House holiday rentals in Northwest Side
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Top-rated house rentals in Northwest Side
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Northwest Side
House rentals with a pool
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4.94 out of 5 average rating, 18 reviewsGlen Ellyn Home
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4.81 out of 5 average rating, 36 reviews30 mins to CHI*3 Kings*Fireplace*2 Desks*BBQ Grill
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4.86 out of 5 average rating, 29 reviews2Bed+2Bath PentHouse in South Loop
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4.94 out of 5 average rating, 35 reviewsWhole House with a Hot Tub!
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4.82 out of 5 average rating, 11 reviewsSchaumburg Oasis with a Pool and Hidden Garden
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New place to stayCity Close, Country Calm
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4.95 out of 5 average rating, 20 reviewsParadise 4BR w/ Pool & Games
Weekly house rentals
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4.9 out of 5 average rating, 48 reviews3BD/2BA Chicago Avondale/Logan Square House
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4.94 out of 5 average rating, 17 reviewsWrigley classic+trendy+2garage
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5 out of 5 average rating, 65 reviewsNo Cleaning Fee Private Apt. Parking Near Airport
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5 out of 5 average rating, 11 reviewsNEW! Large/Beautiful Home with 6BDS/4BTH + Garage!
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4.88 out of 5 average rating, 84 reviewsLuxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |
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4.82 out of 5 average rating, 62 reviewsLogan Square Portrait Room
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4.89 out of 5 average rating, 53 reviewsBrand New Spacious Duplex
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4.93 out of 5 average rating, 86 reviewsHistoric 1920s bungalow near Logan Square !
Private house rentals
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4.8 out of 5 average rating, 79 reviewsEntire 2 BR home w/ office, deck & no clean fee!
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4.98 out of 5 average rating, 84 reviewsCasita Rosalinda - 3BR/2BA Chicago Home
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4.88 out of 5 average rating, 90 reviewsA+amazing beauty, entire 2 BR Skokie historic stay
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4.93 out of 5 average rating, 28 reviewsEntire Home in Historic Logan Square
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4.96 out of 5 average rating, 46 reviewsCulinary DREAM - Pizza Oven/BBQ/Smoker
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4.97 out of 5 average rating, 79 reviewsModern Victorian Charm | A+ Location in OP
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5 out of 5 average rating, 33 reviewsOak Park - Wine House!
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4.97 out of 5 average rating, 99 reviewsUltra Modern, 2800 SQ Ft, Outdoor Gazebo Sleeps 14
Destinations to explore
- Downtown Chicago Holiday rentals
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