Holiday homes & B&B in Chicago

Holiday rental deals in Chicago

We have selected the best vacation rentals in Chicago. Save money with Bluepillow by comparing the best deals from major travel websites in Chicago

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  130€

  Silversmith Hotel Chicago Downtown

  13.7 Exceptional (3222)

  • Hotel

  Located in The Loop, this hotel is within a 5-minute walk of Millennium Park and Art Institute of Chicago. CNA Center and Roosevelt University are also within 10 minutes. Madison-Wabash Station is only

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• from

  98€

  City Suites Hotel

  17 Exceptional (566)

  • Hotel

  Located in Lakeview, this hotel is within a 5-minute walk of Vic Theatre and Briar Street Theatre. Wrigley Field and DePaul University-Lincoln Park are also within 1 mile (2 km). Belmont Station (Red Line)

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• from

  164€

  Villa D' Citta

  18.6 Exceptional (36)

  • Hotel

  Located in Lincoln Park, this bed & breakfast is within a 10-minute walk of Lincoln Hall and DePaul University-Lincoln Park. Lincoln Park Zoo and Park West are also within 2 miles (3 km). Fullerton Station

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• from

  202€

  Wicker Park Inn

  10.3 Exceptional (238)

  • Hotel

  Located in Wicker Park, this bed & breakfast is within 3 mi (5 km) of United Center, John Hancock Center and Water Tower Place. Skydeck Ledge and University of Illinois Chicago are also within 6 mi (10

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• from

  139€

  Villa Dubois Guest House

  11.5 Exceptional (170)

  • Hotel

  Located in Bronzeville, this guesthouse is within 2 miles (3 km) of State Street, Illinois Institute of Technology and Guaranteed Rate Field. McCormick Place and Soldier Field are also within 3 miles (5

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• from

  321€

  LEVEL Chicago – Old Town

  13.2 Exceptional (109)

  • Hotel

  This family-friendly Chicago aparthotel is located near the beach, within a 15-minute walk of State Street, Second City and Michigan Avenue. John Hancock Center and Water Tower Place are also within 1

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Save on Bed & Breakfast in Chicago

Are you looking for an accommodation in Chicago and do you want to save money? Choose from 13 Bed & Breakfasts in Chicago

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  153€

  Ruby Room Inn

  10.3 Exceptional (403)

  • Hotel

  Featuring a garden, Ruby Room Inn is set in Chicago, 2.2 miles from United Center. The property is located 2.6 miles from Water Tower Chicago and 2.7 miles from Michigan Avenue. Free WiFi is included. At

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• from

  148€

  Hyde Park Chicago

  • 1 Guest · 1Bedroom

  Wicker Residential is located in the historical Wicker Park neighborhood here in Chicago, IL. Wicker Park is safe and beautiful location for visitors, tourist and long stays. If you don't mind me, explain:

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• from

  164€

  Villa D' Citta

  18.6 Exceptional (36)

  • Hotel

  Located in Lincoln Park, this bed & breakfast is within a 10-minute walk of Lincoln Hall and DePaul University-Lincoln Park. Lincoln Park Zoo and Park West are also within 2 miles (3 km). Fullerton Station

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• from

  202€

  Wicker Park Inn

  10.3 Exceptional (238)

  • Hotel

  Located in Wicker Park, this bed & breakfast is within 3 mi (5 km) of United Center, John Hancock Center and Water Tower Place. Skydeck Ledge and University of Illinois Chicago are also within 6 mi (10

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• from

  97€

  The Sono Chicago

  11.9 Exceptional (624)

  • Hotel

  One of our bestsellers in Chicago! The Sono Chicago is located in The Old Town neighborhood of Chicago. Lincoln Park Zoo is only 0.7 miles away. Parking is free with permit provided by The Sono Chicago. The

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• from

  105€

  Ray's Bucktown Bed and Breakfast

  12.6 Exceptional (349)

  • Hotel

  Located near numerous restaurants and shops in the Bucktown neighbourhood of Chicago, Ray's Bucktown features a communal sauna, free WiFi, and in-room breakfast service. Live entertainment at the Congress

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The best places to stay in Chicago

Book an apartment in Chicago and choose the right accommodation for your needs

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  76€

  Hotel Audrey

  8.8 Fabulous (1105)

  • Hotel

  Located on Chicago’s Magnificent Mile, this boutique hotel is 5 minutes' walk from Navy Pier. The hotel features a full-service restaurant, rooftop bar and coffee shop. Every modern room at Cambria

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  68€

  Hampton Inn Chicago Downtown/N Loop/Michigan Ave

  9 Exceptional (811)

  • Hotel

  One of our top picks in Chicago.Located in the heart of the city, Hampton Inn Chicago Downtown/N Loop/Michigan Ave is just 2 blocks away from Millennium Park. This hotel offers a 24-hour fitness centre

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  88€

  Loews Chicago Hotel

  9.3 Exceptional (699)

  • Hotel

  One of our top picks in Chicago.A rooftop lounge with views of the city skyline, on-site modern restaurant and a large indoor lap pool highlight the Loews Chicago Hotel. Located near the Chicago River,

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• from

  96€

  Hyatt Centric The Loop Chicago

  11.1 Exceptional (2729)

  • Hotel

  One of our top picks in Chicago.Situated in Chicago’s famed Theatre District, Hyatt Centric The Loop Chicago is within 10 minutes' walk of State Street shopping and the Art Institute of Chicago. This

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• from

  116€

  Ace Hotel Chicago

  12.7 Exceptional (744)

  • Hotel

  Situated among the bustling restaurant scene in the city’s West Loop neighborhood, this downtown Chicago hotel features on-site dining, a rooftop lounge and garden and contemporary guest rooms with free

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• from

  88€

  The Wheeler Mansion

  11.8 Exceptional (188)

  • Hotel

  This family-friendly Chicago hotel is located near the beach, within a 10-minute walk of Wintrust Arena, Glessner House Museum and McCormick Place. National Vietnam Veterans Art Museum is 0.4 mi (0.6 km)

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Nearby cities

• Carlyle
• Algonquin
• Savoy
• Woodland Hills
• Highland Park
• Naperville