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

Change your mind
Book hotels with free cancellation
Treat yourself
Save instantly and earn perks with One Key
Learn about One Key
Be picky
Search almost a million properties worldwide

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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

includes taxes & fees

27 Nov - 28 Nov

A grand hotel lobby with a central staircase, ornate columns, and a decorative ceiling.

2. Hilton Chicago

Downtown Chicago

carol

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

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

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

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

includes taxes & fees

22 Nov - 23 Nov

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

7. theWit Chicago, a Hilton Hotel

Downtown Chicago

Joshua R

includes taxes & fees

22 Nov - 23 Nov

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

8. Hilton Rosemont Chicago O'Hare

Rosemont

MELISSA

includes taxes & fees

27 Nov - 28 Nov

A hotel with a brick facade, a modern glass building to the right, and a well-lit entrance.

9. Hilton Orrington / Evanston

Downtown Evanston

Jinho

includes taxes & fees

2 Dec - 3 Dec

A modern bar area with a marble countertop, bar stools, and a variety of liquor bottles.

10. Hilton Chicago/Oak Lawn

Oak Lawn

Michele

includes taxes & fees

15 Nov - 16 Nov

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Southwest Side Hotel Reviews

L7 Chicago by LOTTE

10/10 Excellent

"Super cute for a girls weekend. Close to shops and good restaurants. Staff goes above and beyond. It was a lovely experience."

Sports Illustrated Resorts Chicago

8/10 Good

"The room was clean although the tv was a bit confusing to use the advertising for the room was different from what is shown on here. Overall very nice property not much noise can be heard even with a train station nearby. Staff was great and helpful. Bar is free most days from 3-7 also a free brunch on Sundays as well starting at 11 did not make it to the other events. Overall I had a really good stay."

The Wade

8/10 Good

"The hotel property was beautiful; however, the staff was less than accommodating. During check-in, three groups waited 10 to 15 minutes before receiving assistance. While we were waiting, a staff member entered the office directly behind the check-in desk, where another employee appeared to be engaged in a conversation. That employee could clearly see the three groups waiting but allowed the door to close and did not offer assistance. The groups continued waiting for several more minutes before the same staff member emerged from the back office to assist guests checking into their rooms. On Monday morning, my wife and I went to have breakfast in the restaurant. A sign at the entrance clearly stated, "Please wait to be seated." We stood there for approximately ten minutes while several staff members looked directly at us without acknowledging our presence. After losing patience, I walked down the stairs and asked if someone would be seating us. One of the staff members then informed us that we could seat ourselves at any available table. While the property itself was impressive, the lack of attentiveness and customer service from the staff detracted significantly from our overall experience."

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"

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."

Explore a world of travel with Expedia

Chicago Holiday Rentals

Book Hilton Hotels in Southwest Side on Expedia.com

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

L7 Chicago by LOTTE

Sports Illustrated Resorts Chicago

Club Quarters Hotel, Central Loop, Chicago

The Wade

The Chicago Hotel Collection - Magnificent Mile

Arlo Chicago

LondonHouse Chicago, Curio Collection by Hilton

Fairmont Chicago at Millennium Park

Hotel Saint Clair- Magnificent Mile

Explore a world of travel with Expedia

Search Hotels by Hilton Hotels in Southwest Side from £96

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

L7 Chicago by LOTTE

Explore a world of travel with Expedia