Vacation rentals in North Side
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Top-rated vacation rentals in North Side
Guests agree: these stays are highly rated for location, cleanliness, and more.
Guest suite in Lincoln Square
5.0 out of 5 average rating, 290 reviewsPrivate Lincoln Square one bed+bath studio apt.
Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336
Sep. 15 – 22
Apartment in Uptown
4.97 out of 5 average rating, 260 reviewsCozy loft in Chicago's Uptown
Located in the heart of Uptown, we offer a private, 3rd floor/walk-up, smoke-free studio apartment in a vintage Queen Anne (hosts live on 1st floor; small family on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. New!Andersonville, recently voted the coolest neighborhood in US (Timeout’s survey) is only a 15-minute stroll. The CTA's Red Line/Wilson station is 3 blocks away. Overnight street-parking decals also available for guests.
Sep. 16 – 23
Guest suite in Portage Park
4.93 out of 5 average rating, 346 reviewsPeaceful Portage Park Apartment
You have the entire apartment all to yourself (kitchen, bathroom, 2 bedrooms and an office). Shared backyard. Portage park is located about halfway between O’hare airport and downtown. It is one of the safest neighborhoods in Chicago. Parking is easy! We’re 2 blocks away from a park (dog park, playground, walking/running path, tennis courts, indoor and Olympic sized outdoor pool). Fairly close to coffee shops and good places to eat We are family friendly House trained dogs are ok : $10/night
Mar. 5 – 12
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for North Side vacation rentals
Other great vacation rentals in North Side
Apartment in Lincoln Square
4.96 out of 5 average rating, 316 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Sep. 28 – Oct. 5
Guest suite in Chicago
4.95 out of 5 average rating, 238 reviewsGreat location, private entry and patio!
Oct. 28 – Nov. 4
Apartment in Andersonville
4.93 out of 5 average rating, 198 reviewsCharming Edgewater/Andersonville Garden 1 bdrm.
Jan. 28 – Feb. 4
Apartment in Park Ridge
4.79 out of 5 average rating, 309 reviewsModern Garden apartment (WHOLE UNIT)
Jul. 1 – 8
Guest suite in Logan Square
4.97 out of 5 average rating, 232 reviewsStylish Studio in Historic Logan Square
Aug. 26 – Sep. 2
Guest suite in Lake View
4.91 out of 5 average rating, 355 reviewsContemporary, private suite w fireplace
Feb. 3 – 10
Apartment in Logan Square
4.87 out of 5 average rating, 481 reviewsLogan Square Studio
Feb. 24 – Mar. 3
Guesthouse in Andersonville
4.91 out of 5 average rating, 339 reviewsPrivate, Charming, Coach House Loft in Andersonville
Oct. 2 – 9
Apartment in Chicago
4.93 out of 5 average rating, 377 reviewsRavenswood Guest House Annex
Feb. 2 – 9
Apartment in Logan Square
4.96 out of 5 average rating, 253 reviewsLogan Square 2nd Floor Chicago Victorian
Feb. 20 – 27
Guest suite in Chicago
4.98 out of 5 average rating, 132 reviewsBnB on Grace Street - Modern 2-Bedroom Guest Suite
Sep. 4 – 11
Guesthouse in West Town
4.9 out of 5 average rating, 145 reviewsCortez House - 2BR - Free Parking - Great Beds
Apr. 24 – May 1
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