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Condo holiday rentals in North Side

Find and book unique condos on Airbnb

Top-rated condo rentals in North Side

Guests agree: These condos are highly rated for location, cleanliness and more.

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Superhost
A stylish living area features a gray sectional sofa and a caramel suede sofa set against a warm exposed brick wall. A round area rug adds color to the polished hardwood floor. A coffee table sits centrally, accompanied by a large plant near the window.
Condo in Chicago
4.89 out of 5 average rating, 115 reviews

Soft Suede and Warm Bricks at a Stylish Rogers Park Home

Dim the lights, play chilled tunes through the Bluetooth speakers, and snuggle up on the caramel suede sofa at this welcoming home. Wander the polished hardwood floors, pluck spices from the open shelving, and serve dinner on the kitchen island. Cleaning fee is $350 for stays of 30 days or less; additional Flat $150 per 30-days for longer term stays. Also, check out our other two listings in the building. Soft Leather & Warm Bricks in Stylish New Home: airbnb.com//h/softleather-warmbricks Soft Palate & Warm Bricks at a Rogers Park Home: airbnb.com//h/softpalate-warmbricks Meet NEW and CHARM with exposed brick,dim LED lighting,rainfall shower with bluetooth wiring, In-unit washer/dryer, open shelving, gourmet kitchen seats 6, stainless steel appliances, wood counters,5 range oven w/Broan hood, soft close cabinets,coffee machine or walk to Starbucks or french coral coffee around the corner. Grocery store(Jewel),Dry Cleaners(will provide you with a discount for staying at The Clark),UPS,Walgreens, Marshalls,LA Fitness, wine shop,Red Line, Metra, CTA Transportation,Evanston,Lake,Beaches, and Restaurants all in walking distance.Loyola and Northwestern 10 minutes away...Only bring your clothes and your ready to go! Free Wifi,Keyless Entry,Towels,Bedding,Ready to cook kitchen, 1 Free Parking space and $25 per diem for each additional vehicle. The entire unit is for your guests alone. Not a shared space. Reservations are set for(4) four people. Additional charges of $40 per person per diem applies. Space accommodates up to 6 guests. Chicago is an Amazing City and I'm here to answer and help out any way I can. Meeting guests upon their arrival is what helps guests become acclimated with the space and provides a sense of comfort. Of course, there are those moments that our schedules will have a conflict due to delayed arrivals with travel and guests will check in on their own, with a four digit code, of their choice. It’s a keyless entry that will allow guests to enter the building and unit smoothly. Guests will always be able to access us for whatever they need. Any issues that arise, need to book another day or two and questions about the city or for recommendations. The condo is five blocks from the lake with its beaches, bike paths, running, and peaceful places to read the morning paper with a cup of coffee. Walk just one street to the CTA Red Line train, which connects to virtually anywhere in the city. La Fitness is across the street for your convenience. Ohare international Airport-25 mins with light traffic. 45 mins with traffic. Take Mannheim Rd N to Thouy E to Clark N to property located on the left hand side. Midway Airport-25 min with light traffic. 45 mins with traffic. I55 N to Lake shore Drive/ (Route 41)N to Sheridan Rd to Howard W to Clark S to property located on the right hand side. Red Line (L Train-CTA) 1 block East of property Bus Line (CTA)-Outside in front of the property Metra -4 blocks North or South of property Kitchen area desk is equipped with a USB electrical outlet for your convenience, as well as all three bedrooms (north walls). Both bathrooms are equipped with Bluetooth to pair your music while getting ready.

Guest favourite
Condo in Chicago
4.86 out of 5 average rating, 245 reviews

The Bright Retreat in Andersonville

Stay in the heart of Andersonville when you book this bright, newly renovated condo. The home is one block from Clark Street near some of Chicago's best restaurants. It is 3 blocks from the Argyle Red Line stop, which will get you to Wrigley in 15 minutes and downtown in 30 minutes. The home includes a fully stocked kitchen, free parking spot (small and medium size cars and SUVs only, not large vehicles), in unit washer & dryer, queen-size bed, and couch with queen-size memory foam mattress.

Guest favourite
A spacious studio is showcased with a king-size bed positioned against a contrasting dark wall. Natural light filters through large windows, highlighting the exposed brick and the vintage stone fireplace. A mirrored wall accents the room, while a desk complements the seating area.
Condo in Chicago
4.94 out of 5 average rating, 276 reviews

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Guest favourite
A modern living area features a blue sectional sofa facing a mounted flat-screen TV. A wooden coffee table is positioned in front of the sofa. A desk and chair are situated near a large window, allowing natural light to brighten the room.
Condo in Chicago
4.87 out of 5 average rating, 158 reviews

Newly updated 1BD/1B in Old Irving Chicago!

Welcome to your home away from home in the heart of one of Chicago's safest and quietest neighborhoods! This beautifully updated 1 bedroom apartment offers everything you need for a comfortable and convenient stay. It is perfect for couples, solo travelers, and business visitors. Book now for a truly unforgettable experience in the Windy City! - 1 free parking spot - 400 MB Wifi - 2 smart T.V. with access to Netflix, Hulu, Amazon and more! - Desk - Easy app paid laundry in the building.

Superhost
The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.
Condo in Chicago
4.96 out of 5 average rating, 157 reviews

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Top Guest favourite
Condo in Chicago
4.99 out of 5 average rating, 299 reviews

Your Chicago Retreat

Enjoy this charming 3-bedroom condo with free on-site parking just three blocks from Lake Michigan. Convenient access to public transit, including the express bus to downtown (9 miles), Navy Pier, and Grant Park. The CTA Jarvis station is only three blocks away. Perfect for families, business travelers, and couples, this condo is also close to Loyola (1.5 miles) and Northwestern universities (2.5 miles). A great home base to explore all that Chicago has to offer!

Guest favourite
A spacious living area with large windows allows natural light to fill the room. A light-colored sectional sofa is complemented by two blue armchairs and a round coffee table. A neutral area rug anchors the space, creating a comfortable environment for relaxation.
Condo in Chicago
4.82 out of 5 average rating, 199 reviews

Alluring Condo w/ Pri. Prkng Cls to Transit &Beach

Our 3 bedroom and 2 bathroom condo has a perfect open layout for any size group that is traveling together. You'll have a ton of open space to share and feel at home, while also choosing from 3 bedrooms to get some privacy as well. Each bedroom has a queen size bed, while the master bedroom also has its own full size private bathroom. Feel free to stay in and cook with our fully equipped kitchen, enjoy the 65 inch Roku TV, and gather around the very large island.

Guest favourite
A living area features a leather sofa and two upholstered chairs, arranged around a glass coffee table. A brick accent wall provides character, while a large television sits atop a wooden console. Artworks adorn the walls, accompanied by natural light from the windows.
Condo in Chicago
4.79 out of 5 average rating, 305 reviews

Logan Square Beauty with 2 Bedrooms W/parking

Our two-bedroom condo is beautifully appointed and has vintage charm everywhere you look. You'll have access to a shared backyard, and all of the amenities of home - while being a 10 minute walk from some of the hottest bars and restaurants in Chicago. One garage parking spot is available during your stay. I provide all the essentials to make your stay easy and comfortable. Toilet paper, soaps, shampoos, towels, linens and even coffee and tea!

Top Guest favourite
Condo in Chicago
4.97 out of 5 average rating, 175 reviews

Chicago Oasis | Spa Bath, Patio & Fireplace

Experience the best of Chicago from this centrally located retreat just minutes from Downtown, top restaurants, shopping, and iconic attractions. Relax in a spa bathroom with a jetted tub and rain shower, cozy up by the fireplace, and enjoy a fully equipped kitchen. A king bedroom and queen Murphy bed comfortably accommodate up to 4 guests. Finish your evenings on the private patio gathered around the fire table.

Superhost
A vibrant living area is highlighted by a deep blue sofa and a colorful area rug. A large wall-mounted television is positioned across from the seating, and modern artwork decorates the walls. The adjoining kitchen is visible in the background, showcasing sleek cabinetry and new appliances.
Condo in Chicago
4.85 out of 5 average rating, 273 reviews

3D Tour! Designer Condo near Logan Square

Scan QR code in photos for a 3D Tour! What you’ll love: - Totally renovated garden unit, completed in 2021. Everything new. - Upscale furnishings & decor. - Gourmet, fully equipped kitchen w/ new appliances, coffee maker and spices. - Remote work station w/ super fast Wi-Fi (600mb). - Serta queen mattress in master. - Bunk beds w/ full and twin sized memory foam mattresses. - Heat & A/C.

Top Guest favourite
An open kitchen and dining area features exposed wooden beams and stylish light fixtures. A modern dining table with black chairs provides seating, while a lounge chair is positioned nearby. Decorative plants and art add warmth to the contemporary space.
Condo in Chicago
4.95 out of 5 average rating, 147 reviews

Modern Izakaya Studio in Wicker Park

The Izakaya Studio is a sleek, design-forward space in the heart of Wicker Park, with a secret whisky room inside. Inspired by the intimate atmosphere of a Japanese izakaya: warm, curated, a little unexpected. The kind of place where you settle in, pour something good, and stop thinking about your plans for a while. Spacious for a studio, and comfortable enough for a longer stay in Chicago.

Top Guest favourite
A bright living area is showcased with large windows allowing natural light. Red and orange artwork adorns the walls, while a gray ottoman centers the room. Seating consists of a gray sofa and an armchair with a geometric pattern, accompanied by decorative lamps on either side.
Condo in Chicago
4.97 out of 5 average rating, 490 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. We 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!

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