Greater Grand Crossing Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was €1,105, price is now €761 per person
€761
per person
24 Sept - 29 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (3,732 reviews)
Won't stay there again

Reviewed on 4 Aug 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was €1,452, price is now €877 per person
€877
per person
6 Sept - 11 Sept
found 21 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (509 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was €1,604, price is now €995 per person
€995
per person
20 Sept - 25 Sept
found 8 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (2,606 reviews)
Everything was great.

Reviewed on 4 Aug 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was €1,290, price is now €807 per person
€807
per person
24 Sept - 29 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.2/10 Very good! (2,858 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,530, price is now €1,115 per person
€1,115
per person
16 Oct - 19 Oct
found 1 day ago
Return flight included
New York (JFK) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)
Fantastic location and nice spacious rooms very quiet at night but let down by toilet that constantly blockedz. Excellent big gym and spa. Amazing terrace view on 16th floor

Reviewed on 4 Aug 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
A busy city street with tall buildings, a bus, and cars.

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.

Find hotels in Downtown Chicago

Top hotels in Greater Grand Crossing

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is €162 per night from 30 Aug to 31 Aug
€162
30 Aug - 31 Aug
includes taxes & fees
8/10 Very good! (10,198 reviews)
"The property is nice but you definitely get what you pay for. The ac in the room could not keep up even on a 75° day and the bathrooms in the lobby were vile but the room was cute and clean. The staff was wonderful."

Reviewed on 4 Aug 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is €166 per night from 30 Aug to 31 Aug
€166
30 Aug - 31 Aug
includes taxes & fees
8/10 Very good! (1,912 reviews)
"Great"

Reviewed on 4 Aug 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is €167 per night from 30 Aug to 31 Aug
€167
30 Aug - 31 Aug
includes taxes & fees
8.8/10 Excellent! (2,948 reviews)
"All is good"

Reviewed on 4 Aug 2026

Hyatt Regency O'Hare Chicago
See all 4,425 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 holiday package cost?
Live it up in Greater Grand Crossing from just €761. 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 holiday 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, organising 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 holiday?
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 organising a luxury city stay with your love or a budget solo adventure, take a look at our holiday packages today.
Can I choose my airline with a Greater Grand Crossing Expedia holiday 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 holiday package?
Plans can change unexpectedly, so yes, you can. You may be able to cancel and rebook your Greater Grand Crossing holiday 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 theatre scene.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.