Holiday rentals in Near North Side, Chicago
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Top-rated holiday rentals in Near North Side, Chicago
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Holiday rentals for every style
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Popular amenities for Near North Side, Chicago holiday rentals
Other great holiday rentals in Near North Side, Chicago
Guest favourite
Flat in Uptown
4.96 out of 5 average rating, 267 reviewsCozy loft in Chicago's Uptown
Guest favourite
Guest suite in Logan Square
4.97 out of 5 average rating, 226 reviewsPrivate Suite w/ offstreet pkg, at Logan Sq Blu Ln
Guest favourite
Loft in Lake View
4.96 out of 5 average rating, 422 reviewsLakeview Loft-Vintage Chicago, Modern Amenities
Guest favourite
Home in Bridgeport
4.95 out of 5 average rating, 123 reviewsCozy & Modern Chic Full House in Trendy Bridgeport
Guest favourite
Home in Uptown
4.9 out of 5 average rating, 334 reviewsPrivate 3rd Floor Apartment
Guest favourite
Home in Lake View
4.98 out of 5 average rating, 206 reviewsWrigleyville Southport Studio
Superhost
Flat in East Rogers Park
4.89 out of 5 average rating, 106 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
Guest favourite
Flat in Little Italy
4.98 out of 5 average rating, 199 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
Quick stats about holiday 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
- Pet-friendly rentals Near North Side
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- Waterfront rentals Near North Side
- Loft rentals Near North Side
- Rentals with breakfast Near North Side
- Rentals with a cinema Near North Side
- Rentals with an EV charger Near North Side
- Rentals with a washing machine and dryer Near North Side
- Family-friendly rentals Near North Side
- Flat rentals Near North Side
- Townhouse rentals Near North Side
- Rentals with a firepit Near North Side
- Rentals with lake access Near North Side
- Rentals with pools Near North Side
- Fitness-friendly rentals Near North Side
- Rentals with beach access Near North Side
- Rentals with a fireplace Near North Side
- Rentals with a patio Near North Side
- Monthly Rentals Near North Side
- Rentals with a hot tub Near North Side
- Apartment rentals Near North Side
- Rentals with outdoor seating Near North Side
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