Compare South Side Guest House Rentals

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Featured Guest Houses in South 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 17 - Dec 18
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 17 - Dec 18
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
Villa Christina

Villa Christina

3 out of 5
6832 S Calumet Ave Chicago IL
At Villa Christina, guests have access to free WiFi in public areas and laundry facilities. There's free parking if you drive.
Parking included
Free WiFi
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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 South Side

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

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

    6500 S Cicero Ave Chicago IL
    $112 nightly
    The price is $132 total per night from Jan 4 to Jan 5
    $132 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    8.8/10 Excellent! (1,237 reviews)
    SpringHill Suites by Marriott Chicago Chinatown

    SpringHill Suites by Marriott Chicago Chinatown

    2357 S WENTWORTH AVE Chicago IL
    $112 nightly
    The price is $131 total per night from Jan 1 to Jan 2
    $131 total
    Jan 1 - Jan 2, 2026
    Total with taxes and fees
    9.4/10 Exceptional! (1,002 reviews)
    Motel 6 - Chicago, IL

    Motel 6 - Chicago, IL

    10022 South Halsted Street Chicago IL
    $80 nightly
    The price is $94 total per night from Dec 17 to Dec 18
    $94 total
    Dec 17 - Dec 18
    Total with taxes and fees
    6.8/10 (203 reviews)

South Side Guest Houses essential information

Accommodation
3 Guest Houses
Lowest Price
$88
Highest Price
$132
Popular accommodation
Villa Dubois Guest House, Mccormick Place Guest House, Villa Christina

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