Apartment holiday rentals in Chicago
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Top-rated apartment rentals in Chicago
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago apartment rentals
Weekly apartment rentals
Rental unit in West Town
Spacious & private! Free parking! Great location!
Rental unit in Forest Park
Walk to Oak Park from Our Sunny Turn of the Century Apt
Rental unit in Andersonville
Andersonville Cozy 1 bedroom basement suite
Rental unit in Logan Square
Logan Square Studio
Rental unit in Chicago
La Cottage
Rental unit in West Town
Fully Furnished Apartment Wicker Park Free Parking
Rental unit in Andersonville
Sunny, Cozy, Colorful Andersonville
Rental unit in Logan Square
King Bed, Huge Spa Shower, Dining Destination
Private apartment rentals
Rental unit in East Rogers Park
Idyllic Lakefront Sanctuary W/ Unforgettable Vista
Rental unit in Logan Square
Modern Logan Square Apartment, steps from train!
Rental unit in Pilsen Historic District
Modern
Rental unit in Portage Park
Cozy & Comfy 1bd In Historic Portage Park Bungalow
Rental unit in Logan Square
Relaxed Bucktown/Wicker Park 1B Apt
Rental unit in Avondale
Cozy Avondale apt right by Belmont blue line stop
Rental unit in Irving Park
⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Rental unit in Wicker Park
Private Studio Apt in the Heart of Wicker Park!
Apartment rentals with a hot tub
Rental unit in West Town
Checkerboard Studio with Private Outdoor Hot Tub and Yard
Rental unit in Chicago
Skyline Serenity: Sauna, Hot Tub, Peloton, Views
Rental unit in Berwyn
“Dream slice of urban homesteading.”
Rental unit in West Loop
Cloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Rental unit in Logan Square
Luxe Suite + Spa House Retreat! Pets Welcome
Rental unit in Streeterville
Lake, City, & River View Condo
Rental unit in The Loop
The Areal Oasis
Rental unit in West Rogers Park
Spacious Beautiful Condo
Quick stats about apartment rentals in Chicago
Total rentals
5.9K properties
Rentals with dedicated workspaces
3.8K properties have a dedicated workspace
Rentals with a pool
750 properties have a pool
Pet-friendly rentals
2K properties allow pets
Family-friendly rentals
2.7K properties are a good fit for families
Total number of reviews
253K reviews
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
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Apartment rentals United States
- Serviced apartment rentals United States
- Rentals with a patio Chicago
- Rentals with beach access Chicago
- Fitness-friendly rentals Chicago
- Guesthouse rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Rentals with a sauna Chicago
- Lakehouse rentals Chicago
- Rentals with a fireplace Chicago
- Family-friendly rentals Chicago
- Bed and breakfasts Chicago
- Rentals with breakfast Chicago
- Rentals with a fire pit Chicago
- Mansion rentals Chicago
- Loft rentals Chicago
- Rentals with an EV charger Chicago
- Beachfront rentals Chicago
- Rentals with lake access Chicago
- House rentals Chicago
- Private suite rentals Chicago
- Rentals with pools Chicago
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- Rentals with an accessible height bed Chicago
- Smoking-friendly rentals Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with a balcony Chicago
- Kid-friendly rentals Chicago
- Monthly Rentals Chicago
- Boutique hotel rentals Chicago
- Waterfront rentals Chicago
- Townhouse rentals Chicago
- Rentals with a home theatre Chicago
- Rentals with outdoor seating Chicago
- Apartment rentals Downtown Chicago
- Apartment rentals Milwaukee
- Apartment rentals Lake Geneva
- Apartment rentals Illinois
- 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