$177 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.
TQO
Tulum Intl. Airport
$499 Roundtrip, found 1 day ago
$499
Roundtrip
found 1 day ago
ORD
O'Hare Intl.
CUN
Cancun Intl.
$609 Roundtrip, just found
$609
Roundtrip
just found
MDW
Midway Intl.
CUN
Cancun Intl.
$611 Roundtrip, found 8 hours ago
$611
Roundtrip
found 8 hours ago
MDW
Midway Intl.
TQO
Tulum Intl. Airport
$680 Roundtrip, found 2 days ago
$680
Roundtrip
found 2 days ago
Airfares from $177 One Way, $350 Round Trip from Chicago to Puerto Aventuras
Prices starting at $350 for return flights and $177 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
$350 Roundtrip, found 8 hours ago
$350
Roundtrip
found 8 hours ago
ORD
Chicago
CUN
Cancun
$359 Roundtrip, found 9 hours ago
$359
Roundtrip
found 9 hours ago
ORD
Chicago
TQO
Tulum
$363 Roundtrip, found 1 hour ago
$363
Roundtrip
found 1 hour ago
ORD
Chicago
CUN
Cancun
$399 Roundtrip, just found
$399
Roundtrip
just found
ORD
Chicago
CZM
Cozumel
$410 Roundtrip, just found
$410
Roundtrip
just found
Puerto Aventuras economy flight packages
Price found within the past 48 hours. Click for updated prices.
5.0-star property
Palmaïa-The House of AïA: All Inclusive Wellness Resort
9.8/10 Exceptional! (659 reviews)
Sep 13 - Sep 18
5 night stay
Chicago (CHI) to Cancun (CUN)
Frontier Airlines • Non-stop • Coach
Cancun (CUN) to Chicago (CHI)
Volaris • Non-stop • Coach
Price was $4,884, price is now $2,034 per person
$2,034
per person
found 2 days ago
Wow! Easily the best resort we have stayed at.
I am not Vegan but the best part of this trip was definitely the food. The all-inclusive is the best deal around by far. There are plenty of non-vegan options but honestly I mostly ate the vegan versions. Everything was top-shelf. Charlies Vegan Tacos were a highlight. And we actually lost some weight while we were there since its so healthy.
The service was incredible. Everywhere we went we were greeted with smiles and hellos. We got to know by name many of the staff.
The Pools are about the best I have seen and the beach (when there is not seaweed) is incredible. And they keep it cleaner than any other beach around.
Every time we ventured out to try something different we came back to the hotel because it was just better.
The free classes like Yoga were amazing as well.
I feel this is a secret that will soon be out.
But thank you to all the staff who were part of this experience.
Reviewed on Aug 8, 2026
4.0-star property
The Pyramid Cancun By Oasis - All Inclusive
7.4/10 Good! (1,809 reviews)
Sep 13 - Sep 18
5 night stay
Chicago (CHI) to Cancun (CUN)
Frontier Airlines • Non-stop • Coach
Cancun (CUN) to Chicago (CHI)
Volaris • Non-stop • Coach
Price was $1,971, price is now $941 per person
$941
per person
found 2 days ago
Excellent
Reviewed on Aug 9, 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
Palmaïa-The House of AïA: All Inclusive Wellness Resort
9.8/10 Exceptional! (659 reviews)
Sep 26 - Oct 1
5 night stay
Chicago (CHI) to Cancun (CUN)
Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $4,947, price is now $2,303 per person
$2,303
per person
found 1 day ago
Wow! Easily the best resort we have stayed at.
I am not Vegan but the best part of this trip was definitely the food. The all-inclusive is the best deal around by far. There are plenty of non-vegan options but honestly I mostly ate the vegan versions. Everything was top-shelf. Charlies Vegan Tacos were a highlight. And we actually lost some weight while we were there since its so healthy.
The service was incredible. Everywhere we went we were greeted with smiles and hellos. We got to know by name many of the staff.
The Pools are about the best I have seen and the beach (when there is not seaweed) is incredible. And they keep it cleaner than any other beach around.
Every time we ventured out to try something different we came back to the hotel because it was just better.
The free classes like Yoga were amazing as well.
I feel this is a secret that will soon be out.
But thank you to all the staff who were part of this experience.
Reviewed on Aug 8, 2026
4.0-star property
The Pyramid Cancun By Oasis - All Inclusive
7.4/10 Good! (1,809 reviews)
Sep 28 - Oct 5
7 night stay
Chicago (ORD) to Cancun (CUN)
United • Roundtrip • BusinessClass
Save 100% on your flight
Price was $3,095, price is now $1,589 per person
$1,589
per person
found 1 day ago
Excellent
Reviewed on Aug 9, 2026
Don't see what you're looking for?
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
El Dorado Royale, All & More Inclusive Adults Only
8.6/10 Excellent! (657 reviews)
Sep 24 - Sep 28
4 night stay
Chicago (CHI) to Cancun (CUN)
American Airlines • Non-stop roundtrip • FirstClass
Price was $2,436, price is now $1,602 per person
$1,602
per person
found 1 hour ago
.
Reviewed on Aug 7, 2026
5.0-star property
Palmaïa-The House of AïA: All Inclusive Wellness Resort
9.8/10 Exceptional! (659 reviews)
Sep 24 - Sep 28
4 night stay
Chicago (CHI) to Cancun (CUN)
American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $4,612, price is now $2,394 per person
$2,394
per person
found 1 hour ago
Wow! Easily the best resort we have stayed at.
I am not Vegan but the best part of this trip was definitely the food. The all-inclusive is the best deal around by far. There are plenty of non-vegan options but honestly I mostly ate the vegan versions. Everything was top-shelf. Charlies Vegan Tacos were a highlight. And we actually lost some weight while we were there since its so healthy.
The service was incredible. Everywhere we went we were greeted with smiles and hellos. We got to know by name many of the staff.
The Pools are about the best I have seen and the beach (when there is not seaweed) is incredible. And they keep it cleaner than any other beach around.
Every time we ventured out to try something different we came back to the hotel because it was just better.
The free classes like Yoga were amazing as well.
I feel this is a secret that will soon be out.
But thank you to all the staff who were part of this experience.
Reviewed on Aug 8, 2026
4.5-star property
Valentin Imperial Rivera Maya All Inclusive - Adults Only
9.4/10 Exceptional! (1,710 reviews)
Sep 24 - Sep 28
4 night stay
Chicago (CHI) to Cancun (CUN)
American Airlines • Non-stop roundtrip • FirstClass
Price was $2,614, price is now $1,732 per person
$1,732
per person
found 1 hour ago
Loved the property and the staff. Very beautiful and private. Property is hard to walk and not alot of pre communication of how things work. The beach waa not really swimmable.
Reviewed on Aug 9, 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.