Apartment holiday rentals in West Side
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Top-rated apartment rentals in West Side
Guests agree: these apartments are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for West Side apartment rentals
Weekly apartment rentals
Apartment in Oak Park
4.98 out of 5 average rating, 126 reviewsPicture Perfect 3Bed Steps from Train and FLW
Apartment in Near West Side
4.93 out of 5 average rating, 218 reviewsThe Upscale Getaway Near Downtown
Apartment in Chicago
4.86 out of 5 average rating, 192 reviewsBold Ukrainian Village 2 Bedroom w/Garage Parking
Apartment in Chicago
4.94 out of 5 average rating, 432 reviewsThe Penthouse Gallery at OHC - No Cleaning Fee!
Apartment in Chicago
4.91 out of 5 average rating, 122 reviewsSpacious & Modern Family Friendly North Center Apt
Apartment in Chicago
4.81 out of 5 average rating, 265 reviewsWelcoming 2BR in Chicago's Best Neighborhood!
Apartment in Chicago
4.95 out of 5 average rating, 129 reviewsThe Grand Kimball Lodge, Logan Square, Sleeps 14
Apartment in Albany Park
4.81 out of 5 average rating, 445 reviewsCozy Apartment with Free On-Site Parking
Pet-friendly apartment rentals
Apartment in Evanston
4.76 out of 5 average rating, 568 reviewsSpacious Evanston Unit - Walk to Northwestern U
Apartment in Chicago
4.93 out of 5 average rating, 187 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.
Apartment in Chicago
4.83 out of 5 average rating, 308 reviewsChic and Charming Vintage Condominium in Lincoln Park
Apartment in Lincoln Park
4.78 out of 5 average rating, 202 reviewsModern Luxury In Old Town - Sleeps 4
Apartment in Chicago
4.91 out of 5 average rating, 300 reviewsSusie's Space. 2BR easy parking & pet friendly
Apartment in Chicago
4.92 out of 5 average rating, 100 reviewsModern designed 2bed/2bath | Heart of Bronzeville!
Apartment in Chicago
4.82 out of 5 average rating, 188 reviewsChicago River West 4 Bedroom / 3 Bathroom
Apartment in Wicker Park
4.87 out of 5 average rating, 239 reviewsSpacious & Stylish Home at the ♥ of Wicker Park
Apartment rentals with a pool
Apartment in Chicago
4.74 out of 5 average rating, 147 reviewsCentral Downtown Location-Modern 2BR Condo
Apartment in Evanston
4.91 out of 5 average rating, 102 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Apartment in Lisle
4.95 out of 5 average rating, 44 reviewsPeaceful Condo in Lisle, Illinois
Apartment in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Apartment in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Apartment in Uptown
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Apartment in Chicago
4.7 out of 5 average rating, 27 reviews1 bedroom in the heart of downtown Chicago.
Room in Naperville
4.5 out of 5 average rating, 6 reviewsPrivate Bedroom with Private Bath - 2nd floor
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Apartment rentals Chicago
- Apartment rentals Chicago
- Apartment rentals Downtown Chicago
- Apartment rentals Milwaukee
- Apartment rentals Illinois
- Rentals with breakfast West Side
- Fitness-friendly rentals West Side
- Flat rentals West Side
- Rentals with a firepit West Side
- Monthly Rentals West Side
- Rentals with a hot tub West Side
- Waterfront rentals West Side
- Pet-friendly rentals West Side
- Smoking-friendly rentals West Side
- Rentals with an EV charger West Side
- Rentals with a sauna West Side
- Rentals with beach access West Side
- Loft rentals West Side
- Private suite rentals West Side
- Hotel rentals West Side
- Family-friendly rentals West Side
- Rentals with a cinema West Side
- Rentals with a washing machine and dryer West Side
- Rentals with pools West Side
- Rentals with outdoor seating West Side
- Rentals with a balcony West Side
- Rentals with a patio West Side
- Rentals with a fireplace West Side
- Guest house rentals West Side
- House rentals West Side
- Rentals with lake access West Side
- Townhouse rentals West Side
- Family-friendly rentals West Side
- Apartment rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom