Holiday rentals in North Side

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Top-rated holiday rentals in North Side

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Guest favourite

Guest suite in Lincoln Square

5.0 out of 5 average rating, 297 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

Guest favourite

Flat in Lincoln Square

4.94 out of 5 average rating, 193 reviews

Spacious, light-drenched studio-private entrance!

Sun-filled private apartment in Lincoln Square! Spacious & well-appointed studio apartment features newly renovated kitchen and 1.5 baths (spa shower!) Located in the Lincoln Square neighborhood, you’ll be steps to restaurants, cafes, pubs & shopping. Close to CTA Brown Line (Rockwell) stop, as well as Western, Foster & Lawrence buses. Just 3.4 miles to Wrigley Field. One block to Swedish Covenant Hospital. Short bus/ride-share to Andersonville, Chicago Lakefront & Foster Beach! Kid friendly.

Guest favourite

Guest suite in Chicago

4.98 out of 5 average rating, 112 reviews

Gorgeous Studio 15 Minutes From Ohare!

Private, cozy and spacious studio apartment. This wonderful apartment is clean and ready to be your home away from home in Chicago! Full kitchen and bath! Spacious Backyard! Free Parking! On a beautiful treelined street in the Dunning neighborhood. Great for couples & business travelers! Close to great restaurants and parks, Rosemont Convention Center (10 minutes), O’ Hare Aiport (15 minutes), Downtown (35-45minutes). *Travel times are non rush hour and can increase depending on time/events*

Guest favourite

Flat in Avondale

4.97 out of 5 average rating, 120 reviews

Designer Avondale Attic

Soak in the beauty of this professionally designed and newly-renovated minimalistic attic in the heart of Chicago's most hip neighborhoods! Every detail of this home was thought through extensively to provide the perfect experience for our guests. Designer furniture, luxury soaps and amenities, a smart TV, high speed wifi, free laundry on site! A quick walk brings you to amazing coffee shops, trendy restaurants, or hop on the Blue Line train to help you get to any part of the city with ease.

Guest favourite

Guest suite in Logan Square

4.97 out of 5 average rating, 226 reviews

Private Suite w/ offstreet pkg, at Logan Sq Blu Ln

Cozy English garden apt (300 sq ft) w/ priv. entrance & free offstreet prking. 4 min walk to Blue Line. Brightly lit / high ceiling. Adjustable Tempupedic memory foam QUEEN bed plus futon in lvng rm. Kitchenette w/ mini-frig, Nespresso & Keurig, toastr ovn, microwv, and waffle maker w/maple syrp. Designer bath. 30+ restaur/bar nearby (see GUIDE BK in LOCATION). Self check-in. Flexible cancel. Early lugg. drop. A space to unwind in -- art-filled and artistic in design, NOT bland or IKEA like!

Guest favourite

Guest suite in Lincoln Square

4.95 out of 5 average rating, 243 reviews

Great location, private entry and patio!

Large 1 bedroom space tastefully decorated and well equipped. Sleeps 4 (5 with available inflatable). Queen bed in BR, full size futon in LR. Spacious enough for 2 to work comfortably. Use of the patio, fire pit and grill. Located in vibrant Lincoln Square. Steps to the Rockwell brown line el station, restaurants, a bagel shop, and yoga/massage studio. A few blocks away are shops, restaurants and a movie theater! Easy street parking with free permits. Level 2 EV charger available.

Guest favourite

Guest suite in Irving Park

4.99 out of 5 average rating, 138 reviews

BnB on Grace Street - Modern 2-Bedroom Guest Suite

Welcome to Bnb on Grace Street in the charming Old Irving Park neighborhood, in one of the original homes built in 1893! Our private guest suite is modern and recently renovated while highlighting original features of the home such as the exposed brick walls. It's just 2 blocks from a major highway and from the El Train blue line, from which you can travel into downtown or out to O'Hare Airport. The suite includes 2 bedrooms, 1 bathroom, a kitchenette/dining area, and living room.

Guest favourite

Flat in Wrigleyville

4.93 out of 5 average rating, 188 reviews

Taj Ma-small at Wrigley

I think you are just going to love my apartment. The space features wonderful large windows in both rooms and has all of the quirky charm that vintage buildings offer up. The location literally can't be beat, with the apartment a four-minute walk from Wrigley Field, the bustling Southport shopping corridor, and both the red line and brown line subway stations. It's also a walk to all of the 'Boystown' nightlife. There is no parking available with the apartment.

Superhost

Flat in East Rogers Park

4.89 out of 5 average rating, 106 reviews

LAKESIDE PIED `A TERRE STEPS TO BEACH

This gem is steps from Hartigan Beach, an eclectic mix of eateries, small theater venues, public transportation and Fine Wines & Spirits. You'll love my place because of the coziness and proximity to a swimming beach, on a friendly tree lined street. Conveniently situated between Loyola and Northwestern Universities. Rent a Divvy bike, call UBER/LYFT, rent a car and explore all that Evanston, Edgewater and Andersonville has to offer!

Guest favourite

Guest suite in Lincoln Square

4.94 out of 5 average rating, 178 reviews

Lincoln Square In-laws Suite: Private Entrance

Garden apartment room with private entrance and ensuite bathroom. All the amenities you'll need for either a work trip, city sightseeing, or just a comfy bed. Located in the vibrant Lincoln Square neighborhood. Only minutes away from the train. Fast wifi, and a large desk for working away from home. P.S. You will most likely find a few beers from a Chicago brewery in the fridge.

Guest favourite

Apartment in Lincoln Square

4.97 out of 5 average rating, 332 reviews

Lincoln Square Gem!

Very nice and updated condo in the heart of Lincoln Square! Lots of fun design elements and artwork await. This sunny condo is in the 2nd floor of a 2-flat building with friendly neighbors. My partner and I live on the first floor. You can walk to all that Lincoln Square has to offer! The Brown Line (Western stop) is just 2.5 blocks away for an easy commute to downtown!

Guest favourite

Flat in Portage Park

4.99 out of 5 average rating, 182 reviews

NW Chicago Apartment in Safe Neighborhood

We have a lower level apartment available located on the northwest side of Chicago. Our neighborhood is mostly Chicago style brick bungalows with plenty of free street parking available. We have easy access to public transportation, including a night owl bus (runs 24 hours) only 3 blocks away. We welcome guests from every culture and background.