Greater Grand Crossing Vacations from ￥344,016

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    Save up to ￥45,448 when you book a flight and hotel together*

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The Latest Greater Grand Crossing Vacation Packages

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was ￥419,975, price is now ￥344,016 per person
￥344,016
per person
Mar 22 - Mar 28
found 5 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Perfect location, comfortable and clean room

Reviewed on Jan 5, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥565,091, price is now ￥431,406 per person
￥431,406
per person
Mar 22 - Mar 28
found 5 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!

Reviewed on Jan 3, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was ￥581,636, price is now ￥458,678 per person
￥458,678
per person
Mar 22 - Mar 28
found 5 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Upon check-in, it was magical! The doormen were amazing, the 'go as often as you'd like' Santa's candy shop, overall hotel decorations and the professionalism of the staff will blow you away!!! This hotel is next level up and puts the Ritz Carlton down a notch, for sure. Our room was truly magnificent and I wish we could have stayed longer!

Reviewed on Jan 6, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥450,266, price is now ￥368,169 per person
￥368,169
per person
Mar 22 - Mar 28
found 5 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in

Reviewed on Dec 25, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was ￥445,109, price is now ￥367,908 per person
￥367,908
per person
Mar 22 - Mar 28
found 5 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.

Reviewed on Dec 18, 2025

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 showing a city

Downtown Chicago

5 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.

Find hotels in Downtown Chicago

Greater Grand Crossing Hotel Deals

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥13,997 per night from Jan 25 to Jan 26
￥13,997
￥16,431 total
Jan 25 - Jan 26
includes taxes & fees
8.8/10 Excellent! (3,660 reviews)
We had a wonderful stay at the Hilton. The staff was exceptionally helpful in providing any information we neede. A shout out to Latis and Christian, who were extremely friendly, always created us with a smile and we’re eager to help. We will definitely stay here again.

Reviewed on Jan 6, 2026

Hilton Chicago/Magnificent Mile Suites
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥21,702 per night from Jan 17 to Jan 18
￥21,702
￥30,074 total
Jan 17 - Jan 18
includes taxes & fees
8.4/10 Very Good! (2,494 reviews)
I paid for a king room and had that for the first half of my stay, but something went wrong with the water heater for the floor(?). It wasn't explained well to us, but we were moved into another room on a higher level which I assumed would have been similar but it was much smaller and had a queen ...

Reviewed on Jan 5, 2026

Hilton Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥22,344 per night from Jan 17 to Jan 18
￥22,344
￥30,143 total
Jan 17 - Jan 18
includes taxes & fees
8.4/10 Very Good! (2,226 reviews)
Room was very clean and staff was great

Reviewed on Jan 6, 2026

Palmer House a Hilton Hotel
See all 4,675 properties in Greater Grand Crossing
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 ￥344,016. 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.

Things to do

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥6,889
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,845
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,263
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.