Vacation rentals in Near North Side, Chicago
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Top-rated vacation rentals in Near North Side, Chicago
Guests agree: these stays are highly rated for location, cleanliness, and more.
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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 favourite
Apartment in Roscoe Village
4.95 out of 5 average rating, 242 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Guest favourite
Apartment in West Town
4.96 out of 5 average rating, 266 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Guest favourite
Apartment in Lincoln Park
4.99 out of 5 average rating, 197 reviewsExplore Lincoln Park from a Polished Apartment
Guest favourite
Guest suite in West Town
4.96 out of 5 average rating, 309 reviewsAugusta's Garden | Noble Square | Wicker Park
Guest favourite
Home in West Loop
4.97 out of 5 average rating, 318 reviewsCozy garden apartment historic Jackson Bvld.
Guest favourite
Guest suite in Logan Square
4.97 out of 5 average rating, 239 reviewsStylish Studio in Historic Logan Square
Guest favourite
Apartment in Humboldt Park
4.98 out of 5 average rating, 110 reviewsHumboldt Park Loft
Guest favourite
Apartment in Lincoln Square
4.94 out of 5 average rating, 193 reviewsSpacious, light-drenched studio-private entrance!
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
- Rentals with a sauna Near North Side
- Monthly Rentals Near North Side
- Rentals with a firepit Near North Side
- Apartment rentals Near North Side
- Rentals with an EV charger Near North Side
- Waterfront rentals Near North Side
- Rentals with a patio Near North Side
- Boutique hotel rentals Near North Side
- House rentals Near North Side
- Rentals with a washer and dryer Near North Side
- Rentals with breakfast Near North Side
- Rentals with a home theater Near North Side
- Rentals with beach access Near North Side
- Rentals with a hot tub Near North Side
- Rentals with outdoor seating Near North Side
- Pet-friendly rentals Near North Side
- Townhouse rentals Near North Side
- Rentals with pools Near North Side
- Rentals with lake access Near North Side
- Fitness-friendly rentals Near North Side
- Hotel rentals Near North Side
- Family-friendly rentals Near North Side
- Rentals with a fireplace Near North Side
- Condo rentals Near North Side
- Kid-friendly rentals Near North Side
- Loft rentals Near North Side
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