Top 10 Southwest Side hotels and places to stay

Relax in style with plush seating and a classic design, featuring a sofa, armchairs, and a bookshelf.

"Stayed many times, great fun!"

includes taxes & fees

24 Aug - 25 Aug

Relax in style with lounge chairs and bar stools amidst a scenic backdrop.

"Beautiful property, will definitely stay there again."

includes taxes & fees

21 Aug - 22 Aug

"Great location & friendly staff."

includes taxes & fees

19 Aug - 20 Aug

Relax in a serene bedroom with a large bed, minimalist decor, and a cityscape painting above.

"It was a good stay the rooms are small tho but if you are going to have fun and just have somewhere to sleep then it’s perfect for a couple people "

includes taxes & fees

4 Aug - 5 Aug

Enjoy a self-service breakfast with a variety of options at this well-equipped breakfast bar.

"Staff are very friendly:) "

includes taxes & fees

6 Aug - 7 Aug

Skylark Motel's exterior features a prominent sign with its name displayed in bold letters.

"Poorly cleaned and not kept up well."

includes taxes & fees

17 Aug - 18 Aug

Stairs lead to a bar area with a counter and seating on the upper level.

"Good Hotel"

includes taxes & fees

24 Aug - 25 Aug

Relax in a serene urban setting with a spacious seating area and unobstructed city views.

"Enjoyed staying here!"

includes taxes & fees

4 Aug - 5 Aug

Enjoy a romantic breakfast on the balcony with a city view, surrounded by a selection of cheeses, fresh fruits, and nuts.

"Great location for shopping and dining. "

includes taxes & fees

4 Aug - 5 Aug

Enjoy a casual dining experience with comfortable seating and a variety of beverages.

"Excellent location and great vibe. "

includes taxes & fees

17 Aug - 18 Aug

Relax in a stylish seating area with plush armchairs and a decorative partition, surrounded by ambient lighting and a patterned rug.

"Excellent Hotel!!"

includes taxes & fees

24 Aug - 25 Aug

Relax in the hotel lobby's spacious seating area, surrounded by a city view and comfortable sofas and armchairs.

"Location, cleanness and staff were very good "

includes taxes & fees

25 Aug - 26 Aug

Experience the grandeur of our lobby, featuring a stunning chandelier, comfortable seating, and a beautiful staircase.

"Great stay"

includes taxes & fees

24 Aug - 25 Aug

Enjoy a drink at the bar, where a geometric ceiling structure and contemporary design create a welcoming atmosphere.

"Great hotel in a great location. Would definitely stay again "

includes taxes & fees

24 Aug - 25 Aug

Located at the corner of a bustling street, Ohio House features a flat roof and large glass windows.

"Great place to stay!"

includes taxes & fees

17 Aug - 18 Aug

Relax in a spacious lobby with a large seating area, sofas, armchairs, and tables for guests.

"the hotel was in an amazing location, very clean and comfortable for 4 people, and the beds were very comfortable!"

includes taxes & fees

14 Aug - 15 Aug

Experience grandeur in this beautifully designed ballroom with high ceilings, arched windows, and elegant table settings.

"Great place to stay."

includes taxes & fees

18 Aug - 19 Aug

Contemporary lounge area with a striking metal structure and large windows offering urban views.

"Great location "

includes taxes & fees

10 Aug - 11 Aug

Relax on the rooftop with wicker lounge chairs and take in the city skyline views.

"nice hotel and nice staff and close to everything "

includes taxes & fees

24 Aug - 25 Aug

Elevators lead to upper floors from this grand corridor, flanked by ornate columns.

"Great place to stay."

includes taxes & fees

24 Aug - 25 Aug

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

Sign in

Sign up, it's free

Learn more about Southwest Side

Explore attractions like Balzekas Museum of Lithuanian Culture and S.S. Peter and Paul Church as you discover things to see and do in Southwest Side.

See all hotels in Southwest Side

Top Southwest Side Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Great time in Chicago and the hotel made it phenomenal! It’s in a very central location and allows access to all the major tourist attractions within walking distance. We really enjoyed Saturday movie night at the pool!"

Palmer House a Hilton Hotel

10/10 Excellent

"The Palmer House has many wonderful qualities to it. It’s a perfect location for those looking to explore Chicago. It’s right next to an elevated train stop and a close walk to many places. It’s a beautiful old historic hotel, incredible lobby, and for the most parts the rooms are well appointed. My room 16-179, was relatively clean… lot of smudges on the two mirrors…, the bed was very comfortable, and the amenities worked well. Perfect for a solo trip. It would not be a good room for two people or a family, seeing as it is way too small."