Greater Grand Crossing Vacations from $199

Book a Hotel + Flight or Car together to unlock savings

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.
Bridgeview Inn Chicago Area

Bridgeview Inn Chicago Area

2 out of 5
Save 100% on your flight
Price was $311, price is now $199 per person
$199
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
6.4/10 (105 reviews)
Newly remodeled room.

Reviewed on Oct 11, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,063, price is now $543 per person
$543
per person
May 3 - May 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The room was excellent

Reviewed on Feb 16, 2026

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

3.5 out of 5
Price was $750, price is now $415 per person
$415
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (999 reviews)
Elevator was broken all three days we were there, so line could back up to get in. Food at the diner was ok but not great, with very little to eat out in the area, we ended up door dashing mostly. Steakhouse was really good, but very expensive $98 ribeye with no sides included expensive, but nice for a date night. Beds were not comfortable and pillows even worse, but will say room was clean.

Reviewed on Feb 17, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $767, price is now $457 per person
$457
per person
May 3 - May 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Nice hotel Great location

Reviewed on Feb 15, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $611, price is now $367 per person
$367
per person
May 3 - May 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
Room neat, clean and cozy. Check in was easy. Small and intimate for quick weekend getaway.

Reviewed on Feb 16, 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 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

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $109 total per night from Feb 18 to Feb 19
$109 total
Feb 18 - Feb 19
Total with taxes and fees
8/10 Very Good! (9,900 reviews)
Nice room and amazing view of lake Michigan. Very clean and staff was friendly. Only down side was our room was extremely hot.

Reviewed on Feb 16, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $144 total per night from Mar 4 to Mar 5
$144 total
Mar 4 - Mar 5
Total with taxes and fees
9.2/10 Wonderful! (3,355 reviews)
The room was excellent

Reviewed on Feb 16, 2026

Hotel Riu Plaza Chicago
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $192 total per night from Feb 27 to Feb 28
$192 total
Feb 27 - Feb 28
Total with taxes and fees
8.4/10 Very Good! (2,638 reviews)
All of the staff we talked to were extremely kind and helpful. We had something sent to the room twice. Both times the items arrived within 10 minutes. The room, which we paid $99 (after tax) to upgrade to, had a really great view of the lake, Navy Pier and Museum Campus. The room was updated. Even ...

Reviewed on Feb 16, 2026

Hilton Chicago
See all 4,674 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 lakeside or experience the acclaimed art scene in this vibrant area.

Greater Salem Baptist Church

Things to do

Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$166
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Picture 7 for Activity Chicago River: 1.5-Hour Guided Architecture Cruise

Chicago River: 1.5-Hour Guided Architecture Cruise

$44
per adult
98% of travellers recommend
Chicago River: 1.5-Hour Guided Architecture Cruise
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.