Greater Grand Crossing Vacations from $490

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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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $828, price is now $490 per person
$490
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
It was very pleasant and safe. I liked that you needed a room key to use the elevator which made us feel safe. The hotel is located very central and walking distance to everything. The staff was very friendly.

Reviewed on May 16, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $991, price is now $577 per person
$577
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,127 reviews)
The hotel was clean, staff was friendly and very helpful. My room was clean and the breakfast buffet was phenomenal. I recommend this hotel and will be a returning customer.

Reviewed on May 18, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $787, price is now $496 per person
$496
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,148 reviews)
Lovely stay and we are at Toro right in the hotel. Fabulous dinner

Reviewed on May 18, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,344, price is now $854 per person
$854
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
The Sable was beautiful and peaceful. We enjoyed our stay and would definitely come back. Thanks for the great customer service.

Reviewed on May 17, 2026

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,025, price is now $653 per person
$653
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Good location close to many attractions like sears tower, the bean, river boat tours... nuce rooms ... public parking 1/2 block from premises .. just an overal great property with excellent convenience for tourists type activities

Reviewed on May 3, 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

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

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $161 total per night from May 25 to May 26
$161 total
May 25 - May 26
Total with taxes and fees
8/10 Very Good! (10,150 reviews)
"Always stay here when I’m trying to save money great location and price"

Reviewed on May 17, 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
$189 nightly
The price is $225 total per night from May 25 to May 26
$225 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (4,176 reviews)
"The hotel was clean, staff was friendly and very helpful. My room was clean and the breakfast buffet was phenomenal. I recommend this hotel and will be a returning customer."

Reviewed on May 18, 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
$123 nightly
The price is $146 total per night from May 25 to May 26
$146 total
May 25 - May 26
Total with taxes and fees
7.8/10 Good! (1,429 reviews)
"I paid for room almost $600 but Expedia didn’t send me breakfast."

Reviewed on May 18, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,576 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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

$22
per child
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.