Greater Grand Crossing Vacations from $237

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Your Greater Grand Crossing Vacation

Organizing your next break just got easier with a vacation package to Greater Grand Crossing. Embrace the best this neighborhood has to offer while making fond memories you won't forget. Your trip to Greater Grand Crossing wouldn't be complete without exploring major attractions nearby such as University of Chicago, Chicago Museum of Science and Industry and Robie House. Expedia is here to help put your travel plans into action. Book your ideal Greater Grand Crossing vacation today.

The Latest Greater Grand Crossing Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago - Schaumburg by IHG

Holiday Inn Chicago - Schaumburg by IHG

3.5 out of 5
Save 100% on your flight
Price was $447, price is now $237 per person
$237
per person
Dec 26 - Dec 31
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
16.4/10 Exceptional! (999 reviews)
Rooms were clean and overall the hotel was nice

Reviewed on Nov 1, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $3,257, price is now $1,529 per person
$1,529
per person
Dec 28 - Jan 3
found 16 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
18/10 Exceptional! (380 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.

Reviewed on Nov 9, 2025

Art Villa

Art Villa

5 out of 5
West Town
Price was $1,349, price is now $647 per person
$647
per person
Dec 25 - Dec 30
found 24 hours ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
20/10 Exceptional! (2 reviews)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $970, price is now $486 per person
$486
per person
Dec 20 - Dec 23
found 2 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
17.6/10 Exceptional! (1,075 reviews)
I didn’t have breakfast. Just coffee from the Starbucks kiosk.

Reviewed on Nov 17, 2025

Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
East Hazel Crest
Save 100% on your flight
Price was $743, price is now $400 per person
$400
per person
Dec 26 - Dec 31
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (MDW)
18.8/10 Exceptional! (160 reviews)
Everything was great

Reviewed on Nov 19, 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

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

Greater Grand Crossing Hotel Deals

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $106 total per night from Dec 10 to Dec 11
$106 total
Dec 10 - Dec 11
Total with taxes and fees
8.4/10 Very Good! (5,272 reviews)
I like the place was a good place and the staff are very welcoming. As one thing I didn't like I booked one bedroom King bed, I end up with two single beds. But they promise me to change in the morning and they didn't. I was not happy about it.

Reviewed on Nov 19, 2025

Embassy Suites by Hilton Chicago Downtown River North
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
$131 nightly
The price is $149 total per night from Nov 26 to Nov 27
$149 total
Nov 26 - Nov 27
Total with taxes and fees
8.4/10 Very Good! (2,065 reviews)
Classy and classic! Never disappoints

Reviewed on Nov 16, 2025

Palmer House a Hilton Hotel
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
$83 nightly
The price is $98 total per night from Dec 7 to Dec 8
$98 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (3,324 reviews)
Awesome location and valet was very helpful

Reviewed on Nov 18, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,612 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Greater Grand Crossing

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.

Auburn Park

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.

Greater Salem Baptist Church

Things to do

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.