$90 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.
$266 Roundtrip, just found
$266
Roundtrip
just found
MDW
Midway Intl.
CUN
Cancun Intl.
$330 Roundtrip, just found
$330
Roundtrip
just found
ORD
O'Hare Intl.
TQO
Tulum Intl. Airport
$384 Roundtrip, found 1 day ago
$384
Roundtrip
found 1 day ago
RFD
Greater Rockford
CUN
Cancun Intl.
$460 Roundtrip, found 5 days ago
$460
Roundtrip
found 5 days ago
Airfares from $90 One Way, $201 Round Trip from Chicago to Playa del Carmen
Prices starting at $201 for return flights and $90 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
$201 Roundtrip, just found
$201
Roundtrip
just found
ORD
Chicago
CUN
Cancun
$210 Roundtrip, just found
$210
Roundtrip
just found
MDW
Chicago
CUN
Cancun
$262 Roundtrip, found 6 days ago
$262
Roundtrip
found 6 days ago
ORD
Chicago
TQO
Tulum
$300 Roundtrip, found 20 hours ago
$300
Roundtrip
found 20 hours ago
MDW
Chicago
TQO
Tulum
$314 Roundtrip, found 20 hours ago
$314
Roundtrip
found 20 hours ago
Playa del Carmen economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Hotelito del Mar
9/10 Wonderful! (67 reviews)
Dec 31 - Jan 7
7 night stay
Chicago (ORD) to Cancun (CUN)
Frontier Airlines • Coach
Cancun (CUN) to Chicago (ORD)
Spirit Airlines • Coach
Price was $2,191, price is now $811 per person
$811
per person
found 1 day ago
Spacious rooms and roof top pool. Just a few blocks from 5th Avenue. Loved it and will be back!
Reviewed on Jul 26, 2019
3.5-star property
Ahau Tulum
8.6/10 Excellent! (249 reviews)
Dec 14 - Dec 22
8 night stay
Chicago (CHI) to Tulum Intl. Airport (TQO)
Spirit Airlines • Non-stop roundtrip • Coach
Price was $5,085, price is now $1,686 per person
$1,686
per person
found 20 hours ago
Overall a wonderful experience.
Reviewed on Jul 25, 2023
3.5-star property
Maya Tulum by G Hotels
7.8/10 Good! (398 reviews)
Jan 3 - Jan 7
4 night stay
Chicago (CHI) to Tulum Intl. Airport (TQO)
American Airlines • Non-stop roundtrip • Coach
Price was $3,222, price is now $1,090 per person
$1,090
per person
found 1 day ago
Pros: We stayed in one of the beachfront bungalows and had our own private beach access, lounge chairs, even hammocks. THUMP THUMP THUMP My spouse is AFAB non-binary, post-chest surgery and was able to lie in the sun without a top -- something hard to do in a lot of beach spaces. The room looked nice and the bed was comfortable; toilet was separate from sinks and shower, which always helps with 2 people. THUMP THUMP THUMP
Cons: The hotel next door plays really loud music from mid-afternoon until midnight or 2am, depending on the night. It's not Maya's fault, but the sound carries over the beach. We chose to go to Tulum because we heard it was quieter than Cancun, but this is unfortunately in the party district. THUMP THUMP THUMP I was able to tune out the music with ear plugs, but this meant that there was no falling asleep to the sound of the waves. My spouse had a harder time with it and had to take sleep aids because the THUMP THUMP THUMP was driving them insane.
The lighting in the room is very ambient and relaxing at night, but there is almost no light by the bathroom mirror. THUMP THUMP THUMP If you want to put on makeup or shave, leave the room and find one of the random mirrors gracing the grounds around the hotel. At night, forget it. The restaurant turned us away at 5pm when they close at 6, told us to come back at 8. When we got food at 9 it was cold and underwhelming.
If the THUMP THUMP THUMP in this review drives you nuts, look for a different hotel.
Reviewed on Feb 15, 2024
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View all tripsPlaya del Carmen business class flight packages
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Hard Rock Hotel Cancun - All Inclusive
7.8/10 Good! (1,307 reviews)
Jan 2 - Jan 6
4 night stay
Chicago (CHI) to Cancun (CUN)
American Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $3,417, price is now $1,969 per person
$1,969
per person
found 18 hours ago
Room was a little dated and worn. Staff were excellent.
Reviewed on Oct 29, 2025
4.0-star property
Family 3 Bedroom Ocean Villa By Wyndham Grand Cancun
7.6/10 Good! (49 reviews)
Jan 2 - Jan 6
4 night stay
Chicago (CHI) to Cancun (CUN)
American Airlines • Non-stop roundtrip • BusinessClass
Price was $6,434, price is now $3,305 per person
$3,305
per person
found 18 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
4.5-star property
Temptation at The Tower Cancún All Inclusive - Adults Only
9/10 Wonderful! (591 reviews)
Jan 1 - Jan 4
3 night stay
Chicago (ORD) to Cancun (CUN)
American Airlines • Roundtrip • BusinessClass
Save 100% on your flight
Price was $4,931, price is now $2,799 per person
$2,799
per person
found 1 day ago
The resort was clean, pleasing, and plenty of space. The food however left something to be desired. I feel that quality was sacrificed for quantity. Even the "nicer" dining areas were somewhat of a disappointment. The Flame was a total disappointment. The grilled chicken wasn't grilled and was very dry. The Strip steak wasn't what a Strip steak should be and was mostly fat and gristle. The food at the grills at the pool and the party were fantastic.
The staff was great.
Reviewed on Mar 19, 2023
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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
Hard Rock Hotel Cancun - All Inclusive
7.8/10 Good! (1,307 reviews)
Dec 28 - Jan 1
4 night stay
Chicago (ORD) to Cancun (CUN)
American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $4,975, price is now $2,882 per person
$2,882
per person
found 1 day ago
Room was a little dated and worn. Staff were excellent.
Reviewed on Oct 29, 2025
4.0-star property
Family 3 Bedroom Ocean Villa By Wyndham Grand Cancun
7.6/10 Good! (49 reviews)
Jan 2 - Jan 9
7 night stay
Chicago (ORD) to Cancun (CUN)
American Airlines • Non-stop roundtrip • FirstClass
Price was $10,128, price is now $4,937 per person
$4,937
per person
found 16 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
4.5-star property
Temptation at The Tower Cancún All Inclusive - Adults Only
9/10 Wonderful! (591 reviews)
Dec 28 - Jan 1
4 night stay
Chicago (ORD) to Cancun (CUN)
American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $5,545, price is now $3,176 per person
$3,176
per person
found 1 day ago
The resort was clean, pleasing, and plenty of space. The food however left something to be desired. I feel that quality was sacrificed for quantity. Even the "nicer" dining areas were somewhat of a disappointment. The Flame was a total disappointment. The grilled chicken wasn't grilled and was very dry. The Strip steak wasn't what a Strip steak should be and was mostly fat and gristle. The food at the grills at the pool and the party were fantastic.
The staff was great.
Reviewed on Mar 19, 2023
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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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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.