Apartment holiday rentals in North Side

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Top-rated apartment rentals in North Side

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Guest favourite

Apartment in Portage Park

4.95 out of 5 average rating, 108 reviews

Comfortable, modern apartment 20 Min from Downtown

Welcome to Chicago! Whatever reason brings you to my lovely city, I'm sure my house will suit your every need. There are three units with separate entrees, out of which the first unit is for your own use; second unit is rented occasional. I live in the garden apartment, but will be rarely home. This modern unit has: -2 bedrooms 1 queen & 1 double bed -2 full bathroom -washer and a dryer -fully equipped kitchen - Wi Fi -50'' flat screen TV -central Air/Heat - back yard with porch -free parking

4–11 Jan

$264 NZD per night

Guest favourite

Apartment in Lincoln Square

4.94 out of 5 average rating, 191 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.

17–24 Jul

$251 NZD per night

Guest favourite

Apartment in West Town

4.98 out of 5 average rating, 219 reviews

Ukrainian Village Garden Retreat

A newly updated 1 bedroom, 1 bathroom apartment in Chicago's historic Ukrainian Village. Located a few blocks from Wicker Park, Ukrainian Village is a small historic district of Chicago filled with historic architecture. Access the apartment via a smart lock, the apartment includes everything you need for a comfortable stay, including a queen-sized bed, full kitchen, fiber high-speed internet (100+ Gbps up and down), smart TV, modern bathroom, in-unit washer & dryer, and free garage parking.

16–23 Jan

$315 NZD per night

Guest favourite

Apartment in Avondale

4.97 out of 5 average rating, 117 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.

6–13 Jul

$267 NZD per night

Guest favourite

Apartment in Chicago

4.9 out of 5 average rating, 257 reviews

Bright & Lofty Bucktown 1br

My top-floor apartment in Bucktown is the perfect space for your trip to Chicago! It's a stylish, modern rehab in a classic Chicago building, so you really see the best of what the city has to offer! It's just off beautiful Holstein Park, and easy walking distance to 2 Blue Line stops - so you can get to the Loop in under a half hour! And plenty of Logan Square favorites along Milwaukee are a 15 minute walk away - book today! Early Check-Ins and Late Check-Outs are difficult to accommodate.

8–15 Jan

$295 NZD per night

Guest favourite

Apartment in Irving Park

4.89 out of 5 average rating, 177 reviews

Historic Chicago neighborhood flat

Private one-bedroom apartment plus queen sleeper sofa in historic Ravenswood Manor. This unit is on the ground floor of a three-flat on a beautiful tree-lined street with plenty of free parking. Close to Brown Line - Francisco Stop - and lots of neighborhood parks. Close to Rockwell and Lincoln Square shopping and restaurants and next to Albany Park, one of Chicago’s most diverse neighborhoods. New fixtures, furniture, appliances, free shared laundry, access to backyard upon request.

6–13 Feb

$255 NZD per night

Guest favourite

Apartment in Chicago

4.96 out of 5 average rating, 238 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

5 Star Reviews! 1 Bedroom Apartment,King Bed, queen sofasleeper, OwnOcc. Bldg. Featuring Central Air, Private Balcony, Deluxe Kitchen Stainless Steel Appliances, Microwave, & More. 55" TV, Direct TV.This outstanding Location is steps from the Roscoe Village Business District and a quick walk to the Train Stop & Bus stops, to Downtown Chicago & United Center(Hawks & Bulls).Walk to Bars, Restaurants & Shops.All stays over 30 days will require Guests to Complete additional "Lease".,

30 Dec – 6 Jan

$239 NZD per night

Guest favourite

Apartment in Chicago

4.93 out of 5 average rating, 187 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.

17–24 Feb

$285 NZD per night

Guest favourite

Apartment in Uptown

4.96 out of 5 average rating, 266 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; apartment on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. Andersonville (one of Chicago’s coolest neighborhood is a 15-minute stroll. CTA's Red Line/Wilson train station is 3 blocks away. Overnight street-parking decals also available for guests.

14–21 Oct

$235 NZD per night

Superhost

Apartment in East Rogers Park

4.89 out of 5 average rating, 105 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!

21–28 Oct

$254 NZD per night

Guest favourite

Apartment in Lincoln Square

4.96 out of 5 average rating, 323 reviews

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

Light-filled, comfy 2-bed 1-bath apartment on a quiet, tree-lined street in Lincoln Square on Chicago's north side. Spacious kitchen stocked with essentials, washer/dryer, and your own private porch. Walk to cute local shops, cafes, grocery stores and the Rockwell brown line stop. Pet and kid-friendly (in one of the city's most family-friendly areas). Street parking is free, easy and doesn't require a permit.

12–19 Nov

$286 NZD per night

Guest favourite

Apartment in Chicago

4.99 out of 5 average rating, 181 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.

1–8 Sep

$268 NZD per night