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Search 165 Chicago to Quintana Roo Resort Vacation Deals and 152 Resorts

At AppleVacations.com, we’ve created 165 custom vacation packages for 152 different resorts in Quintana Roo. Each “Flight + Hotel” package is priced per person. Each “Hotel Only” package is priced per night. Make sure to use the filters to find the perfect Quintana Roo resort deal for you!
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Zoëtry Villa Rolandi Isla Mujeres Cancun - All Inclusive Cancún
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
1 Deal Available!
From $3,356 to $3,356* /person
7 to 7 Day Trips - Nov to Jan
La Casa De La Playa - All Inclusive Playa del Carmen
5.0
Trip Advisor Rating
Hotel + Flight
4 Deals Available!
From $3,303 to $10,984* /person
3 to 7 Day Trips - Nov to Feb
Impression Isla Mujeres by Secrets - All Inclusive Isla Mujeres
4.5
Trip Advisor Rating
Hotel + Flight
4 Deals Available!
From $2,086 to $5,060* /person
3 to 7 Day Trips - Sep to Feb
Impression Moxché by Secrets - All Inclusive Playa del Carmen
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $1,923 to $3,032* /person
3 to 7 Day Trips - Nov to Feb
Hotel Xcaret Arte - All Inclusive Playa del Carmen
Hotel + Flight
4 Deals Available!
From $1,830 to $3,329* /person
3 to 7 Day Trips - Nov to Feb
Secrets Akumal Riviera Maya - All Inclusive Tulum
5.0
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $1,611 to $2,444* /person
3 to 7 Day Trips - Nov to Feb
Hotel Xcaret Mexico - All Inclusive Playa del Carmen
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $1,550 to $3,140* /person
3 to 7 Day Trips - Nov to Jan
Iberostar Grand Paraiso - All Inclusive Playa del Carmen
5.0
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $1,535 to $2,167* /person
3 to 7 Day Trips - Nov to Feb
Secrets Maroma Beach Riviera Cancun - All Inclusive Playa del Carmen
5.0
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $1,317 to $4,402* /person
3 to 7 Day Trips - Nov to Feb
Secrets Tulum Resort & Beach Club - All Inclusive Tulum
4.0
Trip Advisor Rating
Hotel + Flight
4 Deals Available!
From $1,271 to $1,944* /person
3 to 7 Day Trips - Nov to Feb

Top Quintana Roo Destination: Cancún Resort Packages from Chicago

Take an amazing trip from Chicago to the captivating heart of Cancún with a great resort and flight package deal. Our selection of 53 deals caters to every traveler's desires, whether you're looking for a all-inclusive adventure or a adults-only escape. Each meticulously curated package boasts a per-person price, encompassing both flight and hotel costs, with rates ranging from $810 to $3,356, so there’s a perfect getaway for every budget. Our handpicked hotel partners, which include renowned names like Iberostar Hotels & Resorts, Melia Hotels International and Oasis Resorts, offer unparalleled accommodations complete with a range of top-tier amenities such as a spa, a free high speed internet connection and a massage services. Immerse yourself in the charm of Cancún, where every corner invites exploration and relaxation. Seize this opportunity to book a 3-day, 5-day or 7-day adventure with unbeatable resort rates and flight fares from Chicago to Cancún in Quintana Roo.

Grand Oasis Palm - All Inclusive Cancún
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $810 to $1,352* /person
3 to 7 Day Trips - Jan to Feb
Dreams Vista Cancun Golf & Spa Resort - All Inclusive Cancún
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $829 to $1,352* /person
3 to 7 Day Trips - Nov to Feb
The Pyramid Cancun - All Inclusive Cancún
3.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $881 to $1,386* /person
3 to 7 Day Trips - Nov to Feb
Dreams Natura Resort & Spa - All Inclusive Cancún
4.0
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $906 to $1,462* /person
3 to 7 Day Trips - Nov to Feb
Secrets Playa Mujeres Golf & Spa Resort - All Inclusive Cancún
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $917 to $1,692* /person
3 to 7 Day Trips - Nov to Jan
Paradisus Cancun - All Inclusive Cancún
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $956 to $1,826* /person
3 to 7 Day Trips - Nov to Feb
Iberostar Selection Cancun - All Inclusive Cancún
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $967 to $1,744* /person
3 to 7 Day Trips - Nov to Jan
Grand Palladium Costa Mujeres Resort & Spa - All Inclusive Cancún
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $991 to $1,686* /person
3 to 7 Day Trips - Nov to Jan
TRS Coral Hotel- Adults Only - All Inclusive Cancún
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $1,003 to $1,715* /person
3 to 7 Day Trips - Nov to Feb
Secrets The Vine Cancun - All Inclusive Cancún
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $1,034 to $1,734* /person
3 to 7 Day Trips - Nov to Jan
Coral Level at Iberostar Selection Cancun - All Inclusive Cancún
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $1,074 to $2,033* /person
3 to 7 Day Trips - Sep to Feb
Dreams Playa Mujeres Golf & Spa Resort  - All Inclusive Cancún
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $1,132 to $2,231* /person
3 to 7 Day Trips - Nov to Jan

Top Quintana Roo Destination: Playa del Carmen Resort Packages from Chicago

Set out on an unforgettable adventure from Chicago to the enchanting Cancún with AppleVacations.com's exceptional package deals, available in 3-day, 5-day and 7-day options, all thoughtfully designed to cater to your preferences. Whether you're seeking a family-friendly escape, an adults-only retreat, a romantic getaway or an all-inclusive adventure, we have the perfect package for you. Each deal offers incredible value, priced per person, and covering both flights and hotel accommodations. Our prestigious hotel partners, including Iberostar Hotels & Resorts, Experiencias Xcaret Hoteles and Melia Hotels International, ensure an exceptional stay with a range of amenities such as a spa, a free high speed internet connection and a massage services. Prices cater to all budgets, starting as low as $758 per person and reaching $10,984 for those seeking peak experiences. With an average price per person of $1,777, you can create unforgettable memories in Cancún without breaking the bank. Secure your dream vacation today with AppleVacations.com and seize the opportunity for unbeatable value!

Iberostar Quetzal - All Inclusive Playa del Carmen
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $758 to $1,279* /person
3 to 7 Day Trips - Nov to Feb
Grand Palladium Kantenah Resort and Spa - All Inclusive Playa del Carmen
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $808 to $1,407* /person
3 to 7 Day Trips - Nov to Feb
Paradisus La Perla Adult Only - All Inclusive Playa del Carmen
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $1,060 to $1,708* /person
3 to 7 Day Trips - Nov to Feb
Paradisus Playa Del Carmen - Riviera Maya - All Inclusive Playa del Carmen
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $1,154 to $1,732* /person
3 to 7 Day Trips - Nov to Feb
Secrets Moxche Playa del Carmen - All Inclusive Playa del Carmen
4.5
Trip Advisor Rating
Hotel + Flight
4 Deals Available!
From $1,203 to $3,030* /person
3 to 7 Day Trips - Nov to Feb
Secrets Maroma Beach Riviera Cancun - All Inclusive Playa del Carmen
5.0
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $1,317 to $4,402* /person
3 to 7 Day Trips - Nov to Feb
Iberostar Grand Paraiso - All Inclusive Playa del Carmen
5.0
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $1,535 to $2,167* /person
3 to 7 Day Trips - Nov to Feb
Hotel Xcaret Mexico - All Inclusive Playa del Carmen
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $1,550 to $3,140* /person
3 to 7 Day Trips - Nov to Jan
Hotel Xcaret Arte - All Inclusive Playa del Carmen
Hotel + Flight
4 Deals Available!
From $1,830 to $3,329* /person
3 to 7 Day Trips - Nov to Feb
Impression Moxché by Secrets - All Inclusive Playa del Carmen
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $1,923 to $3,032* /person
3 to 7 Day Trips - Nov to Feb
La Casa De La Playa - All Inclusive Playa del Carmen
5.0
Trip Advisor Rating
Hotel + Flight
4 Deals Available!
From $3,303 to $10,984* /person
3 to 7 Day Trips - Nov to Feb
Grand Velas Riviera Maya - All Inclusive Playa del Carmen
5.0
Trip Advisor Rating
All-inclusive
The AAA Five Diamond Grand Velas Riviera Maya is an ultra-luxury all-inclusive resort set on 206 acres of pristine jungle and mangroves and with the finest white sand beach in the Riviera Maya. ...

Top Quintana Roo Destination: Cozumel Resort Packages from Chicago

Discover the scenic allure of Cozumel in Quintana Roo with AppleVacations.com’s handpicked selection of 0 travel packages. Depart from Chicago and embark on a journey tailored to your tastes, be it a adventure. Our premier hotel partners, including iconic names like Iberostar Hotels & Resorts, Experiencias Xcaret Hoteles and Melia Hotels International, ensure that your stay is replete with amenities such as a . Each package is meticulously assembled, covering both your flight and accommodations. With a pricing spectrum that starts from per traveler, diving into Cozumel promises both value and memories. Don’t wait – book your vacation package from Chicago to Cozumel in Quintana Roo today on AppleVacations.com.*

The Westin Cozumel Cozumel
4.5
Trip Advisor Rating
Experience the perfect blend of adventure and relaxation at The Westin Cozumel resort. Enjoy thrilling activities like beach clubs, museum visits, exploring Mayan ruins, scuba diving, boating and eco-...
Fiesta Americana Cozumel - All Inclusive Cozumel
4.5
Trip Advisor Rating
All-inclusive

Fiesta Americana Cozumel is the ideal place to strengthen your relationships and emotional connections. You and your loved ones will share unique and unforgettable moments throughout the resort, cr...

The Explorean Cozumel - All-Inclusive Cozumel
4.5
Trip Advisor Rating
All-inclusive
The Explorean Cozumel All-Inclusive combines relaxation and adventure with a majestic charm that makes your visit to Mexico's largest island truly unique and utterly unforgettable. It's an amazing way...
Iberostar Cozumel - All Inclusive Cozumel
4.5
Trip Advisor Rating
All-inclusive

Iberostar's Premium Collection: Dazzling sandy beaches along with the Palancar and Santa Rosa Wall reefs beckoning offshore make Cozumel a diver's and nature lover's retreat. Relaxed and rejuvenati...

Cozumel Palace - All Inclusive Cozumel
4.5
Trip Advisor Rating
All-inclusive
2019 Resort Added Values
Extra Value: Receive up to a $1500 resort credit (booking dates, travel dates, duration, and usage restrictions may apply).
Free Symbolic Weddings:...
Casa Mexicana Cozumel - European Plan Cozumel
4.5
Trip Advisor Rating
You will realize you are in for something special from the very moment you enter the modern, spacious, and colorful lobby. This hotel is perfect for meeting friends, relaxing on the terrace overlookin...
Presidente Intercontinental Cozumel Resort & Spa - European Plan Cozumel
4.5
Trip Advisor Rating
With breathtaking views of the crystalline water, Presidente InterContinental Cozumel Resort & Spa is located only six miles from the airport and is situated minutes from the abundant coral reefs. Par...
InterContinental Hotels PRESIDENTE COZUMEL RESORT SPA Cozumel
4.5
Trip Advisor Rating
Enjoy an oasis of tranquility on the largest private beach on the island, with white sand and crystal clear, sargassum-free waters. Take in panoramic views of the Caribbean from the comfort of your ro...
Melia Cozumel - All Inclusive Cozumel
4.0
Trip Advisor Rating
All-inclusive
Meliã Cozumel is truly one of the most impressive all-inclusive hideaways in Mexico, featuring an array of amenities, facilities and unlimited amounts of fun. 
This beautiful hotel...
Secrets Aura Cozumel - All Inclusive Cozumel
4.0
Trip Advisor Rating
All-inclusive

The ultimate in romantic all-suite accommodation, this refined Adults only resort offers Unlimited-Luxury® with limitless gourmet dini...

Allegro Cozumel - All Inclusive Cozumel
4.0
Trip Advisor Rating
All-inclusive

The all-inclusive Allegro Cozumel has been designed to offer comfortable accommodations on magnificent Playa San Francisco, one of the most beautiful beaches in Cozumel. The resort’s Ultimate Dive ...

Top Quintana Roo Destination: Puerto Morelos Resort Packages from Chicago

Looking for more destination ideas for a vacation to the Quintana Roo region of Mexico? Try the exciting city of Puerto Morelos. AppleVacations.com has put together an array of 16 travel packages including resorts and flights. Set out from Chicago and journey to a resort destination fitting your traveling companions, be it a dining, family or beach type of hotel. Our partnerships with esteemed hotel brands like Hyatt Inclusive Collection ensure a stay enriched with standout amenities such as a spa, a golf and a children programs. Every package is harmoniously pieced together, encompassing both your flight and 3-day or 5-day sojourns. With prices ranging from an enticing $569 to a luxurious $1,580, and an appealing average of $896 per traveler, your voyage to Puerto Morelos assures both unparalleled value and unforgettable moments. Dive into your next dream vacation now!*

Dreams Sapphire Resort & Spa - All Inclusive Puerto Morelos
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
8 Deals Available!
From $569 to $929* /person
3 to 7 Day Trips - Sep to Feb
Dreams Jade Resort & Spa - All Inclusive Puerto Morelos
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $844 to $1,290* /person
3 to 7 Day Trips - Nov to Jan
Dreams Riviera Cancun Resort & Spa - All Inclusive Puerto Morelos
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $848 to $1,580* /person
3 to 7 Day Trips - Nov to Feb
Margaritaville Beach Resort Riviera Cancun, by Karisma - All Inclusive Puerto Morelos
All-inclusive

Inspired by the lyrics and lifestyle of Jimmy Buffett, Margaritaville Island Reserve Riviera Cancun provides the perfect setting for guests who want to escape the everyday with a tropical change in...

Azul Beach Resort Riviera Cancun By Karisma - All Inclusive Puerto Morelos

Property Location: Radisson on Flagstaff Gardens Melbourne is centrally located in Melbourne, a 4-minute walk from Queen Victoria Market and 8 minutes by foot from Melbourne Central. This l...

Ventus at Hotel Marina El Cid Spa & Beach Resort  - All Inclusive Puerto Morelos
4.5
Trip Advisor Rating

Ventus at Marina El Cid Spa & Beach Resort is the next generation of the El Cid family of resorts, offering exceptional service and singular attention to detail in a luxury setting promising the pe...

Desire Riviera Maya Pearl Resort - All-Inclusive Puerto Morelos
4.5
Trip Advisor Rating
All-inclusive

Lose yourself on the exotic beaches of Puerto Morelos, at Desire Riviera Maya Pearl Resort, as you and your partner immerse yourselves in a deliciously sensual ambiance, where inhibitions do not ex...

The Fives Oceanfront Puerto Morelos - All Inclusive Puerto Morelos
4.5
Trip Advisor Rating
All-inclusive

Hidden amidst the natural beauties of the Mayan Riviera and located in the charming fishing village of Puerto Morelos just 15 miles south of Cancun, The Fives Oceanfront is the perfect destination ...

Ventus Ha' at Marina El Cid Spa & Beach Resort - All Inclusive Puerto Morelos
4.5
Trip Advisor Rating
Be embraced by nature’s delicate touch and intimate atmosphere in our All-inclusive resort located in the magical Riviera Maya. A place of peace, inviting both reflection and exploration of nature, th...
Ocean Coral & Turquesa - All Inclusive Puerto Morelos
4.5
Trip Advisor Rating
All-inclusive
This dazzling all-inclusive resort is located on a prime stretch of beachfront in the heart of the Mexican Caribbean, close to Cancun and neighboring Riviera Maya communities. With sweeping views of t...

Top Quintana Roo Destination: Riviera Maya Resort Packages from Chicago

Set your sights on the captivating allure of Riviera Maya and jet off from Chicago using one of AppleVacations.com's 8 exquisite vacation packages. Whether you're longing for the vibes of dining, the serenity of romance , or the excitement of beach, we've curated the perfect escape for you. Dive into luxury as you lodge at stellar resorts represented by big names like Palladium Hotels, each renowned for their lavish offerings of amenities such as a spa, a restaurant and an exercise gym. With deals ranging from the enticing $772 to the exclusive $2,165, and an appealing average of just $949 per traveler, the allure of Riviera Maya in Quintana Roo is now more accessible than ever. Let AppleVacations.com be the bridge to your dream vacation.*

Grand Palladium White Sand Resort & Spa - All-Inclusive Riviera Maya
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $772 to $1,427* /person
3 to 7 Day Trips - Sep to Jan
TRS Yucatan Hotel - All-Inclusive, Adults Only Riviera Maya
4.5
Trip Advisor Rating
Hotel + Flight
All-inclusive
4 Deals Available!
From $1,126 to $2,165* /person
3 to 7 Day Trips - Nov to Feb
Hard Rock Hotel Riviera Maya - All Inclusive Riviera Maya
4.5
Trip Advisor Rating
All-inclusive

Appealing to luxury travelers, spa enthusiasts and families seeking all-inclusive pampering, this sensational resort provides the perfect setting for relaxation and fun in the sun. Located in Puert...

UNICO 20°87° Riviera Maya - All Inclusive Riviera Maya
4.5
Trip Advisor Rating
All-inclusive
Set on the stunning white beaches of Riviera Maya, UNICO 20°87° immerses you in the culture of the region, from the locally-inspired cocktails and cuisine, to the consistently unique calendar of ...
Desire Riviera Maya Resort - All-Inclusive Riviera Maya
4.5
Trip Advisor Rating
All-inclusive

Desire Riviera Maya Resort is set amongst lingering ocean breezes, powdery white sand and a seductive, picture perfect view of the Caribbean. Additional features include: beach beds, as we...

Barcelo Maya Colonial - All Inclusive Riviera Maya
4.5
Trip Advisor Rating
All-inclusive

Disconnect from the hustle and bustle of everyday life and enjoy a stay at Barceló Maya Colonial – a luxurious, family-friendly resort located in Riviera Maya! The perfect spot to r...

Barcelo Maya Tropical - All Inclusive Riviera Maya
4.5
Trip Advisor Rating
All-inclusive


Welcome to paradise! Set your sights on Barceló Maya Tropical – an amazing resort located along the gorgeous sands of Riviera Maya – and experience a vacation like never before. W...

Catalonia Royal Tulum - All Inclusive Riviera Maya
4.5
Trip Advisor Rating
Fronting the pristine white sands of Xpu-ha Beach, this fetching adults-only resort offers appealing, all-inclusive accommodations ideal for active travelers and couples seeking fun and sun. Surrounde...
Ocean Riviera Paradise - All Inclusive Riviera Maya
4.5
Trip Advisor Rating
All-inclusive
Situated aside a gorgeous beach in the heart of Riviera Maya, the Ocean Riviera Paradise is a five-star resort ideal for families, friends, and couples. Noteworthy for its size, this ...
Hard Rock Hotel Riviera Maya - Heaven Section - All Inclusive Riviera Maya
4.5
Trip Advisor Rating
All-inclusive

A shimmering compliment to the sparkling waters of the Caribbean Sea, this romantic, adults-only resort appeals to honeymooners, spa-lovers and couples looking to tie the knot or fall in love. An i...

Map of Quintana Roo Resorts

FAQs About the Latest Chicago to Quintana Roo Vacation Packages

What cities in Quintana Roo have the highest rated hotels with packages offered that include a flight from Chicago - O'Hare?

In Quintana Roo, the top-rated hotels that offer a flight from ORD are predominantly found in Cancún with 56 top rated hotels, Playa del Carmen with 38 top rated hotels and Cozumel with 18 top rated hotels.

What cities in Quintana Roo have the cheapest packages available from Chicago?

For travelers from Chicago to Quintana Roo, Cancún and Playa del Carmen present the most budget-friendly vacation packages. Prices begin at $810 in Cancún and $758 in Playa del Carmen.

What cities in Quintana Roo have the cheapest packages available from Chicago?

Cancún offers 21 family-friendly packages, 21 luxury packages and 16 adults-only packages. In Playa del Carmen, there are 12 packages tailored for families, 24 luxury options and 16 exclusively for adults.

What resort brands offer Vacations from Chicago to Quintana Roo?

Hyatt Inclusive Collection, Iberostar Hotels & Resorts, Palladium Hotels, Oasis Resorts and Bahia Principe Hotels and Resorts currently have amazing package deals on flights from Chicago to Quintana Roo with resort accommodations included. Here are some of their best deals as of 08-29-2024:

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*Current vacation package prices are listed as of 08-29-2024 and are subject to change based on dates, origins and availability.

While reasonable effort has been made to ensure the accuracy of the information on this website, Apple Vacations does not assume responsibility for any errors or omissions.