$176 Cheap flight deals from Chicago (CHI) to Puerto Aventuras (CUN)
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This Weekend's Flight Deals from Chicago to Puerto Aventuras
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.
$494 Roundtrip, found 5 hours ago
$494
Roundtrip
found 5 hours ago
ORD
O'Hare Intl.
TQO
Tulum Intl. Airport
$508 Roundtrip, found 13 hours ago
$508
Roundtrip
found 13 hours ago
MDW
Midway Intl.
CUN
Cancun Intl.
$546 Roundtrip, found 11 hours ago
$546
Roundtrip
found 11 hours ago
ORD
O'Hare Intl.
CZM
Cozumel Intl.
$622 Roundtrip, found 13 hours ago
$622
Roundtrip
found 13 hours ago
Airfares from $176 One Way, $349 Round Trip from Chicago to Puerto Aventuras
Prices starting at $349 for return flights and $176 for one-way flights to Puerto Aventuras 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
$349 Roundtrip, just found
$349
Roundtrip
just found
ORD
Chicago
CUN
Cancun
$356 Roundtrip, found 2 days ago
$356
Roundtrip
found 2 days ago
ORD
Chicago
CUN
Cancun
$370 Roundtrip, just found
$370
Roundtrip
just found
MDW
Chicago
CUN
Cancun
$408 Roundtrip, found 9 hours ago
$408
Roundtrip
found 9 hours ago
ORD
Chicago
CUN
Cancun
$420 Roundtrip, found 1 hour ago
$420
Roundtrip
found 1 hour ago
Puerto Aventuras economy flight packages
Price found within the past 48 hours. Click for updated prices.
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 $2,777, price is now $912 per person
$912
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
4.0-star property
Hotel Riu Palace Peninsula - All Inclusive
9/10 Wonderful! (4,733 reviews)
Nov 27 - Dec 4
7 night stay
Chicago (CHI) to Cancun (CUN)
Frontier Airlines • Roundtrip • Coach
Price was $4,500, price is now $1,799 per person
$1,799
per person
found 1 day ago
Exelente estancia limpieza y comida vistas …todos súper amables volveríamos con gusto ampliamente recomendable 10/10
Reviewed on Oct 24, 2026
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View all tripsPuerto Aventuras packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
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View all tripsPuerto Aventuras business class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Palace Las Americas - Adults Only- All Inclusive
9.2/10 Wonderful! (5,769 reviews)
Nov 27 - Dec 4
7 night stay
Chicago (CHI) to Cancun (CUN)
Frontier Airlines • Roundtrip • BusinessClass
Save 100% on your flight
Price was $3,728, price is now $1,943 per person
$1,943
per person
found 1 day ago
We had a great experience we enjoyed our stay it was great .
Reviewed on Oct 23, 2026
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 $7,434, price is now $3,575 per person
$3,575
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 $7,461, price is now $3,714 per person
$3,714
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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See all available trips from Chicago to Puerto Aventuras
View all tripsPuerto Aventuras 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 1 day ago
Amazing experience
Reviewed on Oct 24, 2026
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 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
4.0-star property
Family Villas By Wyndham Grand Cancún All Inclusive
7.6/10 Good! (51 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 $4,499, price is now $2,737 per person
$2,737
per person
found 1 day ago
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See all available trips from Chicago to Puerto Aventuras
View all tripsMore About Flying To Puerto Aventuras from Chicago
Route Information for Flights from Chicago to Puerto Aventuras
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | CUN |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Puerto Aventuras
Looking for cheap Chicago to Puerto Aventuras flights? Orbitz has the cheapest air fares for flights from Chicago to Puerto Aventuras. Plus, with our cutting-edge mobile tools, travel planning has never been easier or more wallet-friendly.
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Orbitz is your number one source for low fares for Chicago to Puerto Aventuras flights. Our low price guarantee on domestic and international air tickets give you great savings for a perfect trip to Puerto Aventuras. Need hotels too? You can book them last minute on your mobile phone.
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Puerto Aventuras 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.