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Condo vacation rentals in Northwest Side

Find and book unique condos on Airbnb

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Popular amenities for Northwest Side condo rentals

Weekly condo rentals

Guest favorite
A back deck area is presented with two light brown lounge chairs positioned beside a small glass table. The surrounding greenery is visible, creating a natural view. The deck structure features wooden railings and a sunlight-drenched wood floor.
Condo in Chicago
4.93 out of 5 average rating, 68 reviews

Urban Oasis Getaway. 6 stops to downtown!

LydiaRating, 5 stars2 weeks ago
The hosts are great—very responsive and accommodating. It’s a lovely space, with a fully functioning kitchen and very walkable to a close cta stop that’s a quick 30 minutes downtown. Area around the place is lower income, so if you’re not used to being in a city, you maybe feel less comfortable. Would recommend if you’re comfortable with urban environments though!
Superhost
A welcoming porch area features a wooden deck with two minimalist chairs positioned for relaxation. Natural light filters in through large windows, highlighting the pleasing gray exterior. A decorative 'WELCOME' sign adds a friendly touch, inviting guests to enjoy the serene outdoor space.
Condo in Chicago
4.81 out of 5 average rating, 84 reviews

Apartment in Chicago

AlenaRating, 5 stars1 month ago
Me and my friends had a great time during our stay! The place was clean, well-kept, and in a great location—close to everything we needed. The host was very responsive and helpful throughout. Would definitely recommend!
Top guest favorite
A detailed map displays central Skokie, highlighting various locations such as restaurants and shops along major streets. Key landmarks are marked, including public transport routes and parks, indicating convenient access to amenities and attractions in the area.
Condo in Skokie
4.98 out of 5 average rating, 40 reviews

Free Parking Balcony, Weekly 5% & Monthly 20% Off

InesRating, 5 stars2 weeks ago
We enjoyed our stayed. The place was very clean and comfortable. Mark was great at communicating and accommodating. We would stay there again.
Superhost
A modern kitchen features dark wood cabinetry, stainless steel appliances, and a granite countertop. A gas stove, microwave, and refrigerator are included. A mosaic tile backsplash adds a subtle pattern above the sink area, which is complemented by a sleek faucet.
Condo in Chicago
4.78 out of 5 average rating, 9 reviews

Lincoln Square Condo

BenRating, 5 stars2 weeks ago
Allen's place is great, I stayed for five days and loved it! My highest compliment is that it's super well-equipped, to the point it feels lived-in (in a good way). For example, the kitchen is stocked better than mine, you'll find it easy to make a meal here. The rest of the unit is well thought out, too. My one piece of advice is to pay reallyyy close attention to the check-in instructions. There are multiple entrances to the complex, and they look similar. You might end up trying the wrong lockbox 10 times if you're not careful :) Overall, I highly recommend this place! Friendly neighbors as well!
Guest favorite
A plate of food is presented with a checkered paper liner featuring a hot dog topped with fresh tomatoes and green peppers. A side of crinkle-cut fries is positioned alongside the main dish. A can of beer is visible in the background.
Condo in Chicago
4.95 out of 5 average rating, 96 reviews

Spacious 3BR • Great for Groups • Fast WiFi • Pets

MarketaRating, 5 stars2 weeks ago
Sofia and Brendan were great hosts; very accommodating and on time with their communication. The kitchen was fully stocked with dishes, pots, pans and silverware. They even had a water pitcher to filter water which we greatly appreciated. Also some tea, coffee, creamer and snacks were available. The hosts added an additional bed to the extra sleeping area which was a really nice surprise as this was not visible on the pictures. Plenty of blankets and towels were provided. Aside from some pet hair getting stuck to our clothes from the furniture, the place was very clean and smelled great. Pets are noted on the website so that was not a too much of a surprise. Nothing that would prevent us from returning. But if you have pet allergies or this would bother you, something to note. The condo was about 20 minute walk to the metro. Overall, we were very happy with our stay and would absolutely return. Thank you Sofia and Brendan for a great stay!
Top guest favorite
The exterior of the condo is shown, featuring a well-maintained lawn and a private patio. A dining table and grill are visible on the patio, with a fence providing privacy. The structure has large windows and a distinct architectural design, surrounded by trees.
Condo in Chicago
5 out of 5 average rating, 76 reviews

Modern 2 Bedroom Walk Up Condo in Irving Park

CandaceRating, 5 stars8 months ago
I stayed here for 3 nights and was in town for the Chicago Marathon. Tons of restaurants within walking distance and the bus stop is a short walk, which will drop you at the Red Line train to get you downtown. Place was clean and very cute. Laundry room is a bonus!
Guest favorite
The exterior of a modern three-story condo is depicted, showcasing a facade of light-colored brick and large windows. Lush green leaves partially frame the top of the image, while a bright sky with scattered clouds forms the backdrop.
Condo in Chicago
4.93 out of 5 average rating, 61 reviews

Amazing Fun Condo, City view next to 606 Trail!

StephRating, 5 stars1 week ago
Ken’s place was a great stay! Such a unique home with so much to see inside—decor, art, photos, and trinkets. We enjoyed relaxing in the space between exploring the city. Would recommend to anyone who is considering staying in Chicago!
Top guest favorite
A coffee bar area features a sleek coffee machine and a pod system, neatly arranged on a granite countertop. Disposable cups and a variety of coffee pods are organized in trays, providing convenience for guests. Natural wood cabinetry complements the setup.
Condo in Chicago
5 out of 5 average rating, 28 reviews

Quick Drive to Downtown Chicago & Early Check-In

RoopaRating, 5 stars6 days ago
Thomas is an amazing host! He was very proactive in communicating right from the start of the trip ,was very welcoming and warm. This Airbnb house is spic and span. It is very clean , beautifully decorated and has everything you need to be comfortable in a home. The Kitchen is stocked with all vessels , has basic pantry supplies and has a gas for cooking warm meals. Thomas and his wife were also very thoughtful and considerate and left us a basket full of snacks and coffee pods - that was a really sweet gesture from their end.The coat closet has umbrellas , incase you need one , which I thought was very considerate as well. Thomas also regularly checked in on us to ensure we had a smooth stay - his check in and checkout instructions were uber clear and made it possible to check in and check out without any hassles. There is a starbucks and a bunch of small restaurants on a 10 - 13 min walk from the house.Overall , I would highly recommend his house to other guests.

Pet-friendly condo rentals

Superhost
A living area features two tufted gray sofas and a glass coffee table atop a patterned rug. The space is illuminated by natural light from large windows, with decorative accents including throw pillows and a cozy ottoman.
Condo in Chicago
4.83 out of 5 average rating, 362 reviews

Chic and Charming Vintage Condominium in Lincoln Park

PatrickRating, 5 stars2 weeks ago
We had a terrific stay and would definitely recommend it to others. Great location, especially if you are doing anything around Lincoln Park, DePaul, etc. The dedicated parking space was really helpful (there are 2 of them, but we only had one car). We had six people and were very comfortable. Colin is very responsive as well.
Guest favorite
A spacious living area is highlighted by large windows offering expansive views of the city skyline. A comfortable sofa and two accent chairs are positioned around a coffee table. A dining table with several chairs is visible beside a colorful wall art piece that adds a touch of personality.
Condo in Chicago
4.82 out of 5 average rating, 130 reviews

Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba

ErinRating, 5 stars1 week ago
We were staying in Chicago for a concert at Soldier Field. It was extremely walkable and easy to navigate. The condo is just right with the 2 bedrooms and king sized beds. The provided keurig coffee machine and coffee was nice. Easy walk to Roosevelt station for local transportation.
Top guest favorite
The entryway features a wooden door with a glass panel, leading to a cozy living space. Gray walls complement modern kitchen cabinetry and stainless steel appliances. A comfortable sofa, adorned with white pillows and a soft throw blanket, sits invitingly in the foreground. Decorative elements add character.
Condo in Chicago
4.99 out of 5 average rating, 178 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

RonniRating, 5 starstoday
Beautiful, clean unit and Will was extremely responsive and helpful. Super clean, and the beds and furniture were soooooo comfortable! It looks exactly as it does in the photos and there are so many items included, in case you forgot something! A foot massager?! Amazing 🤣The location is perfect with lots to do close by and no shortage of options for places to eat. I feel extremely fortunate that I came across this one and will definitely book again in the future. Just perfect.
Guest favorite
An open patio space features a light blue sofa adorned with decorative pillows in vibrant colors. A round wooden table sits nearby, complemented by a stylish green side table. Soft lighting from large windows enhances the cozy atmosphere of the room.
Condo in Chicago
4.94 out of 5 average rating, 126 reviews

Urban Oasis | Great for Families w/ Kids

MelissaRating, 5 stars4 days ago
Alex was very responsive and incredibly helpful throughout this process as it was our first time using Airbnb and in Chicago. The home was clean although there were a few areas that could use more of a deep clean. The neighborhood was very relaxed but there isn’t a ton to do (no coffee shops or any local shopping) However it’s only a 6 minute drive or 20 minute walk (we walked and it was really nice) to china town or just to view the river. We only stayed 3 nights and we definitely would stay again!
Superhost
A modern kitchen area features white cabinetry and a central island equipped with a sink and stools. Stainless steel appliances are visible alongside a decorative backsplash. Natural light fills the space through overhead lighting and a nearby entryway.
Condo in Chicago
4.87 out of 5 average rating, 119 reviews

Unique 2BR/2BA FREE Street Parking/WI-FI Near DT

AnneRating, 5 stars3 weeks ago
Excellent séjour en famille chez Cory. Il a été toujours très réactif à nos interrogations. Logement spacieux , confortable. Il été agréable de s’y reposer le soir après de longues marches dans Chicago. Nous recommandons vivement.
Guest favorite
A spacious living area features a sectional sofa in a deep blue hue and a round marble coffee table. A modern light fixture hangs above, while a small workspace with a blue chair is visible in the background. Light-colored walls create a calming ambiance.
Condo in Chicago
4.92 out of 5 average rating, 109 reviews

City Hideaway

ReneeRating, 5 stars2 weeks ago
A really cute, cozy apartment in a great location. Brock was wonderful and very responsive. There was always parking, and it was close to everything. Children upstairs were a bit noisy during the day but overall, my stay was enjoyable and I would definitely recommend the place.
Guest favorite
A modern three-story condominium is showcased, featuring a combination of dark and light brick with large windows. Soft lighting highlights the front entrance and landscaped gravel area, providing a contemporary appeal. Neighboring buildings are visible in the background, contributing to the urban atmosphere.
Condo in Chicago
4.91 out of 5 average rating, 163 reviews

Ultra clean/cozy condo, 10 mins south of Downtown!

AngeliqueRating, 5 stars2 weeks ago
Great host and great stay! Beautiful home. Thank you so much!
Top guest favorite
A vibrant seating area is showcased with a blue couch adorned with colorful throw pillows and a brown leather sofa. A small black coffee table rests on a patterned area rug, which features geometric designs. Large windows allow natural light to fill the space.
Condo in Chicago
4.97 out of 5 average rating, 117 reviews

Steps from the Lake, Lovely 3-Bedroom Condo

CherannRating, 5 stars2 weeks ago
Very close to public transit, grocery stores, and restaurants. Quiet neighborhood and comfortable sleeping.

Condo rentals with a pool

Guest favorite
An outdoor pool area is shown, featuring a clear blue pool surrounded by lounge chairs. Trees provide a touch of greenery, while a modern glass structure offers shaded seating. Sunshine reflects off the water, creating a bright and inviting atmosphere.
Condo in Evanston
4.96 out of 5 average rating, 97 reviews

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

AaronRating, 5 stars1 month ago
I would highly recommend Michelle's listing! The listing is spacious and perfect for a couple or small family (we had our <1 year old). Michelle is communicative, all the instructions are clear, and the location is convenient.
Guest favorite
Condo in Evanston
4.95 out of 5 average rating, 107 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

RemiRating, 5 stars1 month ago
Our Stay at The Bliss of Evanston was great. The host is very responsive and was very accommodating of our requests. The location and view can not be beat.
A serene bedroom is illuminated by soft purple lighting. A spacious bed with a polka dot blanket is centered in the room. Floor-to-ceiling glass doors reveal a view of a vibrant city skyline at night, with city lights twinkling in the background.
Condo in Chicago
4.4 out of 5 average rating, 10 reviews

voco: Balcony & City View

BrookeRating, 5 stars3 weeks ago
Our stay here worked out perfectly. The host was nice, and the location was centrally located to great shopping and restaurants. Very private and safe. The view at night was beautiful.
An outdoor pool area features a clear, blue body of water surrounded by lounge chairs. Lush greenery is placed in large planters along the perimeter, with a backdrop of modern high-rise buildings and a cloudy sky.
Condo in Chicago
4.33 out of 5 average rating, 9 reviews

30 E. Huron #2603 Private Residence

Diego HernanRating, 5 stars25 months ago
Incredible experience. Kevin was very nice and helped us with everything. I would go back again to this amazing apartment and great location.
A cozy living area is highlighted by a wood-burning fireplace, where a warm fire flickers. A sleek coffee table sits in front of a comfortable sectional sofa, complemented by a textured area rug. Two glasses of wine rest atop the table, adding a touch of relaxation.
Condo in Lombard
4.84 out of 5 average rating, 56 reviews

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

LelandRating, 5 stars5 months ago
Briana was responsive before, during and immediately after our stay, always seeking to ensure our comfort and satisfaction. We would have no reservations about staying with them again if they have an opening during a future visit to the area.
Guest favorite
The living area features a comfortable gray sofa facing a modern TV stand. A light rug lies beneath a white coffee table adorned with a small plant. Natural light filters through a large window, complemented by soft curtains. A desk and chair are positioned in the corner.
Condo in Elk Grove Village
4.94 out of 5 average rating, 85 reviews

Just remodeled apartment close to airport and mall

MeagRating, 5 stars2 months ago
I am incredibly particular with places I stay. This place was simple, very clean, had everything you would need to be comfortable. Bed was great! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️
Guest favorite
An outdoor swimming pool is surrounded by lounge chairs, offering a relaxing space. Trees are strategically placed around the area, and large glass walls provide views to the inside. Sunlight reflects off the water, enhancing the serene setting.
Condo in Evanston
4.91 out of 5 average rating, 126 reviews

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

FeiRating, 5 stars2 days ago
可以步行到西北大学,周边环境整洁舒适宜人。屋内设施齐全,很喜欢在厨房cooking。我们全家在这里度过了愉快的一周。下次还会入住。
Guest favorite
Condo in Evanston
4.96 out of 5 average rating, 100 reviews

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

AileenRating, 5 stars1 week ago
Space was clean and in a charming, walkable city. The view in the living room was beautiful. The neighbors were quiet. The coffee in the condo and in the lounge was surprisingly delightful. Our group of friends had a great time, and this would be a perfect place for a family.

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