Apartment holiday rentals in North Side

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.

4.96 out of 5 average rating, 140 reviews

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

BEST LOCATION IN LOGAN SQUARE/AVONDALE with garage parking! 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.

A cozy living area features exposed brick walls, a rustic wooden coffee table, and a large leather sofa. A flat-screen television is positioned in front of the seating, while natural light enters through the windows. A vintage fan rests nearby, and additional storage is provided by a bookshelf.

4.86 out of 5 average rating, 492 reviews

Humboldt Park Traveler's Lodge

Come stay at my gorgeous condo! Featuring exposed brick, a private entrance, stainless steel appliances, and a queen bed -> all on a quiet tree lined street! It's a perfect place to re-energize between big city adventures. Free street parking, and a 5 min walk to some of the best independently owned shops, restaurants, and bars in the city. Also, the massive and incredible Humboldt Park is also just a 5 min walk away! Please reach out for recommendations - I love giving them to people!

A spacious rooftop deck features comfortable wooden seating arranged around a circular table. The area is adorned with vibrant flowers and a decorative rug, all set against a sweeping view of the Chicago skyline under a soft blue sky.

4.94 out of 5 average rating, 189 reviews

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking

Escape into this spacious, Chicago Penthouse! Guests love this home because: - Surrounded by top-notch restaurants/retail - Close to all popular attractions that make Chicago so great - Luxurious, newly-renovated interior filled with natural light - Open-floor plan for entertaining! - Private, spacious roof deck viewing the entire Chicago skyline! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out - Designated parking spot! - Steps away from blue line Damen station (800 feet)

A modern kitchen features sleek gray cabinetry and stainless steel appliances, including a refrigerator and oven. A neutral area rug complements the wood flooring. Natural light is provided by large windows, and stylish wall decor adds a contemporary touch to the space.

4.98 out of 5 average rating, 224 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $10/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

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.

4.88 out of 5 average rating, 149 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.

The living area features exposed brick walls and hardwood floors, with an arrangement of seating including a red armchair and a cozy sofa. A glass coffee table sits on a plush area rug. A wall-mounted flat-screen TV is present, alongside indoor plants and decorative elements.

4.99 out of 5 average rating, 316 reviews

of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D

• 1,750ft² / 162m² . My home is on the second floor of a four flat Itallian Brick Building . You have 2 flight of stairs to Climb to enter. • Walk Score 95 (walk to cafe's, bars, eating, nightlife, etc.) • Biker's paradise • Fully equipped + stocked kitchen • Extremely safe neighborhood • Onsite, secured parking • Onsite washer + dryer ➠ 5 min walk to the Lincoln Park ➠ 10 min drive to Downtown Chicago ➠ 30 min drive to O'Hare Chicago Airport fireplace is not operational.

A modern living area features a green sofa positioned in front of a glass coffee table on a patterned rug. An open kitchen with white cabinetry and stainless steel appliances is visible in the background. Natural light fills the space, enhancing its welcoming atmosphere.

4.97 out of 5 average rating, 155 reviews

Large 2BR, 2BA, patio, sunroom, W/D, L-kitchen

Welcome to our charming home in the peaceful yet centrally located Buena Park neighborhood, housed in an updated antique building. This prime location offers easy access to the Red and Purple train lines, as well as multiple bus routes, making it easy to explore Chicago. You’ll be within walking distance of Wrigley Field, Clark St. bars, Montrose Beach, Lakeview, Boystown, and the iconic Green Mill. A perfect blend of quiet comfort and proximity to Chicago’s best attractions.

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.

4.79 out of 5 average rating, 289 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!

A cozy living area is presented with a daybed adorned with blue linens and colorful throw pillows. Light filters through two windows covered with sheer curtains. A wooden coffee table is positioned in front of a neutral-toned sofa, complemented by a bookshelf displaying various decorative items.

4.88 out of 5 average rating, 180 reviews

Lincoln Park Hideaway - 5 Min Walk to the Park!

800 sq ft 1 Bed 1 Bath Charming garden-level apartment right in the heart of Lincoln Park. Please note that you will need to walk down a short flight of stairs to access the unit. Close to all the best that Chicago has to offer! Walking distance to restaurants, convenience stores, and public transportation. Anything you could want for a nice trip to Chicago to visit friends and family, work relocation, or just explore our gorgeous city!

Superhost

This studio apartment features a modern kitchen with wood cabinetry and black appliances. A small dining table with curved blue chairs and a vibrant orange sofa create an inviting living space. Natural light enters through large windows, illuminating the minimalist decor.

4.79 out of 5 average rating, 175 reviews

Cabin 207 at 747 Lofts

This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot West Loop and Randolph street restaurant row. Walk to bars, shops, restaurants, coffee liquor stores and transportation with ease! You will love our spa baths, in unit laundry and full modern kitchens to make it feel like a home away from home. One of the best pizza spots in Chicago is only steps away!

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.

4.95 out of 5 average rating, 134 reviews

Modern Izakaya Studio in Wicker Park

Stay in a sleek underground izakaya themed studio in one of Chicago's most desirable neighborhoods. Relax and enjoy the quiet zen decor. Find our hidden Japanese whisky room. Kick back in our pillowy loungers and dig into our ramen selection... The Izakaya Studio in the heart of Wicker Park is about giving you a uniquely luxurious guest experience from which to begin your adventures in Chicago.

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.