Holiday rentals in Near North Side, Chicago
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Top-rated holiday rentals in Near North Side, Chicago
Guests agree: these stays are highly rated for location, cleanliness and more.
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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
Rental unit in Roscoe Village
Roscoe Village One Bed Lux Apartment Near Wrigley
Guest favourite
Guest suite in Logan Square
Stylish Studio in Historic Logan Square
Guest favourite
Home in Pilsen Historic District
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
Guest favourite
Rental unit in Little Italy
Spacious 2BR on Quiet St - Free Park/Late Checkout
Guest favourite
Loft in Lake View
Lakeview Loft-Vintage Chicago, Modern Amenities
Guest favourite
Guest suite in Lincoln Square
Great location, private entry and patio!
Guest favourite
Guest suite in Lincoln Square
Private suite in Lincoln Square
Guest favourite
Rental unit in West Town
Turquoise Wonder - Clean, Cozy & Stylish Apt
Quick stats about holiday rentals in Near North Side, Chicago
Total rentals
1.5T 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
52T reviews
Destinations to explore
- Waterfront rentals Near North Side
- Flat rentals Near North Side
- Rentals with breakfast Near North Side
- Rentals with a cinema Near North Side
- Boutique hotel rentals Near North Side
- House rentals Near North Side
- Family-friendly rentals Near North Side
- Loft rentals Near North Side
- Fitness-friendly rentals Near North Side
- Pet-friendly rentals Near North Side
- Rentals with an EV charger Near North Side
- Monthly Rentals Near North Side
- Hotel rentals Near North Side
- Rentals with a firepit Near North Side
- Rentals with pools Near North Side
- Rentals with a sauna Near North Side
- Family-friendly rentals Near North Side
- Rentals with a washing machine and dryer Near North Side
- Rentals with a patio Near North Side
- Townhouse rentals Near North Side
- Rentals with beach access Near North Side
- Rentals with a fireplace Near North Side
- Apartment rentals Near North Side
- Rentals with a hot tub Near North Side
- Rentals with lake access Near North Side
- Rentals with outdoor seating Near North Side
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