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Featured Guest Houses in Chicago

The Plainfield Inn
The Plainfield Inn
3.0 out of 5.0 15106 S Fox River Street, Plainfield, IL
$80
5.0/5 (2 reviews)

Loved the character of the place, the location & the hospitality. Some sort of drawer space would be nice when staying loner as I did so I would not have had to live out of my suitcase. I will definitely consider staying there again when the need arises and I highly recommend it.

Reviewed on Dec 26, 2019
The Plainfield Inn features free WiFi in public areas, express check-in, and express check-out. If you drive, put free parking to good use. This smoke-free guesthouse ...
Mccormick Place Guest House
Mccormick Place Guest House
3.0 out of 5.0 3643 South Indiana Avenue, Chicago, IL
$50
4.2/5 (12 reviews)

Todo súper bien, el servicio el mantenimiento, la manera de contactarlos

Reviewed on Dec 5, 2019
Mccormick Place Guest House features free WiFi in public areas and barbecue grills. You can take advantage of free parking if you drive. Additional amenities ...
Roscoe Village Guesthouse
Roscoe Village Guesthouse
3.5 out of 5.0 2104 W. Roscoe, Chicago, IL
$174
4.0/5 (2 reviews)

This was not a good experience. The place was way over-priced (because of a Cubs baseball game). The location was 1/2 mile away from where promised. The unit above was rented a bunch of 20-somethings who showed up with multiple cases of beer, and they proceeded to drink it all and shout at each other ...

Reviewed on Sep 16, 2018
Roscoe Village Guesthouse features free WiFi in public areas and a garden. You can put free parking to good use if you drive.
Lincoln Park Suites Operated by Roscoe Village Guesthouse
Lincoln Park Suites Operated by Roscoe Village Guesthouse
4.0 out of 5.0 830 W Altgeld, Chicago, IL
$199
Lincoln Park Suites Operated by Roscoe Village Guesthouse features free WiFi in public areas and a garden. If you decide to drive, there's free parking.
Old Town Suites Operated by Roscoe Village Guesthouse
Old Town Suites Operated by Roscoe Village Guesthouse
3.5 out of 5.0 403 W. Eugenie, Chicago, IL
$239
Guests of Old Town Suites Operated by Roscoe Village Guesthouse have access to free WiFi in public areas. A stay here includes free parking.
Chicago Guest House on Henderson Street
Chicago Guest House on Henderson Street
3.0 out of 5.0 1330 W Henderson Street, Chicago, IL
A local mainstay since 1886, Chicago Guest House on Henderson Street offers free WiFi in public areas, a terrace, and laundry facilities. Free parking is available ...
Pilsen Roadhouse
Pilsen Roadhouse
3.0 out of 5.0 1827 S Racine Ave, Chicago, IL
At Pilsen Roadhouse , guests have access to barbecue grills.
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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.

Hotel Options in Chicago

See all 1,935 Properties in Chicago
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.