Vacation rentals in Near North Side, Chicago
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Near North Side, Chicago
Guests agree: these stays are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Near North Side, Chicago vacation rentals
Other great vacation rentals in Near North Side, Chicago
Guest favorite
Apartment in Uptown
4.96 out of 5 average rating, 264 reviewsCozy loft in Chicago's Uptown
Oct 8 – 15
€ 135 per night
Guest favorite
Apartment in Wicker Park
4.95 out of 5 average rating, 171 reviewsWicker Park/Bucktown Location
Jul 10 – 17
€ 148 per night
Superhost
Apartment in West Town
4.92 out of 5 average rating, 326 reviewsBright, Modern Apartment in a Vintage Greystone
Dec 19 – 26
€ 182 per night
Guest favorite
Apartment in West Town
4.96 out of 5 average rating, 262 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Nov 3 – 10
€ 148 per night
Guest favorite
Apartment in Logan Square
4.96 out of 5 average rating, 255 reviewsLogan Square 2nd Floor Chicago Victorian
Feb 20 – 27
€ 153 per night
Guest favorite
Guesthouse in Roscoe Village
4.88 out of 5 average rating, 106 reviewsThe Roscoe Village Guesthouse
Feb 12 – 19
€ 138 per night
Superhost
Apartment in West Town
5.0 out of 5 average rating, 17 reviewsThe Secret West Loop Oasis/walk to Fulton market
Feb 1 – 8
€ 123 per night
Guest favorite
Guest suite in West Loop
4.91 out of 5 average rating, 80 reviewsCozy one-bedroom suite in the heart of West Loop
Jan 26 – Feb 2
€ 165 per night
Quick stats about vacation rentals in Near North Side, Chicago
Total rentals
1.5K properties
Rentals with dedicated workspaces
980 properties have a dedicated workspace
Rentals with a pool
720 properties have a pool
Pet-friendly rentals
750 properties allow pets
Family-friendly rentals
480 properties are a good fit for families
Total number of reviews
52K reviews
Destinations to explore
- Monthly Rentals Near North Side
- Townhouse rentals Near North Side
- Rentals with a sauna Near North Side
- Rentals with breakfast Near North Side
- Hotel rentals Near North Side
- Rentals with a washer and dryer Near North Side
- Rentals with a patio Near North Side
- Rentals with an EV charger Near North Side
- Fitness-friendly rentals Near North Side
- House rentals Near North Side
- Rentals with pools Near North Side
- Rentals with a hot tub Near North Side
- Kid-friendly rentals Near North Side
- Apartment rentals Near North Side
- Rentals with a fireplace Near North Side
- Pet-friendly rentals Near North Side
- Condo rentals Near North Side
- Boutique hotel rentals Near North Side
- Rentals with outdoor seating Near North Side
- Rentals with a fire pit Near North Side
- Rentals with beach access Near North Side
- Wheelchair accessible rentals Near North Side
- Beachfront rentals Near North Side
- Rentals with lake access Near North Side
- Loft rentals Near North Side
- Family-friendly rentals Near North Side
- Rentals with a home theater Near North Side
- Waterfront rentals Near 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