$172 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.
$373 Roundtrip, just found
$373
Roundtrip
just found
ORD
O'Hare Intl.
CZM
Cozumel Intl.
$497 Roundtrip, found 1 day ago
$497
Roundtrip
found 1 day ago
MDW
Midway Intl.
CUN
Cancun Intl.
$501 Roundtrip, found 1 day ago
$501
Roundtrip
found 1 day ago
ORD
O'Hare Intl.
TQO
Tulum Intl. Airport
$533 Roundtrip, found 1 day ago
$533
Roundtrip
found 1 day ago
Airfares from $172 One Way, $349 Round Trip from Chicago to Puerto Aventuras
Prices starting at $349 for return flights and $172 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, found 1 hour ago
$349
Roundtrip
found 1 hour ago
ORD
Chicago
CUN
Cancun
$373 Roundtrip, just found
$373
Roundtrip
just found
ORD
Chicago
CUN
Cancun
$390 Roundtrip, just found
$390
Roundtrip
just found
ORD
Chicago
CUN
Cancun
$419 Roundtrip, found 7 hours ago
$419
Roundtrip
found 7 hours ago
MDW
Chicago
CUN
Cancun
$428 Roundtrip, found 4 days ago
$428
Roundtrip
found 4 days ago
Puerto Aventuras economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Copal Tulum Hotel
8.8/10 Excellent! (1,001 reviews)
Dec 25 - Dec 30
5 night stay
Chicago (CHI) to Cancun (CUN)
Southwest Airlines • Coach
Cancun (CUN) to Chicago (CHI)
American Airlines • Coach
Price was $2,156, price is now $1,028 per person
$1,028
per person
found 1 day ago
Perfect stay. Location better than beach strip
Reviewed on Nov 7, 2026
5.0-star property
Hotelito Azul - A Michelin Key Winner
8.4/10 Very Good! (766 reviews)
Dec 23 - Dec 27
4 night stay
Chicago (CHI) to Cancun (CUN)
Delta • Non-stop roundtrip • Coach
Price was $3,203, price is now $1,523 per person
$1,523
per person
found 1 day ago
Unfortunately the hotel is run down and not maintained. The great reviews are old when the hotel was new and Tulum had tourists. The staff are great and tried to help where they can.
Tulum overall is a dead town, very scammy and extremely over priced - No wonder the tourists have stopped coming. You are better off going somewhere else for holiday.
Reviewed on Nov 8, 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.
5.0-star property
Ocean Coral Riviera Cancun All Inclusive
8.4/10 Very Good! (2,583 reviews)
Jan 3 - Jan 7
4 night stay
Chicago (ORD) to Cancun (CUN)
Frontier Airlines • Roundtrip • PremiumEconomy
Price was $2,097, price is now $1,106 per person
$1,106
per person
found 1 day ago
I originally booked Ocean coral, but due to renovations they offered me their sister's hotel-ocean riviera paradise. It was beautiful. Very kids friendly. Total 9 people traveling and 1 child and we had 3 rooms. Food was delicious I didn't have an issues.
Reviewed on Nov 7, 2026
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View all tripsPuerto Aventuras 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! (143 reviews)
Dec 23 - Dec 30
7 night stay
Chicago (ORD) to Cancun (CUN)
United • Roundtrip • BusinessClass
Price was $10,547, price is now $5,891 per person
$5,891
per person
found 3 hours ago
Restaurant staff and food quality and choices remain five star incredible. However the pool staff and housecleaning was terrible this trip. The pool staff are all talking to each other and don’t seem to care about serving the guests at all. You have to complain to get a drink and that’s not for me. Housekeeping was a disaster. Our room often didn’t get cleaned at all or we had to wait until 5pm for it to get cleaned. They NEED to fix these two things to bring the hotel to the five star rating it boasts. Otherwise - todo bidets, hot tub on balcony, extremely friendly restaurant staff, modern rooms, incredible food choices and restaurant service all remains five stars.
Reviewed on Nov 6, 2026
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View all tripsPuerto Aventuras first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Palace Costa Mujeres - All Inclusive
8.8/10 Excellent! (1,339 reviews)
Dec 15 - Dec 22
7 night stay
Chicago (ORD) to Cancun (CUN)
United • Non-stop • FirstClass
Cancun (CUN) to Chicago (ORD)
Frontier Airlines • Non-stop • FirstClass
Price was $3,827, price is now $2,138 per person
$2,138
per person
found 10 hours ago
Absolutely great experience
Reviewed on Nov 9, 2026
3.5-star property
Cancun Bay All Inclusive Hotel
7.6/10 Good! (1,194 reviews)
Dec 23 - Dec 30
7 night stay
Chicago (ORD) to Cancun (CUN)
American Airlines • Non-stop roundtrip • FirstClass
Price was $4,039, price is now $2,296 per person
$2,296
per person
found 18 hours ago
Very friendly and helpful staff
Beach view amazing
Reviewed on Nov 8, 2026
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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
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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.