When is the best time to go to Gross Point?

The best time to visit Gross Point is during the late spring (May to early June) and early fall (September to October) when the weather is most pleasant for outdoor activities and exploring. During these months, you'll find comfortable temperatures, typically ranging from the mid-60s to high 70s Fahrenheit, making it ideal for walking around the charming downtown area or enjoying the lakefront. The humidity is generally lower than in mid-summer, and there's less chance of extreme weather, providing a consistently good experience. Families often appreciate the shoulder seasons for their milder weather, which is superb for visiting local parks and outdoor attractions without the intense heat or the larger crowds that can sometimes accompany peak summer. Many local events and farmers markets also run during these times. Travelers looking for a relaxed yet engaging trip will find these periods ideal.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Gross Point.

How much is the nightly rate at a Gross Point hotel?

Prices for hotels in Gross Point often vary, but you can find a great deal on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

Top Gross Point Hotels (Chicago)

Upfront pricing
Our total price for your stay includes taxes and fees
Treat yourself
Save 10% or more on over 100,000 hotels worldwide with Member Prices
Learn about One Key
Be picky
Search almost a million properties worldwide

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Gross Point hotels

1. Holiday Inn Express & Suites Prospect Heights by IHG

8.8 mi from Gross Point

Wynton

$101 nightly

Aug 30 - Aug 31

Total with taxes and fees

2. Sable at Navy Pier Chicago, Curio Collection by Hilton

14.2 mi from Gross Point

Dawn

$211 nightly

Sep 7 - Sep 8

Total with taxes and fees

3. The Chicago Hotel Collection Ambassador Gold Coast

12.8 mi from Gross Point

Judy

$143 nightly

Aug 30 - Aug 31

Total with taxes and fees

4. Claridge House Chicago, Tapestry Collection by Hilton

12.8 mi from Gross Point

Timothy

$139 nightly

Sep 7 - Sep 8

Total with taxes and fees

5. Freehand Chicago

13.7 mi from Gross Point

james

$117 nightly

Aug 31 - Sep 1

Total with taxes and fees

6. Congress Plaza Hotel

14.9 mi from Gross Point

Christina

$109 nightly

Sep 8 - Sep 9

Total with taxes and fees

7. La Quinta Inn & Suites by Wyndham Chicago Downtown

14.3 mi from Gross Point

Paige

$158 nightly

Sep 8 - Sep 9

Total with taxes and fees

8. Staypineapple, An Iconic Hotel, The Loop

14.3 mi from Gross Point

Kristie

$167 nightly

Aug 30 - Aug 31

Total with taxes and fees

9. Warwick Allerton - Chicago

13.6 mi from Gross Point

Andrea

$145 nightly

Sep 8 - Sep 9

Total with taxes and fees

10. Palmer House a Hilton Hotel

14.5 mi from Gross Point

suzanne

$198 nightly

Sep 7 - Sep 8

Total with taxes and fees

Breakfast, lunch, dinner and brunch served

11. Arlo Chicago

14.2 mi from Gross Point

Robert

$164 nightly

Sep 7 - Sep 8

Total with taxes and fees

12. The Chicago Hotel Collection - Magnificent Mile

13.6 mi from Gross Point

Shawna

$143 nightly

Aug 31 - Sep 1

Total with taxes and fees

13. Thompson Chicago, by Hyatt

13.1 mi from Gross Point

sheila

$216 nightly

Sep 7 - Sep 8

Total with taxes and fees

Rooftop bar, alfresco dining, open daily

14. The Godfrey Hotel Chicago

13.5 mi from Gross Point

Ryan

$176 nightly

Sep 7 - Sep 8

Total with taxes and fees

15. citizenM Chicago Downtown

14.1 mi from Gross Point

lakadria

$170 nightly

Sep 7 - Sep 8

Total with taxes and fees

16. Embassy Suites by Hilton Chicago Downtown River North

13.7 mi from Gross Point

Bryan

$155 nightly

Aug 16 - Aug 17

Total with taxes and fees

17. The Wade

13.8 mi from Gross Point

Richard

$169 nightly

Aug 23 - Aug 24

Total with taxes and fees

18. Hilton Garden Inn Chicago Central Loop

14.5 mi from Gross Point

Dawn

$169 nightly

Sep 7 - Sep 8

Total with taxes and fees

19. The Royal Sonesta Chicago Downtown

14 mi from Gross Point

Alexis

$221 nightly

Sep 1 - Sep 2

Total with taxes and fees

20. Hilton Chicago

15 mi from Gross Point

kun

$194 nightly

Sep 7 - Sep 8

Total with taxes and fees

View all properties

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

A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

See properties

A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

See properties

A historic castle-like building with intricate stonework and a paved walkway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

See properties

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

See properties

The Chicago Theatre with illuminated marquee and a wet street reflecting lights.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).

See properties

Top Gross Point Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent

"Have stayed here a few times now and always clean and convenient location to what I’m doing in Chicago. Parking is easy ($57 a day). Never have a problem with noise. Will stay again."

Hyatt Regency O'Hare Chicago

8/10 Good

"Visited for my kids Birthday trip & Everything about this property was lovely from the room and Guest service ‘ staff was very nice only thing I hated is the I asked for 2 double rooms but was only accommodated for 1 even though I book in advance but my king room did have a pull out couch so me and my family worked it out ."

Holiday Inn Chicago Dwtn - The Mart by IHG

10/10 Excellent

"As a whole the property and staff were great. I thought the breakfast was a little over priced though. Food certainly wasn’t bad but paying almost $30 a person for a breakfast buffet I expected a bit more variety and options. Selection variety wise it felt a step up from what similar hotels have offered as complimentary. However that’s a minor gripe to an otherwise great experience."

Congress Plaza Hotel

10/10 Excellent

"Beautiful hotel close to everything . Old well maintained Easy to work with staff. The front door valet Jose was perfect. Helpful every time we needed him The only complaint is the parking. The lot was already full and the parking staff at the lot were unhelpful at best. Had to go back to front door man for help. This lot is open to the public as well as the hotel users. If there is a big event nearby plan to park else where"

Eurostars Magnificent Mile

10/10 Excellent

"The hotel is located in walking distance of the Magnificent Mile. The property is modern and eclectic. The views are wonderful. The hotels restaurants was good. The staff were helpful with accommodations. I would personally recommend this hotel. The bilingual staff is highly appreciated. The beet salad was surprisingly scrumptious. The clerk name James was very personable and helpful. "

Find hotels in Gross Point, Chicago

Upfront pricing

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Gross Point hotels

1. Holiday Inn Express & Suites Prospect Heights by IHG

2. Sable at Navy Pier Chicago, Curio Collection by Hilton

3. The Chicago Hotel Collection Ambassador Gold Coast

4. Claridge House Chicago, Tapestry Collection by Hilton

5. Freehand Chicago

6. Congress Plaza Hotel

7. La Quinta Inn & Suites by Wyndham Chicago Downtown

8. Staypineapple, An Iconic Hotel, The Loop

9. Warwick Allerton - Chicago

10. Palmer House a Hilton Hotel

11. Arlo Chicago

12. The Chicago Hotel Collection - Magnificent Mile

13. Thompson Chicago, by Hyatt

14. The Godfrey Hotel Chicago

15. citizenM Chicago Downtown

16. Embassy Suites by Hilton Chicago Downtown River North

17. The Wade

18. Hilton Garden Inn Chicago Central Loop

19. The Royal Sonesta Chicago Downtown

20. Hilton Chicago

Where to stay in Gross Point

Downtown Chicago

The Loop

Magnificent Mile

River North

Theatre District

Top Gross Point Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

Frequently asked questions

Explore a world of travel with Expedia