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2026-06-29

2026-06-30
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Chicago holiday rentals

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240 results

  • Hidden Oasis In The Heart Of Lakeview

    From US$ 260

    648 W Oakdale Ave, Chicago, United States (To the map)

    To the hotel

    price for 1 night
    Book Now From US$ 260
  • Single Family Home With 3 Bedrooms Plus Attic With 2 Beds

    From US$ 264

    3036 North Gresham Avenue, Chicago, United States (To the map)

    To the hotel

    price for 1 night
    Book Now From US$ 264
  • Modern 4 Bedroom Condo In Lakeview

    West Barry Avenue 2100, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Gorgeous Wrigley Greystone

    West Cuyler Avenue 968, Chicago, United States (To the map)

    To the hotel

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

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

    To the hotel

    Book Now
  • Charming Belmont Heights Oasis Home

    From US$ 559

    3035 North Olcott Avenue Belmont Heights, Chicago, United States (To the map)

    To the hotel

    price for 1 night
    Book Now From US$ 559
  • Top 1 Rated 4Br Lincoln Park House - King Bed

    210 W St Paul Ave, Chicago, Il 60614, Usa, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Downtown Mich Ave - 6 Penthouses, Sleep 25

    820 South Michigan Avenue 1207, Chicago, United States (To the map)

    To the hotel

    Book Now
  • 1 Mi To Wrigley! Quintessential Chi-Town Greystone

    3622 N Hermitage Ave Unit 2, Chicago, United States (To the map)

    To the hotel

    Book Now
  • The Retreat - Hot Tub, Theater, Game Room, Fire Pit, Bar, Sleeps 14

    4505 North Harding Avenue, Chicago, United States (To the map)

    To the hotel

    Book Now
  • 4 Mi To Dtwn Chicago Modern Home With Outdoor Space

    Chicago, United States (To the map)

    To the hotel

    Book Now
  • Hello Again, Chicago!

    From US$ 719

    1856 West Huron Street, Chicago, United States (To the map)

    To the hotel

    price for 1 night
    Book Now From US$ 719
  • Pet-Friendly With Pool Table Walk To Wrigley Field

    From US$ 1249

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

    To the hotel

    price for 1 night
    Book Now From US$ 1249
  • 2 Newly Built Luxury Condos With Private Roofdeck

    From US$ 2399

    811 N Sedgwick St, Chicago, United States (To the map)

    To the hotel

    price for 1 night
    Book Now From US$ 2399
  • Commuter-Friendly Bungalow In Chicago'S South Side

    8817 S Merrill Ave, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Luxury Gold Coast Penthouse With Deck & Views

    22 East Elm Street, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Spacious 3-Bed West Loop Townhouse, 1 Car Garage

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

    To the hotel

    Book Now
  • Cozy + Home In Chicago W/ Sauna VIII

    1328 North Leavitt Street, Chicago, United States (To the map)

    The 4-bedroom Cozy + Home In Chicago W/ Sauna VIII is within 350 metres of Debonair Social Club, while The Art Institute of Chicago is approximately a 15-minute drive away. 4 bedrooms and 4 bathrooms…

    To the hotel

    Book Now
  • Modern Townhouse With Contemporary African Art

    719 East 40Th Street, Chicago, United States (To the map)

    To the hotel

    Book Now
  • Tulsa Twilight Terrace Stfrancis

    5829 East 64Th Street, Chicago, United States (To the map)

    To the hotel

    Book Now