Compare Southwest Side Guest House Rentals

Start date: Check-in selected.
To Date
End date: Check-out

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

Hotel Options in Southwest Side

    Hilton Chicago/Magnificent Mile Suites

    Hilton Chicago/Magnificent Mile Suites

    198 E Delaware Pl Chicago IL
    $89 nightly
    The price is $105 total per night from Jan 5 to Jan 6
    $105 total
    Jan 5 - Jan 6, 2026
    Total with taxes and fees
    8.8/10 Excellent! (3,504 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 Jan 4 to Jan 5
    $149 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    9.2/10 Wonderful! (2,133 reviews)
    Palmer House a Hilton Hotel

    Palmer House a Hilton Hotel

    17 E Monroe St Chicago IL
    $140 nightly
    The price is $160 total per night from Dec 28 to Dec 29
    $160 total
    Dec 28 - Dec 29
    Total with taxes and fees
    8.4/10 Very Good! (2,146 reviews)

Southwest Side Guest Houses essential information

Accommodation
 Guest Houses
Lowest Price
$105
Highest Price
$160
Popular accommodation
Hilton Chicago/Magnificent Mile Suites, Silversmith Hotel Chicago Downtown, Palmer House a Hilton Hotel

More to Explore