Gross Point Vacations from $214

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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.
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 $405, price is now $214 per person
$214
per person
Dec 14 - Dec 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine

Reviewed on Oct 4, 2025

Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
Price was $1,020, price is now $524 per person
$524
per person
Dec 31 - Jan 3
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
10/10 Exceptional! (2 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $470, price is now $244 per person
$244
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Healthy breakfast and very clean hotel with friendly staff.

Reviewed on Oct 10, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $918, price is now $510 per person
$510
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.

Reviewed on Oct 11, 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $391, price is now $220 per person
$220
per person
Dec 14 - Dec 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice

Reviewed on Oct 9, 2025

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
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (9,366 reviews)
"Shockingly updated interior of the rooms based on the historic feel of the common areas- I was so pleasantly surprised!"

Reviewed on Oct 10, 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $100 total per night from Nov 10 to Nov 11
$100 total
Nov 10 - Nov 11
Total with taxes and fees
7.8/10 Good! (2,456 reviews)
Great hostel, will book again
"All the staff had great energy and were very helpful. Nice bar/lounge area and cozy space. I had a private room and though it wasn’t huge, it was exactly what we needed for our staycation."

Reviewed on Oct 12, 2025

Freehand 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
$152 nightly
The price is $179 total per night from Nov 9 to Nov 10
$179 total
Nov 9 - Nov 10
Total with taxes and fees
8.4/10 Very Good! (5,074 reviews)
"The onsite parking is worth the money compared to other lots. Walk where you can. The Embassy is in the perfect location for a lot of attractions."

Reviewed on Oct 9, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,266 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
Magnificent Mile - River North showing night scenes, a city and signage

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

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
100% 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
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.