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

$117 nightly

Oct 20 - Oct 21

Total with taxes and fees

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

2. Hyatt Regency O'Hare Chicago

9.8 mi from Gross Point

Christian

$161 nightly

Oct 23 - Oct 24

Total with taxes and fees

A hotel room with a bed, a microwave, a refrigerator, and a coffee machine.

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

10 mi from Gross Point

Arlene

$131 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

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

10 mi from Gross Point

Crystal

$133 nightly

Nov 1 - Nov 2

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

$112 nightly

Oct 21 - Oct 22

Total with taxes and fees

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

6. Claridge House Chicago, Tapestry Collection by Hilton

12.8 mi from Gross Point

Scott

$143 nightly

Nov 9 - Nov 10

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.

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

14.2 mi from Gross Point

Shanequa

$218 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

8. The Chicago Hotel Collection Ambassador Gold Coast

12.8 mi from Gross Point

Christian

$143 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

9. The Whitehall Hotel, BW Premier Collection

13.3 mi from Gross Point

KURT

$143 nightly

Nov 2 - Nov 3

Total with taxes and fees

A bar area with a checkered floor, leather seating, and a bar counter with a visible liquor selection.

10. ACME Hotel Chicago, Outset Collection by Hilton

13.7 mi from Gross Point

alex

$118 nightly

Nov 1 - Nov 2

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

$130 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

12. Congress Plaza Hotel

14.9 mi from Gross Point

Ashya

$108 nightly

Nov 11 - Nov 12

Total with taxes and fees

A grand lobby with a chandelier, plush seating, and a patterned carpet.

13. The Drake

13.3 mi from Gross Point

Carrie

$167 nightly

Nov 12 - Nov 13

Total with taxes and fees

A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.

14. Hilton Vacation Club Hotel Blake Chicago

14.8 mi from Gross Point

Mario

$172 nightly

Nov 3 - Nov 4

Total with taxes and fees

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

15. Best Western Grant Park Hotel

15.3 mi from Gross Point

Colin

$107 nightly

Nov 10 - Nov 11

Total with taxes and fees

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

16. L7 Chicago by LOTTE

14.1 mi from Gross Point

Jeffrey Thomas

$187 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

17. Millennium Hotel Knickerbocker Chicago

13.3 mi from Gross Point

Tracey

$147 nightly

Nov 15 - Nov 16

Total with taxes and fees

A compact hotel room with bunk beds, a dining table with yellow chairs, a black leather sofa, and a potted plant.

18. The Chicago Hotel Collection River North

13.2 mi from Gross Point

israel Xavier

$112 nightly

Nov 1 - Nov 2

Total with taxes and fees

An indoor swimming pool with a glass ceiling, multiple seating areas, and city views.

19. Hilton Garden Inn Chicago Downtown/Magnificent Mile

13.7 mi from Gross Point

Hakeim

$144 nightly

Nov 1 - Nov 2

Total with taxes and fees

A modern rooftop lounge with white seating, a glass ceiling, and city views.

20. The Godfrey Hotel Chicago

13.5 mi from Gross Point

Jo

$147 nightly

Nov 12 - Nov 13

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 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

Hyatt Regency Chicago

10/10 Excellent

"."

Congress Plaza Hotel

10/10 Excellent

"We stayed at the Congress for a Bears game. We selected it based on price and proximity to Soldier Field. The price was incredibly reasonable, so I was a bit concerned about the quality and cleanliness of the room and hotel prior to checking in. We were more than pleased with our room and the hotel overall and feel it was great value for our money. The room was very clean and had been updated quite recently. It was roomie in both the room itself and the bathroom. We also appreciated the amenities in the room, including a coffee maker, refrigerator, a large, walk-in closet, plenty of drawer storage for clothes and extra seating and table. It is also near do much in the city, so it’s a great place to stay. The only issue that I had is I wish the TV had been a bit larger. But other than that, I would highly recommend the Congress."

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good

"The hotel is in a great location. The room was decent and so was the breakfast. We were entitled to vouchers for breakfast, cocktails and dinner as well as water bottles. At check-in, it would have been nice to be told that and get those vouchers. We had to ask for them the next day after reading a message received from the hotel. It would be nice also at check-in to let us know that housekeeping is every other day. Overall we still had a good stay."

Find hotels in Gross Point, Chicago

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Our top choices for Gross Point hotels

1. Heart O' Chicago

2. Hyatt Regency O'Hare Chicago

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

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

5. Carleton of Oak Park

6. Claridge House Chicago, Tapestry Collection by Hilton

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

8. The Chicago Hotel Collection Ambassador Gold Coast

9. The Whitehall Hotel, BW Premier Collection

10. ACME Hotel Chicago, Outset Collection by Hilton

11. DoubleTree by Hilton Chicago - Magnificent Mile

12. Congress Plaza Hotel

13. The Drake

14. Hilton Vacation Club Hotel Blake Chicago

15. Best Western Grant Park Hotel

16. L7 Chicago by LOTTE

17. Millennium Hotel Knickerbocker Chicago

18. The Chicago Hotel Collection River North

19. Hilton Garden Inn Chicago Downtown/Magnificent Mile

20. The Godfrey Hotel Chicago

Where to stay in Gross Point

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Gross Point Hotel Reviews

Hyatt Regency Chicago

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