House vacation rentals in North Side

A spacious kitchen features sleek black countertops and a large central island. Stainless steel appliances include a refrigerator and a gas range. Natural light enters through the windows, illuminating decorative plants and kitchen essentials arranged on shelves.

4.98 out of 5 average rating, 123 reviews

Flat in Lincoln Park 2-Flat Central to Everything

Historic, newly renovated flat in the heart of Lincoln Park, with garage! A block from the famous Blues club "Kingston Mines". Close to great bars and restaurants, including Alinea, the only restaurant in Chicago awarded 3 Michelin Stars. A mile to Lincoln Park Zoo, less than 1-1/2 miles to the lake. Beautiful yard (shared with lower unit) has gas grill, patio, deck, and a garage space. Enjoy the Lincoln Park area in this unique home that offers everything you need for your holiday in Chicago.

An inviting outdoor patio area features sleek white furniture, including a curved sofa and a coffee table atop a striped rug. A hammock is suspended nearby, surrounded by lush greenery and a wooden fence, with the warm glow of lights illuminating the space.

4.96 out of 5 average rating, 200 reviews

The Chicago River House – GIANT wall projector!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

4.83 out of 5 average rating, 107 reviews

Private Roofdeck! Location! Parking! Amazing home!

Large Bucktown home with plenty of space for the whole family! Your group will have the best stay in the perfect location to explore all that Chicago has to offer. Steps away from the 606 walking trail and one block from the Blue Line. This home is situated on a beautiful tree lined street with charming bungalows highlighting Bucktown architecture. The home offers 2 floors of living space with a large kitchen, dining room, living room and 3 bedrooms. Custom bath with w/d. Parking included!

A spacious living room features comfortable seating on soft gray furniture, including a large chaise and armchairs. Natural light brightens the area, while a gas fireplace is set within a stylish stone surround. A large flat-screen TV is mounted above the fireplace.

4.86 out of 5 average rating, 103 reviews

Entire house in Lakeview with yard and garage

Enjoy the luxury and privacy of a house all to yourself in Chicago's trendiest neighborhood. Very well maintained and furnished since this serves as my primary residence that I make available on Airbnb when I’m out of town. Around the corner there is a 7-Eleven and within a 10 minute walk you’ll find Target, Starbucks, Gym, Theaters, Restaurants, Bars, and much more. You can also easily walk to Wrigleyville, Boystown, or the train station which can take you downtown in under 20 minutes.

4.86 out of 5 average rating, 215 reviews

A stylish living area features a comfortable blue couch adorned with decorative pillows. A glass coffee table sits atop an area rug, surrounded by an array of colorful artwork on the walls. A cozy sleeping area is visible in the background, draped with vibrant blankets.

Home in Evanston

SW Evanston Private, Stylish, Spacious Suite

Comfort and convenience abound in this stylish suburban suite! Mid-century and vintage motif meets modern touches and style. Guests have the entire basement, with a private bedroom, bathroom, huge living space, and a private entrance in a quiet house on a beautiful treelined street. Backyard access, coffee, easy street parking. Walking distance to parks and public transportation, a short drive to downtown Evanston and the lakefront, easy access to Chicago, Northwestern. Loyola, Skokie.

Superhost

A spacious living area features a vibrant orange sofa adorned with green and beige throw blankets. A stylish coffee table holds decorative items, while a large houseplant adds a touch of greenery. Natural light fills the room, highlighting the wooden staircase in the background.

4.91 out of 5 average rating, 192 reviews

BoHo House | Chic, 1903 Chicago Workers Cottage

Welcome to BoHo House – a charming, airy bohemian gem built in 1903. This beautifully designed 3BR home is just a short walk from Chicago's popular bars, restaurants, and coffee shops. Enjoy the peaceful private fenced backyard, perfect for your pup to roam, complete with an adorable outdoor space. Host a cozy patio dinner by the fire or unwind indoors with a movie. Just 20 minutes from ORD, 10 minutes to downtown, with 800+ Mbps WiFi, free coffee, and secure 2-car garage parking!

A welcoming living area is presented with a mix of plush seating, including a white chair and a vibrant orange sofa. A wooden shelving unit displays decorative items and books. Soft lighting enhances the wooden floor, while light streams through large windows dressed with sheer coverings.

4.99 out of 5 average rating, 136 reviews

Entire first floor in Lincoln Square!

First floor of a restored 1903 Victorian in Lincoln Square. The home is spacious with high ceilings throughout and a very open feel. You'll have the whole 1st-floor with access to the backyard with chairs & fire pit. Two bedrooms and an office with additional sleeping options (ask me!). Large dining room & eat-in kitchen. Brand new kitchen & huge new bath! Many short-term rentals in this area are third-floor walk-ups. Make your life easier and stay on the first floor!

4.95 out of 5 average rating, 146 reviews

A modern kitchen features an island with seating for two and stainless steel appliances. White cabinetry contrasts with a dark backsplash, while large windows allow natural light to illuminate the workspace. The clean design promotes a functional and inviting cooking area.

Home in Elmhurst

Elmhurst NEW - Super Clean Modern Farmhouse!

Not your average Air BNB!!! 🏡 Newly renovated - CLEAN modern farmhouse in a great location! ✨ ✅Pet Friendly! 🐕 ✅15 min from O'hare. ✈ ✅25 min to Downtown Chicago 🏦 ✅Close to Grocery, restaurants, coffee, shopping, golf, expressways, down town Elmhurst ,Train and Oakbrook and Fashion Outlet Mall. ✅3 great sized bedrooms, 2 living area sofas converts into sleepers ✅Smart TV in family room and Master. ✅ Back patio with dining and seating ✅Large fenced in yard.

A stylish living space is highlighted by a brown leather sofa and a large area rug, with natural light streaming through the window. The modern kitchen is equipped with sleek black cabinetry and stainless steel appliances. Potted plants add a touch of greenery to the setting.

4.96 out of 5 average rating, 280 reviews

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

4.99 out of 5 average rating, 146 reviews

Whole apartment! 2 Bed/2 bath steps from Wrigley!!

Newly rehabbed urban nest among the tree-lined streets of beautiful East Lakeview. Literally 60 seconds to Wrigley Field, close to bars, restaurants, El train/busses, and lakefront. You’ll have loads of space in this 2 bed, 2 bath, plus office and large laundry room with FREE full size W/D. Free parking passes! Owner lives near by and is happy to help with anything you need to make your trip the best it can be. Flexible check in/out times upon request.

A modern kitchen and dining area features sleek cabinetry and a large window allowing natural light. A glass dining table with blue chairs is positioned centrally, adjacent to stainless steel appliances and counter space. Light hardwood flooring enhances the spacious look of the room.

4.96 out of 5 average rating, 123 reviews

Northside Chicago Getaway

This home is a classic Chicago bungalow that has been recently updated. There are some special features including whole home audio, a 75" TV with 9.1 Dolby atmosphere surround sound, a 3-person sauna, complete kitchen, fire pit out back and private parking for 2 cars. The Home is located in the Mayfair Park area of Chicago and offers a taste of the City life but also has a little space to breathe. Hope you enjoy it as much as I have over the years!

A stately Victorian house is surrounded by a landscaped garden featuring lush greenery and colorful plants. The front porch is framed by pillars and features multiple seating areas. A red front door adds a bold contrast to the dark exterior of the home.