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11 Nov - 12 Nov
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12 Nov - 13 Nov
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13 Nov - 15 Nov
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Our top choices for Jackson Park Highlands hotels

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

1. Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 7.3 mi from Jackson Park Highlands
8.2 out of 10, Very good, (2,746 reviews)
"Room was dated but clean, staff was friendly, location was perfect for my needs"
United States
Michelle
The price is £76
includes taxes & fees
8 Dec - 9 Dec
Best Western Grant Park Hotel
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

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

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 8.5 mi from Jackson Park Highlands
9.4 out of 10, Exceptional, (2,783 reviews)
"Best stay, wonderful property."
Canada
Bonnie
The price is £142
includes taxes & fees
23 Nov - 24 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
Exterior

3. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
The Loop, 7.7 mi from Jackson Park Highlands
9.6 out of 10, Exceptional, (1,207 reviews)
"Great location from both airports. Lovely hotel clean and convenient"
United Kingdom
Kanokkan
The price is £99
includes taxes & fees
10 Dec - 11 Dec
Hilton Vacation Club Hotel Blake Chicago
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

4. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 7.3 mi from Jackson Park Highlands
8.8 out of 10, Excellent, (2,202 reviews)
"Great place to stay at"
United States
Aran
The price is £85
includes taxes & fees
24 Nov - 25 Nov
Hilton Garden Inn Chicago Downtown South Loop
A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.

5. Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
The Loop, 7.4 mi from Jackson Park Highlands
9.0 out of 10, Wonderful, (1,000 reviews)
"Fantastic location and facility. Comfortable bed and nice shower! Perfect hotel for the Bears Game!"
United States
Taso
The price is £112
includes taxes & fees
8 Dec - 9 Dec
Le Méridien Essex Chicago
A bar area with a checkered floor, bar stools, and a well-lit sign above the bar.

6. ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
River North, 8.8 mi from Jackson Park Highlands
9.0 out of 10, Wonderful, (1,963 reviews)
"Hotel is great for the price."
United States
alex
The price is £76
includes taxes & fees
7 Dec - 8 Dec
ACME Hotel Chicago, Outset Collection by Hilton
A modern kitchen with a large window, a dining area, and a view of the sea.

7. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
The Loop, 7.3 mi from Jackson Park Highlands
8.8 out of 10, Excellent, (2,532 reviews)
"Wonderful room and great breakfast buffet!"
United States
Nicole
The price is £93
includes taxes & fees
23 Nov - 24 Nov
Homewood Suites by Hilton Chicago Downtown South Loop
A modern rooftop lounge with white seating, a glass ceiling, and city views.

8. The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
River North, 9.1 mi from Jackson Park Highlands
8.8 out of 10, Excellent, (2,609 reviews)
"Had a great stay , view was beautiful and bed was super comfortable."
United States
Tamiya
The price is £96
includes taxes & fees
6 Dec - 7 Dec
The Godfrey Hotel Chicago
A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

9. Hyatt House Chicago/West Loop-Fulton Market

Hyatt House Chicago/West Loop-Fulton Market
3.5 star property
8.8 mi from Jackson Park Highlands
9.0 out of 10, Wonderful, (1,316 reviews)
"Loved the continental breakfast and how close different bars and restaurants were at :)"
United States
Carole
The price is £112
includes taxes & fees
25 Nov - 26 Nov
Hyatt House Chicago/West Loop-Fulton Market
A bar area with a long counter, bar stools, and a mirrored wall.

10. The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 9.2 mi from Jackson Park Highlands
8.4 out of 10, Very good, (3,952 reviews)
"Friendly staff and great location"
United States
Alexis
The price is £72
includes taxes & fees
8 Dec - 9 Dec
The Whitehall Hotel, BW Premier Collection
The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.

11. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
9.7 mi from Jackson Park Highlands
9.0 out of 10, Wonderful, (1,436 reviews)
"Staff was super kind,"
United States
Cloey
The price is £101
includes taxes & fees
22 Nov - 23 Nov
Claridge House Chicago, Tapestry Collection by Hilton
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

12. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 8.8 mi from Jackson Park Highlands
8.8 out of 10, Excellent, (2,584 reviews)
"Great location and beautiful hotel!"
United States
Jodi
The price is £86
includes taxes & fees
8 Dec - 9 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
A couple sitting on a blue couch with a table in front of them, holding drinks and a pizza.

13. Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
4.0 star property
Streeterville, 8.8 mi from Jackson Park Highlands
8.6 out of 10, Excellent, (2,405 reviews)
"Great location and friendly staff."
United States
Grace
The price is £70
includes taxes & fees
9 Dec - 10 Dec
Hotel Saint Clair- Magnificent Mile
A multi-story building with a prominent entrance featuring a large archway and a sign.

14. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 7.5 mi from Jackson Park Highlands
8.6 out of 10, Excellent, (3,536 reviews)
"Enjoyed my stay will book again!"
United States
Jordan
The price is £143
includes taxes & fees
26 Nov - 27 Nov
Hilton Chicago
A cozy room with a sofa, a dining table, and a window with a view of buildings.

15. LIVN - West Loop Chicago

LIVN - West Loop Chicago
4.0 star property
8.1 mi from Jackson Park Highlands
9.2 out of 10, Wonderful, (413 reviews)
"It was a fantastic stay!"
United States
Elzbieta
The price is £108
includes taxes & fees
12 Nov - 13 Nov
LIVN - West Loop Chicago
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

16. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 7.6 mi from Jackson Park Highlands
8.0 out of 10, Very good, (10,176 reviews)
"Rooms were excellent, staff was helpful, and this short trip was easier to manage this close to our destination."
United States
Skylar
The price is £103
includes taxes & fees
23 Nov - 24 Nov
Congress Plaza Hotel
A dining table set for six with a cityscape view through large windows.

17. Swissotel - Chicago

Swissotel - Chicago
4.5 star property
8.4 mi from Jackson Park Highlands
9.0 out of 10, Wonderful, (3,580 reviews)
"Great hotel"
United States
Daniel Michael
The price is £142
includes taxes & fees
26 Nov - 27 Nov
Swissotel - Chicago
A snack bar with various packaged snacks and beverages.

18. Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District
4.0 star property
Theatre District, 8.3 mi from Jackson Park Highlands
8.8 out of 10, Excellent, (1,717 reviews)
"Great location, friendly staff, convenient parking"
United States
Lisa
The price is £95
includes taxes & fees
23 Nov - 24 Nov
Cambria Hotel Chicago Loop - Theatre District
A hotel lobby with a bar area, seating, and a large window.

19. Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop
3.0 star property
The Loop, 8 mi from Jackson Park Highlands
9.2 out of 10, Wonderful, (1,443 reviews)
"Will definitely stay again!!"
United States
Jasmine
The price is £113
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Chicago Central Loop
A hotel bathroom with a large mirror, a sink, and a vanity.

20. Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
3.5 star property
Theatre District, 8.4 mi from Jackson Park Highlands
9.0 out of 10, Wonderful, (1,564 reviews)
"Great resort and clean.. very good location"
United States
Christopher
The price is £129
includes taxes & fees
23 Nov - 24 Nov
Sports Illustrated Resorts Chicago
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.
View all properties

Compare popular hotels in Jackson Park Highlands

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
9.4
Exceptional
2,783 reviews
View
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
8.8
Excellent
2,202 reviews
View
A modern kitchen with a large window, a dining area, and a view of the sea.
Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
8.8
Excellent
2,532 reviews
View
A multi-story building with a prominent entrance featuring a large archway and a sign.
Hilton Chicago
4.0 star property
8.6
Excellent
3,536 reviews
View
A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.
Le Méridien Essex Chicago
4.0 star property
9.0
Wonderful
1,000 reviews
View

Where to stay in Jackson Park Highlands

Find the best Jackson Park Highlands areas for the activities you enjoy most. Learn more about Jackson Park Highlands
Learn more about Jackson Park Highlands
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.

A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.
Photo by © City of Chicago
Open Photo by © City of Chicago

Magnificent Mile

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

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

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

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

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Top Jackson Park Highlands Hotel Reviews

Exterior
Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago

10/10 Excellent

Great location from both airports. Lovely hotel clean and convenient
United Kingdom
Kanokkan
Reviewed October 31, 2026
Hilton Vacation Club Hotel Blake Chicago

Frequently Asked Questions

When is the best time to go to Jackson Park Highlands?

Jackson Park Highlands isn't typically considered a tourist destination; it's a residential neighbourhood. Therefore, the "best time to go" isn't really applicable in the same way it would be for a holiday spot.

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 Jackson Park Highlands.

How much is the nightly rate at a Jackson Park Highlands hotel?

Hotel prices in Jackson Park Highlands often vary, but you can find a great deal from £75 on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.