$183 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.
$467 Roundtrip, just found
$467
Roundtrip
just found
ORD
O'Hare Intl.
TQO
Tulum Intl. Airport
$508 Roundtrip, found 2 hours ago
$508
Roundtrip
found 2 hours ago
MDW
Midway Intl.
CUN
Cancun Intl.
$546 Roundtrip, just found
$546
Roundtrip
just found
ORD
O'Hare Intl.
CZM
Cozumel Intl.
$622 Roundtrip, found 2 hours ago
$622
Roundtrip
found 2 hours ago
Airfares from $183 One Way, $299 Round Trip from Chicago to Playa del Carmen
Prices starting at $299 for return flights and $183 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
$299 Roundtrip, just found
$299
Roundtrip
just found
ORD
Chicago
CUN
Cancun
$356 Roundtrip, found 1 day ago
$356
Roundtrip
found 1 day ago
ORD
Chicago
CUN
Cancun
$378 Roundtrip, found 15 hours ago
$378
Roundtrip
found 15 hours ago
MDW
Chicago
CUN
Cancun
$408 Roundtrip, found 2 hours ago
$408
Roundtrip
found 2 hours ago
ORD
Chicago
CUN
Cancun
$421 Roundtrip, just found
$421
Roundtrip
just found
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
7.8/10 Good! (1,073 reviews)
Nov 30 - Dec 6
6 night stay
Chicago (CHI) to Cancun (CUN)
American Airlines • Coach
Cancun (CUN) to Chicago (CHI)
Viva Aerobus • Coach
Price was $1,969, price is now $828 per person
$828
per person
found 1 day ago
Nice
Reviewed on Oct 21, 2026
4.0-star property
Delek Holbox
8.8/10 Excellent! (304 reviews)
Nov 27 - Dec 4
7 night stay
Chicago (CHI) to Cancun (CUN)
Frontier Airlines • Roundtrip • Coach
Price was $2,913, price is now $1,184 per person
$1,184
per person
found 1 day ago
Un lugar relajado. La atención del personal inmejorable. Hugo, a cargo del Staff es extraordinario. Puedes ver el fenómeno impresionante de la bioluminiscencia en la misma Playa del Hotel, es maravilloso. Definitivamente volvería.
Reviewed on Oct 14, 2026
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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
Hotel Mousai Cancun Adults Only - All Inclusive
9.8/10 Exceptional! (139 reviews)
Nov 27 - Dec 4
7 night stay
Chicago (CHI) to Cancun (CUN)
Frontier Airlines • Roundtrip • BusinessClass
Price was $7,441, price is now $3,582 per person
$3,582
per person
found 1 day ago
This experience was mind blowing. Have visited multiple hotels but this one is one of its kind. Property, room, cleanliness, amenities were all top notch, but what really stood out was the staff and the food. Food is michelin star grade, without a question. Restaurants DAO, NOI, Bocados were out of this world… When talking abouts staff, i’m basically speechless. Intelligence paired with kindness, manner and they were all seeking to make every single of your moments unforgettable: special thanks to Marcia our concierge, Jose & Jesus the mixologists, and the best waiters EVER Manuel and Yamil on the rooftop, Fernando at NOI. Honestly, i could write this review for hours, was a lifetime exoerience for us to be there. Everything was way beyond our expectations. One thing to keep in mind though: beach is not the best, this is not your place if that is your point. But honestly, Isla mujeres is like 40min away from there, with Playa Norte which is one of the TOP beaches in Mexico. There is also a construction going on next to the hotel, they are bulding Lemuria their new property, but there were little to no discomcofrts about that. They even pay attention to crank up the music when there is noise.
Reviewed on Oct 22, 2026
5.0-star property
Hotel Mousai Cancun Ocean Front Adults Only - All Inclusive
8.4/10 Very Good! (17 reviews)
Nov 27 - Dec 4
7 night stay
Chicago (CHI) to Cancun (CUN)
Frontier Airlines • Roundtrip • BusinessClass
Price was $7,444, price is now $3,601 per person
$3,601
per person
found 1 day ago
I really liked this hotel and the comfort it provides is unmatched. Every one of the staff members is really attentive and nice. The only reason I’m giving it 4 starts instead of 5 is the food. Out of all the restaurants around this hotel, just one met my expectations.
Reviewed on Jun 1, 2026
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View all tripsPlaya del Carmen first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Hotel Riu Palace Kukulkan - Adults Only - All Inclusive
9.2/10 Wonderful! (5,642 reviews)
Dec 14 - Dec 18
4 night stay
Chicago (CHI) to Cancun (CUN)
United • FirstClass
Cancun (CUN) to Chicago (CHI)
American Airlines • FirstClass
Price was $2,619, price is now $1,561 per person
$1,561
per person
found 19 hours ago
Everything was great
Reviewed on Oct 23, 2026
4.0-star property
Hotel Riu Palace Peninsula - All Inclusive
9/10 Wonderful! (4,733 reviews)
Dec 2 - Dec 7
5 night stay
Chicago (ORD) to Cancun (CUN)
United • FirstClass
Cancun (CUN) to Chicago (ORD)
American Airlines • FirstClass
Price was $3,288, price is now $1,773 per person
$1,773
per person
found 1 day ago
5.0-star property
Hotel Mousai Cancun Adults Only - All Inclusive
9.8/10 Exceptional! (139 reviews)
Dec 14 - Dec 18
4 night stay
Chicago (CHI) to Cancun (CUN)
United • FirstClass
Cancun (CUN) to Chicago (CHI)
American Airlines • FirstClass
Price was $3,993, price is now $2,367 per person
$2,367
per person
found 19 hours ago
This experience was mind blowing. Have visited multiple hotels but this one is one of its kind. Property, room, cleanliness, amenities were all top notch, but what really stood out was the staff and the food. Food is michelin star grade, without a question. Restaurants DAO, NOI, Bocados were out of this world… When talking abouts staff, i’m basically speechless. Intelligence paired with kindness, manner and they were all seeking to make every single of your moments unforgettable: special thanks to Marcia our concierge, Jose & Jesus the mixologists, and the best waiters EVER Manuel and Yamil on the rooftop, Fernando at NOI. Honestly, i could write this review for hours, was a lifetime exoerience for us to be there. Everything was way beyond our expectations. One thing to keep in mind though: beach is not the best, this is not your place if that is your point. But honestly, Isla mujeres is like 40min away from there, with Playa Norte which is one of the TOP beaches in Mexico. There is also a construction going on next to the hotel, they are bulding Lemuria their new property, but there were little to no discomcofrts about that. They even pay attention to crank up the music when there is noise.
Reviewed on Oct 22, 2026
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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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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.