Compare Southwest Side Guest House Rentals

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Featured Guest Houses in 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 16 - Dec 17
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

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
Dec 16 - Dec 17
Total with taxes and fees
Mccormick Place Guest House features free WiFi in public areas and a garden. You can take advantage of free parking if you drive. Additional amenities include barbecue grills and a picnic area.
Parking included
Free WiFi
Chicago Avenue Inn

Chicago Avenue Inn

2 out of 5
3305 W Chicago Ave Chicago IL
$110 nightly
The price is $126 total per night
$126 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
Chicago Avenue Inn features free WiFi in public areas, microwave in a common area, and refrigerator in a common area.
Wrigleyville Inn

Wrigleyville Inn

3 out of 5
914 W Newport Ave Chicago IL
Guests of Wrigleyville Inn enjoy free WiFi in public areas, a terrace, and laundry facilities. Free parking is included with your stay.
Oakwood at 73 E. LAKE

Oakwood at 73 E. LAKE

2 out of 5
73 East Lake Street Chicago IL
Stay at this guesthouse in Chicago. Popular attractions Chicago Riverwalk and Millennium Park 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.

Hotel Options in Southwest Side

    Hilton Chicago/Magnificent Mile Suites

    Hilton Chicago/Magnificent Mile Suites

    198 E Delaware Pl Chicago IL
    $81 nightly
    The price is $95 total per night from Jan 5 to Jan 6
    $95 total
    Jan 5 - Jan 6, 2026
    Total with taxes and fees
    8.8/10 Excellent! (3,467 reviews)
    Silversmith Hotel Chicago Downtown

    Silversmith Hotel Chicago Downtown

    10 S Wabash Ave Chicago IL
    $127 nightly
    The price is $149 total per night from Dec 21 to Dec 22
    $149 total
    Dec 21 - Dec 22
    Total with taxes and fees
    9.2/10 Wonderful! (2,109 reviews)
    Palmer House a Hilton Hotel

    Palmer House a Hilton Hotel

    17 E Monroe St Chicago IL
    $132 nightly
    The price is $150 total per night from Dec 30 to Dec 31
    $150 total
    Dec 30 - Dec 31
    Total with taxes and fees
    8.4/10 Very Good! (2,123 reviews)

Southwest Side Guest Houses essential information

Accommodation
5 Guest Houses
Lowest Price
$88
Highest Price
$150
Popular accommodation
Villa Dubois Guest House, Mccormick Place Guest House, Chicago Avenue Inn, Wrigleyville Inn, Oakwood at 73 E. LAKE

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