Default HTG hotel image

Hotels in Jackson Park Highlands, Chicago

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Filter by

Star rating

Guest rating

Selecting then applying a filter from this group will update the results on a new page

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, (3,283 reviews)
"Great stay!"
United States
Alan
The price is CA $227
CA $312 total
includes taxes & fees
Oct 24 - Oct 25
Hilton Chicago
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

2. 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, (10,240 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 person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

3. The Wade

The Wade
4.5 star property
Streeterville, 14.1 km from Jackson Park Highlands
8.6 out of 10, Excellent, (2,104 reviews)
"Great stay"
United States
Fernanda
The price is CA $211
CA $251 total
includes taxes & fees
Oct 25 - Oct 26
The Wade
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, (2,865 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
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

5. 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, (2,162 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
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

6. 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, (3,670 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
A spacious lobby with a central coffee table, sofas, and a large mirror.

7. 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, (2,357 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 14 - Oct 15
The Chicago Hotel Collection Ambassador Gold Coast
A cozy room with a sofa, a dining table, and a window with a view of buildings.

8. LIVN - West Loop Chicago

LIVN - West Loop Chicago
4.0 star property
13.1 km from Jackson Park Highlands
9.4 out of 10, Exceptional, (294 reviews)
"It was a very nice place to stay"
Canada
chidubem
The price is CA $238
CA $279 total
includes taxes & fees
Sep 29 - Sep 30
LIVN - West Loop Chicago
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

9. 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, (2,717 reviews)
"Amazing place to stay"
United States
Shanequa
The price is CA $450
CA $583 total
includes taxes & fees
Oct 22 - Oct 23
Sable at Navy Pier Chicago, Curio Collection by Hilton
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, (2,673 reviews)
"Great stay, close to great food and ambiance in West Loop."
United States
Victoria
The price is CA $248
CA $294 total
includes taxes & fees
Oct 25 - Oct 26
Crowne Plaza Chicago West Loop by IHG
A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

11. Carleton of Oak Park

Carleton of Oak Park
3.0 star property
22.6 km from Jackson Park Highlands
9.2 out of 10, Wonderful, (1,169 reviews)
"Rooms were clean and the staff was amazing!"
United States
Suzanne
The price is CA $158
CA $175 total
includes taxes & fees
Oct 6 - Oct 7
Carleton of Oak Park
A modern kitchen with a large window, a dining area, and a view of the sea.

12. 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, (2,482 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 grand lobby with a central bar, high ceilings, and classical architecture.

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

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
4.0 star property
Theatre District, 13 km from Jackson Park Highlands
8.6 out of 10, Excellent, (1,007 reviews)
"The hotel was absolutely stunning! Loved the convenience of it being right down town!"
United States
Amanda
The price is CA $281
CA $335 total
includes taxes & fees
Oct 4 - Oct 5
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
A cityscape at dusk with high-rise buildings, including a Hilton hotel.

14. 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, (4,969 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 hotel lobby with a reception desk, marble flooring, and elegant chandeliers.

15. Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 13.1 km from Jackson Park Highlands
9.2 out of 10, Wonderful, (2,408 reviews)
"We enjoyed our stay; everything was nearby to walk. Staff was great super nice and we felt so welcomed."
United States
Carmen
The price is CA $280
CA $376 total
includes taxes & fees
Oct 25 - Oct 26
Silversmith Hotel Chicago Downtown
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

16. 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, (2,305 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 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 hotel entrance with a glass door, a sign above the door, and two potted plants on either side.

18. Hampton Inn Majestic Chicago Theatre District

Hampton Inn Majestic Chicago Theatre District
3.0 star property
Theatre District, 13 km from Jackson Park Highlands
9.2 out of 10, Wonderful, (1,001 reviews)
"I loved the location, the breakfast, the comfortable bed and the proximity of public transportation."
United States
Jacqueline
The price is CA $290
CA $345 total
includes taxes & fees
Oct 25 - Oct 26
Hampton Inn Majestic Chicago Theatre District
A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

19. River Hotel

River Hotel
4.0 star property
The Loop, 13.7 km from Jackson Park Highlands
8.8 out of 10, Excellent, (5,447 reviews)
"Great place to travel!"
United States
Jared
The price is CA $263
CA $313 total
includes taxes & fees
Oct 25 - Oct 26
River Hotel
A modern building with a colorful facade and a red circular seating area.

20. citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 13.6 km from Jackson Park Highlands
9.4 out of 10, Exceptional, (4,361 reviews)
"Great location and friendly staff"
United States
Kimberly
The price is CA $291
CA $346 total
includes taxes & fees
Oct 25 - Oct 26
citizenM Chicago Downtown
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

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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"It was clean, location was fantastic, close walk to some of the sights we wanted to see & the lakeshore. Didn’t have any issues with safety. Service at the restaurant they have there was extremely slow. We would stay at the hotel again."
Brandi 3-night trip
Posted 2 hours ago
Congress Plaza Hotel

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.

Explore a world of travel with Expedia