Gross Point Vacations from $813

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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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,401, price is now $813 per person
$813
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,076 reviews)
Everything was perfect

Reviewed on Mar 26, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,714, price is now $1,038 per person
$1,038
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,646 reviews)
Hotel is beautiful and located in an excellent area. Everything is around you

Reviewed on Mar 28, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,321, price is now $1,418 per person
$1,418
per person
Jun 4 - Jun 8
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
10/10 makes you feel at home. One of the best hotels I’ve ever stayed in.

Reviewed on Mar 23, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,322, price is now $836 per person
$836
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
The rooms are extremely clean and have everything you need. The staff is so accommodating and friendly. The view is amazing

Reviewed on Mar 27, 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

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
$115 nightly
The price is $135 total per night from Apr 5 to Apr 6
$135 total
Apr 5 - Apr 6
Total with taxes and fees
8/10 Very Good! (10,005 reviews)
Good overall

Reviewed on Mar 29, 2026

Congress Plaza Hotel
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
$122 nightly
The price is $143 total per night from Apr 5 to Apr 6
$143 total
Apr 5 - Apr 6
Total with taxes and fees
9/10 Wonderful! (4,007 reviews)
Nice location and awesome room

Reviewed on Mar 29, 2026

Hilton Chicago/Magnificent Mile Suites
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 $152 total per night from Apr 12 to Apr 13
$152 total
Apr 12 - Apr 13
Total with taxes and fees
8.6/10 Excellent! (5,792 reviews)
Great spot in the shopping district. Good breakfast and nice to have the snacks and drinks for the happy hour time.

Reviewed on Mar 28, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,448 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.
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Kid Friendly Vacations

Discover the most popular places to visit in Gross Point

Wrigley Field

Wrigley Field

4.5/5(2,149 reviews)

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

4.5/5(336 reviews)

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
Chicago Skyline at North Beach

Naval Base Great Lakes

4.5/5(461 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$66
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
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.