Compare Chicago Guest House Rentals

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 Chicago

Don't see what you're looking for?
See all available properties in Chicago
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 Chicago

    Congress Plaza Hotel

    Congress Plaza Hotel

    520 South Michigan Avenue Chicago IL
    $155 nightly
    The price is $184 total per night from Jun 29 to Jun 30
    $184 total
    Jun 29 - Jun 30
    Total with taxes and fees
    8/10 Very Good! (10,138 reviews)
    The Chicago Hotel Collection - Magnificent Mile

    The Chicago Hotel Collection - Magnificent Mile

    166 E Superior Street Chicago IL
    $154 nightly
    The price is $183 total per night from Jun 28 to Jun 29
    $183 total
    Jun 28 - Jun 29
    Total with taxes and fees
    7.8/10 Good! (1,495 reviews)
    Hotel Riu Plaza Chicago

    Hotel Riu Plaza Chicago

    150 East Ontario Street Chicago IL
    $203 nightly
    The price is $242 total per night from Jun 30 to Jul 1
    $242 total
    Jun 30 - Jul 1
    Total with taxes and fees
    9.4/10 Exceptional! (4,306 reviews)

Chicago guest houses give you a warm welcome to the Windy City

Chicago lies next to Lake Michigan, Illinois. It’s a city famous for its architecture, music and seriously trendy shopping malls. It never fails to impress visitors, and Chicago guest houses are ideally located for travelers to enjoy all that the “Windy City” has to offer.

About Chicago guest houses

Whether you want to take in some Chicago Blues in downtown, or gain a bird’s eye view of the city from Sear’s Tower, you’ve got everything right on your doorstep. Most Chicago guest houses are centrally located, meaning you never have to go too far to find a bar, a place to eat, attractions for children, or top shopping spots.

Expect spacious, comfortable guest rooms in your Chicago guest house, free Wi-Fi, a laundry service, excellent food and room service facilities, and that all-important expert local knowledge.

Shopping

Chicago is a large city with excellent shopping malls and boutique stores. Visit Michigan Avenue for major brand flagship stores, or if you are after something quirky and unique, Randolph Street Market is the place to go. Don’t miss the opportunity to visit State Street, with its stunning 19th-century architecture and high-end boutiques. It also boasts the world’s second-largest department store, Macy’s.

Chicago guest houses are within easy reach of all these locations, so you won’t have too far to carry those heavy shopping bags.

Tourist attractions

Visitor attractions in Chicago range from sophisticated art galleries to kid-friendly theme parks. For a free day out, visit the city’s inland beaches. Chicago is also brimming with culture. Make sure to visit the Museum of Contemporary Art, which has one of the country’s most extensive collections of modern art. The Wrigley Field Baseball Stadium is a must-see for sports fans. Built in 1914, it’s an iconic piece of architectural design.

Getting around

Although Chicago is a large city, the central location of most Chicago guest houses means you can easily enjoy all there is to see on foot. To explore a little further out, hop onto Chicago’s subway system, or hire a car from one of the many vehicle rental offices located across the city.

Chicago Guest Houses essential information

Accommodation
8 Guest Houses
Lowest Price
$125
Highest Price
$242
Popular accommodation
Mccormick Place Guest House, Chicago Avenue Inn, Villa Dubois Guest House, Wrigleyville Inn, Villa Christina, Oakwood at AMLI RIVER NORTH, Oakwood at 73 E. LAKE

More to Explore