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Playa del Carmen

$99+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Nov 4 — Nov 111
Tue 11/4
Tue 11/11
1 adult, Economy
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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 October 5, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$239
(Cheapflightsfares)

One-way from

$99
(Booking.com)

Popular in

March

Cheapest in

September

Average price

$396
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 (CHI) to Playa del Carmen
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One-way flight from Chicago (CHI) to Playa del Carmen
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Highest demand for flights based on searches. 5% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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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 October 5, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/4. 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.
Sun 10/265:05 amORD - CUN
1 stop7h 39mSpirit Airlines
Thu 10/301:49 pmCUN - ORD
1 stop11h 14mSpirit Airlines
Deal found 10/4$239
This Cheapflightsfares deal was found by Cheapflights users on 10/5. 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.
Mon 10/275:05 amORD - CUN
1 stop7h 39mSpirit Airlines
Fri 10/319:09 amCUN - ORD
1 stop12h 24mSpirit Airlines
Deal found 10/5$240
This Gotogate deal was found by Cheapflights users on 10/4. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/14:30 pmORD - CUN
1 stop26h 40mMultiple Airlines
Fri 12/511:42 amCUN - ORD
Nonstop4h 08mMultiple Airlines
Deal found 10/4$242
This Mytrip deal was found by Cheapflights users on 10/4. 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.
Tue 10/216:30 amORD - CUN
Nonstop3h 45mMultiple Airlines
Tue 10/289:09 amCUN - ORD
1 stop7h 14mMultiple Airlines
Deal found 10/4$243
This Cheapflightsfares deal was found by Cheapflights users on 10/4. 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.
Sat 12/66:00 amORD - CUN
Nonstop3h 37mSpirit Airlines
Fri 12/1211:42 amCUN - ORD
Nonstop4h 08mSpirit Airlines
Deal found 10/4$244
This Kiwi.com deal was found by Cheapflights users on 10/2. 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.
Wed 11/125:10 amORD - CUN
1 stop7h 25mMultiple Airlines
Tue 11/181:28 pmCUN - ORD
Nonstop4h 08mMultiple Airlines
Deal found 10/2$245
This Cheapflightsfares deal was found by Cheapflights users on 10/3. 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.
Sat 10/186:58 pmORD - CUN
1 stop13h 06mSpirit Airlines
Sat 10/259:09 amCUN - ORD
1 stop12h 24mSpirit Airlines
Deal found 10/3$247
This Priceline deal was found by Cheapflights users on 10/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/25:10 amORD - CUN
1 stop7h 25mMultiple Airlines
Thu 11/61:28 pmCUN - ORD
Nonstop4h 08mMultiple Airlines
Deal found 10/3$248
This CheapOair deal was found by Cheapflights users on 10/5. 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 12/66:00 amORD - CUN
Nonstop3h 37mSpirit Airlines
Sat 12/1312:34 pmCUN - ORD
1 stop11h 31mSpirit Airlines
Deal found 10/5$249
This Cheapflightsfares deal was found by Cheapflights users on 10/3. 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.
Sun 10/265:05 amORD - CUN
1 stop7h 39mSpirit Airlines
Sat 11/19:09 amCUN - ORD
1 stop7h 14mSpirit Airlines
Deal found 10/3$250
This Kiwi.com deal was found by Cheapflights users on 10/3. 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 11/156:00 amORD - CUN
Nonstop3h 44mSpirit Airlines
Sat 11/2211:53 amCUN - ORD
Nonstop4h 00mSpirit Airlines
Deal found 10/3$251
This Southwest deal was found by Cheapflights users on 10/5. 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.
Sat 11/153:40 pmMDW - CUN
Nonstop3h 45mSouthwest
Fri 11/212:15 pmCUN - MDW
Nonstop3h 45mSouthwest
Deal found 10/5$252

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 October 5, 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

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/15

3:40 pm-8:25 pm

Nonstop3h 45m

Cancun

Fri 11/21

2:15 pm-5:00 pm

Nonstop3h 45m

$252

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Sat 11/1

8:20 am-7:50 pm

2 stops11h 30m

Cancun

Thu 11/6

2:15 pm-5:00 pm

Nonstop3h 45m

$276

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Thu 10/30

7:10 am-2:45 pm

1 stop7h 35m

Cancun

Sun 11/2

1:27 pm-4:27 pm

Nonstop4h 00m

$296

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 11/29

6:45 am-3:34 pm

1 stop7h 49m

Cancun

Wed 12/10

6:00 am-1:12 pm

1 stop8h 12m

$316

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sun 12/7

6:45 am-9:20 pm

2 stops13h 35m

Cancun

Fri 12/12

6:00 am-1:12 pm

1 stop8h 12m

$321

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 10/14

7:55 am-2:20 pm

1 stop6h 25m

Cancun

Sat 10/25

11:35 am-7:05 pm

1 stop7h 30m

$331

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Tue 11/11

9:34 am-9:20 pm

2 stops10h 46m

Cancun

Tue 11/18

8:00 am-6:08 pm

2 stops11h 08m

$331

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

Wed 10/22

8:00 am-3:25 pm

1 stop7h 25m

Cancun

Sat 10/25

1:45 pm-8:50 pm

1 stop7h 05m

$331

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Tue 11/11

10:46 am-9:20 pm

2 stops9h 34m

Cancun

Tue 11/18

8:00 am-8:29 pm

2 stops13h 29m

$331

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

Sat 11/15

10:46 am-9:20 pm

2 stops9h 34m

Cancun

Tue 11/18

8:00 am-3:26 pm

1 stop8h 26m

$331

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/4

Showing 1-10 of 40 results
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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 October 3, 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 October 5, 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 September 28, 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 at noon 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 October 5, 2025.

The most flights from CHI to PL9 are scheduled on a Saturday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 on average).

How much does it cost to fly round-trip from Chicago 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 October 5, 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
4,237 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,953 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,041 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,075 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,147 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 Southwest, United Airlines, and Delta fly from Chicago to Playa del Carmen in about 3h 45m. The time it takes to get you to your destination can typically vary by up to 4h 04m. Airlines will cover a distance of 1434 mi. This flight may include one or multiple stops.

  • 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: Spirit Airlines (100%), Frontier (81%), Emirates( 79%).

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

    While on average a flight from Chicago to Playa del Carmen is generally $482, our data shows the cheapest flight currently is $89. When looking at the most popular route, (Chicago O'Hare Intl - Cancun), you can expect to pay $218 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 October 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$147Average$338FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$161Average$520FlexibilityNo cancel feeOn-time69%
DeltaCheapest$168Average$500FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$174Average$457FlexibilityNo cancel feeOn-time62%
VolarisCheapest$183Average$546FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$191Average$436FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$205Average$685FlexibilityNo cancel feeOn-time67%
VivaCheapest$237Average$292FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$266Average$598FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$268Average$521FlexibilityNo cancel feeOn-time71%

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