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)

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Our top choices for Gross Point hotels

A three-tiered fruit basket on a wooden table against a wall with framed pictures.

1. Heart O' Chicago

6.6 mi from Gross Point

Anthony

$85 nightly

Oct 12 - Oct 13

Total with taxes and fees

A spacious lobby with a central coffee table, sofas, and a large mirror.

2. The Chicago Hotel Collection Ambassador Gold Coast

12.8 mi from Gross Point

Laura

$188 nightly

Sep 29 - Sep 30

Total with taxes and fees

A modern dining area with a large table, chairs, and a coffee station.

3. avid hotel Chicago O’Hare – Des Plaines by IHG

9.6 mi from Gross Point

Sarai

$139 nightly

Sep 28 - Sep 29

Total with taxes and fees

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

4. Hilton Chicago/Magnificent Mile Suites

13.3 mi from Gross Point

Brian

$197 nightly

Oct 1 - Oct 2

Total with taxes and fees

The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.

5. Claridge House Chicago, Tapestry Collection by Hilton

12.8 mi from Gross Point

Christie

$180 nightly

Sep 20 - Sep 21

Total with taxes and fees

A historic building with a glass entrance, large columns, and decorative planters with flowers.

6. Warwick Allerton - Chicago

13.6 mi from Gross Point

Monique

$157 nightly

Oct 1 - Oct 2

Total with taxes and fees

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

7. Carleton of Oak Park

13.9 mi from Gross Point

Alan

$109 nightly

Oct 12 - Oct 13

Total with taxes and fees

An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

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

14.2 mi from Gross Point

Ashraf

$314 nightly

Oct 1 - Oct 2

Total with taxes and fees

A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

9. River Hotel

14 mi from Gross Point

steve

$152 nightly

Sep 27 - Sep 28

Total with taxes and fees

An outdoor rooftop lounge with seating, a fire feature, and a view of the city skyline at night.

10. The Chicago Hotel Collection - Magnificent Mile

13.6 mi from Gross Point

Patricia

$144 nightly

Sep 29 - Sep 30

Total with taxes and fees

11. Hotel 55 Chicago Downtown

13.7 mi from Gross Point

Angel

$208 nightly

Sep 27 - Sep 28

Total with taxes and fees

A spacious lobby with a checkered floor, a large sofa, and multiple chairs.

12. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

13.7 mi from Gross Point

Marissa

$180 nightly

Sep 20 - Sep 21

Total with taxes and fees

A modern lobby with a grey sofa, checkered ottomans, and a coffee table. There are black chairs, a blue sofa, and a TV on a stand.

13. Aloft by Marriott Chicago Mag Mile

13.8 mi from Gross Point

Jerry

$179 nightly

Sep 20 - Sep 21

Total with taxes and fees

A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.

14. Travelodge by Wyndham Downtown Chicago

14.9 mi from Gross Point

Matthew

$155 nightly

Sep 29 - Sep 30

Total with taxes and fees

A historic building with a prominent casino sign, surrounded by modern skyscrapers.

15. Hotel Felix River North/Magnificent Mile

13.5 mi from Gross Point

Scott

$183 nightly

Sep 27 - Sep 28

Total with taxes and fees

A modern building with a glass facade and a curved structure.

16. Hyatt Regency O'Hare Chicago

9.8 mi from Gross Point

Joanne

$186 nightly

Oct 4 - Oct 5

Total with taxes and fees

A grand lobby with a central bar, high ceilings, and classical architecture.

17. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

14.4 mi from Gross Point

Scott

$159 nightly

Sep 27 - Sep 28

Total with taxes and fees

A modern lounge area with seating, a coffee table, and a view of the city at night.

18. Moxy Chicago Downtown

13.6 mi from Gross Point

Justin

$200 nightly

Sep 20 - Sep 21

Total with taxes and fees

A modern building with a colorful facade and a red circular seating area.

19. citizenM Chicago Downtown

14.1 mi from Gross Point

Germaine

$193 nightly

Sep 20 - Sep 21

Total with taxes and fees

A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

20. Congress Plaza Hotel

14.9 mi from Gross Point

Manuel

$162 nightly

Sep 27 - Sep 28

Total with taxes and fees

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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 cityscape with tall skyscrapers and a historic tower.

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.

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A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.

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.

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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.

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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.

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A river with a city skyline in the background, surrounded by green trees and grass.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

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Top Gross Point Hotel Reviews

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"Nice place to stay"

Hilton Chicago

10/10 Excellent

"My stay at the Chicago Hilton was truly exceptional. From the moment I arrived, I was impressed by the beautiful and elegant surroundings, outstanding amenities, and impeccable service. The staff were gracious, attentive, and professional, making the entire experience feel warm and welcoming. The hotel itself is absolutely gorgeous, with amenities that exceeded my expectations. I look forward to staying here again and would highly recommend the Chicago Hilton to anyone seeking a memorable and luxurious experience in Chicago."

Warwick Allerton - Chicago

10/10 Excellent

"It was our first time in Chicago, and we would definitely stay here again. The hotel is clean, quiet, and so pretty. (with an art deco vibe) It’s also located in a great area, very easily walkable to most shops/attractions/etc that were already on our list. The staff was so friendly. I wish I got the name of the lovely lady who was so generous to my friends and I. Overall such a nice comfy place to stay at!"

Find hotels in Gross Point, Chicago

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Be picky

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Our top choices for Gross Point hotels

1. Heart O' Chicago

2. The Chicago Hotel Collection Ambassador Gold Coast

3. avid hotel Chicago O’Hare – Des Plaines by IHG

4. Hilton Chicago/Magnificent Mile Suites

5. Claridge House Chicago, Tapestry Collection by Hilton

6. Warwick Allerton - Chicago

7. Carleton of Oak Park

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

9. River Hotel

10. The Chicago Hotel Collection - Magnificent Mile

11. Hotel 55 Chicago Downtown

12. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

13. Aloft by Marriott Chicago Mag Mile

14. Travelodge by Wyndham Downtown Chicago

15. Hotel Felix River North/Magnificent Mile

16. Hyatt Regency O'Hare Chicago

17. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

18. Moxy Chicago Downtown

19. citizenM Chicago Downtown

20. Congress Plaza Hotel

Where to stay in Gross Point

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Gross Point Hotel Reviews

Hotel Saint Clair- Magnificent Mile

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