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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

  • Lux Apts With Lake Views And Top Amenities

    1000M Apartments, Chicago, United States ( Show map )

    Conveniently located approximately a 25-minute walk from the Merchandise Mart, the 6-room Lux Apts With Lake Views And Top Amenities Chicago apartment offers…

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    From US$ 815
    price for 1 night
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  • Sleek 1-Bedroom Apt In Chicago - East Park Tower 0610 Rep

    5242 South Hyde Park Boulevard, Chicago, United States ( Show map )

    To enjoy your vacation in Chicago, stay at the 58 m² Sleek 1-Bedroom Apt In Chicago - East Park Tower 0610 Rep, which is 350…

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    From US$ 222
    price for 1 night
    Book Now From US$ 222
  • Cozy Beautiful Downtown Unit Chi In Prime River North Location Near Mag Mile - 1

    North Orleans Street 870, Chicago, United States ( Show map )

    The spacious 2-bedroom Cozy Beautiful Downtown Unit Chi In Prime River North Location Near Mag Mile - 1 Chicago apartment lies approximately 2 km from…

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    From US$ 583
    price for 1 night
    Book Now From US$ 583
  • Jeffjack Heated Pool Penthouse In Chicago'S West Loop

    601 West Jackson Boulevard, Chicago, United States ( Show map )

    The spacious 2-bedroom Jeffjack Heated Pool Penthouse In Chicago'S West Loop Apartment is located nearly a 25-minute walk from Millennium Public Park and…

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    From US$ 364
    price for 1 night
    Book Now From US$ 364
  • Beautifully Remodeled Second Floor Flat In River North - 2N

    North Orleans Street 858, Chicago, United States ( Show map )

    The 1-room Beautifully Remodeled Second Floor Flat In River North - 2N Chicago lies 2.4 km from Wrigley Building and just 10 minutes on foot…

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    From US$ 230
    price for 1 night
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  • Chateau De Woodlawn - Peaceful 3 Bedroom Apartment.

    6554 South Rhodes Avenue, Chicago, United States ( Show map )

    The 108 m² Chateau De Woodlawn - Peaceful 3 Bedroom Apartment. The leading research center "Oriental Institute Museum" is 2 km away, while Lincoln Memorial United…

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    From US$ 265
    price for 1 night
    Book Now From US$ 265
  • The Upscale Getaway Near Downtown

    2331 West Harrison Street Unit 3, Chicago, United States ( Show map )

    The 111 m² The Upscale Getaway Near Downtown Apartment Chicago is nestled in a residential area of Chicago, about 10 minutes' drive from the public…

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    From US$ 734
    price for 1 night
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  • Splendid & Fully Furnished 1Br Apartment - Broadway 204 Rep

    3122 North Broadway Apt 204, Chicago, United States ( Show map )

    To enjoy your vacation in Chicago, stay at the spacious 1-bedroom Splendid & Fully Furnished 1Br Apartment - Broadway 204 Rep Chicago, which is around 25…

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    From US$ 255
    price for 1 night
    Book Now From US$ 255
  • Uptown Gem

    1020 West Lawrence Avenue #522, Chicago, United States ( Show map )

    The 42 m² Uptown Gem Apartment Chicago includes a sunbathing terrace and is situated only a 5-minute walk from Paper Machete. Just 250 metres…

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    From US$ 521
    price for 1 night
    Book Now From US$ 521
  • Mccormick Place Amazing 2Br Suite With City View And Optional Parking For Up To 8 Guests Near Soldier Field And Lakefront Trail

    2036 South Michigan Avenue Apt 304, Chicago, United States ( Show map )

    To enjoy your vacation in Chicago, stay at the spacious 2-bedroom Mccormick Place Amazing 2Br Suite With City View And Optional Parking For Up…

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    From US$ 389
    price for 1 night
    Book Now From US$ 389
  • Comfortable 2Br Chicago Apt - Sunnyside 2F

    3150 West Sunnyside Avenue, Chicago, United States ( Show map )

    The spacious 84 m² Comfortable 2Br Chicago Apt - Sunnyside 2F lies 4.6 km from the baseball stadium "Wrigley Field" and merely a 5-minute stroll…

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    From US$ 201
    price for 1 night
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  • Stylish 1Br In Lakeview Chicago - Brompton 1 Rep

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

    Stylish 1Br In Lakeview Chicago - Brompton 1 Rep apartment lies within a 3-km distance of the 35-acre beautifully landscaped Lincoln Park Zoo and…

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    From US$ 332
    price for 1 night
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  • South Loop 3Br Group Comfort Near Downtown, Grant Park, Soldier Field And Mccormick Place

    2112 South Michigan Avenue Unit 4, Chicago, United States ( Show map )

    Situated merely 5 minutes' stroll from Cermak-McCormick Place underground station, the spacious 111 m² South Loop 3Br Group Comfort Near Downtown, Grant Park, Soldier…

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    From US$ 461
    price for 1 night
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  • Perfect Stay - Modern 2Br Unit - Barry Gb

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

    The spacious 102 m² Perfect Stay - Modern 2Br Unit - Barry Gb Chicago apartment lies within a 7-km distance of the Skydeck Chicago and only…

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  • 1Br Adorable Apt With In-Unit Laundry - Lake 206 Rep

    630 West Lake Street, Chicago, United States ( Show map )

    The spacious 1Br Adorable Apt With In-Unit Laundry - Lake 206 Rep Chicago is situated 6 minutes' walk from the Merchandise Mart and 20 km…

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    From US$ 579
    price for 1 night
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  • Perfect Wrigleyville Stay

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

    Staying at the 130 m² Perfect Wrigleyville Stay Chicago apartment, guests can visit Northalsted Market Days, located about 5 minutes' walk away. Just 450 m…

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    From US$ 600
    price for 1 night
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  • Chic 1 Bedroom W Parking

    33 South Ashland Avenue, Chicago, United States ( Show map )

    Located around 10 minutes' walk from Ashland underground station, Chic 1 Bedroom W Parking Chicago apartment also boasts proximity to The Spirit by by Omri &…

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    From US$ 126
    price for 1 night
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  • Indulging 2Br Apartment In Festive Boystown - Buckingham 1

    641 West Buckingham Place, Chicago, United States ( Show map )

    To enjoy your vacation in Chicago, stay at the spacious 1-bedroom Indulging 2Br Apartment In Festive Boystown - Buckingham 1 Chicago, which is around 7…

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    From US$ 170
    price for 1 night
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  • Bootlegger House Sleeps 10-20 Free Tv & Parking

    3153 North Pine Grove Avenue, Chicago, United States ( Show map )

    The 325 m² Bootlegger House Sleeps 10-20 Free Tv & Parking Apartment Chicago is located 11 minutes' walk from Briar Street Theatre and 1.1 km…

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    From US$ 633
    price for 1 night
    Book Now From US$ 633
  • The Wrigleyville Garden 200 Steps To Wrigley-2Br

    3618 North Racine Avenue B, Chicago, United States ( Show map )

    The Wrigleyville Garden 200 Steps To Wrigley-2Br Chicago apartment is located just 500 metres from Alta Vista Terrace District and just a 5-minute…

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    From US$ 136
    price for 1 night
    Book Now From US$ 136