Compare Northwest 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

Featured Guest Houses in Northwest 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
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.
Free WiFi
Air conditioning
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.
Parking included
Free WiFi
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.
Don't see what you're looking for?
See all available properties in Northwest Side
View all properties
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 Northwest 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 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
    $134 nightly
    The price is $153 total per night from Dec 30 to Dec 31
    $153 total
    Dec 30 - Dec 31
    Total with taxes and fees
    8.4/10 Very Good! (2,123 reviews)

Northwest Side Guest Houses essential information

Accommodation
5 Guest Houses
Lowest Price
$88
Highest Price
$153
Popular accommodation
Villa Dubois Guest House, Mccormick Place Guest House, Chicago Avenue Inn, Wrigleyville Inn, Oakwood at 73 E. LAKE

More to Explore