Gross Point Vacations from $528

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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 $806, price is now $528 per person
$528
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Very pet friendly. Small room but fine for the 2 overnights in city. The Shower head in 1003 leaks & reduced the flow but otherwise decent. Spot Hero parking ($35 night) around the corner for easy in and out. Central location to most areas of interest @$125 value

Reviewed on Mar 24, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,180, price is now $664 per person
$664
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
My only complaint was the sheets were rough and made my skin and my daughter's skin itchy.... maybe the detergent? Otherwise the room was very clean, breakfast was great, bag check was easy and valet was quick and not too pricey! All the staff were pleasant and professional!

Reviewed on Mar 26, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was $1,069, price is now $640 per person
$640
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,076 reviews)
Staff was soooo friendly

Reviewed on Mar 25, 2026

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $879, price is now $540 per person
$540
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,675 reviews)
We loved our stay. Two adults and our eight-year-old son took a weekend trip to Chicago. This hotel was very close to the field museum and walking distance to magnificent mile. Short Uber ride to nearby shopping and Willis Tower. The staff were awesome and upgraded our room at a low price. We felt very safe and staff were very helpful. The eighth floor had a beautiful pool, spa and sauna, great view of lake mi, open late too. We dined for breakfast at yoke and Niu B for dinner. Delicious. At checkout we purchased a future Hilton grand vacation at a great discount too. Let’s go. :)

Reviewed on Mar 25, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,096, price is now $704 per person
$704
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Staff was really nice

Reviewed on Mar 24, 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
$110 nightly
The price is $129 total per night from Apr 1 to Apr 2
$129 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (10,024 reviews)
The rooms are very outdated and the bathroom was a mess when I arrived. (Like hair in the shower) The hotel is very conveniently located so that is a huge plus and not super expensive. I felt safe the whole time, and staff was helpful when I arrived.

Reviewed on Mar 25, 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 6 to Apr 7
$143 total
Apr 6 - Apr 7
Total with taxes and fees
9/10 Wonderful! (3,982 reviews)
Good location, parking only a couple blocks away, very clean and quiet room.

Reviewed on Mar 26, 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 $153 total per night from Apr 5 to Apr 6
$153 total
Apr 5 - Apr 6
Total with taxes and fees
8.6/10 Excellent! (5,775 reviews)
The pillows in the rooms were very hard and so was the bed. In the pool area there where not enough towels for people and it seemed very cold for a indoor pool.

Reviewed on Mar 25, 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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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(2,149 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
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.