Greater Grand Crossing Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Greater Grand Crossing
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $2,082
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
The staff were helpful, the room was nice and clean, and the buffet breakfast was amazing. We enjoyed our stay.
Reviewed on Aug 28, 2026
Where to stay in Greater Grand Crossing
Find the best Greater Grand Crossing areas and neighborhoods for the activities you enjoy most. Learn more about Greater Grand Crossing
Downtown Chicago
4 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Greater Grand Crossing Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $146
CA $174 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very good! (10,197 reviews)
"Room and bathroom were dirty and bathtub didn’t work."
Reviewed on Aug 28, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $173
CA $205 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very good! (2,113 reviews)
"Staff was very nice, hotel is in a great location"
Reviewed on Aug 28, 2026
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (876 reviews)
"Clean rooms, great location"
Reviewed on Aug 28, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
How much does a Greater Grand Crossing vacation package cost?
Live it up in Greater Grand Crossing from just CA $1,347. Choose from a wonderful selection of hotels, flights and rental cars to suit every budget and style. Pick up even better deals when you add some activities or tours to your package.
How do I get a cheap travel package to Greater Grand Crossing?
Just imagine all the fabulous things you could do in Greater Grand Crossing with extra cash in your wallet. Watch your savings stack up when you bundle your travel bookings into a Greater Grand Crossing vacation package. You have plenty of choice when you book with Expedia too. In fact, you can select from over 550 airlines and 1,000,000 properties around the world. Whether you're taking off with the entire family or going it alone, organizing a getaway to Greater Grand Crossing is better with a package.
Where should I stay in Greater Grand Crossing?
A visit to Greater Grand Crossing isn't complete without seeing University of Chicago and Chicago Museum of Science and Industry. Reserve a room close by for quick access to these famous sights.
How far in advance should I book my Greater Grand Crossing vacation?
While not all airlines advertise ticket prices early, customers are usually able to look up international flights on Expedia up to 12 months in advance. This is the time when you can nab some incredible bargains. If you're purchasing tickets last minute, you might still be in luck. Low prices occasionally become available just weeks prior to departure.
What does an Expedia Greater Grand Crossing travel package include?
That depends on you. You can select from a variety of Greater Grand Crossing packages, such as a hotel, rental car and flight. You can also book a hotel with a flight, or a rental car with a flight. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your ideal Greater Grand Crossing break looks like, get set to save!
What should I know before booking a Greater Grand Crossing travel package?
You'll pick up great savings when you bundle your hotels, flights and rental cars into a package. Not only that, booking everything in one place just makes things easier. So why waste your time or money? Whether you're organizing a luxury city stay with your love or a budget solo adventure, take a look at our vacation packages today.
Can I choose my airline with a Greater Grand Crossing Expedia vacation package?
Yes, and with more than 550 airlines to choose from worldwide, you have loads of choice. Take a look at the available options and see which airline best suits your needs and budget.
If I'm not able to travel, can I cancel my Greater Grand Crossing vacation package?
Plans can change unexpectedly, so yes, you can. You may be able to cancel and rebook your Greater Grand Crossing vacation package at no cost if you've booked in the last 24 hours. For older bookings, you can still make the necessary changes, but your car rental company, hotel or airline may charge a fee. Want more information? Take a look at our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.
Stay near popular Greater Grand Crossing attractions
Martin Luther King Drive
You can enjoy some culture when you stop by Martin Luther King Drive in Chicago. Amble around the area's beaches or experience its theater scene.
Auburn Park
After visiting Auburn Park, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.
Third World Press
You can learn about the history of Chicago with a stop at Third World Press. Amble around the area's beaches or experience its theater scene.
Greater Salem Baptist Church
After visiting Greater Salem Baptist Church, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the acclaimed art scene in this vibrant area.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.