A lush green valley with a winding road, steep mountains, and a misty atmosphere.

Hilton Hotels Hillside hotels

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Check prices for these dates

Tonight
5 Sept - 6 Sept
Tomorrow
6 Sept - 7 Sept
Next weekend
11 Sept - 13 Sept
In two weeks
18 Sept - 20 Sept

Our top choices for Hillside Hilton Hotels

A hotel room with a sofa, armchairs, a dining table, and a view of the city at night.
A bar area with a bar counter, multiple chairs, and a chandelier.
A restaurant with a central round table surrounded by chairs, a buffet counter with food and drinks, and a large window with a cityscape view.
A terrace with outdoor seating, a view of a control tower, and flags.

1. Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport
O'Hare
United States
marlo
HK$1,948
HK$2,287 total
includes taxes & fees
27 Sept - 28 Sept
Hilton Chicago O'Hare Airport
A large, historic building with a central courtyard surrounded by trees.
A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.
A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.
A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.

2. Hilton Chicago

Hilton Chicago
Downtown Chicago
United States
Lori
HK$1,560
HK$2,085 total
includes taxes & fees
7 Sept - 8 Sept
Hilton Chicago
A grand lobby with ornate ceiling artwork, chandeliers, and a central staircase.
A long dining table with chairs, overhead lighting, and a marble wall with a decorative ceiling.
An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.
A grand lobby with ornate ceiling artwork, chandeliers, and a prominent 'P' emblem.

3. Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
Downtown Chicago
United States
G.
HK$1,827
HK$2,405 total
includes taxes & fees
7 Sept - 8 Sept
Palmer House a Hilton Hotel
A spacious hotel lobby with a central fountain, elegant chandeliers, and a high ceiling with skylights.
A spacious living room with a view of the ocean, a chandelier, and a traditional red cabinet.
A luxurious lobby with a central fountain, seating areas, and a high ceiling with skylights.
A coastal cityscape with a beach, high-rise buildings, and lush greenery.

4. The Drake

The Drake
Downtown Chicago
United States
Katarzyna
HK$1,717
HK$2,042 total
includes taxes & fees
8 Sept - 9 Sept
The Drake
A spacious indoor area with a high ceiling, large windows, and a central seating area with sofas and tables.
A rooftop bar with seating areas, large windows, and a city view.
A modern lounge with a fireplace, comfortable seating, and large windows offering city views.
A bar area with a large TV screen, multiple shelves of bottles, and orange bar stools.

5. theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel
Downtown Chicago
United States
Samuel
HK$2,293
HK$2,956 total
includes taxes & fees
1 Oct - 2 Oct
theWit Chicago, a Hilton Hotel
A cityscape at dusk with high-rise buildings, including a Hilton hotel.
A hotel room with a sofa, armchair, a flat-screen TV, a bed, and a view of the city and ocean.
A dining table set for a meal with a floral centerpiece, surrounded by chairs, in a room with a cityscape view.
A modern hotel lobby with a central seating area, a reception desk, and a cityscape mural on the wall.

6. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
Canada
Jeremy
HK$1,245
HK$1,481 total
includes taxes & fees
8 Sept - 9 Sept
Hilton Chicago/Magnificent Mile Suites
A bar area with wooden tables and chairs, a counter with a coffee machine, and shelves with bottles.
A bar area with a long counter, multiple shelves of bottles, and a television screen. There are several chairs and tables arranged for dining.
A spacious lobby with a high ceiling, large windows, and modern lighting fixtures.
A grand ballroom with ornate chandeliers, elegant draped tables, and a luxurious carpet.

7. Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare
Rosemont
United States
Cecilia Oviedo
HK$1,215
HK$1,385 total
includes taxes & fees
6 Sept - 7 Sept
Hilton Rosemont Chicago O'Hare
A large hotel with a central courtyard, a lake, and a bridge.
A room with a large window, a bed, and a sofa.
A spacious, modern interior with large windows offering views of a golf course and a lake.
A golf course with a swimming pool, lounge area, and a pond.

8. Hilton Chicago/Oak Brook Hills Resort & Conference Center

Hilton Chicago/Oak Brook Hills Resort & Conference Center
Oak Brook
United States
chauncey
HK$1,054
HK$1,300 total
includes taxes & fees
7 Sept - 8 Sept
Hilton Chicago/Oak Brook Hills Resort & Conference Center
An outdoor dining area with wicker chairs and tables, overhead lighting, and a view of the street.
A grand staircase with white balusters, carpeted steps, and a piano in the background.
A Hilton hotel with a brick facade, large windows, and a modern glass extension.
A café interior with a menu board, wooden tables, chairs, and a brick wall.

9. Hilton Orrington / Evanston

Hilton Orrington / Evanston
Downtown Evanston
United States
Tara
HK$1,319
HK$1,510 total
includes taxes & fees
8 Sept - 9 Sept
Hilton Orrington / Evanston
A modern bar area with a long counter, multiple bar stools, and a variety of bottles on shelves.
A spacious indoor area with a long table, multiple chairs, a sofa, and several gaming machines.
A spacious lobby with a reception desk, seating area, and a modern chandelier.
An indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

10. Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn
Oak Lawn
United States
Samantha
HK$1,087
HK$1,250 total
includes taxes & fees
29 Sept - 30 Sept
Hilton Chicago/Oak Lawn
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Top Hillside Hotel Reviews

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Great hotel and a nice spot for everything you need, walked around and explored! 10/10 great experience!"
Seth 2-night trip
Posted 1 hour ago
Hyatt Regency Chicago
L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Great location. Clean and nice. Thanks!"
DENNIS 2-night trip
Posted 1 hour ago
L7 Chicago by LOTTE
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"The staff were amazing and helpful!"
Jake 1-night trip
Posted 2 hours ago
Fairmont Chicago at Millennium Park
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"close to everything, valet was helpful friendly and welcoming. easy to check in and out, great vibes on a stay night with dj in lobby"
melissa 1-night trip
Posted 2 hours ago
The Chicago Hotel Collection - Magnificent Mile
Warwick Allerton - Chicago

Warwick Allerton - Chicago

10/10 Excellent
"Room, especially the bathroom was clean. It has the basic needs a guest could ask for. Worth the price."
Sharon 3-night trip
Posted 3 hours ago
Warwick Allerton - Chicago
The Wade

The Wade

10/10 Excellent
"Great hotel"
Allison 2-night trip
Posted 4 hours ago
The Wade
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

8/10 Good
"Clean hotel, very close and convenient to the CTA train."
Lindsey 2-night trip
Posted 5 hours ago
The Allegro Royal Sonesta Hotel Chicago Loop
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

8/10 Good
"Me and wife stay 3 nights is Hampton Inn from Aug 31 to Sept3 2026.It is 40 stories hotel. The hotel location is excellent, beautiful in Chicago, very close to Michgan Ave Magnificent Mile, the most beautiful area, high rise buildings and shopping stores. Close to Lake, close to chicago River side, close to Millennium park. Breakfast was ok, not high level, just so, so, Baggage in and out room service was not available when we reached we took our own bags to room. No swimming pool was available. Close to hospital block, .For food Asian food Indian restaurant available on walking distance. I recommend this hotel to tourists coming for Chicago buildings, and other attractions. Mahboob Mian Canada."
Mahboob 3-night trip
Posted 21 hours ago
Hampton Inn Chicago Downtown/Magnificent Mile
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

10/10 Excellent
"We thoroughly enjoyed our stay at Kasa- check in instructions were clear and hassle free. The unit was spacious and clean, with a terrific view. Highly recommended!"
James 3-night trip
Posted 2 days ago
Kasa Magnificent Mile Chicago

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