Gross Point Vacations from $358

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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
Save 100% on your flight
Price was $623, price is now $358 per person
$358
per person
May 5 - May 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,573 reviews)
Clean room, I’m always glad to stay here

Reviewed on Feb 27, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,030, price is now $512 per person
$512
per person
May 5 - May 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,422 reviews)
The hotel was beautiful, the rooms were clean, and the staff were amazing and friendly

Reviewed on Mar 4, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,084, price is now $618 per person
$618
per person
May 5 - May 9
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

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $975, price is now $557 per person
$557
per person
May 5 - May 9
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

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $719, price is now $433 per person
$433
per person
May 5 - May 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,271 reviews)
Clean and comfortable great staff!

Reviewed on Mar 4, 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
$86 nightly
The price is $101 total per night from Mar 5 to Mar 6
$101 total
Mar 5 - Mar 6
Total with taxes and fees
8/10 Very Good! (9,911 reviews)
Very beautiful historical hotel. The place may need a few more finishing touches. We experienced only one hiccup. We stayed for 2 nights. I asked the housekeeper if she could just make up the bed or freshen it up without new linen on that Saturday morning and let her know I left a tip on the bed ...

Reviewed on Mar 4, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$140 nightly
The price is $165 total per night from Mar 8 to Mar 9
$165 total
Mar 8 - Mar 9
Total with taxes and fees
9.4/10 Exceptional! (3,452 reviews)
Nice room, but very cold on the floor and in the bathroom.

Reviewed on Mar 4, 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
$120 nightly
The price is $141 total per night from Mar 5 to Mar 6
$141 total
Mar 5 - Mar 6
Total with taxes and fees
8.6/10 Excellent! (5,713 reviews)
Love the hotel just wish the pool water was warmer

Reviewed on Mar 2, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,558 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

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.