Vacation rentals in North Side

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in North Side

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite

Guest suite in Lincoln Square

5.0 out of 5 average rating, 290 reviews

Private 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

$250 CAD per night
Guest favourite

Apartment in Uptown

4.97 out of 5 average rating, 260 reviews

Cozy 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

$189 CAD per night
Guest favourite

Guest suite in Portage Park

4.93 out of 5 average rating, 346 reviews

Peaceful 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

$205 CAD per night

Popular amenities for North Side vacation rentals

Other great vacation rentals in North Side

Guest favourite

Apartment in Lincoln Square

4.96 out of 5 average rating, 316 reviews

Bright family-friendly Lincoln Square 2-bed 1-bath

Sep. 28 – Oct. 5

$230 CAD per night
Guest favourite

Guest suite in Chicago

4.95 out of 5 average rating, 238 reviews

Great location, private entry and patio!

Oct. 28 – Nov. 4

$196 CAD per night
Guest favourite

Apartment in Andersonville

4.93 out of 5 average rating, 198 reviews

Charming Edgewater/Andersonville Garden 1 bdrm.

Jan. 28 – Feb. 4

$188 CAD per night
Superhost

Apartment in Park Ridge

4.79 out of 5 average rating, 309 reviews

Modern Garden apartment (WHOLE UNIT)

Jul. 1 – 8

$210 CAD per night
Guest favourite

Guest suite in Logan Square

4.97 out of 5 average rating, 232 reviews

Stylish Studio in Historic Logan Square

Aug. 26 – Sep. 2

$267 CAD per night
Guest favourite

Guest suite in Lake View

4.91 out of 5 average rating, 355 reviews

Contemporary, private suite w fireplace

Feb. 3 – 10

$137 CAD per night
Guest favourite

Apartment in Logan Square

4.87 out of 5 average rating, 481 reviews

Logan Square Studio

Feb. 24 – Mar. 3

$188 CAD per night
Guest favourite

Guesthouse in Andersonville

4.91 out of 5 average rating, 339 reviews

Private, Charming, Coach House Loft in Andersonville

Oct. 2 – 9

$272 CAD per night
Guest favourite

Apartment in Chicago

4.93 out of 5 average rating, 377 reviews

Ravenswood Guest House Annex

Feb. 2 – 9

$163 CAD per night
Guest favourite

Apartment in Logan Square

4.96 out of 5 average rating, 253 reviews

Logan Square 2nd Floor Chicago Victorian

Feb. 20 – 27

$198 CAD per night
Guest favourite

Guest suite in Chicago

4.98 out of 5 average rating, 132 reviews

BnB on Grace Street - Modern 2-Bedroom Guest Suite

Sep. 4 – 11

$224 CAD per night
Superhost

Guesthouse in West Town

4.9 out of 5 average rating, 145 reviews

Cortez House - 2BR - Free Parking - Great Beds

Apr. 24 – May 1

$209 CAD per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. North Side