South Side Guest Houses

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 prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for South Side guest houses

Villa Dubois Guest House

Bronzeville

Stefano

includes taxes & fees

16 Jul - 17 Jul

Chicago Avenue Inn

Humboldt Park

Zoe

includes taxes & fees

12 Aug - 13 Aug

View all properties

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

Top South Side Hotel Reviews

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

10/10 Excellent

"The hotel was in a convenient location, clean with friendly and helpful staff members. The cons to this hotel were you have to pay $30 per day for parking due to the fact it is close to the airport and it doesn't have a swimming pool."

Carlton Inn Midway

8/10 Good

"My problem was with hsving the shuttle fetch me from the airport. I couldn't get thru to th hotel, so ended up taking an uber. I explained the matter to the Gen Manager, who agreed to cover the cost of the Uber. I found the staff extremely pleasant, professional, and efficient; and the breakfast quite nice. Shuttle to the airport the next morning was perfect."

Motel 6 - Chicago, IL

10/10 Excellent

"This motel 6 is exactly what you pay for. It’s definitely for saving a buck—thin bed sheets and messy landowner special in the rooms being paint and stain jobs, etc. that being said, it had good space and decent location for a 1/4th of the price of hotels in downtown Chicago. We came for a wedding. The property is gated in which gives a safer feel especially in leaving your cars and they don’t enter the rooms during your stay unless requested so you’ll have privacy."

Find out more about South Side