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Featured Chicago Guest Houses

$50
Villa Dubois Guest House

Villa Dubois Guest House

2.0 out of 5.0 3722 S Calumet Ave, Chicago, IL
4.6/5
(5 Reviews)
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and luggage storage are also provided.
 
$30
Mccormick Place Guest House

Mccormick Place Guest House

3.0 out of 5.0 3643 South Indiana Avenue, Chicago, IL
4.2/5
(4 Reviews)
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a picnic area, and barbecue grills are also on offer.
 
$70
The Plainfield Inn

The Plainfield Inn

3.0 out of 5.0 15106 S Fox River Street, Plainfield, IL
5/5
(1 Reviews)
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, express check-in, and express check-out are also on offer.
 
$109
Roscoe Village Guesthouse

Roscoe Village Guesthouse

3.5 out of 5.0 2104 W. Roscoe, Chicago, IL
5/5
(1 Reviews)
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden is also provided.
 
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Pilsen Roadhouse

Pilsen Roadhouse

3.0 out of 5.0 1827 S Racine Ave, Chicago, IL
This guesthouse features barbecue grills.
 
$104
Chicago Guest House on Henderson Street

Chicago Guest House on Henderson Street

3.0 out of 5.0 1330 W Henderson Street, Chicago, IL
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a picnic area are also on offer.
 
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Chicago Cozy Home in Rogers Park Neighborhood Walk to Train Redline Loyola Stop

Chicago Cozy Home in Rogers Park Neighborhood Walk to Train Redline Loyola Stop

Chicago, IL
A garden is available at this guesthouse.
 
$99
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
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden is also provided.
 
$156
Chicago Guest House Discover Vibrant Wrigleyville From This Captivating Home!

Chicago Guest House Discover Vibrant Wrigleyville From This Captivating Home!

Chicago, IL
A garden is available at this guesthouse.
 
$139
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
Free WiFi in public areas is available at this guesthouse. Take advantage of the free self parking.
 

Gay Friendly Accommodation in Chicago

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Comfort Suites Michigan Avenue Loop

Comfort Suites Michigan Avenue Loop

3.0 out of 5.0 320 N. Michigan Avenue, Chicago, IL
4.4/5
(46 Reviews)
This aparthotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Self parking, express check-out, and dry cleaning are also offered.
 
$99
Best Western Plus Hawthorne Terrace Hotel

Best Western Plus Hawthorne Terrace Hotel

2.5 out of 5.0 3434 N. Broadway Avenue, Chicago, IL
4.4/5
(8 Reviews)
This hotel features a fitness center and a spa tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the sauna and free full breakfast each morning.
 
$119
Hyatt Regency McCormick Place

Hyatt Regency McCormick Place

4.0 out of 5.0 2233 S Martin Luther King Dr, Chicago, IL
4.1/5
(92 Reviews)
This eco-friendly hotel includes 3 restaurants, an indoor pool, and a 24-hour health club. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Unwind with a drink at one of the 2 bars/lounges and enjoy perks like a free casino shuttle.
 
$67
Hotel Versey Days Inn by Wyndham Chicago

Hotel Versey Days Inn by Wyndham Chicago

3.0 out of 5.0 644 West Diversey Parkway, Corner Diversey/Clark/Broadway, Chicago, IL
4.1/5
(79 Reviews)
This hotel features free WiFi in public areas, concierge services, and valet parking. Business travelers can take advantage of the laundry service. There's luggage storage and multilingual staff can provide around-the-clock assistance.
 
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Top Trending Hotels in Chicago

See all 2,596 Properties in Chicago
Eurostars Magnificent Mile, previously Dana Hotel $94
Eurostars Magnificent Mile, previously Dana Hotel

Eurostars Magnificent Mile, previously Dana Hotel

660 North State Street, Chicago, IL
     
    4.0 out of 5.0 Stars

    Located in River North, this spa hotel is steps from Chinese Consulate and State Street. Water Tower Place and Michigan Avenue are also within 10 minutes. Chicago Station (Red Line) and Grand Station (Red Line) are within a 5-minute walk.

    Warwick Allerton - Chicago $79
    Warwick Allerton - Chicago

    Warwick Allerton - Chicago

    701 North Michigan Avenue, Chicago, IL
       
      4.0 out of 5.0 Stars

      This family-friendly Chicago hotel is located in the entertainment district, just steps from Northwestern Memorial Hospital and Michigan Avenue. Chicago Water Tower and Water Tower Place are also within 5 minutes. Chicago Station (Red Line) is 6 minutes by foot and Grand Station (Red Line) is 8 minutes.

      Hyatt Regency Chicago $129
      Hyatt Regency Chicago

      Hyatt Regency Chicago

      151 East Wacker Dr, Chicago, IL
         
        4.0 out of 5.0 Stars

        Located in The Loop, this eco-friendly hotel is steps from Chicago Riverwalk and Michigan Avenue Bridge. Grant Park and Chicago Theatre are also within 10 minutes. State Station is 9 minutes by foot and Randolph-Wabash Station is 9 minutes.

        Radisson Blu Aqua Hotel Chicago $118
        Radisson Blu Aqua Hotel Chicago

        Radisson Blu Aqua Hotel Chicago

        221 N Columbus Dr, Chicago, IL
           
          4.5 out of 5.0 Stars

          Located in The Loop, this luxury hotel is within a 5-minute walk of Chicago Riverwalk, Grant Park, and Aon Center. Chicago Theatre and Chicago Cultural Center are also within 10 minutes. Randolph-Wabash Station is 8 minutes by foot and State Station is 8 minutes.

          *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.