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Featured Guest Houses in Chicago

Estimated price for 1 night/2 adults

The Plainfield Inn
The Plainfield Inn
3.0 out of 5.0 15106 S Fox River Street, Plainfield, IL
$70
5.0/5 (1 reviews)

Steps to downtown Plainfield, and close to great restaurants.

Reviewed on Apr 14, 2019
Situated in Plainfield, this guesthouse is within 6 mi (10 km) of Westfield Louis Joliet Shopping Mall, Mistwood Golf Club, and Naperbrook Golf Course. Bolingbrook ...
Mccormick Place Guest House
Mccormick Place Guest House
3.0 out of 5.0 3643 South Indiana Avenue, Chicago, IL
$30
4.1/5 (9 reviews)

Beautiful house in an interesting area.. Attentiveness of staff, via texts, was supurb. Would stay again..

Reviewed on May 6, 2019
Located in Bronzeville, this guesthouse is 1.8 mi (3 km) from McCormick Place and 2.8 mi (4.6 km) from Soldier Field. Millennium Park and Grant Park are also ...
Villa Dubois Guest House
Villa Dubois Guest House
2.0 out of 5.0 3722 S Calumet Ave, Chicago, IL
$30
Located in Bronzeville, this guesthouse is within 1 mi (2 km) of Lakefront Trail and State Street. McCormick Place and Soldier Field are also within 3 mi (5 ...
Pilsen Roadhouse
Pilsen Roadhouse
3.0 out of 5.0 1827 S Racine Ave, Chicago, IL
Located in Lower West Side, this guesthouse is within 2 mi (3 km) of University of Illinois Chicago, UIC Pavilion, and State Street. Willis Tower and McCormick ...
Private and Spacious Home in Chicago Rogers Park
Private and Spacious Home in Chicago Rogers Park
Chicago, IL
This historic guesthouse is located in Chicago (Rogers Park), close to Loyola University Chicago and Aragon Entertainment Center. Area attractions also include ...
Chicago Guest House on Henderson Street
Chicago Guest House on Henderson Street
3.0 out of 5.0 1330 W Henderson Street, Chicago, IL
$150
Located in Lakeview, this guesthouse is within a 15-minute walk of Vic Theatre and Wrigley Field. Briar Street Theatre and DePaul University-Lincoln Park are ...
Private Northside Guest House 1 mi From Wrigleyfield
Private Northside Guest House 1 mi From Wrigleyfield
Chicago, IL
Located in North Center, this guesthouse is within 3 mi (5 km) of Wrigley Field, Vic Theatre, and Briar Street Theatre. Lincoln Park and DePaul University-Lincoln ...
Coach House in Popular Lincoln Park Neighborhood
Coach House in Popular Lincoln Park Neighborhood
Chicago, IL
Located in Lincoln Park, this property is within a 10-minute walk of Park West and Lincoln Park Zoo. Chicago History Museum and Second City are also within 15 ...
Naperville's Timeless Beauty
Naperville's Timeless Beauty
Naperville, IL
Situated in Naperville, this romantic property is 2.9 mi (4.7 km) from Seven Bridges Golf Club and 3.1 mi (5 km) from Four Lakes Alpine Snowsports. Morton Arboretum ...
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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.

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Estimated price for 1 night/2 adults