Skokie Vacation Rentals
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$1,000+
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50 rentals in Skokie.
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Private Apartment With A Private Entrance To Our Cozy Newly Renovated Apartment
2 bedrooms
1 bathroom
Sleeps 4
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*Stylish & Spacious Getaway by Evanston/Skokie/NU
2 bedrooms
1 bathroom
Sleeps 5
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CHICAGO DOWNTOWN, CUBS- IN JUST 15 miles !!
2 bedrooms
1 bathroom
Sleeps 4
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Your home away from home! Best Location, Includes Breakfast! Free parking ideal!
4 bedrooms
2 bathrooms
Sleeps 11
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Heart of Oak Park, train ride to downtown Chicago. WIFI & Cable Included!
2 bedrooms
1 bathroom
Sleeps 5
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The entire FLAT. Stay Like You Own! Central AIR. TWO FULL BATHROOMS. Unique.
Edgewater, Magnolia Glen, Far North Side
2 bedrooms
2 bathrooms
Sleeps 5
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Soft Leather and Warm Bricks at a Stylish Rogers Park Home
Rogers Park, Far North Side
3 bedrooms
2 bathrooms
Sleeps 7
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Well-located Town Home for 6 People with Car Port And Private Entrance.
2 bedrooms
3 bathrooms
Sleeps 6
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Soft Suede and Warm Bricks at a Sylish Rogers Park Home
Rogers Park, Far North Side
3 bedrooms
2 bathrooms
Sleeps 8
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Mid Century Elegance in Evanston Vintage Apartment. WINTER SPECIAL!
3 bedrooms
2 bathrooms
Sleeps 6
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Retro Apartment in Andersonville
Andersonville, Edgewater, West Edgewater, Far North Side
2 bedrooms
1 bathroom
Sleeps 4
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Beautiful Chicago Mansion ~ 20 Minutes Downtown/O'Hare On Blue Line
Irving Park, Northwest Side
7 bedrooms
3 bathrooms
Sleeps 16
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Comfortable home in historic Oak Park- open For Thanksgiving and Christmas!!!
2 bedrooms
1 bathroom
Sleeps 4
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Sunny Jumbo Studio in the Heart of Oak Park
1 bedroom
1 bathroom
Sleeps 2
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Nice and cozy aptartment in two unit building. 20min from the airport. Sleeps 5!
Dunning, Northwest Side, Belmont Central
3 bedrooms
1 bathroom
Sleeps 5
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Charming apartment, fantastic location! Spacious 4 bedroom, a rare find!
4 bedrooms
1 bathroom
Sleeps 5
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2 other travelers have booked this property
Complete rehab, Easy transportation locale, Safe neighborhood
Northwest Side, Hermosa, Logan Square
2 bedrooms
1 bathroom
Sleeps 4
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Oak Park Beauty Sleeps 1 to 8 Guests
3 bedrooms
1 bathroom
Sleeps 6
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2 other travelers have booked this property
Beach House Chicago
Rogers Park, Far North Side
2 bedrooms
2 bathrooms
Sleeps 6
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1 other traveler has booked this property
Stunning New 6 Bedroom Home w/ Parking in Chicago (Superhosts)
Albany Park, Mayfair, Far North Side
6 bedrooms
4 bathrooms
Sleeps 14
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Peaceful Country Home near O’hare airport
3 bedrooms
2 bathrooms
Sleeps 10
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STYLISH, MODERN 3/1 APT .3 MILES FROM LINCOLN SQ! -GOATHOTE
Lincoln Square, Ravenswood, Far North Side
4 bedrooms
1 bathroom
Sleeps 8
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Condo
2 bedrooms
2 bathrooms
Sleeps 4
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Comfy Quarters
1 bedroom
2 bathrooms
Sleeps 2
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1 other traveler has booked this property
Newly Remodeled Modern Apartment
3 bedrooms
2 bathrooms
Sleeps 8
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Cute, cozy modern apartment 20 min ohare and midway airports and 30 min to dt
3 bedrooms
1 bathroom
Sleeps 6
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Modern 3 bedroom in Heart of Wrigleyville
Buena Park, Uptown, Far North Side
3 bedrooms
3 bathrooms
Sleeps 8
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Dorothy's Place
South Austin, West Side, Austin
3 bedrooms
1 bathroom
Sleeps 5
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Oak Park's Historic Getaway w/FHS
3 bedrooms
2 bathrooms
Sleeps 8
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Contemporart Celebrity themed private parking runs to downtown
South Austin, West Side, Austin
2 bedrooms
1 bathroom
Sleeps 4
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LUXE* TOWN HOUSE DUPLEX MIN FROM DOWNTOWN CHICAGO
Garfield Park, West Garfield Park, West Side
4 bedrooms
2 bathrooms
Sleeps 20
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Private Floor - 8 miles from ORD + Shopping/Food
Belmont Cragin, Northwest Side, Belmont Central
1 bedroom
1 bathroom
Sleeps 3
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5 Bedroom Oak Park Bungalow - 18 mins to city cntr
5 bedrooms
2 bathrooms
Sleeps 12
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Modern and Spacious 2bed/1bath apartment
West Ridge (West Rogers Park), Far North Side
2 bedrooms
1 bathroom
Sleeps 4
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Spacious homely feeling apartment in Jefferson Park
Albany Park, Far North Side
3 bedrooms
1 bathroom
Sleeps 5
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$99 +Chicago / Airport / Lake -in just 20 minutes!!
Jefferson Park, Far North Side
2 bedrooms
1 bathroom
Sleeps 6
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Heart of Evanston
2 bedrooms
1 bathroom
Sleeps 5
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1 other traveler has booked this property
Beautiful Fully Furnished Apartment, 20 minutes from Downtown Chicago.
1 bedroom
1 bathroom
Sleeps 4
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Fully Furnished and rehabbed townhouse with off-street parking and yard
3 bedrooms
2 bathrooms
Sleeps 6
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Eclectic Vibe - Oak Park/Forest Park, Pets OK
0 bedrooms
1 bathroom
Sleeps 3
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Private 1 Bdrm Suite w/Spa 25 Min Train Dwtn Chicago
1 bedroom
1 bathroom
Sleeps 2
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Beautiful and Quiet Space in North Side Chicago
Lincoln Square, Budlong Woods, Far North Side
3 bedrooms
1 bathroom
Sleeps 6
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ITALIAN garden apartment ! GREAT location ! Kids friendly!!
Old Irving Park, Northwest Side
1 bedroom
1 bathroom
Sleeps 5
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Entire Apartment with Complete Privacy Near O'hare
Far North Side
1 bedroom
1 bathroom
Sleeps 4
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Modern Victorian With Old World Charm
2 bedrooms
1 bathroom
Sleeps 6
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Governors Manor in Great Location with 6 Bedrooms
North Side, Logan Square
5 bedrooms
3 bathrooms
Sleeps 16
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Perfect Urban Hideaway Long Term Stays Welcome!
Edgewater Beach, Edgewater, Far North Side
3 bedrooms
1 bathroom
Sleeps 6
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Free Breakfast Buffet. Queen Suite in 'The Glen' | Staybridge
1 bedroom
1 bathroom
Sleeps 2
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Elegant, Urban Retreat, Child/Family Friendly!
3 bedrooms
1 bathroom
Sleeps 8
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