Greater Grand Crossing Vacations from $269

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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.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Save 100% on your flight
Price was $431, price is now $269 per person
$269
per person
May 5 - May 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8/10 Very Good! (503 reviews)
Was an wonderful experience. The staff was very kind and helpful. The view was amazing. Highly recommend any time of the year!

Reviewed on Jan 12, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,246, price is now $739 per person
$739
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,422 reviews)
Great breakfast buffet! Great location to Michigan Ave. I would stay here again.

Reviewed on Mar 3, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $634, price is now $405 per person
$405
per person
May 29 - Jun 1
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (467 reviews)
Room was amazing and beautiful and comfortable Only issue was when we arrived they had a plumbing issue and the whole place smelled horrific like a sewer. We didn’t go eat at the restaurant because the smell made us nauseous

Reviewed on Mar 1, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $605, price is now $416 per person
$416
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,136 reviews)
Front desk staff are gems! They knew my name after 1 interaction and were very attentive. The room amenities were very nice-- espresso, bottled water, chocolates, steamer, toiletries.

Reviewed on Mar 1, 2026

The Drake

The Drake

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $934, price is now $645 per person
$645
per person
May 5 - May 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,334 reviews)
The room was spacious and neatly kept. The staff was super nice and made sure that we had what we needed during our stay.

Reviewed on Mar 1, 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
$86 nightly
The price is $101 total per night from Mar 5 to Mar 6
$101 total
Mar 5 - Mar 6
Total with taxes and fees
8/10 Very Good! (9,909 reviews)
There was no hot water in the shower the whole time we were there.

Reviewed on Mar 3, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$140 nightly
The price is $165 total per night from Mar 8 to Mar 9
$165 total
Mar 8 - Mar 9
Total with taxes and fees
9.4/10 Exceptional! (3,449 reviews)
Great breakfast buffet! Great location to Michigan Ave. I would stay here again.

Reviewed on Mar 3, 2026

Hotel Riu Plaza Chicago
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
$120 nightly
The price is $141 total per night from Mar 5 to Mar 6
$141 total
Mar 5 - Mar 6
Total with taxes and fees
8.6/10 Excellent! (5,711 reviews)
Love the hotel just wish the pool water was warmer

Reviewed on Mar 2, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,696 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

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$61
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Flyover in Chicago

Flyover in Chicago

$38
per adult
98% of travellers recommend
Flyover in 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.