Book Guest Houses in Far Southwest Side, IL

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Top Guest Houses in Far Southwest Side

Villa Dubois Guest House

Villa Dubois Guest House

2 out of 5
3722 S Calumet Ave Chicago IL
$75 nightly
The price is $88 total per night
$88 total
Dec 28 - Dec 29
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

Mccormick Place Guest House

3 out of 5
3643 South Indiana Avenue Chicago IL
$75 nightly
The price is $88 total per night
$88 total
Jan 19 - Jan 20, 2026
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

Chicago Avenue Inn

2 out of 5
3305 W Chicago Ave Chicago IL
$109 nightly
The price is $124 total per night
$124 total
Jan 13 - Jan 14, 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

Wrigleyville Inn

3 out of 5
914 W Newport Ave Chicago IL
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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
Oakwood at 73 E. LAKE

Oakwood at 73 E. LAKE

2 out of 5
73 East Lake Street Chicago IL
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Stay at this guesthouse in Chicago. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Oakwood at AMLI RIVER NORTH

Oakwood at AMLI RIVER NORTH

2 out of 5
71 West Hubbard Street Chicago IL
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Stay at this guesthouse in Chicago. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
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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 Far Southwest Side

Silversmith Hotel Chicago Downtown

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)

Far Southwest Side Guest Houses essential information

Accommodation
6 Guest Houses
Lowest Price
$88
Highest Price
$179
Popular accommodation
Villa Dubois Guest House, Mccormick Place Guest House, Chicago Avenue Inn, Wrigleyville Inn, Oakwood at 73 E. LAKE, Oakwood at AMLI RIVER NORTH

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