop7h 04m

$494

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Fri 7/31

9:19 am-8:15 pm

2 stops10h 56m

Cancun

Tue 8/4

8:05 am-4:15 pm

1 stop8h 10m

$496

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 7/30

11:05 am-8:15 pm

1 stop9h 10m

Cancun

Tue 8/4

8:05 am-10:36 pm

1 stop14h 31m

$498

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 8/3

9:55 am-1:30 pm

Nonstop3h 35m

Cancun

Fri 8/7

12:50 pm-9:00 pm

1 stop8h 10m

$499
Quickest round-trip

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Thu 7/23

9:55 am-1:30 pm

Nonstop3h 35m

Cancun

Thu 7/30

4:10 pm-7:45 pm

Nonstop3h 35m

$504

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 7/25

6:30 am-2:55 pm

1 stop8h 25m

Cancun

Sat 8/1

10:05 am-1:40 pm

Nonstop3h 35m

$516

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 6/23

8:40 am-3:05 pm

1 stop6h 25m

Cancun

Tue 6/30

3:05 pm-6:35 pm

Nonstop3h 30m

$518

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Mon 6/15

5:00 am-1:40 pm

2 stops8h 40m

Cancun

Thu 6/18

12:40 pm-7:35 pm

1 stop6h 55m

$532

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/11

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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

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 14, 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.

How much does it cost to fly round-trip from Chicago Midway Airport to Playa del Carmen?

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 14, 2026.
See what other customers who have flown with Southwest,Delta, andAeromexico 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
4,299 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,299 reviews
Southwest
8.0
Very good
4,299 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,453 reviews
Southwest
8.0
Very good
4,299 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Aeromexico
7.4
Good
1,513 reviews
Southwest
8.0
Very good
4,299 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.6
Fair
2,951 reviews
Southwest
8.0
Very good
4,299 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 9h 17m. Fly via Delta to get the fastest option. There are 1434 mi between Chicago Midway Airport and Playa del Carmen.

  • What are the most reliable airlines from Chicago Midway Airport to Playa del Carmen?

    The top 3 most reliable airlines when flying from Chicago Midway Airport to Playa del Carmen are Southwest (64%), Frontier (17%) and Volaris (17%).

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

    Looking at all options, your cheapest flight can be booked for $107. While the most popular route (Chicago Midway - Cancun) can be booked for $348 on average, our data indicates $326 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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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

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 May 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$198Average$515FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$293Average$509FlexibilityNo cancel feeOn-time63%
AeromexicoCheapest$309Average$401FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$377Average$3,633FlexibilityNo cancel feeOn-timeN/A

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