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An airport with multiple runways, parked airplanes, and a large terminal building.

Hilton Hotels hotels in Southwest Side, Chicago

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Our top choices for Southwest Side Hilton Hotels

A spacious corridor with a patterned carpet, wooden panel walls, and a ceiling with a unique light fixture.

A buffet setup with various food items and serving utensils, illuminated by overhead lights.

A spacious hallway with a patterned carpet, wooden ceiling, and benches along the walls.

A bar area with a bar counter, multiple chairs, and a chandelier.

1. Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4.0 star property

O'Hare

8.6 out of 10, Excellent, (2,599 reviews)

8.6/10

Excellent

(2,599 reviews)

"Enjoyed our stay"

Cassandra L

The price is €195

€195

includes taxes & fees

12 Dec - 13 Dec

Hilton Chicago O'Hare Airport

A multi-story building with a prominent entrance featuring a large archway and a sign.

A spacious hotel lobby with a large seating area, a flat-screen TV, and a view of the ocean.

A spacious lobby with a grand piano, comfortable seating areas, and a fireplace.

A spacious lobby with a patterned carpet, seating area, and a fireplace.

2. Hilton Chicago

Hilton Chicago

4.0 star property

Downtown Chicago

8.6 out of 10, Excellent, (3,541 reviews)

8.6/10

Excellent

(3,541 reviews)

"Enjoyed my stay will book again!"

Jordan

The price is €172

€172

includes taxes & fees

22 Nov - 23 Nov

Hilton Chicago

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.

A golf course with multiple holes, water hazards, and sand bunkers.

A modern hotel room with a wooden floor, a dining area with a chandelier, a sofa, and a view of the outdoors.

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

Hilton Chicago/Oak Brook Hills Resort & Conference Center

4.0 star property

Oak Brook

9.0 out of 10, Wonderful, (1,001 reviews)

9.0/10

Wonderful

(1,001 reviews)

"excelent , convenient location, nice pool , healthy breakfast options"

Thomas

The price is €124

€124

includes taxes & fees

4 Dec - 5 Dec

Hilton Chicago/Oak Brook Hills Resort & Conference Center

A grand lobby with a staircase, ornate chandeliers, and a clock on the wall.

A grand lobby with ornate ceiling artwork, a bar area, and seating arrangements.

A grand lobby with ornate ceiling artwork, chandeliers, and a prominent 'P' emblem.

A banquet hall with round tables, chandeliers, and ornate wall decorations.

4. Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property

Downtown Chicago

8.6 out of 10, Excellent, (2,725 reviews)

8.6/10

Excellent

(2,725 reviews)

"Beautiful hotel with wonderful staff!"

Christy

The price is €166

€166

includes taxes & fees

24 Nov - 25 Nov

Palmer House a Hilton Hotel

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

A dining table set for a meal with a floral centerpiece, surrounded by chairs, in a room with a cityscape view.

A hotel room with a sofa, armchair, a flat-screen TV, a bed, and a view of the city and ocean.

A hotel room with a desk, chair, sofa, and armchair. There are two artworks on the wall, a TV mounted on the wall, and a window with curtains.

5. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 star property

Downtown Chicago

9.0 out of 10, Wonderful, (5,067 reviews)

9.0/10

Wonderful

(5,067 reviews)

"Great place to stay"

Melissa

The price is €111

€111

includes taxes & fees

10 Dec - 11 Dec

Hilton Chicago/Magnificent Mile Suites

A spacious hotel lobby with a central fountain, multiple seating areas, and a high ceiling with decorative woodwork.

A spacious lobby with a central fountain, multiple seating areas, and a high ceiling with natural light.

A grand chandelier with multiple candle-like lights and crystal decorations.

A hotel room with a large window offering a view of the sea, a sitting area with a sofa and armchairs, a dining table with chairs, and a chandelier.

6. The Drake

The Drake

4.0 star property

Downtown Chicago

9.0 out of 10, Wonderful, (1,662 reviews)

9.0/10

Wonderful

(1,662 reviews)

"Enjoyable stay"

Joseph

The price is €149

€149

includes taxes & fees

26 Nov - 27 Nov

The Drake

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.

A spacious indoor area with a high ceiling, large windows, and a central seating area with sofas and tables.

A spacious lobby with a large window, a central floral arrangement, and modern seating.

7. theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 star property

Downtown Chicago

9.0 out of 10, Wonderful, (1,163 reviews)

9.0/10

Wonderful

(1,163 reviews)

"Loved our stay, the staff were so helpful and nice!"

Charlotte

The price is €190

€190

includes taxes & fees

23 Nov - 24 Nov

theWit Chicago, a Hilton Hotel

A modern lobby with a fireplace, leather seating, and a green plant.

A spacious lobby with a high ceiling, large windows, and modern lighting fixtures.

A hotel entrance with a covered walkway, glass doors, and outdoor seating.

A grand ballroom with ornate chandeliers, elegant draped tables, and a luxurious carpet.

8. Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 star property

Rosemont

8.4 out of 10, Very good, (1,003 reviews)

8.4/10

Very good

(1,003 reviews)

"Nice stay"

Jossue

The price is €154

€154

includes taxes & fees

25 Nov - 26 Nov

Hilton Rosemont Chicago O'Hare

An outdoor dining area with wicker chairs and tables, overhead lighting, and a view of the street.

A modern hotel room with a round table, leather chairs, a sofa, and a large window.

A grand staircase with a wooden handrail and white balusters, leading to a landing with a chandelier.

A conference room with a large oval table, six chairs, and two potted plants.

9. Hilton Orrington / Evanston

Hilton Orrington / Evanston

4.0 star property

Downtown Evanston

8.6 out of 10, Excellent, (178 reviews)

8.6/10

Excellent

(178 reviews)

"We had a great stay at the Hilton Orrington Evanston! It’s an older hotel, but the location is fantastic, with great coffee and restaurants nearby. The staff was super friendly and even gave us a ride to the game! We really enjoyed our time here and would absolutely recommend it."

Michelle

The price is €116

€116

includes taxes & fees

15 Dec - 16 Dec

Hilton Orrington / Evanston

A modern bar area with a long counter, multiple bar stools, and a variety of bottles on shelves.

A tall, multi-story hotel with a prominent 'Hilton' sign at the entrance.

A spacious restaurant with high ceilings, large windows, and a variety of seating arrangements including tables and chairs.

A spacious lobby with a reception desk, seating area, and a modern chandelier.

10. Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

3.5 star property

Oak Lawn

8.4 out of 10, Very good, (1,436 reviews)

8.4/10

Very good

(1,436 reviews)

"Great hotel!"

Robert

The price is €127

€127

includes taxes & fees

22 Nov - 23 Nov

Hilton Chicago/Oak Lawn

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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Top Southwest Side Hotel Reviews

A hot tub with a metal ladder, surrounded by white tiled walls and floor, with a large window providing a view of the cityscape.

A modern hotel entrance with glass doors, a visible reception desk, and signage for Hilton Garden Inn and Homewood Suites.

A hotel room with two beds, a desk, a chair, and a large window offering a city view.

A modern outdoor patio with tables and chairs, a glass railing, and a view of a high-rise building.

Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

10/10 Excellent

Good location, perfect for the marathon stat & finish. Good rooms, beds, showers and gym / pool. Would have no hesitation in recommending this hotel.

Justin

Reviewed October 13, 2025Reviewed October 13, 2025

Hilton Garden Inn Chicago Downtown South Loop

A modern restaurant interior with a bar area, seating, and a wooden table.

A modern interior with a dining area, sofas, and artwork on the walls.

A modern hotel room with two beds, a cityscape mural, a nightstand, and a lamp.

A person sitting on a blue couch with a dog beside them, holding a glass of wine, and a pizza on a wooden board on a table.

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

10/10 Excellent

Incredibly friendly staff in the hotel, so helpful too. Hotel is in a great location, walkable to all the downtown attractions and Navy Pier. Would highly recommend the St Clair.

Adrienne

Reviewed September 18, 2024Reviewed September 18, 2024

Hotel Saint Clair- Magnificent Mile

A multi-story hotel with a prominent sign reading "Crowne Plaza."

A spacious lobby with a seating area, a reception desk, and a large screen.

A hotel room with a sofa, a small table with a bottle and glasses, a bed with a white comforter, and a view of the city through a window with curtains.

A modern lobby with seating arrangements, a reception desk, and a bar area.

Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

10/10 Excellent

great

Trpimir

Reviewed October 2, 2025Reviewed October 2, 2025

Crowne Plaza Chicago West Loop by IHG

A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

Transparent igloo-like structures with seating inside, set on a wooden deck with snow on the ground, surrounded by tall buildings.

A modern hotel lobby with a central seating area, a staircase, and a wall with a vertical garden.

A modern lobby with a seating area, a bar, and a green wall.

DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

8/10 Good

Good location, but.. an old hotel where rooms look old, tired and untidy. Very load air conditioning that makes it impossible to conduct normal conversation. Terrible staff unable to issue an invoice for the stay for an international traveller. The automatic parking that was unprepared for user with mobile from a different country. But the location was good.

Slawomir

Reviewed May 24, 2026Reviewed May 24, 2026

DoubleTree by Hilton Chicago - Magnificent Mile

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Hilton Hotels hotels in Southwest Side, Chicago

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Southwest Side Hilton Hotels

1. Hilton Chicago O'Hare Airport

2. Hilton Chicago

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

4. Palmer House a Hilton Hotel

5. Hilton Chicago/Magnificent Mile Suites

6. The Drake

7. theWit Chicago, a Hilton Hotel

8. Hilton Rosemont Chicago O'Hare

9. Hilton Orrington / Evanston

10. Hilton Chicago/Oak Lawn

Top Southwest Side Hotel Reviews

Hilton Garden Inn Chicago Downtown South Loop

10/10 Excellent

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