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 favorite
Apartment in West Town
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
Dec 3 – 10
G$28,599 GYD per night
Guest favorite
Apartment in Lincoln Park
4.83 out of 5 average rating, 208 reviewsCozy Lincoln Park Studio - Steps to Zoo!
Dec 5 – 12
G$29,599 GYD per night
Guest favorite
Loft in Lake View
4.96 out of 5 average rating, 416 reviewsLakeview Loft-Vintage Chicago, Modern Amenities
Feb 5 – 12
G$31,650 GYD per night
Guest favorite
Guest suite in Lincoln Square
4.91 out of 5 average rating, 419 reviewsCozy, Quiet, Garden Getaway!
Mar 17 – 24
G$21,413 GYD per night
Guest favorite
Condo in Lincoln Square
4.98 out of 5 average rating, 329 reviewsLincoln Square Gem!
Oct 4 – 11
G$30,183 GYD per night
Guest favorite
Apartment in Avondale
4.97 out of 5 average rating, 117 reviewsDesigner Avondale Attic
Jul 11 – 18
G$25,255 GYD per night
Guest favorite
Apartment in West Town
4.92 out of 5 average rating, 326 reviewsBright, Modern Apartment in a Vintage Greystone
Jan 16 – 23
G$29,649 GYD 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
Feb 25 – Mar 4
G$28,961 GYD 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
- Boutique hotel rentals Near North Side
- Townhouse rentals Near North Side
- Rentals with an EV charger Near North Side
- Rentals with beach access Near North Side
- Monthly Rentals Near North Side
- Rentals with a patio Near North Side
- Fitness-friendly rentals Near North Side
- Rentals with a hot tub Near North Side
- Hotel rentals Near North Side
- Rentals with a sauna Near North Side
- Rentals with lake access Near North Side
- Waterfront rentals Near North Side
- Condo rentals Near North Side
- House rentals Near North Side
- Rentals with outdoor seating Near North Side
- Wheelchair accessible rentals Near North Side
- Rentals with a fireplace Near North Side
- Pet-friendly rentals Near North Side
- Rentals with a fire pit Near North Side
- Rentals with a washer and dryer Near North Side
- Loft rentals Near North Side
- Rentals with pools Near North Side
- Family-friendly rentals Near North Side
- Rentals with a home theater Near North Side
- Apartment rentals Near North Side
- Rentals with breakfast Near North Side
- Beachfront rentals Near North Side
- Kid-friendly rentals Near North Side
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