HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Playa del Carmen

$100+ Cheap flights from Chicago (CHI) 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
ago. 25 — sep. 11
lun. 8/25
lun. 9/1
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago 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.

Cheapflights Tip: The best prices from Chicago to Playa del Carmen are usually found in September or October, booked 66 days in advance, depart on a Monday or Tuesday and return on a Friday

Cheap flight deals from Chicago to Playa del Carmen

Keep the following information in mind while searching for Chicago to Playa del Carmen flight deals. Data was last updated agosto 20, 2025.

Round-trip from

$238
(Cheapflightsfares)

One-way from

$100
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$413
From Chicago (CHI) to Playa del Carmen
Search Deals
One-way flight from Chicago (CHI) to Playa del Carmen
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

Find flight deals from Chicago to Playa del Carmen

Cheapest flights from Chicago to Playa del Carmen
Explore the most affordable flight options available from Chicago to Playa del Carmen. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 8/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/145:05 amORD - CUN
1 stop7h 54mSpirit Airlines
jue. 9/182:07 pmCUN - ORD
1 stop8h 41mSpirit Airlines
Deal found 8/19$238
This Cheapflightsfares deal was found by Cheapflights users on 8/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/295:17 pmORD - CUN
1 stop14h 54mSpirit Airlines
sáb. 10/42:07 pmCUN - ORD
1 stop8h 41mSpirit Airlines
Deal found 8/18$239
This FlightHub deal was found by Cheapflights users on 8/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/88:50 pmORD - CUN
1 stop12h 52mSpirit Airlines
mié. 11/121:35 pmCUN - ORD
1 stop8h 25mSpirit Airlines
Deal found 8/19$240
This Mytrip deal was found by Cheapflights users on 8/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/226:10 amORD - CUN
Nonstop3h 29mSpirit Airlines
jue. 8/281:42 pmCUN - ORD
1 stop10h 17mSpirit Airlines
Deal found 8/19$241
This Mytrip deal was found by Cheapflights users on 8/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/1012:25 pmORD - CUN
1 stop12h 25mMultiple Airlines
mar. 10/149:09 amCUN - ORD
1 stop12h 24mMultiple Airlines
Deal found 8/19$242
This Booking.com deal was found by Cheapflights users on 8/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/256:40 pmORD - CUN
1 stop13h 24mSpirit Airlines
sáb. 11/110:55 amCUN - ORD
Nonstop4h 03mSpirit Airlines
Deal found 8/20$243
This FlightHub deal was found by Cheapflights users on 8/18. 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.
sáb. 9/205:17 pmORD - CUN
1 stop14h 54mSpirit Airlines
mar. 9/239:16 amCUN - ORD
1 stop12h 42mSpirit Airlines
Deal found 8/18$244
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/288:25 amORD - CUN
Nonstop3h 53mMultiple Airlines
mié. 11/51:35 pmCUN - ORD
1 stop8h 25mMultiple Airlines
Deal found 8/20$245
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
jue. 10/308:56 pmORD - CUN
1 stop12h 21mMultiple Airlines
mar. 11/41:28 pmCUN - ORD
Nonstop4h 08mMultiple Airlines
Deal found 8/18$247
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
jue. 10/308:15 amORD - CUN
Nonstop3h 53mMultiple Airlines
sáb. 11/110:55 amCUN - ORD
Nonstop4h 03mMultiple Airlines
Deal found 8/18$248
This Frontier deal was found by Cheapflights users on 8/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/308:15 amORD - CUN
Nonstop3h 53mFrontier
dom. 11/21:28 pmCUN - ORD
Nonstop4h 08mFrontier
Deal found 8/20$249
This Southwest deal was found by Cheapflights users on 8/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/289:40 amMDW - CUN
Nonstop3h 35mSouthwest
sáb. 11/112:00 pmCUN - MDW
Nonstop3h 35mSouthwest
Deal found 8/19$271

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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 agosto 20, 2025.
Use the filters below to find and compare flights from Chicago to Playa del Carmen that are best for you.

Fly from

Chicago

Fly to

Playa del Carmen

Route

Depart

Return

Price

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

vie. 9/12

8:56 pm-9:15 am

1 stop12h 19m

Cancun

mié. 9/17

2:07 pm-10:48 pm

1 stop8h 41m

$238

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

mar. 10/28

9:40 am-1:15 pm

Nonstop3h 35m

Cancun

sáb. 11/1

12:00 pm-3:35 pm

Nonstop3h 35m

$271

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

dom. 8/24

9:29 am-1:14 pm

Nonstop3h 45m

Cancun

mar. 8/26

3:38 pm-7:36 pm

Nonstop3h 58m

$271

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

sáb. 11/15

3:40 pm-8:25 pm

Nonstop3h 45m

Cancun

mié. 11/19

1:45 pm-4:30 pm

Nonstop3h 45m

$271

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

sáb. 9/6

9:29 am-1:14 pm

Nonstop3h 45m

Cancun

sáb. 9/13

3:38 pm-7:36 pm

Nonstop3h 58m

$271

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

mar. 10/28

9:40 am-1:15 pm

Nonstop3h 35m

Cancun

mar. 11/4

1:45 pm-4:30 pm

Nonstop3h 45m

$271

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

dom. 11/2

10:40 am-3:25 pm

Nonstop3h 45m

Cancun

jue. 11/6

2:15 pm-5:00 pm

Nonstop3h 45m

$271

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

sáb. 11/15

3:40 pm-8:25 pm

Nonstop3h 45m

Cancun

jue. 11/20

1:45 pm-4:30 pm

Nonstop3h 45m

$271

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

dom. 10/26

8:25 am-12:05 pm

Nonstop3h 40m

Cancun

sáb. 11/1

2:00 pm-5:45 pm

Nonstop3h 45m

$271

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

sáb. 9/6

10:43 am-2:28 pm

Nonstop3h 45m

Cancun

mié. 9/10

12:20 pm-4:18 pm

Nonstop3h 58m

$276

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 39 results
1
2
3
4

Best time to book a flight from Chicago to Playa del Carmen

Have a flexible travel schedule? Discover the best time to fly to Playa del Carmen from Chicago 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 to Playa del Carmen

How far ahead should I book a flight from Chicago to Playa del Carmen?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Playa del Carmen. Price data was last updated on August 8, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Playa del Carmen, you should look to book at least 66 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago to Playa del Carmen?

Currently, January is the cheapest month in which you can book a flight from Chicago to Playa del Carmen (average of $360). Flying from Chicago 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 CHI to PL9?

Find hourly flight availability from Chicago 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 agosto 20, 2025.

When flying from Chicago to Playa del Carmen, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

Use this chart to determine the cheapest time to fly round-trip from Chicago to Playa del Carmen. Price data was last updated on August 17, 2025.

Travelers seeking maximum savings on their Chicago to Playa del Carmen flight should consider departing on Wednesday 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.

Weekly flight availability from Chicago to Playa del Carmen

Explore weekly flight availability from Chicago to Playa del Carmen. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated agosto 20, 2025.

The most flights from CHI to PL9 are scheduled on a Monday (7 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (6 on average).

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 agosto 20, 2025.
See what other customers who have flown with Southwest, United Airlines, and American Airlines from Chicago 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
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,928 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,039 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,207 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Chicago 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 to Playa del Carmen?

    Airlines like Spirit Airlines, Southwest, and United Airlines fly from Chicago to Playa del Carmen in about 3h 35m. The time it takes to get you to your destination can typically vary by up to 8h 44m. Airlines will cover a distance of 1434 mi. This flight may include one or multiple stops.

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

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $100. However, be on the lookout for offers from Volaris and Southwest, as they are both options that can get you from Chicago to Playa del Carmen for a low price.

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

    Before booking your flight to Playa del Carmen from Chicago, check out the most reliable airlines to get you to your destination on time: Emirates (84%), United Airlines (83%), Spirit Airlines( 81%).

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

    While on average a flight from Chicago to Playa del Carmen is generally $599, our data shows the cheapest flight currently is $88. When looking at the most popular route, (Chicago O'Hare Intl - Cancun), you can expect to pay $202 for that flight.

  • Can I find deals for flights from Chicago to Playa del Carmen that include hotel bookings?

    Yes. In addition to deals on Chicago to Playa del Carmen flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago 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 Chicago to Playa del Carmen.

  • Can I find deals for business class flights from Chicago to Playa del Carmen?

    Yes. Cheapflights offers flight deals from Chicago 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 to Playa del Carmen?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Playa del Carmen (average of $360). Flying from Chicago 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.

Top 10 airlines flying from Chicago to Playa del Carmen

Discover the top 10 airlines that operate flights from Chicago 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 agosto 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$124Average$326FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$161Average$514FlexibilityNo cancel feeOn-time69%
DeltaCheapest$168Average$512FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$170Average$458FlexibilityNo cancel feeOn-time62%
VolarisCheapest$179Average$544FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$191Average$471FlexibilityNo cancel feeOn-timeN/A
VivaCheapest$250Average$294FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$266Average$622FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$269Average$513FlexibilityNo cancel feeOn-time71%
AviancaCheapest$552Average$896FlexibilityNo cancel feeOn-time71%

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.