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2026-02-28

2026-03-01

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Vacation Rentals in Chicago

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716 properties found

  • South Loop 3 Bedroom Apt

    1314 South Wabash Avenue, Chicago, United States ( Show map )

    South Loop 3 Bedroom Apt Chicago is located 2.3 km from the Skydeck Chicago and 25 minutes' walk from the scenic Chicago Riverwalk Walkway. Millennium…

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  • Exquisite Rogers Park 1 Bedroom, 1 Bath Apartment Near Evanston

    2324 West Touhy Avenue, Chicago, United States ( Show map )

    Exquisite Rogers Park 1 bedroom, 1 bath Apartment Near Evanston Chicago is also located around a 5-minute walk from Indian Boundary Park. Jarvis Beach…

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    From US$ 261
    price for 1 night
    Book Now From US$ 261
  • Boutique Garden House Chicago 3-Story Sleeps 12

    7131 South Michigan Avenue, Chicago, United States ( Show map )

    The 4-bedroom Boutique Garden House Chicago 3-Story Sleeps 12 offers proximity to nearby tourist spots, such as Oriental Institute Museum, situated 3.8 km…

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    From US$ 629
    price for 1 night
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  • Forrestville Ave Large Suite

    4510 South Forrestville Avenue, Chicago, United States ( Show map )

    The 1-room Forrestville Ave Large Suite lies in the Bronzeville district of Chicago and provides guests with Wi-Fi, and parking nearby. The 130…

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    From US$ 145
    price for 1 night
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  • Club Salon Sleeps 10-20 Free Parking & Tv

    3152 North Pine Grove Avenue, Chicago, United States ( Show map )

    Located a 25-minute walk from a shopping hub like Gallagher Way, the spacious 2-bedroom Club Salon Sleeps 10-20 Free Parking & Tv Apartment…

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    From US$ 326
    price for 1 night
    Book Now From US$ 326
  • Stylish & Bright Gem Overlooks Lovely Park With Great Amenities

    3850 West Diversey Avenue, Chicago, United States ( Show map )

    Staying at the spacious Bright Apt In Front Of Lovely Park - Logan Square Chicago, guests can relax on a patio only an 11-minute walk…

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    From US$ 201
    price for 1 night
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  • Parisian Retreat 6Min To Main Quandrangle U Of C

    6502 South Maryland Avenue 1, Chicago, United States ( Show map )

    The 1500 m^2 Parisian Retreat 6Min To Main Quandrangle U Of C Apartment Chicago offers proximity to such tourist attractions as Woodlawn Baptist Church…

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    From US$ 310
    price for 1 night
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  • Stylish Studio Apartment In Portage Park - Pensacola 2N

    5060 West Pensacola Avenue, Chicago, United States ( Show map )

    Located 10 minutes' stroll from Montrose underground station, Stylish Studio Apartment In Portage Park - Pensacola 2N Chicago also boasts proximity to Saint John's Lutheran Church.

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    From US$ 282
    price for 1 night
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  • Mccormick Place 3Br Luxury Penthouse Duplex With Personal Rooftop And Optional Parking For 8 Guests In Chicago South Loop

    2036 South Michigan Avenue 710, Chicago, United States ( Show map )

    The 2-room Mccormick Place 3Br Luxury Penthouse Duplex With Personal Rooftop And Optional Parking For 8 Guests In Chicago South Loop is located about…

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    From US$ 595
    price for 1 night
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  • Chicago 2Br City Escape With Optional Parking Near Mccormick Place, Navy Pier, Shedd Aquarium, And Millennium Park

    2112 South Michigan Avenue Unit 5, Chicago, United States ( Show map )

    Located 10 minutes by car from the Skydeck Chicago, the 88 m² Chicago 2Br City Escape With Optional Parking Near Mccormick Place, Navy Pier, Shedd…

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    From US$ 520
    price for 1 night
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  • Iklektik House // Robin

    2334 West Erie Street 2R, Chicago, United States ( Show map )

    Situated only an 8-minute walk from Holy Rosary Catholic Church, the 37 m^2 Iklektik House // Robin Apartment Chicago provides convenient access to numerous…

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    From US$ 461
    price for 1 night
    Book Now From US$ 461
  • Chic 2 Bedroom 1 Parking Sleeps 6

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

    To enjoy your vacation in Chicago, stay at the spacious 2-bedroom Chic 2 Bedroom 1 Parking Sleeps 6, which is around 10 minutes by…

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  • Afrique Francaise De Woodlawn 2

    6554 South Rhodes Avenue 2, Chicago, United States ( Show map )

    Located just 6 minutes' walk from first house of prayer, Afrique Francaise de Woodlawn 2 Apartment Chicago gives quick access to various tourist spots in…

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    From US$ 82
    price for 1 night
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  • Perfect Place To Enjoy The City Or Just Relax

    1902 South Sawyer Avenue, Chicago, United States ( Show map )

    To enjoy your vacation in Chicago, stay at the 93 m^2 Perfect Place To Enjoy The City Or Just Relax, which is just 1.2…

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    From US$ 107
    price for 1 night
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  • Modern Imd Condo - Workspace - Free Parking

    2329 West Harrison Street Unit 1, Chicago, United States ( Show map )

    The spacious 111 m² Modern Imd Condo - Workspace - Free Parking Chicago lies within a 6-km distance of the Buckingham Fountain and around a 10…

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    From US$ 216
    price for 1 night
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  • Stylish Cozy 3Br 420 Friendly Apartment With Gym Near Mccormick Place, Grant Park And Soldier Field

    2112 South Michigan Avenue Unit 3, Chicago, United States ( Show map )

    To enjoy your vacation in Chicago, stay at the spacious 2-bedroom Stylish Cozy 3Br 420 Friendly Apartment With Gym Near Mccormick Place, Grant Park…

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    From US$ 906
    price for 1 night
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  • 2 Bedroom Apt Near U Chicago Campus & The Lakefront!

    1024 E Hyde Park Blvd Apt 1S, Chicago, United States ( Show map )

    Overlooking the inner courtyard, 1-room 2 Bedroom Apt Near U Chicago Campus & The Lakefront! The Sprawling hands-on Museum of Science and Industry is…

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    From US$ 331
    price for 1 night
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  • Spacious South Loop 2Br Apartment Near Mccormick Place, Soldier Field & Downtown Chicago

    2036 South Michigan Avenue Unit 603, Chicago, United States ( Show map )

    Spacious South Loop 2Br Apartment Near Mccormick Place, Soldier Field & Downtown Chicago includes a patio and is situated a 5-minute walk from the indoor…

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    From US$ 1410
    price for 1 night
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  • Walk To Lake Michigan Chicago Apt With Deck

    3975 S Ellis Ave, Chicago, United States ( Show map )

    Walk To Lake Michigan Chicago Apt With Deck is located a 25-minute walk from Dorchester Commons Shopping Center and within a 900-metre distance…

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    From US$ 201
    price for 1 night
    Book Now From US$ 201
  • Group-Friendly 2Br With Optional Parking And Gym Access Near Mccormick Place And Soldier Field

    2036 South Michigan Avenue Unit 306, Chicago, United States ( Show map )

    The spacious 2-bedroom Group-Friendly 2Br With Optional Parking And Gym Access Near Mccormick Place And Soldier Field Chicago apartment provides swift access to…

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    From US$ 509
    price for 1 night
    Book Now From US$ 509