Apartment holiday rentals in North Side
Find and book unique apartments on Airbnb
Top-rated apartment rentals in North Side
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 North Side apartment rentals
Weekly apartment rentals
Rental unit in Chicago
4.8 out of 5 average rating, 215 reviews⚡️NEW! Sunny & Cozy 3BDRM, 10min/ORD, 20min/DT❤️
Rental unit in Chicago
4.9 out of 5 average rating, 379 reviewsSunny Logan Square Artists' home
Rental unit in Chicago
4.98 out of 5 average rating, 283 reviewsAndersonville Cozy 1 bedroom basement suite
Rental unit in Chicago
4.84 out of 5 average rating, 335 reviewsDugout in Wrigleyville
Rental unit in Chicago
4.79 out of 5 average rating, 159 reviewsChicago Lincoln Park Getaway
Rental unit in Chicago
4.95 out of 5 average rating, 286 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Rental unit in Chicago
4.94 out of 5 average rating, 111 reviewsSunny, modern 1 bdrm apartment with lofted ceiling
Rental unit in Chicago
4.99 out of 5 average rating, 109 reviewsLuxury 2-story 2-bedroom 3-bath Lincoln Park Apt
Private apartment rentals
Rental unit in Chicago
4.89 out of 5 average rating, 150 reviewsComfortable, modern apartment 20 Min from Downtown
Rental unit in Chicago
4.89 out of 5 average rating, 122 reviewsBeautiful garden unit in Logan Square!
Rental unit in Chicago
4.95 out of 5 average rating, 231 reviewsEntire 1st Floor Apt near O'Hare/ORD & Blue Line
Rental unit in Chicago
4.9 out of 5 average rating, 170 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Rental unit in Chicago
4.91 out of 5 average rating, 409 reviewsThe Grotto of Logan Square
Rental unit in Chicago
4.93 out of 5 average rating, 197 reviewsCharming Apt. near Wrigley/Cubs, Ravenswood/Uptown
Rental unit in Chicago
4.96 out of 5 average rating, 233 reviewsPelotoning while Airbnb'ing in Chicago!
Rental unit in Chicago
4.87 out of 5 average rating, 179 reviewsLovely and Cozy Suite on Southport !
Apartment rentals with a hot tub
Rental unit in Chicago
4.81 out of 5 average rating, 69 reviewsQuiet but in the Heart of City walk Everywhere
Rental unit in Chicago
4.87 out of 5 average rating, 31 reviewsThe Areal Oasis
Rental unit in Chicago
4.88 out of 5 average rating, 50 reviewsSpacious Beautiful Condo
Rental unit in Chicago
4.85 out of 5 average rating, 53 reviewsPrivate Rooftop Views from Penthouse Suite
Rental unit in Chicago
5 out of 5 average rating, 20 reviewsSkyline Oasis: City & Lake Views
Rental unit in Chicago
5 out of 5 average rating, 21 reviewsLake, City, & River View Condo
Rental unit in Chicago
4.99 out of 5 average rating, 74 reviewsBelmont Pleasures - hot tub / arcade gaming room
Rental unit in Chicago
4.94 out of 5 average rating, 49 reviews420 friendly apt with 2 queens,1full roller,1 twin
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Saugatuck Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Bend Holiday rentals
- South Side Holiday rentals
- Schaumburg Holiday rentals
- Chicago Holiday rentals
- Serviced apartment rentals United States
- Flat rentals United States
- Flat rentals Chicago
- Flat rentals Downtown Chicago
- Flat rentals Milwaukee
- Flat rentals Illinois
- Rentals with outdoor seating North Side
- Smoking-friendly rentals North Side
- Townhouse rentals North Side
- Waterfront rentals North Side
- Rentals with a hot tub North Side
- House rentals North Side
- Rentals with a balcony North Side
- Monthly Rentals North Side
- Rentals with a firepit North Side
- Rentals with beach access North Side
- Bed and breakfasts North Side
- Rentals with an EV charger North Side
- Rentals with breakfast North Side
- Beachfront rentals North Side
- Rentals with a fireplace North Side
- Rentals with lake access North Side
- Rentals with a patio North Side
- Private suite rentals North Side
- Family-friendly rentals North Side
- Loft rentals North Side
- Hotel rentals North Side
- Rentals with pools North Side
- Fitness-friendly rentals North Side
- Apartment rentals North Side
- Rentals with a washing machine and dryer North Side
- Family-friendly rentals North Side
- Pet-friendly rentals North Side
- 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
- Things to do United States
- Art and culture United States
- Wellness United States
- Nature and outdoors United States
- Entertainment United States
- Sightseeing United States
- Food and drink United States
- Sports activities United States
- Things to do Illinois
- Art and culture Illinois
- Food and drink Illinois
- Sightseeing Illinois
- Things to do North Side