Book Guest Houses in Southwest Side, IL
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Top Guest Houses in Southwest Side
Villa Dubois Guest House
3722 S Calumet Ave Chicago IL
$55 nightly
The price is $65 total per night
$65 total
Dec 24 - Dec 25
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a communal living room, and express check-in are also on offer.
Parking included
Free WiFi
Mccormick Place Guest House
3643 South Indiana Avenue Chicago IL
$75 nightly
The price is $88 total per night
$88 total
Dec 24 - Dec 25
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a picnic area, and barbecue grills are also on offer.
Parking included
Free WiFi
Chicago Avenue Inn
3305 W Chicago Ave Chicago IL
$108 nightly
The price is $123 total per night
$123 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
This guesthouse includes free WiFi in public areas and a virtual front desk.
Free WiFi
Air conditioning
Wrigleyville Inn
914 W Newport Ave Chicago IL
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, laundry facilities, and a virtual front desk are also on offer.
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.
Top hotels in Southwest Side
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
$127 nightly
The price is $149 total per night from Jan 4 to Jan 5
$149 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.2/10 Wonderful! (2,147 reviews)
Southwest Side Guest Houses essential information
Accommodation | 5 Guest Houses |
|---|---|
Lowest Price | $65 |
Highest Price | $174 |
Popular accommodation | Villa Dubois Guest House, Mccormick Place Guest House, Chicago Avenue Inn, Wrigleyville Inn, Oakwood at 73 E. LAKE |
Explore More Ways to Travel with Travelocity
- Motels in Kedzie Station
- Apartments in Sox-35th Station
- Condos in Sox-35th Station
- Motels in Chicago Wrightwood Station
- Apartments in 35th-Bronzeville-IIT Station
- Condos in 35th-Bronzeville-IIT Station
- Extended Stay Hotels in 35th-Bronzeville-IIT Station
- Motels in 35th-Bronzeville-IIT Station
- Resorts in 35th-Bronzeville-IIT Station
- 3 Star Hotels in Gage Park
- Gage Park Hotels
- Extended Stay Hotels in 47th Station
- Pet Friendly Hotels in Englewood
- Romantic Getaways & Hotels in Englewood
- Englewood Hotels
- Brighton Park Hotels
- Downtown Chicago Hotels
- Apartments in 35th-Archer Station
- West Englewood Hotels
- Extended Stay Hotels in 51st Station
- 4 Star Hotels in Ducktown
- Ducktown Hotels
- Chicago Lawn Hotels
- Arcade Hotels in Archer Heights
- Cheap Hotels in Archer Heights
- Hotels with Shopping in Archer Heights
- Archer Heights Hotels
- West Elsdon Hotels
- Extended Stay Hotels in Chicago
- Hotels with Hot Tubs in Chicago
- Chicago Hotels
- Motels in Chicago
- Hotels near Bridgeport Art Center
- Guest Houses in Ashland-63rd Station
- Hotels near Ashland-63rd Station
- Hotels near Midway Intl.
- Inns in King Drive Station
- Motels in King Drive Station
- Condos in Pulaski Station
- Extended Stay Hotels in Pulaski Station
- Apartments in Midway Station
- Hotels near Marquette Park
- 3 Star Hotels in Canaryville
- Canaryville Hotels
- Condos in Chicago 35th Street-Lou Jones-Bronzeville Station
- Extended Stay Hotels in Chicago 35th Street-Lou Jones-Bronzeville Station
- Guest Houses in Chicago 35th Street-Lou Jones-Bronzeville Station
- Hostels in Chicago 35th Street-Lou Jones-Bronzeville Station
- Motels in Chicago 35th Street-Lou Jones-Bronzeville Station
- West Lawn Hotels
- B&B in South Side
- Castles in South Side
- Motels in South Side
- Hotels near Zhou B Art Center
- Glendale Hotels
- Motels in Chicago Western Avenue Station
- Mckinley Park Hotels
- Condos in Garfield Station
- 5 Star Hotels in Corwith
- Flights to Chicago
- Flights from Midway Intl.
- Delta Atlanta (ATL) to Chicago (MDW) flights
- Delta Minneapolis (MSP) to Chicago (MDW) flights
- Delta Washington (DCA) to Chicago (MDW) flights
- Volaris Durango (DGO) to Chicago (MDW) flights
- Flights from Atlanta (ATL) to Chicago (MDW)
- Flights from Austin (AUS) to Chicago (MDW)
- Flights from Nashville (BNA) to Chicago (MDW)
- Flights from Boston (BOS) to Chicago (MDW)
- Flights from Baltimore (BWI) to Chicago (MDW)
- Flights from Charlotte (CLT) to Chicago (MDW)
- Flights from Columbus (CMH) to Chicago (MDW)
- Flights from Denver (DEN) to Chicago (MDW)
- Flights from Dallas (DFW) to Chicago (MDW)
- Flights from Detroit (DTW) to Chicago (MDW)
- Flights from Newark Liberty Intl. Airport (EWR) to Chicago (MDW)
- Flights from Fort Lauderdale (FLL) to Chicago (MDW)
- Flights from Houston (IAH) to Chicago (MDW)
- Flights from New York (JFK) to Chicago (MDW)
- Flights from Las Vegas (LAS) to Chicago (MDW)
- Flights from Los Angeles (LAX) to Chicago (MDW)
- Flights from New York (LGA) to Chicago (MDW)
- Flights from Kansas City (MCI) to Chicago (MDW)
- Flights from Orlando (MCO) to Chicago (MDW)
- Flights from Minneapolis (MSP) to Chicago (MDW)
- Flights from Portland (PDX) to Chicago (MDW)
- Flights from Philadelphia (PHL) to Chicago (MDW)
- Flights from Phoenix (PHX) to Chicago (MDW)
- Flights from Raleigh (RDU) to Chicago (MDW)
- Flights from Fort Myers (RSW) to Chicago (MDW)
- Flights from San Diego (SAN) to Chicago (MDW)
- Flights from San Francisco (SFO) to Chicago (MDW)
- Flights from Orange County (SNA) to Chicago (MDW)
- Flights from Tampa (TPA) to Chicago (MDW)