South Side Hotels with WiFi, Chicago: South Side Hotel Guide

A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

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 availability on South Side Hotels with WiFi

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for South Side hotels with wifi

A hotel room with a bed, a desk, a chair, a TV, and a colorful rug.

A Holiday Inn Express & Suites hotel with a modern facade, multiple parking spaces, and a well-lit entrance.

A hotel reception desk with a modern design, including a digital display and a sign indicating it is a non-smoking property.

A coffee station with two espresso machines, a coffee grinder, and various coffee-related items.

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

Bedford Park

Roberto

€145

includes taxes & fees

1 Nov - 2 Nov

A modern living room with a sofa, two blue chairs, a round coffee table, and a unique ceiling design.

A modern hotel room with a bed, a sofa, a desk, and artwork on the walls.

A modern lobby with a sofa, a coffee table, and a large digital art display.

A modern restaurant with a bar area, multiple seating options, and a contemporary design.

2. SpringHill Suites by Marriott Chicago Chinatown

Chinatown

olivia

€180

includes taxes & fees

31 Oct - 1 Nov

A modern bar area with a bar counter, seating, and large windows offering a view of the street.

A hotel room with a bed, a seating area with a table and a plant, a window with a city view, and a radiator.

A modern lobby with a vending machine, a statue, and an exit sign.

A modern bar area with a curved counter, multiple stools, and pendant lighting. A menu board is visible on the wall, and a coffee machine is on the counter.

3. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Allen

€146

includes taxes & fees

1 Nov - 2 Nov

An outdoor café with tables and chairs, a red umbrella, and a flower-lined walkway.

A modern multi-story building with a prominent central tower, large windows, and a pedestrian walkway.

A hotel room with a bed, a desk, a chair, a sofa, a coffee table, and a painting on the wall.

A restaurant with a bar area, seating, and a television screen displaying a sports event.

4. Hyatt Place Chicago-South/University Medical Center

Hyde Park

Denise

€220

includes taxes & fees

2 Nov - 3 Nov

A modern hotel room with large windows, a sofa, chairs, a dining table, and a coffee table.

A spacious living area with a modern chandelier, comfortable seating, and a fireplace.

A multi-story hotel with a modern design, featuring a prominent entrance with a marquee and outdoor seating area.

A bar area with a marble countertop, multiple shelves of bottles, and a large TV screen. There are several bar stools and a round table with a vase of flowers.

5. Sophy Hyde Park

Hyde Park

amy

€307

includes taxes & fees

31 Oct - 1 Nov

A modern hotel room with a large bed, a bedside table, a nightstand, and a wall-mounted light fixture.

A modern hotel room with a large bed, a nightstand, a wall-mounted lamp, and a door.

A room with a window, a white shelf, a colorful striped rug, and a large number '6' on the wall.

6. Motel 6 - Chicago, IL

Washington Heights

Nazli

€93

includes taxes & fees

15 Oct - 16 Oct

A Marriott hotel with a brick facade, a covered entrance, and landscaped areas with trees and shrubs.

A bar area with a black marble countertop, wicker bar stools, and a variety of bottles and glasses on shelves.

A hotel room with two beds, a desk, and a chair.

7. Chicago Marriott Midway

Bedford Park

Carolyn

€168

includes taxes & fees

2 Nov - 3 Nov

A hotel lobby with a reception desk, seating area, and a cityscape mural on the ceiling.

A spacious hotel lobby with seating areas, a reception desk, and a large window offering a view.

A spacious lobby with a modern design, featuring a large sofa, multiple chairs, a coffee table, and a mural of an airplane.

A Best Western hotel with a brick facade, multiple windows, and a covered parking area.

8. Best Western Inn & Suites - Midway Airport

Burbank

David L

€112

includes taxes & fees

1 Nov - 2 Nov

View all properties

Top South Side Hotel Reviews

Jaslin Hotel

8/10 Good

"The location is close to my son’s apartment who is studying in Chicago. We hoped to get a view of the north side but we didn’t, Bed to small for two though but since we were doing à lot of walking we didn’t care that much, we were so tired that we slept fast.😀"

Chicago Lake Shore Hotel

10/10 Excellent

"Everything was clean they are busy updating this hotel. I like to location close to the hospital and free parking."

Holiday Inn Chicago – Midway Airport S by IHG

8/10 Good

"The hotel was nice. I loved the restaurant. The location though was a bit much. Will stay again, but definitely plan time to get to where u need to be."

Best Western Inn & Suites - Midway Airport

10/10 Excellent

"Free parking and breakfast were a huge win,"

Carlton Inn Midway

10/10 Excellent

"The room was lovely and clean, breakfast was good, staff was very pleasant"

Explore a world of travel with Expedia

Flights to Chicago

Things to do in Central Chicago

Room 1

Change your mind

Treat yourself

Be picky

Check availability on South Side Hotels with WiFi

Our top choices for South Side hotels with wifi

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

2. SpringHill Suites by Marriott Chicago Chinatown

3. Holiday Inn Chicago – Midway Airport S by IHG