Apartment holiday rentals in Chicago
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Top-rated apartment rentals in Chicago
Guests agree: these apartments 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 Chicago apartment rentals
Weekly apartment rentals
Rental unit in Logan Square
Logan Square Studio
Rental unit in Edgewater
Ravenswood Guest House Annex
Rental unit in Lake View
Private Queen Bedroom and En Suite Bath
Rental unit in Forest Park
Walk to Oak Park from Our Sunny Turn of the Century Apt
Rental unit in West Town
Turquoise Wonder - Clean, Cozy & Stylish Apt
Rental unit in Irving Park
Spacious 1BR apartment in a central location
Rental unit in Logan Square
Logan Square 2nd Floor Chicago Victorian
Rental unit in Near North Side
Great Location Studio II
Private apartment rentals
Rental unit in Logan Square
Modern Logan Square Apartment, steps from train!
Rental unit in Irving Park
⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Rental unit in Berwyn
The Green Bungalow: Charming 1-BR apt. with patio
Rental unit in Avondale
Cozy Avondale apt right by Belmont blue line stop
Rental unit in Logan Square
Relaxed Bucktown/Wicker Park 1B Apt
Rental unit in Oak Park
Cozy and Character-Rich Chicago Style, Tv NFL PASS
Rental unit in Lake View
Private 2 Bedroom Malt Row, N Center, Wrigley Home
Rental unit in Avondale
Attic apartment in a hip neighborhood!
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 West Rogers Park
Spacious Beautiful Condo
Rental unit in The Loop
The Areal Oasis
Rental unit in Streeterville
Lake, City, & River View Condo
Quick stats about flat 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
- Serviced apartment rentals United States
- Flat rentals United States
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Lakehouse rentals Chicago
- Rentals with an EV charger Chicago
- Loft rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Family-friendly rentals Chicago
- Rentals with an accessible-height bed Chicago
- Monthly Rentals Chicago
- Fitness-friendly rentals Chicago
- Townhouse rentals Chicago
- Rentals with a balcony Chicago
- Smoking-friendly rentals Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Mansion rentals Chicago
- Rentals with a fireplace Chicago
- Private suite rentals Chicago
- Beachfront rentals Chicago
- House rentals Chicago
- Rentals with lake access Chicago
- Rentals with a sauna Chicago
- Rentals with pools Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Waterfront rentals Chicago
- Family-friendly rentals Chicago
- Bed and breakfasts Chicago
- Rentals with a patio Chicago
- Boutique hotel rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Rentals with beach access Chicago
- Flat rentals Downtown Chicago
- Flat rentals Milwaukee
- Flat rentals Lake Geneva
- Flat rentals Illinois
- Flat 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