$147 Cheap flight deals from Chicago (CHI) to Puerto Aventuras (CUN)
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
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.
$495 Roundtrip, just found
$495
Roundtrip
just found
ORD
O'Hare Intl.
TQO
Tulum Intl. Airport
$499 Roundtrip, found 2 days ago
$499
Roundtrip
found 2 days ago
MDW
Midway Intl.
CUN
Cancun Intl.
$548 Roundtrip, just found
$548
Roundtrip
just found
MDW
Midway Intl.
TQO
Tulum Intl. Airport
$680 Roundtrip, found 2 days ago
$680
Roundtrip
found 2 days ago
Airfares from $147 One Way, $350 Round Trip from Chicago to Puerto Aventuras
Prices starting at $350 for return flights and $147 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, just found
$350
Roundtrip
just found
ORD
Chicago
CUN
Cancun
$359 Roundtrip, found 13 hours ago
$359
Roundtrip
found 13 hours ago
ORD
Chicago
TQO
Tulum
$371 Roundtrip, found 6 hours ago
$371
Roundtrip
found 6 hours ago
ORD
Chicago
CUN
Cancun
$399 Roundtrip, just found
$399
Roundtrip
just found
ORD
Chicago
CZM
Cozumel
$410 Roundtrip, found 3 hours ago
$410
Roundtrip
found 3 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! (1,053 reviews)
Sep 30 - Oct 6
6 night stay
Chicago (CHI) to Cancun (CUN)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,663, price is now $770 per person
$770
per person
found 1 day ago
The hotel was really nice. We chose the ocean view and it was amazing waking up to the ocean. We went during the sargassum season so there was a lot on the beach. Overall it was a nice clean hotel and everyone was very helpful.
Reviewed on Aug 9, 2026
5.0-star property
Palmaïa-The House of AïA: All Inclusive Wellness Resort
9.8/10 Exceptional! (659 reviews)
Sep 17 - Sep 21
4 night stay
Chicago (CHI) to Cancun (CUN)
Volaris • Non-stop roundtrip • Coach
Price was $3,784, price is now $1,779 per person
$1,779
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
Don't see what you're looking for?
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.
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
Majestic Mirage Costa Mujeres, All Suite Resort - All Inclusive
9/10 Wonderful! (346 reviews)
Sep 14 - Sep 19
5 night stay
Chicago (CHI) to Cancun (CUN)
United • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $3,001, price is now $1,736 per person
$1,736
per person
just found
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 6 hours 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
5.0-star property
Hotel Mousai Cancun Adults Only - All Inclusive
9.6/10 Exceptional! (124 reviews)
Sep 14 - Sep 19
5 night stay
Chicago (CHI) to Cancun (CUN)
United • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $4,982, price is now $2,828 per person
$2,828
per person
just found
Hotel Mousai sets a standard that very few hotels can even imagine. Not only with breathtaking views, top shelf cocktails, 5 star dining, incomparable accommodations, but the personalized butler service is truly one of a kind.
Reviewed on Aug 5, 2026
Don't see what you're looking for?
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
If you have been putting off a well-deserved vacation due to a tight budget, now is the time to visit Orbitz.com. We offer you huge savings on Chicago to Puerto Aventuras flights, great hotel rooms, and stellar vacation packages. Let Orbitz show you how to cheaply plan the perfect trip.
Guaranteed low prices on flights from Chicago to Puerto Aventuras
Low fares, discounted rates, great deals, and special promotions—all of these can be found through Orbitz. Get cheap fares on Chicago to Puerto Aventuras flights and amazing deals on luxury hotels. You can even accumulate loyalty or frequent flyer miles or points on qualifying flights from Chicago to Puerto Aventuras so you can earn flight rewards on your favorite airlines.
Mobile planning for flights from Chicago to Puerto Aventuras
Worried about unexpected flight delays or other travel disruptions on your Chicago to Puerto Aventuras flights? You can opt to receive free alerts sent to you and six of your contacts via email, voicemail, or text. The Orbitz mobile app also lets you access up-to-date flight information from your iPhone, iPad, and mobile Android devices. Our mobile technology let you check baggage claim and gate details, view your itinerary for your flights from Chicago to Puerto Aventuras, and book exclusive hotel deals—even on the same day.
Take advantage of low fares on Chicago to Puerto Aventuras flights and vacation packages
Orbitz has the best prices available on flights from Chicago to Puerto Aventuras. Take advantage of our low fare sales and discounts and begin to plan your next trip. We also give you great savings on hotels, car rentals, and vacation packages.
Flights from Chicago
- Chicago to Orlando
- Chicago to Houston
- Chicago to New York
- Chicago to Phoenix
- Chicago to Dallas
- Chicago to Los Angeles
- Chicago to New Orleans
- Chicago to Washington
- Chicago to London
- Chicago to Paris
- Chicago to Toronto
- Chicago to Rome
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Sacramento
- Chicago to Montreal
- Chicago to Kansas City
- Chicago to Atlantic City
- Chicago to Hartford
Puerto Aventuras Airports
More Destinations
- Flights from Toluca to Akumal
- Flights from Atlanta to Akumal
- Flights from Charlotte to Akumal
- Flights from Chicago to Akumal
- Flights from Dallas to Akumal
- Flights from Denver to Akumal
- Flights from Detroit to Akumal
- Flights from Houston to Akumal
- Flights from Miami to Akumal
- Flights from Minneapolis - St. Paul to Akumal
- Flights from Nashville to Akumal
- Flights from New York to Akumal
- Flights from Orlando to Akumal
- Flights from Philadelphia to Akumal
- Flights from Phoenix to Akumal
- Flights from Washington to Akumal
- Flights from Tijuana to Akumal
- Flights from Newark to Akumal
- Flights from Richmond to Akumal
- Flights from Boston to Xpu-Ha
- Flights from Chicago to Xpu-Ha
- Flights from Detroit to Xpu-Ha
- Flights from Los Angeles to Xpu-Ha
- Flights from Minneapolis - St. Paul to Xpu-Ha
- Flights from New York to Xpu-Ha
- Flights from Orlando to Xpu-Ha
- Flights from Washington to Xpu-Ha
- Flights from Sacramento to Xpu-Ha
- Flights from Newark to Xpu-Ha
- Flights from Birmingham to Xpu-Ha
- Flights from Atlanta to Playa del Carmen
- Flights from Austin to Playa del Carmen
- Flights from Boston to Playa del Carmen
- Flights from Charlotte to Playa del Carmen
- Flights from Chicago to Playa del Carmen
- Flights from Cleveland to Playa del Carmen
- Flights from Dallas to Playa del Carmen
- Flights from Denver to Playa del Carmen
- Flights from Detroit to Playa del Carmen
- Flights from Houston to Playa del Carmen
- Flights from Kansas City to Playa del Carmen
- Flights from Los Angeles to Playa del Carmen
- Flights from Mexico City to Playa del Carmen
- Flights from Miami to Playa del Carmen
- Flights from Minneapolis - St. Paul to Playa del Carmen
- Flights from Nashville to Playa del Carmen
- Flights from New Orleans to Playa del Carmen
- Flights from New York to Playa del Carmen
- Flights from Orlando to Playa del Carmen
- Flights from Philadelphia to Playa del Carmen
- Flights from Phoenix to Playa del Carmen
- Flights from Portland to Playa del Carmen
- Flights from Salt Lake City to Playa del Carmen
- Flights from San Antonio to Playa del Carmen
- Flights from San Francisco to Playa del Carmen
- Flights from Seattle to Playa del Carmen
- Flights from Toronto to Playa del Carmen
- Flights from Vancouver to Playa del Carmen
- Flights from Washington to Playa del Carmen
- Flights from Sacramento to Playa del Carmen
- Flights from Monterrey to Playa del Carmen
- Flights from Omaha to Playa del Carmen
- Flights from Querétaro to Playa del Carmen
- Flights from Tijuana to Playa del Carmen
- Flights from Des Moines to Playa del Carmen
- Flights from Pittsburgh to Playa del Carmen
- Flights from Fort Lauderdale to Playa del Carmen
- Flights from Newark to Playa del Carmen
- Flights from Richmond to Playa del Carmen
- Flights from Oakland to Playa del Carmen
- Flights from Atlantic City to Playa del Carmen
- Flights from Oklahoma City to Playa del Carmen
- Flights from Baton Rouge to Playa del Carmen
- Flights from Covington to Playa del Carmen
- Flights from Acapulco (ACA) to Cozumel (CZM)
- Flights from Atlanta (ATL) to Cozumel (CZM)
- Flights from Watertown (ATY) to Cozumel (CZM)
- Flights from Nashville (BNA) to Cozumel (CZM)
- Flights from Akron (CAK) to Cozumel (CZM)
- Flights from Chattanooga (CHA) to Cozumel (CZM)
- Flights from Evansville (EVV) to Cozumel (CZM)
- Flights from Houston (HOU) to Cozumel (CZM)
- Flights from Ironwood (IWD) to Cozumel (CZM)
- Flights from Jacksonville (JAX) to Cozumel (CZM)
- Flights from Quzhou (JUZ) to Cozumel (CZM)
- Flights from Lyndonville (LLX) to Cozumel (CZM)
- Flights from Lincoln (LNK) to Cozumel (CZM)
- Flights from Orlando (MCO) to Cozumel (CZM)
- Flights from Melbourne (MLB) to Cozumel (CZM)
- Flights from Miami (MPB) to Cozumel (CZM)
- Flights from Punta Gorda Airport (PGD) to Cozumel (CZM)
- Flights from Port of Spain (POS) to Cozumel (CZM)
- Flights from Presidente Prudente (PPB) to Cozumel (CZM)
- Flights from Rochester (ROC) to Cozumel (CZM)
- Flights from Salisbury (SBY) to Cozumel (CZM)
- Flights from Shageluk (SHX) to Cozumel (CZM)
- Flights from Santa Rosa (STS) to Cozumel (CZM)
- Flights from Vero Beach (VRB) to Cozumel (CZM)
- Flights from Penticton (YYF) to Cozumel (CZM)
- Flights from St. John's (YYT) to Cozumel (CZM)
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.