Gross Point Vacations from $372

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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 Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $644, price is now $372 per person
$372
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,573 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well. The location is excellent and i would go back.

Reviewed on Mar 4, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $882, price is now $409 per person
$409
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,422 reviews)
Definitely will be coming back ! Clean, safe, and very helpful staff ! Breakfast buffet was also a big plus !!!

Reviewed on Mar 5, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $1,114, price is now $634 per person
$634
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Had a great stay!! Kelly at the front desk was so sweet

Reviewed on Feb 22, 2026

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Price was $675, price is now $396 per person
$396
per person
May 1 - May 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
The room was great and clean , there was a toilet issue but the staff members gladly were readily available to fix it all ! The amenities including the hot tub, and pool as well as the in room service breakfast was 5/5 . Would absolutely stay here again .

Reviewed on Feb 17, 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 $683, price is now $405 per person
$405
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,070 reviews)
Very nice & clean hotel and near the Bean and shops are walkable.

Reviewed on Mar 3, 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

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

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
$101 nightly
The price is $118 total per night from Mar 30 to Mar 31
$118 total
Mar 30 - Mar 31
Total with taxes and fees
8/10 Very Good! (9,916 reviews)
Great location! Friendly staff

Reviewed on Mar 5, 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
$135 nightly
The price is $159 total per night from Mar 15 to Mar 16
$159 total
Mar 15 - Mar 16
Total with taxes and fees
9.4/10 Exceptional! (3,458 reviews)
Definitely will be coming back ! Clean, safe, and very helpful staff ! Breakfast buffet was also a big plus !!!

Reviewed on Mar 5, 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
$130 nightly
The price is $153 total per night from Mar 22 to Mar 23
$153 total
Mar 22 - Mar 23
Total with taxes and fees
8.6/10 Excellent! (5,716 reviews)
Old property bad food long lines

Reviewed on Mar 5, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,545 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
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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

4.5/5(2,128 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(332 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
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier

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.