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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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
ene. 1 — ene. 81
jue. 1/1
jue. 1/8
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Playa del Carmen are usually found in September or July, 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

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 diciembre 2, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 12/1. 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.
vie. 12/129:14 pmORD - CUN
1 stop13h 22mSpirit Airlines
vie. 12/1911:50 amCUN - ORD
Nonstop4h 03mSpirit Airlines
Deal found 12/1$217
This Cheapflightsfares deal was found by Cheapflights users on 11/30. 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. 12/79:14 pmORD - CUN
1 stop13h 22mSpirit Airlines
sáb. 12/1311:50 amCUN - ORD
Nonstop4h 03mSpirit Airlines
Deal found 11/30$223
This Cheapflightsfares deal was found by Cheapflights users on 11/29. 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.
sáb. 12/136:05 amORD - CUN
Nonstop3h 50mSpirit Airlines
dom. 12/2111:50 amCUN - ORD
Nonstop4h 03mSpirit Airlines
Deal found 11/29$225
This Super.com deal was found by Cheapflights users on 11/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/145:00 amORD - CUN
1 stop7h 13mSpirit Airlines
dom. 12/2111:50 amCUN - ORD
Nonstop4h 03mSpirit Airlines
Deal found 11/30$230
This Cheapflightsfares deal was found by Cheapflights users on 12/1. 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. 12/85:00 amORD - CUN
1 stop7h 13mSpirit Airlines
jue. 12/112:36 pmCUN - ORD
1 stop10h 33mSpirit Airlines
Deal found 12/1$232
This Expedia deal was found by Cheapflights users on 11/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/85:00 amORD - CUN
1 stop7h 13mSpirit Airlines
vie. 12/122:36 pmCUN - ORD
1 stop10h 33mSpirit Airlines
Deal found 11/30$233
This Expedia deal was found by Cheapflights users on 12/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/139:14 pmORD - CUN
1 stop13h 22mSpirit Airlines
sáb. 12/2011:50 amCUN - ORD
Nonstop4h 03mSpirit Airlines
Deal found 12/1$235
This Cheapflightsfares deal was found by Cheapflights users on 11/30. 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. 12/79:14 pmORD - CUN
1 stop13h 22mSpirit Airlines
vie. 12/122:36 pmCUN - ORD
1 stop10h 33mSpirit Airlines
Deal found 11/30$238
This SmartFares deal was found by Cheapflights users on 12/1. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/66:00 amMDW - CUN
1 stop8h 33mAeromexico
mar. 12/91:33 pmCUN - MDW
1 stop11h 14mAeromexico
Deal found 12/1$302
This Aeromexico deal was found by Cheapflights users on 11/30. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/229:50 amMDW - CUN
1 stop5h 40mAeromexico
jue. 1/111:25 amCUN - MDW
1 stop11h 57mAeromexico
Deal found 11/30$320
This Aeromexico deal was found by Cheapflights users on 11/30. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/56:00 amMDW - CUN
1 stop7h 05mAeromexico
vie. 12/124:34 pmCUN - MDW
1 stop8h 13mAeromexico
Deal found 11/30$321
This Delta deal was found by Cheapflights users on 11/30. 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.
sáb. 12/66:00 amMDW - CUN
1 stop8h 33mDelta
mié. 12/103:15 pmCUN - MDW
1 stop9h 32mDelta
Deal found 11/30$327

Find 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 diciembre 2, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$214
(Mytrip)

One-way from

$100
(Mytrip)

Popular in

March

Cheapest in

September

Average price

$502
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 (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. 5% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 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 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 diciembre 2, 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

sáb. 2/28

6:04 am-2:56 pm

1 stop7h 52m

Cancun

sáb. 3/7

3:10 pm-10:56 pm

1 stop8h 46m

$287

ChicagoCancún

MDW - CUN

MDWCUN

Chicago Midway

dom. 2/22

5:25 am-1:55 pm

1 stop7h 30m

Cancun

jue. 2/26

4:10 pm-6:50 pm

Nonstop3h 40m

$314

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

dom. 12/7

6:45 am-3:33 pm

1 stop7h 48m

Cancun

mié. 12/10

6:00 am-1:12 pm

1 stop8h 12m

$317

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

sáb. 2/28

1:11 am-12:34 pm

1 stop10h 23m

Cancun

sáb. 3/7

6:01 am-12:55 pm

1 stop7h 54m

$319

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

lun. 2/16

1:11 am-1:47 pm

1 stop11h 36m

Cancun

lun. 2/23

11:18 am-11:00 pm

1 stop12h 42m

$319

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

dom. 3/1

1:11 am-5:38 pm

1 stop15h 27m

Cancun

sáb. 3/7

6:01 am-12:55 pm

1 stop7h 54m

$319

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

vie. 2/6

5:30 am-8:02 pm

2 stops13h 32m

Cancun

mar. 2/10

6:01 am-12:55 pm

1 stop7h 54m

$323

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

mié. 2/18

6:15 am-6:47 pm

2 stops11h 32m

Cancun

mar. 2/24

11:18 am-11:00 pm

1 stop12h 42m

$323

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

dom. 1/18

5:30 am-6:47 pm

2 stops12h 17m

Cancun

jue. 1/22

2:12 pm-11:00 pm

1 stop9h 48m

$323

ChicagoCancún

ORD - CUN

ORDCUN

Chicago O'Hare Intl

mar. 1/13

7:05 am-3:30 pm

1 stop7h 25m

Cancun

jue. 1/15

8:00 am-1:40 pm

1 stop6h 40m

$326

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/1

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 November 28, 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 $135). Flying from Chicago to Playa del Carmen in July is currently the most expensive (average of $217). 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 diciembre 2, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Playa del Carmen at noon. If you’re flexible enough to do this you can expect to save up to 41% on your trip compared to booking a flight in the evening.

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 November 29, 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. Thursday mornings 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 diciembre 2, 2025.

The most flights from CHI to PL9 are scheduled on a Tuesday (10 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 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 diciembre 2, 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
4,253 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
United Airlines
7.4
Good
9,065 reviews
Southwest
8.0
Very good
4,253 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
American Airlines
7.2
Good
11,041 reviews
Southwest
8.0
Very good
4,253 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Spirit Airlines
6.3
Okay
8,156 reviews
Southwest
8.0
Very good
4,253 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Frontier
5.8
Fair
3,094 reviews
Southwest
8.0
Very good
4,253 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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 JetBlue, Southwest, and Delta fly from Chicago to Playa del Carmen in about 7h 30m. The time it takes to get you to your destination can typically vary by up to 22m. 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 Frontier, with whom users have recently found tickets for as low as $73. However, be on the lookout for offers from Viva and Spirit Airlines, 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: Spirit Airlines (89%), American Airlines (82%), Frontier( 80%).

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

    While on average a flight from Chicago to Playa del Carmen is generally $625, our data shows the cheapest flight currently is $91. When looking at the most popular route, (Chicago O'Hare Intl - Cancun), you can expect to pay $207 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 $135). Flying from Chicago to Playa del Carmen in July is currently the most expensive (average of $217). 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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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 diciembre 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
AeromexicoCheapest$145Average$411FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$161Average$514FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$165Average$346FlexibilityNo cancel feeOn-time65%
DeltaCheapest$168Average$494FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$178Average$468FlexibilityNo cancel feeOn-time62%
VolarisCheapest$179Average$550FlexibilityNo cancel feeOn-time79%
VivaCheapest$237Average$300FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$266Average$579FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$268Average$529FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$287Average$425FlexibilityNo cancel feeOn-time62%

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