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  • Polk Street Coach House Apartment, Little Italy/Medical Dist

    Chicago, United States

    4.95

    Guesthouse

    Sleeps: 6
  • Urban Comfort in the Heart of Chicago

    Chicago, United States

    4.95

    Condo

    Sleeps: 4
  • Great location. Free parking.

    Chicago, United States

    4.85

    Condo

    Sleeps: 2
  • Best in Chicago, private, amazing garden space

    Chicago, United States

    4.75

    Entire place

    Sleeps: 5
  • Stunning Retro Apartment in Andersonville

    Chicago, United States

    4.80

    Entire place

    Sleeps: 4
  • Fully Furnished Apartment Wicker Park Free Parking

    Chicago, United States

    4.85

    Entire place

    Sleeps: 2
  • Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!

    Chicago, United States

    4.71

    Entire place

    Sleeps: 10
  • 2nd floor of 1908 brick two-flat in Logan Square

    Chicago, United States

    4.75

    Entire place

    Sleeps: 6
  • 2BR Bursting w/ Character in Hip Logan Square!

    Chicago, United States

    4.61

    Entire place

    Sleeps: 4
  • The Woodsman's Gallery at OHC - No Cleaning Fee!

    Chicago, United States

    4.57

    Entire place

    Sleeps: 6
  • Lakeview Loft-Vintage Chicago, Modern Amenities

    Chicago, United States

    4.80

    Loft

    Sleeps: 4
  • Restored Apartment in Historic Victorian Home

    Chicago, United States

    4.66

    Entire place

    Sleeps: 2
  • Unique Lincoln Park Duplex Apt

    Chicago, United States

    4.80

    Condo

    Sleeps: 2
  • Modern Chicago Loft with a Complimentary Garage Spot

    Chicago, United States

    4.61

    Entire place

    Sleeps: 2
  • The Penthouse Gallery at OHC - No Cleaning Fee!

    Chicago, United States

    4.71

    Condo

    Sleeps: 6
  • Explore Chicago from an Urban Sanctuary with Free Parking

    Chicago, United States

    4.61

    Entire place

    Sleeps: 2
  • King Bed, Huge Spa Shower, Dining Destination

    Chicago, United States

    4.80

    Entire place

    Sleeps: 4
  • Private suite in Lincoln Square

    Chicago, United States

    4.85

    Guest Suite

    Sleeps: 4
  • Peaceful River West Apt with free parking

    Chicago, United States

    4.90

    Entire place

    Sleeps: 4
  • Unwind in Style Steps from the Magnificent Mile

    Chicago, United States

    4.90

    Entire place

    Sleeps: 4
  • Top Floor Escape | Modern Amenities | Lush Garden

    Chicago, United States

    4.85

    Entire place

    Sleeps: 5
  • Private Lincoln Square Garden Apt

    Chicago, United States

    4.61

    Guest Suite

    Sleeps: 4
  • Cozy, Quiet, Garden Getaway!

    Chicago, United States

    4.57

    Guest Suite

    Sleeps: 2
  • Andersonville Living

    Chicago, United States

    4.61

    Entire place

    Sleeps: 6
  • Ravenswood Guest House Annex

    Chicago, United States

    4.66

    Entire place

    Sleeps: 4
  • Sophisticated Flat in Historic Building

    Chicago, United States

    4.80

    Entire place

    Sleeps: 2
  • Lincoln Square Gem!

    Chicago, United States

    4.85

    Condo

    Sleeps: 4
  • A Vintage Pink House in the Heart of Chicago

    Chicago, United States

    4.75

    Entire place

    Sleeps: 3
  • iKlektik House Chicago / Cardinal

    Chicago, United States

    4.57

    Entire place

    Sleeps: 4
  • Lovely, bright, 3-bedroom Avondale flat. Private.

    Chicago, United States

    4.80

    Entire place

    Sleeps: 5
  • Peaceful Portage Park Apartment

    Chicago, United States

    4.66

    Guest Suite

    Sleeps: 5
  • Charming, Spacious 3BR Lakeview Apt Near Transit

    Chicago, United States

    4.85

    Entire place

    Sleeps: 5
  • CLEAN Cozy Vintage Chicago Apartment near Downtown

    Chicago, United States

    4.66

    Entire place

    Sleeps: 4
  • Get Cozy at a Powder-Blue Residence in the Heart of Pilsen

    Chicago, United States

    4.75

    Entire place

    Sleeps: 4
  • Eclectic and Colorful Retro Apartment near Logan Square

    Chicago, United States

    4.75

    Entire place

    Sleeps: 6
  • Remodeled 2BR Pet Friendly Apartment Irving Park

    Chicago, United States

    5.00

    Entire place

    Sleeps: 6
  • Cozy Coach House

    Chicago, United States

    4.75

    Guesthouse

    Sleeps: 2
  • Lincoln Pk-parking-wifi-King bd-crib-kid friendly

    Chicago, United States

    4.90

    Entire place

    Sleeps: 4
  • Bright family-friendly Lincoln Square 2-bed 1-bath

    Chicago, United States

    4.80

    Entire place

    Sleeps: 5
  • Private Lincoln Square one bed+bath studio apt.

    Chicago, United States

    4.95

    Guest Suite

    Sleeps: 2
  • Cozy garden apartment historic Jackson Bvld.

    Chicago, United States

    4.90

    Entire place

    Sleeps: 2
  • Spacious Old Town Loft in a Great Location.

    Chicago, United States

    4.80

    Entire place

    Sleeps: 15
  • Lincoln Park/Lake View/Wrigley/Walk to El/Parking

    Chicago, United States

    4.85

    Entire place

    Sleeps: 4
  • Redesigned Lower Level Studio in Historic Building

    Chicago, United States

    4.90

    Entire place

    Sleeps: 4
  • Sunny Apartment Just 2 Blocks from Wrigley and Boystown

    Chicago, United States

    4.90

    Condo

    Sleeps: 4
  • Contemporary, private suite w fireplace

    Chicago, United States

    4.57

    Guest Suite

    Sleeps: 3
  • The Grotto of Logan Square

    Chicago, United States

    4.57

    Entire place

    Sleeps: 2
  • Bright, Modern Apartment in a Vintage Greystone

    Chicago, United States

    4.61

    Entire place

    Sleeps: 4
  • Amazing Penthouse Skyline Views!

    Chicago, United States

    4.66

    Entire place

    Sleeps: 14
  • The Craftsman Gallery at OHC - No Cleaning Fee!

    Chicago, United States

    4.57

    Entire place

    Sleeps: 8
  • Gorgeous, cozy 1-bedroom Suite in Andersonville

    Chicago, United States

    4.80

    Guest Suite

    Sleeps: 2
  • Wrigleyville 75 yards from Wrigley Field

    Chicago, United States

    4.66

    Entire place

    Sleeps: 10
  • Beautifully Renovated 2BR in Historic Lincoln Park

    Chicago, United States

    4.80

    Condo

    Sleeps: 5
  • Luxe, Private Suite w/Own Entrance-2023 Renovated

    Chicago, United States

    4.61

    Guest Suite

    Sleeps: 2
  • Secret Garden | Noble Square | Wicker Park

    Chicago, United States

    4.80

    Guest Suite

    Sleeps: 3
  • An elegant Chicago Northside Getaway

    Chicago, United States

    5.00

    Entire place

    Sleeps: 6
  • The Roscoe House near Wrigley Field

    Chicago, United States

    4.80

    Entire place

    Sleeps: 8
  • Pilsen Modernist, Creative, Lightfilled Loft

    Chicago, United States

    4.57

    Loft

    Sleeps: 3
  • Northside Chicago Favorite with parking!

    Chicago, United States

    4.95

    Condo

    Sleeps: 6
  • Private, Charming, Coach House Loft in Andersonville

    Chicago, United States

    4.57

    Guesthouse

    Sleeps: 2
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