Vacation Packages w/ Airfare, Hotel & Tours to Luxury Vacations in North America from ORD - Chicago in August

Thinking about traveling to North America from Chicago? Discover North America in August, the perfect month for luxury travelers seeking a blend of excitement and exclusivity. Imagine soaring over the breathtaking landscapes of Banff National Park in a private helicopter, where turquoise lakes and t... read more

Iconic Hotels: Hotel Monteleone, New Orleans

Discover the enchanting heart of New Orleans at the iconic Hotel Monteleone. Nestled in the historic French Quarter, this timeless hotel exudes old-world elegance and modern comfort. Immerse yourself in jazz at famous clubs, savor local flavors, and stroll along the Mississippi River.

From
ORD $681 * Per Person

3+ Nights

2 People

* Vacation is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes air, airport taxes, and hotel. Additional baggage charges may apply. Rates are available for 1 to 9 travelers.

Beach Getaway at Hyatt Regency Grand Reserve Puerto Rico

At the Hyatt Regency Grand Reserve Puerto Rico, you'll be able to enjoy a luxurious beach vacation just steps away from the pristine ocean. Revel in upscale amenities in a secluded location on Coco Beach close to the expansive El Yunque National Forest, providing easy access for amazing activities both on and off the resort. Relax in the stunning lagoon-style pool, indulge in delicious Caribbean cuisine, and soak up year-round sunshine on this splendid beach vacation in Puerto Rico.

From
ORD $1,212 * Per Person

3+ Nights

2 People

* Vacation is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes air, airport taxes, transfers, and hotel. Additional baggage charges may apply. Rates are available for 1 to 9 travelers.

Puerto Rican Paradise

Are you craving a Caribbean vacation without the hassle of a passport? The Caribe Hilton is the answer you've been waiting for! Escape for 3, 4, 5, or 6 nights in San Juan, Puerto Rico, on the spectacular grounds of this historic resort. Spend your days relaxing at the spa, lounging under a cascading waterfall, and soaking up the pristine beach. Whatever paradise is for you, it's waiting at the Caribe Hilton.

From
ORD $661 * Per Person

3+ Nights

2 People

Simply Maui

Pack your bags, we're going to Hawaii! During this magnificent trip, explore the Maui hotspot of Lahaina. Discover the scenery behind this historic whaling village and immerse yourself in the intriguing Hawaiian culture! Prepare to enjoy days at your luxurious accommodation while treating yourself to the best of Hawaii while taking in the gorgeous views of the Pacific.

From
ORD $1,760 * Per Person

4+ Nights

2 People

Hilton Hawaii Hopper: Waikoloa Village & Waikiki Beach Resort

Experience two of Hawaii's most beautiful islands! Start your vacation on the Big Island where you'll stay at the luxurious Hilton Waikoloa Village, beloved for its stunning salt-water lagoon pool and local Luau's.

Next, you're off to Honolulu to stay at the renowned Hilton Hawaiian Village Waikiki Beach Resort. Located on the widest stretch of beach in Waikiki, you'll enjoy over 22 acres of beautiful gardens, pools, and delicious on-site restaurants. Sit back and relax in Hawaiian paradise, or head off the resort to explore more of Hawaii's attractions! You can hike through the Hawaii Volcanoes National Park, get wild at the Honolulu Zoo, and beach-hop around the islands.

From
ORD $2,640 * Per Person

7+ Nights

2 People

* Vacation package is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes air, airport taxes and hotels. Additional baggage charges may apply. Rates are available for 1 to 9 travelers.

What travelers are saying about our trips to NorthAmerica

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Beachfront Oasis at Fairmont El San Juan Puerto Rico

Experience true bliss when you travel to Puerto Rico and stay in the phenomenal Fairmont El San Juan Hotel. You'll be staying right on the two-mile long Isla Verde Beach, surrounded by tall palm trees and lush greenery. Dive into any of the hotel's dazzling swimming pools, lay back with poolside service, and enjoy lively entertainment at the hotel's renowned nightclub.

From
ORD $1,152 * Per Person

3+ Nights

2 People

* Vacation is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes air, airport taxes, transfers, hotel and breakfast daily. Additional baggage charges may apply. Rates are available for 1 to 9 travelers.

Hilton Waikoloa Village, Hawaii vacation package

Beach Days and Hawaiian Leis: Hilton Waikoloa Village

Get ready to make your Hawaiian dreams a reality! Stay in paradise in Waikoloa Village as you relax by the hotel's pools, soak up the Hawaiian sun, and lounge in the utmost comfort. Check out gorgeous beaches, try your hands at some water-sports, and immerse yourself in Hawaii's local culture and customs. It doesn't matter how you choose to spend your days because this getaway will fulfill all of your Hawaiian dreams.

From
ORD $1,985 * Per Person

4+ Nights

2 People

* Vacation is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes air, airport taxes, and hotels Additional baggage charges may apply. Rates are available for 1 to 9 travelers.

Iconic Hotels: Fairmont Copley Plaza Boston

Experience the allure of historic Boston with an exciting stay at the iconic Fairmont Copley Plaza Boston. Fall in love with the city's rich heritage along the Freedom Trail, savor exquisite New England cuisine, and indulge in rejuvenating spa treatments with panoramic city views. Uncover the city's cultural gems at the Museum of Fine Arts, the Paul Revere Trail, and even take a cruise to see Boston in a new light.

From
ORD $698 * Per Person

3+ Nights

2 People

The Palmer House, a Hilton Hotel - Dining Area

Iconic Hotels: Palmer House, Chicago

Discover Chicago's vibrant energy from the heart of the city at Palmer House, a Hilton Hotel, where you can immerse yourself in the perfect blend of historic elegance and modern comfort. Located amidst the iconic landmarks, you'll find yourself steps away from the Magnificent Mile, Art Institute, and Millennium Park. Whether you're exploring the city or simply unwinding in luxurious accommodations, Palmer House promises an exceptional Chicago vacation.

From
ORD $601 * Per Person

3+ Nights

2 People

Iconic Hotels: Hotel del Coronado, San Diego

Immerse yourself in the sun, sand, and sea of San Diego with a stay at the iconic Hotel del Coronado, Curio Collection by Hilton. Situated in a 19th-century Victorian building, this historic resort offers an oceanfront paradise filled with endless activities, oasis-like pools, world-class dining, and a superb location just five miles from Downtown San Diego. Iconic for a reason, the Hotel del Coronado is sure to provide the perfect beachfront San Diego vacation.

From
ORD $1,231 * Per Person

3+ Nights

2 People

Beyond the Basics: New York City

Unveil the magic of New York City while enjoying the ideal balance between free-spirited exploration and expertly guided, unique tours. Immerse yourself in the city's dynamic energy, diverse culture, and iconic landmarks, plus uncover the secrets of the past with an exclusive Brooklyn Bridge & DUMBO Tour and pay homage to resilience and hope with a 9/11 Memorial and One World Trade Center Tour.

From
ORD $1,256 * Per Person

3+ Nights

2 People

* Vacation is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes air, airport taxes, hotel, tours and daily breakfast. Additional baggage charges may apply. Rates are available for 1 to 9 travelers.

Iconic Hotels: The Plaza Hotel, New York City

Get lost in the "Big Apple" during this marvelous NYC vacation. With a once-in-a-lifetime stay at the iconic Plaza Hotel, you'll have a chance to discover Manhattan at ease with a prime location next to Central Park. Whether you'd like to sample authentic New York Style pizza, shop on 5th Avenue, or enjoy views of Lady Liberty, you'll get the full New York City experience on this trip!

From
ORD $2,472 * Per Person

3+ Nights

2 People

Iconic Hotels: The Driskill, Austin

Spend 3 - 5 nights in the colorful capital of Texas: Austin! Explore the city filled with artistic wonders, from intriguing museums to fascinating street art. Taste the diverse flavors of the city, visit some of the state's most incredible landmarks, including the Texas State Capitol, and embrace Austin's natural beauty. With a stay at the 4-star Driskill Hotel, this is the ultimate way to experience Austin!

From
ORD $1,381 * Per Person

3+ Nights

2 People

Iconic Hotels: The Beverly Hills Hotel

Live in luxury at the world-renowned 5-star Beverly Hills Hotel! Indulge in a lavish escape to glamorous Beverly Hills, where timeless elegance meets modern sophistication. Unwind in an iconic hotel, dine at Michelin-starred restaurants, and embrace the glam of the 90210. Explore Rodeo Drive's designer boutiques, embrace Hollywood's allure, and visit the Griffith Observatory for incredible views of Los Angeles.

From
ORD $3,438 * Per Person

3+ Nights

2 People

* Vacation is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes air, airport taxes and hotel. Additional baggage charges may apply. Rates are available for 1 to 9 travelers.

Iconic Hotels: Bellagio Hotel & Casino, Las Vegas

Spend 3, 4 or 5 nights exploring the famous Las Vegas Strip while staying at the iconic 5-star Bellagio Hotel & Casino. With this centrally-located resort, you'll have easy access to the top restaurants, bars, and other popular casinos in the area. Whether you'd like to snap pictures in front of the Bellagio Fountain or try your luck at the tables, this Vegas trip is everything you need and more!