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Hotels in Jackson Park Highlands, Chicago

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Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11

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Our top choices for Jackson Park Highlands hotels

A large, historic building with a central courtyard surrounded by trees.

1. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 12 km from Jackson Park Highlands
8.6 out of 10, Excellent, (3,277 reviews)
"Great stay!"
United States
Alan
The price is CA $227
CA $312 total
includes taxes & fees
Oct 24 - Oct 25
Hilton Chicago
A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

2. The Wade

The Wade
4.5 star property
Streeterville, 14.1 km from Jackson Park Highlands
8.6 out of 10, Excellent, (2,101 reviews)
"Great stay"
United States
Fernanda
The price is CA $211
CA $251 total
includes taxes & fees
Sep 27 - Sep 28
The Wade
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

3. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 12.3 km from Jackson Park Highlands
8.0 out of 10, Very good, (10,224 reviews)
"Easy check in, rooms were clean, convenient location."
United States
John
The price is CA $227
CA $270 total
includes taxes & fees
Oct 26 - Oct 27
Congress Plaza Hotel
A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.

4. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 12.2 km from Jackson Park Highlands
7.8 out of 10, Good, (2,861 reviews)
"Great stay will be returning"
United States
Tremecka
The price is CA $216
CA $257 total
includes taxes & fees
Oct 25 - Oct 26
Travelodge by Wyndham Downtown Chicago
A spacious lobby with a central coffee table, sofas, and a large mirror.

5. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 15.7 km from Jackson Park Highlands
8.0 out of 10, Very good, (2,350 reviews)
"Loved my stay the staff was nice and the location was great."
United States
Marta
The price is CA $253
CA $301 total
includes taxes & fees
Oct 25 - Oct 26
The Chicago Hotel Collection Ambassador Gold Coast
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

6. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 11.7 km from Jackson Park Highlands
8.8 out of 10, Excellent, (2,159 reviews)
"Great place to stay at"
United States
Aran
The price is CA $264
CA $314 total
includes taxes & fees
Oct 25 - Oct 26
Hilton Garden Inn Chicago Downtown South Loop
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

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 13.7 km from Jackson Park Highlands
9.4 out of 10, Exceptional, (2,713 reviews)
"Amazing place to stay"
United States
Shanequa
The price is CA $448
CA $582 total
includes taxes & fees
Oct 23 - Oct 24
Sable at Navy Pier Chicago, Curio Collection by Hilton
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

8. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Theatre District, 12.9 km from Jackson Park Highlands
8.8 out of 10, Excellent, (3,669 reviews)
"Great location"
United States
Julian
The price is CA $206
CA $245 total
includes taxes & fees
Oct 25 - Oct 26
Club Quarters Hotel, Central Loop, Chicago
An outdoor seating area with wicker chairs, a glass-top table, and a sofa with cushions.

9. Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
4.0 star property
Theatre District, 13.1 km from Jackson Park Highlands
9.0 out of 10, Wonderful, (2,783 reviews)
"Great Stay"
United States
Lavaniel
The price is CA $271
CA $358 total
includes taxes & fees
Sep 27 - Sep 28
Hyatt Centric The Loop Chicago
A multi-story hotel with a prominent sign reading "Crowne Plaza."

10. Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG
3.5 star property
13.6 km from Jackson Park Highlands
9.0 out of 10, Wonderful, (2,670 reviews)
"It is a great location with nice rooms"
United States
Phillip
The price is CA $239
CA $284 total
includes taxes & fees
Sep 27 - Sep 28
Crowne Plaza Chicago West Loop by IHG
A cityscape at dusk with high-rise buildings, including a Hilton hotel.

11. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Streeterville, 14.9 km from Jackson Park Highlands
9.0 out of 10, Wonderful, (4,968 reviews)
"Very nice hotel, friendly staff, good location"
United States
Brian
The price is CA $246
CA $293 total
includes taxes & fees
Oct 25 - Oct 26
Hilton Chicago/Magnificent Mile Suites
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.

12. Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Streeterville, 14.2 km from Jackson Park Highlands
8.6 out of 10, Excellent, (3,346 reviews)
"I really liked the location of the hotel."
United States
Carmina
The price is CA $256
CA $304 total
includes taxes & fees
Sep 27 - Sep 28
Aloft by Marriott Chicago Mag Mile
A spacious lobby with a checkered floor, a large sofa, and multiple chairs.

13. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Streeterville, 14.2 km from Jackson Park Highlands
9.0 out of 10, Wonderful, (1,017 reviews)
"I was happy with my stay"
United States
Lora J
The price is CA $253
CA $301 total
includes taxes & fees
Sep 27 - Sep 28
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
A modern kitchen with a large window, a dining area, and a view of the sea.

14. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
The Loop, 11.7 km from Jackson Park Highlands
8.8 out of 10, Excellent, (2,480 reviews)
"Great overall stay within walking distance of so much."
United States
Cecilia
The price is CA $296
CA $352 total
includes taxes & fees
Oct 25 - Oct 26
Homewood Suites by Hilton Chicago Downtown South Loop
A hotel room with a large bed, two armchairs, a desk, and a view of a cityscape through large windows.

15. The Buckingham Hotel

The Buckingham Hotel
3.5 star property
The Loop, 12.6 km from Jackson Park Highlands
9.0 out of 10, Wonderful, (1,002 reviews)
"Beautiful hotel"
United States
Ibrahim
The price is CA $218
CA $276 total
includes taxes & fees
Sep 27 - Sep 28
The Buckingham Hotel
A cozy room with a sofa, a dining table, and a window with a view of buildings.

16. LIVN - West Loop Chicago

LIVN - West Loop Chicago
4.0 star property
13.1 km from Jackson Park Highlands
9.2 out of 10, Wonderful, (292 reviews)
"It was a very nice place to stay"
Canada
chidubem
The price is CA $242
CA $284 total
includes taxes & fees
Sep 27 - Sep 28
LIVN - West Loop Chicago
A modern hotel room with a sofa, armchairs, a coffee table, a flat-screen TV, and a patterned wall.

17. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
The Loop, 12.4 km from Jackson Park Highlands
9.6 out of 10, Exceptional, (1,244 reviews)
"The room was clean and the building was nostalgic."
United States
John
The price is CA $447
CA $531 total
includes taxes & fees
Oct 14 - Oct 15
Hilton Vacation Club Hotel Blake Chicago
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

18. Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 12.9 km from Jackson Park Highlands
8.6 out of 10, Excellent, (2,303 reviews)
"Great stay overall"
United States
Nathan
The price is CA $206
CA $245 total
includes taxes & fees
Oct 25 - Oct 26
Central Loop Hotel
A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.

19. Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
The Loop, 11.9 km from Jackson Park Highlands
9.0 out of 10, Wonderful, (1,001 reviews)
"This hotel was perfect. Room was a great size, clean, very friendly staff. Perfect for our work trip!"
United States
amanda
The price is CA $324
CA $410 total
includes taxes & fees
Sep 27 - Sep 28
Le Méridien Essex Chicago
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

20. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 14.1 km from Jackson Park Highlands
8.8 out of 10, Excellent, (2,578 reviews)
"Great location!"
United States
Madelyn
The price is CA $275
CA $327 total
includes taxes & fees
Oct 25 - Oct 26
DoubleTree by Hilton Chicago - Magnificent Mile
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.
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Where to stay in Jackson Park Highlands

Find the best Jackson Park Highlands areas and neighborhoods for the activities you enjoy most.
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

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.
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.
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.
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.

Top Jackson Park Highlands Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Clean room and easy check in"
Carly 1-night trip
Posted less than an hour ago
The Chicago Hotel Collection Ambassador Gold Coast

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?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Jackson Park Highlands hotel for you.
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 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.

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