Vacation rentals in Near North Side, Chicago
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Top-rated vacation rentals in Near North Side, Chicago
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Vacation rentals for every style
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Popular amenities for Near North Side, Chicago vacation rentals
Other great vacation rentals in Near North Side, Chicago
Guest favorite
Condo in Little Italy
4.96 out of 5 average rating, 131 reviewsPrivate hot tub - King bed suite - Free parking
Guest favorite
Apartment in Lincoln Park
5.0 out of 5 average rating, 200 reviewsExplore Lincoln Park from a Polished Apartment
Guest favorite
Condo in Lincoln Park
4.96 out of 5 average rating, 448 reviewsUnique Lincoln Park Duplex Apt
Guest favorite
Loft in Lake View
4.96 out of 5 average rating, 425 reviewsLakeview Loft-Vintage Chicago, Modern Amenities
Guest favorite
Guest suite in North Center
4.96 out of 5 average rating, 107 reviewsModern Garden Apartment in Lincoln Square
Guest favorite
Apartment in Edgewater
4.99 out of 5 average rating, 108 reviewsNewly Renovated, Spacious 2BR in Andersonville
Guest favorite
Home in West Town
4.95 out of 5 average rating, 179 reviewsParadise on the Park
Guest favorite
Apartment in Wrigleyville
4.93 out of 5 average rating, 193 reviewsTaj Ma-small at Wrigley
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
- Fitness-friendly rentals Near North Side
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- Rentals with a fire pit Near North Side
- Pet-friendly rentals Near North Side
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- Townhouse rentals Near North Side
- Rentals with beach access Near North Side
- Family-friendly rentals Near North Side
- Rentals with pools Near North Side
- Rentals with a hot tub Near North Side
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