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2026-06-07

2026-06-08

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Chicago holiday rentals

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109 properties found

  • Pet-Friendly With Pool Table Walk To Wrigley Field

    1045 W Dakin St Unit 1, Chicago, United States ( Show map )

    Staying at Pet-Friendly With Pool Table Walk To Wrigley Field Villa Chicago, guests can visit the Boystown neighborhood, which is about a 20-minute…

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    From US$ 1249
    price for 1 night
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  • Spacious 3-Bed West Loop Townhouse, 1 Car Garage

    920 W Van Buren St, Chicago, United States ( Show map )

    Spacious 3-Bed West Loop Townhouse, 1 Car Garage Chicago villa offers proximity to nearby tourist spots, such as Chicago Symphony Center Concert Hall, situated…

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  • Spacious 3Br Urban Getaway W Gym

    2550 South Wabash Avenue, Chicago, United States ( Show map )

    Situated just 6 minutes' walk from Trinity Episcopal Church, Spacious 3Br Urban Getaway W Gym Chicago villa offers opportunities for cycling in the area. Midway…

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  • Chic 4-Bedroom Haven: Designer'S Dream Home

    2655 West Huron Street, Chicago, United States ( Show map )

    Chic 4-Bedroom Haven: Designer'S Dream Home Chicago offers easy access to such tourist spots as the Komoda building, located only a 5-minute walk…

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    From US$ 1155
    price for 1 night
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  • Modern 4 Bedroom Condo In Lakeview

    West Barry Avenue 2100, Chicago, United States ( Show map )

    Modern 4 Bedroom Condo In Lakeview Chicago villa offers quick access to such tourist spots as the Le Thrift Luxury Emporium, situated only a 5…

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  • Charming 5 Bedrooms 2 Bathrooms

    8027 South Kimbark Avenue, Chicago, United States ( Show map )

    Situated 4.6 km from the Frederick C. The Sprawling hands-on Museum of Science and Industry is located just a few steps from this accommodation…

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  • Personal Gym Luxury Balcony Condo

    5105 N East River Rd Unit 3F, Chicago, Il 60656, Usa, Chicago, United States ( Show map )

    The 1-bedroom Personal Gym Luxury Balcony Condo Chicago villa is located around 10 minutes by car from Rosemont Theatre, giving access to various tourist…

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    From US$ 233
    price for 1 night
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  • Game Room, Firepit, Playground, Gym, Billiard

    2146 N Kilpatrick Ave, Chicago, United States ( Show map )

    Located 4.4 km from the 184-acre Garfield Park Conservatory, Game Room, Firepit, Playground, Gym, Billiard Chicago villa gives access to various tourist sites in…

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  • 6 Mi To Dtwn: Dog-Friendly Condo W/ Hot Tub!

    4839 S Vincennes Ave Unit 2, Chicago, United States ( Show map )

    Situated only 6 minutes' stroll from Harold Washington Cultural Center, 6 Mi To Dtwn Dog-Friendly Condo With Hot Tub! The Sprawling hands-on Museum…

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    From US$ 362
    price for 1 night
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  • White Sox Best House

    3801 South Calumet Avenue, Chicago, United States ( Show map )

    Situated around 400 metres from Ida B Wells House, White Sox Best House Chicago villa offers easy access to numerous tourist spots in the area.

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    From US$ 162
    price for 1 night
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  • Breathtaking Downtown Penthouse A - Sleeps 11

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

    Breathtaking Downtown Penthouse A - Sleeps 11 Villa Chicago offers quick access to such tourist spots as the long-standing Carl Hammer Gallery, situated only a…

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    From US$ 329
    price for 1 night
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  • Chicago 1Br, Stylish Stay With Workspace

    3114 W Waveland Ave Unit 1A, Chicago, Il 60618, Usa, Chicago, United States ( Show map )

    Located about 25 minutes' walk from Riverview Plaza Shopping Center, the 1-bedroom Chicago 1Br, Stylish Stay With Workspace villa provides access to various tourist…

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  • Suite 2 On Southport 4 Queen Beds

    2501 North Southport Avenue, Chicago, United States ( Show map )

    Situated only a 6-minute stroll from Saint Josaphat Catholic Church, Suite 2 On Southport 4 Queen Beds Chicago villa offers quick access to numerous…

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    From US$ 614
    price for 1 night
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  • Huge Projector And Designated Workspace, Near Wrigley

    3116 W Waveland Ave, Unit 2B, Chicago, Il 60618, Usa, Chicago, United States ( Show map )

    Staying at the 1-bedroom Huge Projector And Designated Workspace, Near Wrigley Chicago villa, guests can easily reach the 35-acre beautifully landscaped Lincoln Park…

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    From US$ 992
    price for 1 night
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  • Extended Stay: Walk To Uic Campus & Train!

    1070 W 15Th St Unit 147, Chicago, United States ( Show map )

    To enjoy your vacation in Chicago, stay at the spacious 116 m² Extended Stay Walk To Uic Campus And Train! The apartment is 3.2 km…

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  • Luxe 4Br With Hot Tub & Game Room

    1654 West Ohio Street, Chicago, United States ( Show map )

    Staying at Luxe 4Br With Hot Tub & Game Room Chicago villa, guests can easily reach the RR #1 Chicago, located just 0.6 km away. The…

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    From US$ 967
    price for 1 night
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  • Chicago Home With Spacious Yard 14 Mi To Dtwn

    Chicago, United States ( Show map )

    Located only 1.7 km from the Historic Pullman Foundation Exhibit Hall, Chicago Home With Spacious Yard 14 Mi To Dtwn gives access to various tourist…

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    From US$ 112
    price for 1 night
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  • Cozy Wicker Park Home With Movie Room

    1523 North Artesian Avenue, Chicago, United States ( Show map )

    Located merely 6 minutes' walk from the Richard's Fabulous Finds, the 4-bedroom Cozy Wicker Park Home With Movie Room Chicago offers quick access to…

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  • Sleeps 18 • 8Br • Game Room • Gym • Theater

    4038 N Central Ave, Chicago, Il 60634, Usa, Chicago, United States ( Show map )

    Sleeps 18 • 8Br • Game Room • Gym • Theater Chicago villa offers quick access to such tourist spots as Romanian Eastern Orthodox Church of Saint Mary, situated…

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  • Hello Again, Chicago!

    1856 West Huron Street, Chicago, United States ( Show map )

    Situated just an 8-minute walk from the Shit Fountain, Hello Again, Chicago! The holiday home is in the immediate vicinity of the Oak Magnificent…

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    From US$ 719
    price for 1 night
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