Compare Chicago Guest House Rentals

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Featured Guest Houses in Chicago

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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 Chicago

    Congress Plaza Hotel

    Congress Plaza Hotel

    520 South Michigan Avenue, Chicago, IL
    The price is $188 per night from Jun 12 to Jun 13
    per night
    Jun 12 - Jun 13
    7.4/10 Good! (4,221 reviews)
    Hyatt Regency Chicago

    Hyatt Regency Chicago

    151 East Wacker Dr, Chicago, IL
    The price is $220 per night from Jun 18 to Jun 19
    per night
    Jun 18 - Jun 19
    8.6/10 Excellent! (2,634 reviews)
    Warwick Allerton - Chicago

    Warwick Allerton - Chicago

    701 North Michigan Avenue, Chicago, IL
    The price is $165 per night from Jun 26 to Jun 27
    per night
    Jun 26 - Jun 27
    7.2/10 Good! (1,420 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.


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

Number of reviews
8 Guest Houses
Lowest Price
Highest Price
Popular accommodation
Villa Dubois Guest House, Mccormick Place Guest House, Villa Christina, Wrigleyville Inn, Chicago Guest House on Henderson Street, Oakwood at AMLI RIVER NORTH, Oakwood at 73 E. LAKE, Oakwood Chicago River North