Gross Point Vacations from $720

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Your Gross Point Vacation

Enjoy amazing adventures when you book a Gross Point vacation package. Whether you're a history buff, foodie or just a traveler who loves to experience new places, there's something for everyone in this exciting city. Every good trip to Gross Point has to include a bit of sightseeing. What to check out first? Bahai House of Worship and Langdon Park Beach are key attractions. Whatever your travel plans or the size of your budget, organizing your ultimate tailored Gross Point vacation is a piece of cake with Expedia.

The Latest Gross Point Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,118, price is now $720 per person
$720
per person
May 15 - May 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
The breakfast was incredibly delicious. The hotel in general is a 10 out of 10.

Reviewed on Mar 20, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,344, price is now $780 per person
$780
per person
May 21 - May 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
Beautiful room. Property upgraded to 2-bedroom. Facilities are great with huge gym. Great stay in Chicago.

Reviewed on Mar 14, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,466, price is now $887 per person
$887
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Spacious room with great views and washer and dryer

Reviewed on Mar 17, 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 $1,278, price is now $788 per person
$788
per person
May 21 - May 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Great location, views, & amenities.

Reviewed on Mar 20, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,600, price is now $1,668 per person
$1,668
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,332 reviews)
Exceptional hotel in the best location!

Reviewed on Mar 17, 2026

Where to stay in Gross Point

Find the best Gross Point areas and neighborhoods for the activities you enjoy most. Learn more about Gross Point
Downtown Chicago showing a city

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

Gross Point 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
$116 nightly
The price is $136 total per night from Apr 1 to Apr 2
$136 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (9,976 reviews)
Everything was clean and the staff were very nice!

Reviewed on Mar 20, 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
$162 nightly
The price is $190 total per night from Mar 29 to Mar 30
$190 total
Mar 29 - Mar 30
Total with taxes and fees
9.4/10 Exceptional! (3,576 reviews)
The breakfast was incredibly delicious. The hotel in general is a 10 out of 10.

Reviewed on Mar 20, 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
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $153 total per night from Mar 29 to Mar 30
$153 total
Mar 29 - Mar 30
Total with taxes and fees
8.6/10 Excellent! (5,757 reviews)
Hotel is conveniently located, clean and rooms were spacious. Evening reception and breakfast selections are fantastic. The only downside was the pool area is small with limited seating but the kiddos still enjoyed. Staff was very professional and helpful. Would stay again.

Reviewed on Mar 20, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,478 properties in Gross Point
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 Gross Point

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$26
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
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
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.