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

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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

Oscar

$108 nightly

Oct 28 - Oct 29

Total with taxes and fees

A hotel lobby with a sofa, chairs, a TV, and artwork on the walls.

2. Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

10 mi from Gross Point

Jaishiri

$119 nightly

Nov 24 - Nov 25

Total with taxes and fees

A modern lounge area with leather sofas, a coffee table, and a patterned rug.

3. Holiday Inn Chicago O'Hare – Rosemont by IHG

10 mi from Gross Point

Nilantay Morshed

$132 nightly

Nov 24 - Nov 25

Total with taxes and fees

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

4. Claridge House Chicago, Tapestry Collection by Hilton

12.8 mi from Gross Point

Scott

$117 nightly

Nov 22 - Nov 23

Total with taxes and fees

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

5. Carleton of Oak Park

13.9 mi from Gross Point

Brad

$109 nightly

Oct 28 - Oct 29

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.

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

14.2 mi from Gross Point

Angela

$160 nightly

Nov 23 - Nov 24

Total with taxes and fees

7. ACME Hotel Chicago, Outset Collection by Hilton

13.7 mi from Gross Point

alex

$101 nightly

Nov 23 - Nov 24

Total with taxes and fees

A bar area with a long counter, bar stools, and a mirrored wall.

8. The Whitehall Hotel, BW Premier Collection

13.3 mi from Gross Point

Benjamin

$99 nightly

Nov 23 - Nov 24

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.

9. Aloft by Marriott Chicago Mag Mile

13.8 mi from Gross Point

Jena

$102 nightly

Nov 22 - Nov 23

Total with taxes and fees

10. Arlo Chicago

14.2 mi from Gross Point

Daniel

$138 nightly

Nov 23 - Nov 24

Total with taxes and fees

A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

11. DoubleTree by Hilton Chicago - Magnificent Mile

13.8 mi from Gross Point

Poua

$103 nightly

Nov 23 - Nov 24

Total with taxes and fees

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

12. citizenM Chicago Downtown

14.1 mi from Gross Point

Katarina

$116 nightly

Nov 23 - Nov 24

Total with taxes and fees

A modern hotel lobby with a bar area, seating arrangements, and a television screen.

13. Cambria Hotel Chicago Loop - Theatre District

14.2 mi from Gross Point

Vansh

$111 nightly

Nov 23 - Nov 24

Total with taxes and fees

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

14. Moxy Chicago Downtown

13.6 mi from Gross Point

Justin

$122 nightly

Nov 23 - Nov 24

Total with taxes and fees

A modern hotel with a glass facade, multiple floors, and a visible entrance.

15. Hyatt Place Chicago/Downtown - The Loop

14.2 mi from Gross Point

Cordula

$118 nightly

Nov 23 - Nov 24

Total with taxes and fees

A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

16. Hyatt House Chicago/West Loop-Fulton Market

13.9 mi from Gross Point

Georgianna

$143 nightly

Nov 23 - Nov 24

Total with taxes and fees

An outdoor dining area with tables and umbrellas, overlooking a river with a bridge and high-rise buildings in the background.

17. Holiday Inn Chicago Dwtn - The Mart by IHG

13.8 mi from Gross Point

Pamela

$147 nightly

Nov 22 - Nov 23

Total with taxes and fees

A modern hotel lobby with a reception desk, marble flooring, and elegant chandeliers.

18. Silversmith Hotel Chicago Downtown

14.4 mi from Gross Point

William

$141 nightly

Nov 24 - Nov 25

Total with taxes and fees

A modern interior with a bar area, seating, and decorative wooden panels.

19. Best Western Grant Park Hotel

15.3 mi from Gross Point

Colin

$98 nightly

Nov 23 - Nov 24

Total with taxes and fees

A grand ballroom with a central dance floor, ornate ceiling, and chandeliers.

20. Millennium Hotel Knickerbocker Chicago

13.3 mi from Gross Point

Tracey

$110 nightly

Nov 25 - Nov 26

Total with taxes and fees

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Compare popular hotels in Gross Point

Property	Star rating	Guest rating
avid hotel Chicago O’Hare – Des Plaines by IHG	3.5 star property	9.4 Exceptional 1,882 reviews	View
Holiday Inn Chicago O'Hare – Rosemont by IHG	3.0 star property	9.0 Wonderful 3,208 reviews	View
Holiday Inn Express & Suites Chicago O'Hare Airport by IHG	3.0 star property	8.8 Excellent 2,070 reviews	View
Hyatt Regency Chicago	4.0 star property	9.4 Exceptional 3,506 reviews	View
L7 Chicago by LOTTE	4.5 star property	9.6 Exceptional 5,114 reviews	View

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 large, historic building with a central tower and multiple windows, located near a body of water.

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

The Wade

10/10 Excellent

"Great stay"

The Royal Sonesta Chicago Downtown

8/10 Good

"First the good: the location is great, right on the river and easily walkable to the Loop of the Magnificent Mile, etc. I arrived early and asked to check my bag, but my room was ready, which was nice. Somehow I got a fabulous upgrade to a comfortable spacious corner room on the 38th floor with the most spectacular views (views plural). When I returned later to rest before dinner, I couldn’t stop looking out the windows—what a show at sunset! The bed was very comfortable, although really really high off the ground. Everything seemed clean. Now the not-so-good: lighting was very sparse in the room—half the room had no lighting at all. No place to charge devices—hello, this is 2026. I had a little trouble with the temperature and there was no way to call downstairs—everything has to be handled in the app. So do stay here, but bring a charging station to plug into the wall—which is far from the bed."

Find hotels in Gross Point, Chicago

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Our top choices for Gross Point hotels

1. Heart O' Chicago

2. Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

3. Holiday Inn Chicago O'Hare – Rosemont by IHG

4. Claridge House Chicago, Tapestry Collection by Hilton

5. Carleton of Oak Park

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

7. ACME Hotel Chicago, Outset Collection by Hilton

8. The Whitehall Hotel, BW Premier Collection

9. Aloft by Marriott Chicago Mag Mile

10. Arlo Chicago

11. DoubleTree by Hilton Chicago - Magnificent Mile

12. citizenM Chicago Downtown

13. Cambria Hotel Chicago Loop - Theatre District

14. Moxy Chicago Downtown

15. Hyatt Place Chicago/Downtown - The Loop

16. Hyatt House Chicago/West Loop-Fulton Market

17. Holiday Inn Chicago Dwtn - The Mart by IHG

18. Silversmith Hotel Chicago Downtown

19. Best Western Grant Park Hotel

20. Millennium Hotel Knickerbocker Chicago

Compare popular hotels in Gross Point

Where to stay in Gross Point

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Gross Point Hotel Reviews

The Wade

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