Greater Grand Crossing Vacations from $186

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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.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $342, price is now $186 per person
$186
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.4/10 Exceptional! (317 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.

Reviewed on Oct 28, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,413, price is now $729 per person
$729
per person
Dec 27 - Jan 2
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.4/10 Exceptional! (1,264 reviews)
Clean, quiet and comfortable room, courteous staff. We received a $25k food credit through Expedia and got exceptional pastries and coffee at the adjacent cafe.

Reviewed on Nov 22, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,292, price is now $680 per person
$680
per person
Dec 27 - Jan 2
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) 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

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $564, price is now $307 per person
$307
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.4/10 Exceptional! (2,241 reviews)
Staff, amenities, cleanliness, and location. Makes this hotel a good stay for your next vacation everything was wonderful. Thank you will stay again.

Reviewed on Nov 24, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $352, price is now $200 per person
$200
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
Really great spot in the city right in the middle like a five minute walk to to everything around you the staff was great. The rooms were beautiful.

Reviewed on Nov 24, 2025

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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

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
$128 nightly
The price is $146 total per night from Dec 21 to Dec 22
$146 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (2,091 reviews)
Rooms are small and tile in bathroom looked dirty

Reviewed on Nov 24, 2025

Palmer House a Hilton Hotel
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
$87 nightly
The price is $102 total per night from Dec 21 to Dec 22
$102 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (5,291 reviews)
All above.

Reviewed on Nov 24, 2025

Embassy Suites by Hilton Chicago Downtown River North
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! (3,359 reviews)
Clean rooms, friendly and helpful staff. TV lets you quickly sign into the main streaming services. Good location.

Reviewed on Nov 24, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,635 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
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Beach Vacations
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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

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
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$45
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.