$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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Feb 22 — Mar 11
1 adult, Economy
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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 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 CarmenExplore 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 January 23, 2026.
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 January 23, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 1/21. 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 3/16:05 am
ORD
- CUN
Nonstop3h 49m
Spirit Airlines
Fri 3/611:59 am
CUN
- ORD
Nonstop3h 54m
Spirit Airlines
Deal found 1/21![Spirit Airlines logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 1/22. 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.
Tue 2/36:23 am
ORD
- CUN
1 stop14h 03m
Multiple Airlines
Fri 2/61:21 pm
CUN
- ORD
1 stop7h 17m
Multiple Airlines
Deal found 1/22![Multiple Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
Sun 2/226:05 am
ORD
- CUN
Nonstop3h 49m
Multiple Airlines
Thu 3/56:27 pm
CUN
- ORD
Nonstop4h 10m
Multiple Airlines
Deal found 1/20![Multiple Airlines logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 2/288:59 am
ORD
- CUN
1 stop5h 51m
Multiple Airlines
Thu 3/56:27 pm
CUN
- ORD
Nonstop4h 10m
Multiple Airlines
Deal found 1/21![Multiple Airlines logo]()
$229
This Expedia deal was found by Cheapflights users on 1/21. 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.
Sat 2/288:59 am
ORD
- CUN
1 stop5h 51m
Multiple Airlines
Wed 3/47:19 pm
CUN
- ORD
Nonstop4h 09m
Multiple Airlines
Deal found 1/21![Multiple Airlines logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 1/316:05 am
ORD
- CUN
Nonstop3h 49m
Spirit Airlines
Sat 2/711:59 am
CUN
- ORD
Nonstop3h 54m
Spirit Airlines
Deal found 1/21![Spirit Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 1/22. 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 2/218:59 am
ORD
- CUN
1 stop5h 51m
Multiple Airlines
Wed 2/257:19 pm
CUN
- ORD
Nonstop4h 09m
Multiple Airlines
Deal found 1/22![Multiple Airlines logo]()
$232
This CheapOair deal was found by Cheapflights users on 1/22. 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.
Tue 2/107:55 am
ORD
- CUN
Nonstop4h 12m
Multiple Airlines
Wed 2/181:25 pm
CUN
- ORD
1 stop11h 22m
Multiple Airlines
Deal found 1/22![Multiple Airlines logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
Mon 2/236:10 am
ORD
- CUN
Nonstop4h 04m
Multiple Airlines
Thu 3/51:25 pm
CUN
- ORD
1 stop6h 46m
Multiple Airlines
Deal found 1/21![Multiple Airlines logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 1/22. 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.
Fri 2/66:05 am
ORD
- CUN
Nonstop3h 49m
Multiple Airlines
Wed 2/117:19 pm
CUN
- ORD
Nonstop4h 09m
Multiple Airlines
Deal found 1/22![Multiple Airlines logo]()
$235
This Super.com deal was found by Cheapflights users on 1/22. 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.
Wed 2/46:05 am
ORD
- CUN
Nonstop3h 49m
Spirit Airlines
Mon 2/911:59 am
CUN
- ORD
Nonstop3h 54m
Spirit Airlines
Deal found 1/22![Spirit Airlines logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 1/22. 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.
Tue 2/247:55 am
ORD
- CUN
Nonstop4h 12m
Multiple Airlines
Wed 2/251:25 pm
CUN
- ORD
1 stop6h 46m
Multiple Airlines
Deal found 1/22![Multiple Airlines logo]()
$237
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 January 23, 2026.
Most accurate provider | Mytrip 3 stars |
|---|---|
Most trusted provider | Mytrip 3 stars |
Round-trip from | $226 (Cheapflightsfares) |
One-way from | $99 (CheapOair) |
Popular in | December |
Cheapest in | September |
Average price | $393 |
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 January 23, 2026.
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
Tue 3/3
8:43 am-1:33 pm
Nonstop3h 50m
Cancun
Tue 3/10
2:18 pm-6:09 pm
Nonstop3h 51m
$301
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sat 2/21
1:11 am-8:02 pm
1 stop17h 51m
Cancun
Thu 3/5
8:38 am-11:00 pm
1 stop15h 22m
$321
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Wed 2/25
6:30 am-9:11 pm
2 stops13h 41m
Cancun
Thu 3/5
6:01 am-11:00 pm
1 stop17h 59m
$330
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Thu 3/5
12:45 pm-9:11 pm
1 stop7h 26m
Cancun
Tue 3/10
8:00 am-4:55 pm
1 stop8h 55m
$336
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Tue 3/10
6:15 am-5:27 pm
2 stops11h 12m
Cancun
Tue 3/17
10:00 am-9:10 pm
1 stop11h 10m
$336
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Fri 2/6
7:05 am-9:11 pm
1 stop13h 06m
Cancun
Tue 2/10
1:33 pm-11:56 pm
2 stops11h 23m
$336
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Sat 2/7
6:15 am-6:47 pm
2 stops11h 32m
Cancun
Sat 2/14
8:00 am-2:10 pm
1 stop7h 10m
$336
ChicagoCancún
ORD - CUN
ORDCUN
Chicago O'Hare Intl
Mon 3/30
7:59 pm-9:00 am
1 stop13h 01m
Cancun
Wed 4/1
4:45 pm-8:30 am
1 stop15h 45m
$336
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Mon 3/9
7:45 am-1:20 pm
1 stop5h 35m
Cancun
Fri 3/13
8:30 am-12:10 pm
Nonstop3h 40m
$340
ChicagoCancún
MDW - CUN
MDWCUN
Chicago Midway
Fri 2/20
6:00 am-4:45 pm
1 stop9h 45m
Cancun
Wed 2/25
12:05 pm-10:31 pm
2 stops11h 26m
$341
Showing 1-10 of 46 results
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 January 16, 2026.
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 $148). 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 January 23, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago to Playa del Carmen in the afternoon. If you’re flexible enough to do this you can expect to save up to 24% on your trip compared to booking a flight at noon.
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 January 23, 2026.
The most flights from CHI to PL9 are scheduled on a Monday (13 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (11 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 January 23, 2026.
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.
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Chicago to Playa del Carmen
See prices for flight routes from nearby airports that may be better suited for you.
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 January 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$129 | Average$394 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$134 | Average$339 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$140 | Average$363 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$166 | Average$1,245 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$180 | Average$412 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$220 | Average$297 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$250 | Average$425 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$259 | Average$522 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$523 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$279 | Average$387 | FlexibilityNo cancel fee | On-time67% |