
Apartment holiday rentals in North Side
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Top-rated apartment rentals in North Side
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Explore Chicago from an Urban Sanctuary with Free Parking
A vintage lovers dream! This loft was designed with a love for the past. Starting in the kitchen, you’ll see the beautiful zinc alloy countertops are complemented by gorgeous antique mirror backsplashes. You’ll have access to a stovetop, microwave, coffeemaker, as well as basic tools and kitchen supplies. There is a lovely throwback SMEG 50’s refrigerator and the shelves are all reclaimed wood. This antique lumber detail can be found throughout the loft, from the floors all the way to the night stands. The bathroom door may be recycled wood and the mirrors antique, but the shower fixtures are all Grohe. There is also a hair-dryer as well as complimentary toiletries and clean towels for your use. At the end of the day, you can sit on our funky wicker swing chair and think of all the chic guests who may have used the closet doors that were brought in from NY’s Plaza hotel! You’ll surely have the sweetest of dreams when you go to sleep on the memory foam mattress following a quick binge using the complimentary netflix. Additional amenities include self-controlled A/C and closet space with hangers, an iron and ironing board. This loft is very well kept, professionally cleaned and sanitized after each and every use. When booking this studio you will have full and private access to the entire apartment. There is a shared deck and lounge area you are welcome to use. For your convenience, we have arranged luggage drop-off/storage before and after your stay at the restaurant right down stairs - do note this is a courtesy. Our check-in and check-out process is automatic and seamless, once you book you will receive a private entry code ahead of your stay. Check-in any time after three pm as late as you'd like, check-out on or before 11 am. Due to our cleaning schedule we cannot accommodate early check-ins or late check-outs. The provided free parking spot is located a block away from the Airbnb unit Someone who’s offsite will be available as needed Set between South Old Irving and Kilbourn parks, the studio is located in one of Chicago's most historical neighborhoods. Sample the craft beer taverns and cocktail bars lining North Milwaukee Avenue. Wrigley Field is about 10 minutes away by car. The quickest and most inexpensive way to get around is via Uber or Lyft. If reaching the apartment by vehicle, there is free street parking in the surrounding neighborhood (please follow the local laws and signs). Public Transportation guide to the apartment: From Chicago O'Hare Int'l Airport: Take the Blue Train line to Irving Park Station and then transfer to the CTA #53 Milwaukee bus line to reach the apartment. You can also take the Blue Train line to Jefferson Park Station and then transfer to the CTA #56 Milwaukee bus line to reach the apartment. To/From Downtown Chicago: The CTA #56 Milwaukee bus is a very convenient and direct way to reach the Downtown Chicago Loop with a station just below the apartment. To/From Wrigley Field: Easily catch a game via the 77 or 152 buses, with a station just close by the apartment. Train and bus maps can be found and downloaded here: https://www.transitchicago.com/maps/ Please note that the provided free parking spot is located a block away from the Airbnb unit.
4.92 out of 5 average rating, 795 reviews
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.
4.99 out of 5 average rating, 111 reviews
Paradise on the Boulevard!
Amazing 2 bedroom garden apartment, located in the heart of the highly desirable Logan Square. This luxurious space with heated polished concrete floors & spa inspired bathroom is situated on the Historic Logan Boulevard, just steps from CTA Blue Line. Fabulous restaurants and coffee shops across the street. The apartment has a private entrance & access to a fabulous shared backyard space. The owner's treehouse deck can be reserved by request. Peace, convenience & excitement are right here.
4.99 out of 5 average rating, 108 reviews
Bright Apartment
Relax in this sunny one-bedroom garden apartment in Albany Park (best for guests under 6'2"). Ideally located between downtown Chicago and O’Hare, you can reach most places in 20–30 minutes. We’re just 5 minutes from the Montrose Blue Line, Kimball Brown Line, and I-90/94. Please note some areas have lower ceilings. Noise disclaimer: Our 100+ year-old home has lots of charm, and like many vintage buildings, you may hear some light neighbor noise—part of the authentic city living experience.
4.91 out of 5 average rating, 150 reviews
Cozy & Comfy 1bd In Historic Portage Park Bungalow
Make yourself at home in my comfortable Portage Park one bedroom garden apartment. This spacious condo is bright and airy with warm furnishings, a kitchenette with an island, private bedroom with a full bed and a modern bathroom with a glass walk-in shower. Portage Park is Chicago’s largest Polish neighborhood and is home to vintage charm, heaps of history and classic Chicago-style bungalows. The National Veterans Art Museum is a poignant must-see while you’re here with its combat-era art.
4.87 out of 5 average rating, 271 reviews
Modern 2 bdrm apt near O'hare-Downtown. King bed.
Step into the vibrant Gladstone Park neighborhood, a mere mile from the blue line. Picture yourself minutes away from O'Hare airport, the Rosemont Convention Center, Fashion Outlet mall, and the thrilling Rosemont Casino. Your spacious haven awaits – a sunny 2-bedroom, 1-bath apartment, brimming with all essential amenities. Feel the convenience with in-unit washer and dryer, hassle-free parking on-site, and free street parking. Don't miss out – book your stay now for a colorful experience.
4.87 out of 5 average rating, 149 reviews
An elegant Chicago Northside Getaway
Welcome to Bluebird Inn, an intimate, thoughtfully designed urban inn that will serve as an oasis as you embark on your exploration of Chicago. Nestled above the Long Room, a beloved neighborhood tavern and coffee house (Bad Johnny's, Nice Guy Food Co., Cash's Kitchen and AJ's Bakery & Diner), you can start your day downstairs with breakfast and coffee and stop in for a nitecap before heading up to retire for the evening. Settle in & enjoy the amenities and approachable luxury.
5.0 out of 5 average rating, 377 reviews
Comfortable Vintage North Side Retreat for 8
If you love Mid-Century Modern decor you will love this apartment. The light-filled main family room and sun porch is the perfect place to recharge after a long day of sightseeing. There are 3 bedrooms and a sofa that pulls out into a queen bed to comfortably accommodate 8 guests. A large dining table and functional kitchen means you have the option to cook in or dine out while exploring the city. I provide all the essentials to make your stay easy and comfortable.
4.92 out of 5 average rating, 258 reviews
Cozy Jefferson Park 2BR Apt
A lovely 2nd floor apartment flooded with natural light in a 2-unit building located in Jefferson Park. Conveniently located near O’hare airport, filled with small businesses, dive bars, and family-owned restaurants. Downtown Chicago will take 20-40 minutes, depending on traffic. My partner and I live in the unit below and can answer any questions you may have throughout your stay. We have created a warm and safe place for all to feel welcome!
4.94 out of 5 average rating, 143 reviews
Balcony • Near O’Hare + Transit
This upstairs 1‑bedroom apartment is your quiet, bright home base just 10 minutes from O’Hare Airport and near the Blue Line for easy city access. Enjoy a full kitchen, fast Wi‑Fi, king bed, and Smart TV for relaxing evenings. • Private balcony seating • Dedicated workspace & fast Wi‑Fi • King bed + blackout curtains • Self‑check‑in + private entrance While there’s no in‑unit laundry, optional wash‑and‑fold service ($25/load) is available.
4.94 out of 5 average rating, 305 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.
4.95 out of 5 average rating, 441 reviews
Vibrant & Chic Apt On Quiet St in Andersonville
Welcome to this thoughtfully remodeled 1925’s two-flat building located in the Second Coolest Neighborhood in the US. While this stylish space is the perfect relaxing stay, its location makes it easy for you to get around. *Free street parking You are only: 5 min walk to Clark St & Exceptional restaurants & bars 6 min drive to Lakefront & Lakeshore Drive... 17 min drive to Downtown Chicago...
4.98 out of 5 average rating, 239 reviewsPopular amenities for North Side apartment rentals
Weekly apartment rentals

Sun drenched 2 bedroom 1 bath with Kitchen & W/D
4.94 out of 5 average rating, 272 reviews
💙⚾️ 💙Great Apt, 3 miles West of Wrigley Field 💙⚾️💙
4.98 out of 5 average rating, 132 reviews
Sloth Apt • King Bed • Parking • Walk 2 Blue Line
4.98 out of 5 average rating, 108 reviews
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4.97 out of 5 average rating, 211 reviews
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4.93 out of 5 average rating, 175 reviews
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4.97 out of 5 average rating, 142 reviews
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King Sleep Number Bed – No Cleaning Fee
4.96 out of 5 average rating, 119 reviewsPrivate apartment rentals

Huge Pet Friendly East Albany Park Apartment
4.9 out of 5 average rating, 221 reviews
Modern 1-Bedroom w/ off-street parking space
4.94 out of 5 average rating, 143 reviews
Stylish 2BR Andersonville — Walk to Lake & Cafés
4.98 out of 5 average rating, 162 reviews
Charming 2 Bedroom Apartment w/Private Entrance
4.96 out of 5 average rating, 103 reviews
Relax & Walk to Wrigley Field from this Comfy Home
4.95 out of 5 average rating, 331 reviews
Cozy and Spacious! Logan Square Apartment
4.95 out of 5 average rating, 345 reviews
Cozy & Spacious Sunny 2 bedroom apartment.
4.98 out of 5 average rating, 113 reviews
Sunny Logan Square Artists' home
4.89 out of 5 average rating, 468 reviewsApartment rentals with a hot tub

Checkerboard Studio, Private Outdoor Hot Tub, Yard
4.86 out of 5 average rating, 537 reviews
33rd-Floor Penthouse with Breathtaking Views
4.83 out of 5 average rating, 145 reviews
The Velvet Manor | Luxe 3BR • Jacuzzi • Garage
5.0 out of 5 average rating, 5 reviews
Hygge Hideaway
5.0 out of 5 average rating, 50 reviews
Level One Bedroom Suite | Fulton Market
4.69 out of 5 average rating, 35 reviews
Spacious and Ideally located in the Lakeview area
5.0 out of 5 average rating, 5 reviews
Luxury 3BD Penthouse – Private Patio+Skyline Views
4.83 out of 5 average rating, 40 reviews
Stylish Unit in Wicker Park| Whirlpool Tub|Balcony
4.66 out of 5 average rating, 50 reviewsDestinations to explore
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