$95 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.
$294 Roundtrip, just found
$294
Roundtrip
just found
MDW
Midway Intl.
CUN
Cancun Intl.
$394 Roundtrip, just found
$394
Roundtrip
just found
RFD
Greater Rockford
CUN
Cancun Intl.
$543 Roundtrip, found 5 days ago
$543
Roundtrip
found 5 days ago
RFD
Greater Rockford
CZM
Cozumel Intl.
$746 Roundtrip, found 5 days ago
$746
Roundtrip
found 5 days ago
Airfares from $95 One Way, $202 Round Trip from Chicago to Puerto Aventuras
Prices starting at $202 for return flights and $95 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
$202 Roundtrip, found 11 hours ago
$202
Roundtrip
found 11 hours ago
ORD
Chicago
CUN
Cancun
$229 Roundtrip, found 2 hours ago
$229
Roundtrip
found 2 hours ago
MDW
Chicago
CUN
Cancun
$241 Roundtrip, found 1 day ago
$241
Roundtrip
found 1 day ago
ORD
Chicago
TQO
Tulum
$363 Roundtrip, found 2 days ago
$363
Roundtrip
found 2 days ago
MDW
Chicago
TQO
Tulum
$367 Roundtrip, found 1 day ago
$367
Roundtrip
found 1 day 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! (1,026 reviews)
May 3 - May 8
5 night stay
Chicago (CHI) to Cancun (CUN)
American Airlines • Coach
Cancun (CUN) to Chicago (CHI)
Spirit Airlines • Coach
Price was $1,496, price is now $635 per person
$635
per person
found 1 day 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Room service phone did not work, TVs are outdated and bathroom was clogged Other than that it was okay Loved that it’s very well located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! (389 reviews)
Apr 30 - May 4
4 night stay
Chicago (CHI) to Cancun (CUN)
Southwest Airlines • Coach
Cancun (CUN) to Chicago (CHI)
Frontier Airlines • Coach
Price was $3,133, price is now $1,025 per person
$1,025
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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View all tripsPuerto Aventuras business class 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! (1,026 reviews)
May 14 - May 19
5 night stay
Chicago (ORD) to Cancun (CUN)
United • Roundtrip • BusinessClass
Save 100% on your flight
Price was $1,968, price is now $1,083 per person
$1,083
per person
found 1 day 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
4.5-star property
Valentin Imperial Rivera Maya All Inclusive - Adult Only
9.4/10 Exceptional! (1,718 reviews)
Apr 30 - May 6
6 night stay
Chicago (CHI) to Cancun (CUN)
American Airlines • BusinessClass
Cancun (CUN) to Chicago (CHI)
United • BusinessClass
Price was $5,663, price is now $3,179 per person
$3,179
per person
found 1 day ago
We stayed 4 nights at Valentin Imperial Riviera Maya and overall had a great experience. Transportation arranged through the resort was smooth and comfortable, and check-in was pleasant with champagne offered while we waited. Afterward, a golf cart took us to our room.
The room was modern with nice built-in tech like Bluetooth speakers and electronic “Do Not Disturb” panels. Two small drawbacks were the smoke detector above the bed flashing all night and a very loud coffee machine.
The food was excellent. We especially enjoyed L’Olivo (Italian), La Hacienda (Mexican), and Mar y Tierra (steak & seafood). The breakfast buffet had great variety, Cafe Sisal was perfect for coffee and desserts, and the food trucks were great for lunch.
Activities were a highlight - carbine shooting, Zumba, and pool games. Israel, Carlos, and Pablo from the entertainment team were fantastic. The property is beautiful and very clean, and seeing coatis and iguanas around the resort was a fun touch. The beach itself is beautiful, although we were unlucky with heavy seaweed during our stay so swimming wasn’t possible.
The only real downside was the pool lounge situation. Guests reserve chairs very early (around 5 AM). When I moved unattended items after confirming with staff it was allowed, another guest threatened me. The resort should remind guests at check-in and clear chairs before the pool opens at 7 AM.
Overall we had a great stay and would absolutely return to this resort.
Reviewed on Mar 7, 2026
4.0-star property
Fiesta Americana Cancun Villas
8.4/10 Very Good! (1,106 reviews)
May 14 - May 19
5 night stay
Chicago (ORD) to Cancun (CUN)
United • Roundtrip • BusinessClass
Save 100% on your flight
Price was $2,604, price is now $1,473 per person
$1,473
per person
found 1 day ago
The staff were always very helpful and kind. The breakfast buffet may seem expensive, but it's worth $30 for the variety of traditional Mexican foods and attentive service while enjoying a great view of the ocean. The property is well kept though a bit dated and rooms are spacious. You can access the ocean right in front of the resort by walking down concrete steps, but we walked a few minutes to the beach on either side of the property to enjoy a more traditional beachfront. It's an easy walk to many good restaurants and a grocery store. We cooked at least one meal a day in our little kitchen. One area that could be improved is pool cleanliness. The water looked stagnant in some areas in the mornings and our toddler kept on getting dirty streaks on his swimsuit, which I finally figured out was from some film on the side of the pool.
Reviewed on Mar 19, 2025
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View all tripsPuerto Aventuras first class flight packages
Price found within the past 48 hours. Click for updated prices.
5.0-star property
Paraiso de la Bonita, Adult All-Inclusive, a Luxury Collection Resort
9.4/10 Exceptional! (85 reviews)
Apr 30 - May 3
3 night stay
Chicago (CHI) to Cancun (CUN)
American Airlines • Non-stop • FirstClass
Cancun (CUN) to Chicago (CHI)
United • Non-stop • FirstClass
Price was $2,063, price is now $1,862 per person
$1,862
per person
found 1 day ago
Yes, had an amazing stay! The staff were all wonderful and kind. Made the trip even more memorable.
Reviewed on Feb 1, 2026
5.0-star property
Excellence Coral Playa Mujeres - Adults Only All Inclusive
9.2/10 Wonderful! (420 reviews)
Apr 30 - May 3
3 night stay
Chicago (CHI) to Cancun (CUN)
American Airlines • Non-stop • FirstClass
Cancun (CUN) to Chicago (CHI)
United • Non-stop • FirstClass
Price was $3,072, price is now $2,166 per person
$2,166
per person
found 1 day ago
4.5-star property
Secrets Playa Mujeres Golf & Spa Resort - Adults Only - All Inclusive
8.8/10 Excellent! (1,000 reviews)
Apr 30 - May 3
3 night stay
Chicago (CHI) to Cancun (CUN)
American Airlines • Non-stop • FirstClass
Cancun (CUN) to Chicago (CHI)
United • Non-stop • FirstClass
Price was $3,030, price is now $2,418 per person
$2,418
per person
found 1 day ago
Lovely resort with friendly staff and wonderful food. The views are beautiful and were perfect to celebrate our anniversary!
Reviewed on Mar 31, 2025
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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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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.