Condo vacation rentals in North Side

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Top-rated condo rentals in North Side

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Guest favorite

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

4.95 out of 5 average rating, 103 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 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. Free parking on Lawndale Ave.

Guest favorite

Condo in Chicago

4.89 out of 5 average rating, 111 reviews

Convenient & Spacious 3BR Condo w/Free Parking

Get cozy in this spacious 3-bedroom condo, conveniently located 3 blocks from the Halsted Orange Line overlooking Palmisano Park and only 5 minutes' drive to McCormick Place. Clean, neat, modern and comfortable, the condo offers spacious living space with an open kitchen, washer/dryer, and an outdoor balcony perfect for families and groups. Hungry? Our complex offers a few delicious high rated yelp restaurant options to fulfill your appetite. We look forward to hosting you and your guests!

Superhost

A bright and open dining area features a wooden table surrounded by multiple white chairs. Large windows allow natural light to fill the space, highlighting a modern living room setup with a green sofa and a decorative plant.

Condo in Chicago

4.8 out of 5 average rating, 160 reviews

Massive Old Town Home Steps to Wells St & Beach

Start your Windy City adventures in my spacious 3rd-floor duplex in the heart of Chicago's vibrant Old Town neighborhood! This 8 bed, 4 bath home comfortably sleeps up to 20 guests, making it perfect for large groups or families. Enjoy modern furnishings, a fully equipped kitchen and two cozy living areas to relax in after exploring the city. Steps from popular restaurants, bars, boutiques and the lake, you’ll be immersed in local charm. (Please note, parties and large events are not allowed)

Superhost

A spacious living room features a bright red sectional sofa arranged around a glass coffee table. Natural light floods in through multiple windows, while a decorative fireplace is positioned against the neutral-toned wall. Framed art enhances the atmosphere, creating a welcoming space for relaxation.

Condo in Chicago

4.92 out of 5 average rating, 153 reviews

Stunning, Spacious, & Sunny 2bed Uptown Condo

Welcome to your home away from home in Uptown! My bright and inviting condo offers a perfect blend of comfort and convenience, with your own sunny living room to relax, fully-equipped kitchen and separate dining room, spacious private bedroom, serene sunroom with full bed for extra guests, and a workspace for business travelers. Just steps from the lakefront and Montrose Beach, and a 6-minute walk to the Wilson Red Line, this location is excellent for exploring all that Chicago has to offer.

Guest favorite

A modern kitchen is equipped with sleek white cabinetry and a glossy black countertop. Stainless steel appliances, including a refrigerator and dishwasher, are visible. Ample natural light enters through a window with classic blinds, enhancing the spacious layout and functionality of the area.

Condo in Chicago

4.91 out of 5 average rating, 101 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

This bright and airy 2 bedroom/2 bath condo has been completely renovated with a designer’s eye and creative touch. The condo comes with 2 parking spaces in the adjacent private gated parking lot. The covered patio space on the back deck offers spectacular views of the Chicago skyline – enjoy your morning coffee or evening cocktail overlooking the city. L Train Stops & tons of restaurants, bars and entertainment within walking distance. Please contact me for discounts on monthly stays!

Guest favorite

A bright living area is illustrated with large windows allowing natural light to fill the space. A comfortable beige sectional sofa provides seating, while a wooden coffee table sits on an area rug. A desk with modern design and a chair are present, enhancing the workspace.

Condo in Chicago

4.92 out of 5 average rating, 113 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

Experience a calm and soothing stay in a space bathed with light and nestled amongst the trees. This top floor unit in a 3-flat condominium building offers you the serenity of a neighborhood with tree lined streets, and the convenience of being 3 miles from the heart of downtown Chicago. As a bonus, you're a 2min walk from public transportation. For something closer to home, Wicker Park and Humboldt Park offer great dining and culture steps away. We look forward to hosting you!

Guest favorite

Condo in Chicago

4.98 out of 5 average rating, 133 reviews

Luxurious River North 3BR/2BA- Free Onsite Parking

Experience an urban oasis unlike any other: - Complimentary parking for one vehicle in our attached lot - Spacious, recently renovated kitchen - Immersive entertainment with large-screen TVs - Unwind with a game of poker or foosball at our dedicated tables - Conveniently located within walking distance of the Magnificent Mile - Surrounded by an array of vibrant bars, restaurants, and nightlife - Embrace our inviting patio Indulge in a memorable stay at our 3rd-floor condo!

Guest favorite

A spacious living area features a grey sofa adorned with patterned pillows. Two blue accent chairs complement the glass coffee table, with a striped rug underneath. A colorful abstract artwork adorns the wall above the seating area, and a glimpse of the kitchen is visible in the background.

Condo in Chicago

4.91 out of 5 average rating, 148 reviews

Brilliant Downtown Chicago 3-Bedroom Condominium

Situated in downtown Chicago, right next to the Godfrey Hotel, this spacious and bright 3-bedroom, 2-bathroom condominium is perfectly suited to deliver the best adventures the Windy City has to offer. Our vacation home includes four sleeping areas with 1 King & 3 Queen sized memory foam mattresses and features everything from a fully-stocked kitchen to smart gadgets like Alexa. PARKING: We offer a $30 per day parking credit. This credit pays for most or all parking costs.

Guest favorite

The modern kitchen features sleek cabinets with wood accents and a large island. Stylish pendants hang above the island, which is complemented by gold bar stools. Stainless steel appliances and an elegant backsplash complete the gourmet kitchen setup, providing a functional and inviting space.

Condo in Chicago

4.98 out of 5 average rating, 160 reviews

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

Top guest favorite

A spacious bedroom is highlighted by a large bed with a soft gray blanket and multiple decorative pillows. Two windows allow natural light to fill the room, with a piece of framed artwork displayed on the wall. Wooden nightstands flank the bed.

Condo in Chicago

4.98 out of 5 average rating, 272 reviews

Near Lake Michigan & Wrigley Field

Available 2B/2B condo with 2 King Size Beds. One block from the Aragon Ballroom and Riviera with great views of Uptown and two blocks from Lake Michigan. It’s also a perfect place to stay if your in town for a Cubs game. You can see the stadium from the rooftop deck. Walking distance to everything you need, 2 train stations, groceries, gym, restaurants/ bars. The perfect place to come and go as you please with easy key code entry.

Guest favorite

The exterior of a three-story red brick building is displayed, showcasing large windows and a classic architectural style. A pathway leads to the entrance, flanked by greenery. The surrounding area features tree-lined streets, reflecting a vibrant neighborhood ambiance.

Condo in Chicago

4.83 out of 5 average rating, 339 reviews

Lively Wicker Park 2br, Steps to Damen Blue Line

Rehabbed 2BR 1BA garden unit in the very popular neighborhood of Wicker Park/Bucktown! 2 queen beds and full of amenities. Just a block from everything this neighborhood has to offer and 2 blocks from the 'L' to take you downtown or to O'hare Airport. Premium location to effortlessly walk from our quiet side street and be in the heart of all the entertainment! I provide all the essentials to make your stay easy and comfortable!

Top guest favorite

A classic Chicago 2-flat is presented, featuring brick construction and large windows. Steps lead to the entrance, surrounded by landscaped green areas, including shrubs and flowers. A low fence borders the property, providing a clear view of the well-maintained front yard.

Condo in Chicago

4.97 out of 5 average rating, 111 reviews

Steps from the Lake, Lovely 3-Bedroom Condo

Enjoy all that Chicago has to offer in this beautiful Edgewater home. Lakefront beaches are steps away, as is the red-line Granville stop. This condo is walking distance to the Loyola campus, many restaurants, grocery stores, gyms, antique stores, and more! There is ample street parking on Lakewood, often there is a space right outside the house. We provide daily parking passes for you to use during your stay.

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What guests are saying

Chic and Charming Vintage Condominium in Lincoln Park

4.84 out of 5 average rating, 354 reviews3 weeks ago

Colin's place is cute, clean, and VERY convenient! Just a short walk to the Fullerton or Armitage L stations. Tons of closeby restaurants, and a very good coffee shop/diner just downstairs below us! It is on a busy corner, so be warned the traffic & evening pedestrian noise can be loud, especially in the corner turret bedroom, but the heater makes pretty good white noise. Thanks for a perfect homebase for our girl weekend away!

Condo in Chicago

What guests are saying

A Stones Throw from U Chicago South Campus!

4.87 out of 5 average rating, 234 reviews2 weeks ago

Great location within walking distance of University of Chicago and in a safe neighbourhood. Basement apartment with 2 bedrooms. Bed was comfortable & extra pillows & blankets were provided. Toilet & kitchen facilities were slightly dated but functional. Appreciated the use of washer/dryer & complimentary coffee/tea. Very hospitable host!

Condo in Chicago

What guests are saying

Foosball, Steps from Wrigley, Private Parking

4.92 out of 5 average rating, 114 reviews1 day ago

We enjoyed our stay so much! This was our first time in Chicago and we were there primarily to watch the Cubs at Wrigley Field. This was the perfect location to walk to Wrigley Field. The home was beautiful and in a beautiful neighborhood. If we ever get to go back we will definitely stay here again.

Condo in Chicago

What guests are saying

RockStar Pad W3A BoysTown/Wrigley Field/Parking

4.99 out of 5 average rating, 163 reviewstoday

We had a great stay! The apartment is beautiful and comfortable. There are tons of nice touches throughout, and we definitely relaxed when we were there! The only issue we had is that ubers kept getting the wrong directions/address, but when we used the gyro shop as a pick up/drop off spot, we were fine. The location is in walking distance of Wrigley Field, and great restaurants and thrift shops, and public transit. Highly recommend this apartment if you are visiting Chicago!

Condo in Chicago

What guests are saying

Modern Luxury In Old Town - Sleeps 4

4.78 out of 5 average rating, 219 reviews3 weeks ago

What a perfect location and neighborhood! We were able to walk to the Lincoln Park Zoo, to Second City, and various wonderful bakeries and restaurants! We always felt safe, no matter the time of day or night. Robert was a very responsive host, but, honestly, we didn't need him for much.... his home was clean, pretty well-stocked, and the beds were very comfortable. I would definitely recommend this place!

Condo in Chicago

What guests are saying

Old Town Pied-à-Terre w/Pvt Terrace and Parking

4.91 out of 5 average rating, 289 reviews1 week ago

We knew going in that the only thing to worry about would be the garbage trucks, and as predicted by prior reviews, they came bright and early and were not easily drowned out by the sound of the white noise machines. But all told, this was a fantastic place to bunk for our family while we did a few days of exploring and catching up with local family members in the Chinatown area. We had more than enough space for our family of 4, and a very comfortable place to lay low while our 2 year old napped in the afternoons. We also were only a walk from downtown and Lincoln Park which was fantastic. Even better, there were many toys for our toddler and 7-year-old and that was an unexpected bonus. Given the benefits of the parking space, this place was a great find despite the early garbage truck visits :). Recommend for other families for sure!

Condo in Chicago

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