I thought Wood Ducks were the most amazingly colorful and photogenic ducks until I spotted this incredible bird on the lakefront. What a handsome beautiful duck.

Search Resorts in South Side

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for South Side resorts

Eaglewood Resort and Spa

Itasca

Sherelle

3.908.378 ₫ total

includes taxes & fees

1 Jan - 2 Jan 2026

Hilton Chicago/Oak Brook Hills Resort & Conference Center

Oak Brook

Ana

3.365.309 ₫ total

includes taxes & fees

28 Dec - 29 Dec

Couples treatment room(s), sauna, body treatments, aromatherapy

Wind Creek Southland Casino and Hotel

East Hazel Crest

WILLIAM

4.747.407 ₫ total

includes taxes & fees

29 Dec - 30 Dec

View all properties

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

Top South Side Hotel Reviews

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent

"The staff was super friendly, and the room was clean! Great location."

SpringHill Suites by Marriott Chicago Chinatown

10/10 Excellent

"Everything was wonderful! From the welcoming feeling when we walked in the door with the bright ambiance and the pleasant smell. They have nice & helpful front desk staff, along with convenient parking . Rooms were spacious, clean and the bed was so comfortable. We were sad to have missed out on the breakfast because we slept in but we had heard it was very good."

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

10/10 Excellent

"Clean room, great Dove amenities, very friendly front staff. Extremely close to Midway airport with free shuttle - drivers were VERY kind and gracious and a pleasure to deal with. Close to many restaurants within easy walking distance if you want a snack. "