$138 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.
$349 Roundtrip, found 4 hours ago
$349
Roundtrip
found 4 hours ago
ORD
O'Hare Intl.
TQO
Tulum Intl. Airport
$486 Roundtrip, found 2 days ago
$486
Roundtrip
found 2 days ago
MDW
Midway Intl.
CUN
Cancun Intl.
$494 Roundtrip, found 3 hours ago
$494
Roundtrip
found 3 hours ago
ORD
O'Hare Intl.
CZM
Cozumel Intl.
$544 Roundtrip, found 11 hours ago
$544
Roundtrip
found 11 hours ago
Airfares from $138 One Way, $249 Round Trip from Chicago to Puerto Aventuras
Prices starting at $249 for return flights and $138 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
$249 Roundtrip, found 4 hours ago
$249
Roundtrip
found 4 hours ago
ORD
Chicago
CUN
Cancun
$327 Roundtrip, found 2 days ago
$327
Roundtrip
found 2 days ago
ORD
Chicago
TQO
Tulum
$333 Roundtrip, found 1 day ago
$333
Roundtrip
found 1 day ago
MDW
Chicago
CUN
Cancun
$351 Roundtrip, found 1 day ago
$351
Roundtrip
found 1 day ago
ORD
Chicago
CZM
Cozumel
$355 Roundtrip, found 17 hours ago
$355
Roundtrip
found 17 hours ago
Puerto Aventuras 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 15 - Jul 19
4 night stay
Chicago (CHI) to Cancun (CUN)
Frontier Airlines • Non-stop • Coach
Cancun (CUN) to Chicago (CHI)
American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,491, price is now $681 per person
$681
per person
found 2 days 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Room service phone did not work, TVs are outdated and bathroom was clogged Other than that it was okay Loved that it’s very well located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 15 - Jul 19
4 night stay
Chicago (CHI) to Cancun (CUN)
Volaris • Non-stop roundtrip • Coach
Price was $2,328, price is now $919 per person
$919
per person
found 2 days ago
Its all about the Staff here in addition to the splendid property and food!
Reviewed on Jun 23, 2024
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View all tripsPuerto Aventuras packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Ventura - All Inclusive
8.6/10 Excellent! (531 reviews)
Jul 19 - Jul 22
3 night stay
Chicago (MDW) to Cancun (CUN)
Frontier Airlines • Non-stop • PremiumEconomy
Cancun (CUN) to Chicago (MDW)
Aeromexico • Non-stop • PremiumEconomy
Price was $1,732, price is now $1,199 per person
$1,199
per person
found 15 hours ago
Well satisfy for what pay, and all the amenities.
Reviewed on May 3, 2026
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See all available trips from Chicago to Puerto Aventuras
View all tripsPuerto Aventuras business class flight packages
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Fiesta Americana Condesa Cancun All Inclusive
8.8/10 Excellent! (3,922 reviews)
Jul 15 - Jul 21
6 night stay
Chicago (CHI) to Cancun (CUN)
Frontier Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $3,097, price is now $1,618 per person
$1,618
per person
found 1 day ago
Staff was fantastic, food was good for an all inclusive, but not a wow factor. Pool heater was under repair, hot water had challenges in the room but staff fixed promptly. Spa was good. Staff was friendly and attentive.
Reviewed on Mar 27, 2026
4.0-star property
Family 3 Bedroom Ocean Villa By Wyndham Grand Cancun
7.6/10 Good! (49 reviews)
Jul 15 - Jul 21
6 night stay
Chicago (CHI) to Cancun (CUN)
Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $8,480, price is now $3,931 per person
$3,931
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
5.0-star property
Live Aqua Cancun - Adults Only - All-Inclusive
9.2/10 Wonderful! (1,981 reviews)
Jul 15 - Jul 21
6 night stay
Chicago (CHI) to Cancun (CUN)
Frontier Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $3,312, price is now $1,703 per person
$1,703
per person
found 1 day ago
Tranquil and relaxing.
Reviewed on Apr 4, 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.
5.0-star property
Live Aqua Cancun - Adults Only - All-Inclusive
9.2/10 Wonderful! (1,981 reviews)
Jul 16 - Jul 21
5 night stay
Chicago (CHI) to Cancun (CUN)
American Airlines • Non-stop • FirstClass
Cancun (CUN) to Chicago (CHI)
Frontier Airlines • Non-stop • FirstClass
Save 100% on your flight
Price was $2,827, price is now $1,538 per person
$1,538
per person
found 1 day 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 16 - Jul 21
5 night stay
Chicago (CHI) to Cancun (CUN)
American Airlines • Non-stop • FirstClass
Cancun (CUN) to Chicago (CHI)
Frontier Airlines • Non-stop • FirstClass
Price was $7,129, price is now $3,370 per person
$3,370
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
3.5-star property
Tago Tulum by G Hotels
9.2/10 Wonderful! (414 reviews)
Jul 16 - Jul 21
5 night stay
Chicago (CHI) to Cancun (CUN)
United • Non-stop roundtrip • FirstClass
Price was $3,211, price is now $1,577 per person
$1,577
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
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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.