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2026-06-04

2026-06-05

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Vacation Rentals in Chicago

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956 properties found

  • Cozy & Modern 3Br Apartment - Division 201W 301W Rep

    2153 West Division Street Apt 201W, Chicago, United States ( Show map )

    The spacious 2-bedroom Cozy & Modern 3Br Apartment - Division 201W 301W Rep Chicago lies 2.1 km from the live music venue "Congress Theater" and nearly…

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    From US$ 501
    price for 1 night
    Book Now From US$ 501
  • Chicago Charm

    2139 West Granville Avenue, Chicago, United States ( Show map )

    Situated 5 minutes' walk from Saint Henry Catholic Church, the spacious Chicago Charm Apartment looks out onto the garden. Loyola Lakefront Park is located 2.7…

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    From US$ 254
    price for 1 night
    Book Now From US$ 254
  • Avenir West Loop Penthouses With Iconic City Views

    730 North Milwaukee Avenue, Chicago, United States ( Show map )

    Offering a rooftop swimming pool, Avenir West Loop Penthouses With Iconic City Views Chicago apartment is located merely a 5-minute walk from Chicago Dramatists…

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    From US$ 354
    price for 1 night
    Book Now From US$ 354
  • Stunning Condo #2 - Downtown River North

    811 N Sedgwick St, Chicago, United States ( Show map )

    Situated within 25 minutes' walk of the super - tall skyscraper "Willis Tower", the 2-bedroom Stunning Condo #2 - Downtown River North Chicago villa features a…

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    From US$ 39
    price for 1 night
    Book Now From US$ 39
  • City-View Chicago 3-Br Rooftop

    1619 North Clybourn Avenue C, Chicago, United States ( Show map )

    The spacious 3-bedroom City-View Chicago 3-Br Rooftop apartment lies 2.5 km from the Holy Name Cathedral and around 5 minutes' walk from…

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    From US$ 949
    price for 1 night
    Book Now From US$ 949
  • Lincoln Park Apartment With Backyard!

    722 West Wrightwood Avenue, Chicago, United States ( Show map )

    To enjoy your vacation in Chicago, stay at the spacious Lincoln Park Apartment With Backyard! The Oak Magnificent Mile Street is 4.3 km away, while…

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    From US$ 204
    price for 1 night
    Book Now From US$ 204
  • The Black And White Suite

    611 East 41St Street, Chicago, United States ( Show map )

    Offering a location approximately a 25-minute walk from the Guaranteed Rate Field, the 4-bedroom The Black And White Suite Chicago villa gives access…

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    From US$ 313
    price for 1 night
    Book Now From US$ 313
  • La Villita - Gateway To Chicago

    2419 South Troy Street, Chicago, United States ( Show map )

    La Villita - Gateway To Chicago Apartment offers proximity to a number of tourist attractions, such as Our Lady of Tepeyac Parish, located approximately 5 minutes'…

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    From US$ 215
    price for 1 night
    Book Now From US$ 215
  • Condo Apartment Near Midway Airport

    5470 South Archer Avenue 1A, Chicago, United States ( Show map )

    The spacious Condo Apartment Near Midway Airport Chicago is located 3.1 km from Hawthorne Works Museum and 10 minutes by car from the Chicago Portage…

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    From US$ 130
    price for 1 night
    Book Now From US$ 130
  • Flexhome Ukrainian Village • 2Br • Walkable + Private Balcony - Sleeps 6

    908 N Damen Ave, Chicago, Il 60622, Usa, Chicago, United States ( Show map )

    The 55 m² Flexhome Ukrainian Village 2Br - Private Balcony & Walkable Location Chicago apartment offers easy access to such tourist sites as the Holy Trinity Orthodox…

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    From US$ 493
    price for 1 night
    Book Now From US$ 493
  • Chic & Updated Studio Apt In East Lakeview - Barry S1

    713 West Barry Avenue, Chicago, United States ( Show map )

    Located 3.1 km from the Chicago History Museum, Chic & Updated Studio Apt In East Lakeview - Barry S1 Chicago is 25 minutes' walk from a top…

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    From US$ 157
    price for 1 night
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  • 1Br Stylish Apartment, Perfect For Getaway - Oakdale 201

    West Oakdale Avenue 541, Chicago, United States ( Show map )

    The spacious 10-room 1Br Stylish Apartment, Perfect For Getaway - Oakdale 201 Chicago is situated just a 6-minute walk from the Brewster Building and…

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    From US$ 431
    price for 1 night
    Book Now From US$ 431
  • Wrigley Garden Unit

    820 W. Newport Ave, Chicago, United States ( Show map )

    The 1-room Wrigley Garden Unit Apartment Chicago lies approximately 800 metres from the Church of Our Lady of Mount Carmel and a mere 5…

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    From US$ 180
    price for 1 night
    Book Now From US$ 180
  • Designer Themed 4 Bedroom In Best Location With Patio And Fireplace

    329 West Schiller Street Back, Chicago, United States ( Show map )

    Located around 5 minutes' walk from Eva's Cafe, the 3-bedroom Designer Themed 4 Bedroom In Best Location With Patio And Fireplace Chicago villa gives…

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    From US$ 679
    price for 1 night
    Book Now From US$ 679
  • Spacious 5-Br Apt Next To Transit Free Parking

    1847 South Millard Avenue, Chicago, United States ( Show map )

    Spacious 5-Br Apt Next To Transit Free Parking Chicago is located a 12-minute stroll from Holly Spring Missionary Baptist Church and 3.4 km…

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    From US$ 376
    price for 1 night
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  • 2Br Airy & Tidy Apt With Free Covered Parking - Central Modern

    North Central Avenue 4722, Chicago, United States ( Show map )

    To enjoy your vacation in Chicago, stay at 2Br Airy & Tidy Apt With Free Covered Parking - Central Modern Chicago, which is only 1.3 km from…

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    From US$ 205
    price for 1 night
    Book Now From US$ 205
  • Retro 2 Bedroom Home 6 Mins To United Center With Parking

    408 South Hamlin Boulevard, Chicago, United States ( Show map )

    The spacious Retro 2 Bedroom Home 6 Mins To United Center With Parking Chicago apartment is located a 19-minute walk from the 184 - acre…

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    From US$ 238
    price for 1 night
    Book Now From US$ 238
  • Game Day Getaway - 3Br In Vibrant Wrigleyville

    3824 North Clark Street, Chicago, United States ( Show map )

    The spacious Game Day Getaway - 3Br In Vibrant Wrigleyville Chicago apartment offers easy access to such tourist sites as Grassroots, located a 6-minute walk…

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    From US$ 252
    price for 1 night
    Book Now From US$ 252
  • Modern 2 Bedroom In Avondale

    3137 North Monticello Avenue Apt 1, Chicago, United States ( Show map )

    The 56 m² Modern 2 Bedroom In Avondale Chicago apartment offers easy access to such tourist sites as Saint Wenceslaus Roman Catholic Church, located about…

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    From US$ 356
    price for 1 night
    Book Now From US$ 356
  • Penthouse Level, Stunning Wrigley Stay

    820 West Newport Avenue Unit 3, Chicago, United States ( Show map )

    Located approximately a 5-minute walk from Addison underground station, the 1-room Penthouse Level, Stunning Wrigley Stay Chicago apartment also boasts proximity to Lake…

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    From US$ 170
    price for 1 night
    Book Now From US$ 170