All Hotels by Hilton Hotels in Southwest Side - 2026 Updated Prices

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Our top choices for Southwest Side Hilton Hotels

A modern reception area with a check-in counter, seating, and a decorative wall.

1. Hilton Chicago O'Hare Airport

O'Hare

Cassandra L

₹22,645 total

includes taxes & fees

27 Nov - 28 Nov

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

2. Hilton Chicago

Downtown Chicago

carol

₹14,974 total

includes taxes & fees

27 Nov - 28 Nov

A large hotel with a central courtyard, a lake, and a bridge.

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

Oak Brook

Thomas

₹13,587 total

includes taxes & fees

28 Nov - 29 Nov

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

4. Palmer House a Hilton Hotel

Downtown Chicago

Christy

₹17,888 total

includes taxes & fees

24 Nov - 25 Nov

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

5. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Melissa

₹13,338 total

includes taxes & fees

22 Nov - 23 Nov

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

6. The Drake

Downtown Chicago

stephanie

₹15,645 total

includes taxes & fees

22 Nov - 23 Nov

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

7. theWit Chicago, a Hilton Hotel

Downtown Chicago

Joshua R

₹19,963 total

includes taxes & fees

22 Nov - 23 Nov

A bar area with wooden tables and chairs, a counter with a coffee machine, and shelves with bottles.

8. Hilton Rosemont Chicago O'Hare

Rosemont

MELISSA

₹13,961 total

includes taxes & fees

27 Nov - 28 Nov

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

9. Hilton Orrington / Evanston

Downtown Evanston

Jinho

₹12,148 total

includes taxes & fees

2 Dec - 3 Dec

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

10. Hilton Chicago/Oak Lawn

Oak Lawn

Michele

₹13,340 total

includes taxes & fees

15 Nov - 16 Nov

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Top Southwest Side Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

8/10 Good

"The staff at the concierge were very knowledgeable and helpful day 1 until 4, On my second night, oct 29th, except for the lady staff who was in the lobby bar, she was not accommodating and just giving us a negative answer when we are asking if there if coffee is included in the drinks voucher, she did not even us told us that there was Keurig coffee maker an the right side corner, she is the only one that"

L7 Chicago by LOTTE

10/10 Excellent

"Best hotel sleep in years, which is wild given the central location in a busy city. In-room amenities like the steamer, robe, kettle and yoga mat really elevated my stay. No onsite food except that expensive restaurant downstairs, but there’s an amazing pub literally across the street that’s huge, reasonable and open late. Free coffee in lobby was nice too. Only drawback was the lack of a desk chair in the room. There was a lounger and a table but trying to work from it for more than a few hours was a little rough in my back. I’d definitely stay again."

Arlo Chicago

10/10 Excellent

"Arlo Chicago was perfect! If you are in a wheelchair, the ADA King room was fully accessible with a low sitting bed, walk-in shower, open sinks, and enough space to get around room. It was quiet with electric blinds making it easy to open/close. The location is within walking distance of just about anything, or a bus stop and train station right out front or a block down to access train. The famous Bean site was a 2 minute walk, the Riverwalk about 5 minutes, and so much more. The parking was so easy. You pull right at back door & unload, and the parking garage is literally at the end of that alley. That was my biggest concern being my first overnight stay in a wheelchair where I must transfer in/out my chair. There is a bar and restaurant inside the hotel, drinks (for a fee) already in the room, a refrigerator, alcohol, water, soda, coffee machine, toiletries, robes, etc. The view was awesome. Thank you for the amazing staff who were so kind & helpful...especially Terell who was more than accommodating in helping us register with parking garage online. The room was clean, common areas welcoming, and I will only stay at this location in the future. My only criticism is that the ADA room had a heavy door and was a sharp right angle to enter, which could potentially be an issue for an electric wheelchair user if they were traveling alone...but the staff would have helped. Be prepared financially, but our room was worth the rate & reasonable for all the amenities."

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Room 1

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

The Chicago Hotel Collection - Magnificent Mile

L7 Chicago by LOTTE

Arlo Chicago

LondonHouse Chicago, Curio Collection by Hilton

The Wade

Congress Plaza Hotel

Fairmont Chicago at Millennium Park

Hotel Saint Clair- Magnificent Mile

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Search Hotels by Hilton Hotels in Southwest Side from ₹12,148

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

The Chicago Hotel Collection - Magnificent Mile

Explore a world of travel with Expedia