$152 Cheap flight deals from Chicago (CHI) to Playa del Carmen (CUN)
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This Weekend's Flight Deals from Chicago to Playa del Carmen
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
ORD
O'Hare Intl.
CUN
Cancun Intl.
$400 Roundtrip, just found
$400
Roundtrip
just found
ORD
O'Hare Intl.
TQO
Tulum Intl. Airport
$486 Roundtrip, found 9 hours ago
$486
Roundtrip
found 9 hours ago
MDW
Midway Intl.
TQO
Tulum Intl. Airport
$486 Roundtrip, found 9 hours ago
$486
Roundtrip
found 9 hours ago
MDW
Midway Intl.
CUN
Cancun Intl.
$493 Roundtrip, just found
$493
Roundtrip
just found
Airfares from $152 One Way, $249 Round Trip from Chicago to Playa del Carmen
Prices starting at $249 for return flights and $152 for one-way flights to Playa del Carmen were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
ORD
Chicago
CUN
Cancun
$249 Roundtrip, found 1 hour ago
$249
Roundtrip
found 1 hour ago
ORD
Chicago
CUN
Cancun
$318 Roundtrip, found 10 hours ago
$318
Roundtrip
found 10 hours ago
ORD
Chicago
TQO
Tulum
$333 Roundtrip, found 8 hours ago
$333
Roundtrip
found 8 hours ago
ORD
Chicago
CZM
Cozumel
$363 Roundtrip, found 9 hours ago
$363
Roundtrip
found 9 hours ago
MDW
Chicago
CUN
Cancun
$383 Roundtrip, found 4 days ago
$383
Roundtrip
found 4 days ago
Playa del Carmen economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Ocean Dream Cancun by GuruHotel
7.6/10 Good! (1,040 reviews)
Jul 17 - Jul 24
7 night stay
Chicago (CHI) to Cancun (CUN)
Roundtrip • Coach
Price was $2,263, price is now $880 per person
$880
per person
found 1 day ago
Room service phone did not work, TVs are outdated and bathroom was clogged Other than that it was okay Loved that it’s very well located
Reviewed on Sep 16, 2025
3.5-star property
Tago Tulum by G Hotels
9.2/10 Wonderful! (414 reviews)
Jul 23 - Jul 27
4 night stay
Chicago (CHI) to Cancun (CUN)
American Airlines • Non-stop roundtrip • Coach
Price was $2,210, price is now $916 per person
$916
per person
found 1 day ago
Its all about the Staff here in addition to the splendid property and food!
Reviewed on Jun 23, 2024
4.0-star property
Family 3 Bedroom Ocean Villa By Wyndham Grand Cancun
7.6/10 Good! (49 reviews)
Jul 12 - Jul 17
5 night stay
Chicago (CHI) to Cancun (CUN)
Volaris • Non-stop • Coach
Cancun (CUN) to Chicago (CHI)
American Airlines • Non-stop • Coach
Price was $7,223, price is now $3,055 per person
$3,055
per person
found 1 day ago
This property is not equipped to handle the amount of people staying here. Peope are running to the pool and beach at 7 a.m. to get lounge chairs bc there are not enough on the property. The dining facilities are not large enough. My party was turned away a few times bc the various reataurants were full or at capacity (only one restaurant takes a reservation which is a scramble to get at 8 a.m. each morning).The room was outdated and needs renovating and new decor. It was hard to get anyone to help with anything. Once, I did connect with someone he/she was nice, polite, and helpful. The hotel is understaffed and needs more lounge chairs and umbrellas.
Reviewed on Apr 11, 2022
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View all tripsPlaya del Carmen business class flight packages
Price found within the past 48 hours. Click for updated prices.
5.0-star property
Live Aqua Cancun - Adults Only - All-Inclusive
9.2/10 Wonderful! (1,975 reviews)
Jul 6 - Jul 12
6 night stay
Chicago (CHI) to Cancun (CUN)
Frontier Airlines • Roundtrip • BusinessClass
Save 100% on your flight
Price was $3,425, price is now $1,858 per person
$1,858
per person
found 5 hours ago
Tranquil and relaxing.
Reviewed on Apr 4, 2026
4.0-star property
Family 3 Bedroom Ocean Villa By Wyndham Grand Cancun
7.6/10 Good! (49 reviews)
Jul 2 - Jul 7
5 night stay
Chicago (ORD) to Cancun (CUN)
Frontier Airlines • Roundtrip • BusinessClass
Price was $6,648, price is now $3,218 per person
$3,218
per person
found 11 hours ago
This property is not equipped to handle the amount of people staying here. Peope are running to the pool and beach at 7 a.m. to get lounge chairs bc there are not enough on the property. The dining facilities are not large enough. My party was turned away a few times bc the various reataurants were full or at capacity (only one restaurant takes a reservation which is a scramble to get at 8 a.m. each morning).The room was outdated and needs renovating and new decor. It was hard to get anyone to help with anything. Once, I did connect with someone he/she was nice, polite, and helpful. The hotel is understaffed and needs more lounge chairs and umbrellas.
Reviewed on Apr 11, 2022
5.0-star property
Grand Fiesta Americana Coral Beach Cancun - All Inclusive
9.2/10 Wonderful! (4,072 reviews)
Jul 6 - Jul 12
6 night stay
Chicago (CHI) to Cancun (CUN)
Frontier Airlines • Roundtrip • BusinessClass
Save 100% on your flight
Price was $4,551, price is now $2,452 per person
$2,452
per person
found 5 hours ago
Very enjoyable stay. Friendly staff, great amenities. A bit difficult for our party of 10 to get early dinner reservations (earliest was 8:30/9ish each night). Food was great though. Would definitely come back.
Reviewed on Mar 5, 2026
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See all available trips from Chicago to Playa del Carmen
View all tripsMore About Flying To Playa del Carmen from Chicago
Route Information for Flights from Chicago to Playa del Carmen
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | CUN |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Playa del Carmen
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Your Perfect Playa del CarmenVacation Package
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With the best deals and easy searching options, Orbitz make it easy and fun to find cheap Chicago to Playa del Carmen flights, a great hotel, or a full vacation package. With Orbitz’s low price guarantee, you always get great discounts on air ticket prices.
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Playa del Carmen Airports
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.