Compare South Side Guest House Rentals
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured Guest Houses in South Side

Villa Dubois Guest House
3722 S Calumet Ave, Chicago, IL
$99 nightly
The price is $116 total per night
$116 total
Oct 22 - Oct 23
Total with taxes and fees
Villa Dubois Guest House features free WiFi in public areas, coffee in a common area, and microwave in a common area. If you plan to drive, free parking is available. Helpful staff can provide luggage storage and a safe deposit box at the front desk. Additional amenities include a refrigerator in a common area, express check-in, and express check-out.
Parking included
Free WiFi

Mccormick Place Guest House
3643 South Indiana Avenue, Chicago, IL
$99 nightly
The price is $116 total per night
$116 total
Oct 21 - Oct 22
Total with taxes and fees
Mccormick Place Guest House features free WiFi in public areas and barbecue grills. You can take advantage of free parking if you drive. Additional amenities include a picnic area and a garden.
Parking included
Free WiFi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Hotel Options in South Side

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
6500 S Cicero Ave, Chicago, IL
$131 nightly
The price is $154 total per night from Nov 9 to Nov 10
$154 total
Nov 9 - Nov 10
Total with taxes and fees
8.8/10 Excellent! (1,157 reviews)

Motel 6 - Chicago, IL
10022 South Halsted Street, Chicago, IL
$75 nightly
The price is $88 total per night from Oct 21 to Oct 22
$88 total
Oct 21 - Oct 22
Total with taxes and fees
6.6/10 (136 reviews)

SpringHill Suites by Marriott Chicago Chinatown
2357 S WENTWORTH AVE, Chicago, IL
$152 nightly
The price is $178 total per night from Nov 9 to Nov 10
$178 total
Nov 9 - Nov 10
Total with taxes and fees
9.4/10 Exceptional! (1,014 reviews)
South Side Guest Houses essential information
Accommodation | 3 Guest Houses |
---|---|
Lowest Price | $88 |
Highest Price | $178 |
Popular accommodation | Villa Dubois Guest House, Mccormick Place Guest House, Villa Christina |
More to Explore
More to Explore
- Motels in Chicago 27th Street Station
- Cottages in Halsted Station
- Inns in Halsted Station
- Motels in Halsted Station
- 5 Star Hotels in Grand Boulevard
- Hotels with WiFi in Grand Boulevard
- Motel 6 Hotels in Grand Boulevard
- Hotels with Shopping in Grand Boulevard
- B&B in Chicago 35th Street-Lou Jones-Bronzeville Station
- Condo Rentals in Chicago 35th Street-Lou Jones-Bronzeville Station
- Guest Houses in Chicago 35th Street-Lou Jones-Bronzeville Station
- Guest Houses in Chicago 59th Street Station
- Hotels near United Center
- Apartments in Sox-35th Station
- Resorts in Sox-35th Station
- Hotels near University of Chicago
- Hotels near Smart Museum of Art
- Hotels near Soldier Field
- Resorts in Garfield Station
- Condo Rentals in Chicago 47th Street Station
- Cottages in Chicago 47th Street Station
- Guest Houses in Chicago 47th Street Station
- Condo Rentals in Chicago 55th-56th-57th Street Station
- Extended Stay Hotels in Chicago 55th-56th-57th Street Station
- Extended Stay Hotels in Chicago McCormick Place Station
- Guest Houses in Chicago McCormick Place Station
- Motels in Cermak-Chinatown Station
- B&B in 47th Station
- Motels in 47th Station
- Apartments in Ashland-63rd Station
- Inns in Ashland-63rd Station
- B&B in Chicago 75th Street Station
- Vacation Homes in Chicago 75th Street Station
- Hotels near McCormick Place
- Hotels with Free Parking in Downtown Chicago
- Downtown Chicago Hotels
- Hotels near Elijah Muhammad House
- Cheap Hotels in Chicago
- Hotels with Hot Tubs in Chicago
- Romantic Getaways & Hotels in Chicago
- Chicago Hotels
- Motels in Chicago
- Resorts in Chicago
- Beach Resorts & in Hyde Park
- Cheap Hotels in Hyde Park
- Hilton Hotels in Hyde Park
- Historic Hotels in Hyde Park
- Hotels with Bar in Hyde Park
- Pet Friendly Hotels in Hyde Park
- Hyde Park Hotels
- Hotels near Midway Intl.
- 4 Star Hotels in Kenwood
- Hotels near 4944 S Woodlawn Ave
- Cabin Rentals in 35th-Bronzeville-IIT Station
- Condo Rentals in 35th-Bronzeville-IIT Station
- Hostels in 35th-Bronzeville-IIT Station
- Hotels near Court Theatre
- Flights to Chicago
- Flights from Atlanta to Chicago
- Flights from Austin to Chicago
- Flights from Boston to Chicago
- Flights from Charlotte to Chicago
- Flights from Chicago
- Flights from Cincinnati to Chicago
- Flights from Cleveland to Chicago
- Flights from Columbus to Chicago
- Flights from Dallas to Chicago
- Flights from Denver to Chicago
- Flights from Detroit to Chicago
- Flights from Houston to Chicago
- Flights from Kansas City to Chicago
- Flights from Las Vegas to Chicago
- Flights from Los Angeles to Chicago
- Flights from Memphis to Chicago
- Flights from Miami to Chicago
- Flights from Minneapolis - St. Paul to Chicago
- Flights from Nashville to Chicago
- Flights from New Orleans to Chicago
- Flights from New York to Chicago
- Flights from Orlando to Chicago
- Flights from Philadelphia to Chicago
- Flights from Phoenix to Chicago
- Flights from Portland to Chicago
- Flights from Raleigh to Chicago
- Flights from San Francisco to Chicago
- Flights from Seattle to Chicago
- Flights from St. Louis to Chicago
- Flights from Toronto to Chicago
- Flights from Washington to Chicago
- Flights from Omaha to Chicago
- Flights from Pittsburgh to Chicago
- Flights from Fort Lauderdale to Chicago
- Flights from Newark to Chicago
- Flights from Tampa to Chicago