Apartment holiday rentals in Woodlawn

4.97 out of 5 average rating, 137 reviews

A cozy seating area features a green sectional sofa adorned with decorative pillows in various patterns. A small wooden coffee table sits at the center, topped with a book and a small plant. Exposed brick walls complement large windows dressed with dark curtains.

Apartment in Wicker Park

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

Apartment in Little Italy

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.

4.94 out of 5 average rating, 260 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.

4.98 out of 5 average rating, 228 reviews

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.

Apartment in Lake View

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

4.96 out of 5 average rating, 143 reviews

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.

Apartment in Avondale

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.

Apartment in Old Town Triangle

A modern teal sectional sofa with a tufted design is positioned next to a round marble coffee table. A white fur pillow and a patterned throw are draped on the couch. A black and white cowhide rug adds texture to the wooden floor.

4.76 out of 5 average rating, 328 reviews

Chic Home! Walk to Nightlife-Comedy-Restaurants!

Stay in the heart of Chicago Old Town! This bright, cool and comfortable one bedroom, one bath is decked out in mid century modern furniture, exposed brick, new appliances and has a true city feeling! It comfortably sleeps two (3rd person can sleep on the couch), just 2 blocks to Lincoln Park, and 3 blocks to the famous Second City & stellar Old Town bars. Not to mention a quick 5 minute Uber ride to river north district (downtown Chicago)!

4.9 out of 5 average rating, 177 reviews

A modern kitchen with white cabinetry features stainless steel appliances, including a refrigerator and microwave. An island with seating for three is complemented by decorative vases of flowers. Natural light fills the space through large east-facing windows.

Apartment in Gold Coast

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)

Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier.

4.98 out of 5 average rating, 422 reviews

A dining area showcases a long wooden table surrounded by six metal wire chairs. Natural light enters through two large windows, highlighting the warm wood finishes of the space. A sideboard with glass cabinets is visible against the wall, complemented by decorative art pieces.

Apartment in Lake View

Prime Lakeview Apt: Walk to Wrigley Field

Escape to our bright & airy 2-bedroom apartment on a quiet, tree-lined street in Chicago's vibrant Lakeview. Perfect for 4 guests, this stylish retreat features a full kitchen, cozy fireplace, and is just a short walk from Wrigley Field, Lake Michigan, Boystown and the 'El' train for easy downtown loop access. Enjoy the best of Chicago from this classic home! Street parking passes available upon request.

4.95 out of 5 average rating, 137 reviews

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.

Apartment in Wicker Park

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.

Apartment in Noble Square

A spacious living room features three large windows allowing natural light to fill the space. Comfortable seating includes a leather couch and an armchair. A television is mounted on the wall, and a decorative area rug lies beneath a wooden table set for dining.

4.97 out of 5 average rating, 874 reviews

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

A modern kitchen features wooden cabinetry and a countertop complemented by a tile backsplash. A stainless steel stove and microwave are installed, along with a double sink and a dishwasher. Utensils and dishes are organized on a drying rack, contributing to a functional cooking space.

4.99 out of 5 average rating, 101 reviews

Comfy 2 Bedroom Apartment w/ Office

Located a few blocks from the University of Chicago and 1 mile west of Chicago's beautiful lakefront, this 1st floor Condo offers plenty of comfort and space. 2 Bedrooms include firm Queen-size mattress and plenty of space. Dedicated office space

A modern living area features a stylish seating arrangement with gray sofas and patterned chairs placed on a geometric rug. The backdrop includes a dark accent wall with a chevron pattern, complemented by recessed lighting. A kitchen with black cabinetry and stainless steel appliances is visible in the background.

4.88 out of 5 average rating, 176 reviews

The En Bronze ~ 7mins To Dining & Downtown Chicago

Welcome to the ‘En Bronze’. This super swank, extremely spacious Airbnb is located in the heart of historic Bronzeville. We are centrally located — a mere 7 minute drive to downtown Chicago, McCormick Place and Chicago’s beautiful Lake Front!

Apartment in Lincoln Park

A stylish living area features a white sofa with bright yellow cushions, set against exposed brick walls. A flat-screen TV is positioned above a modern fireplace. A wooden staircase leads to the upper level, while a kitchen bar with dark countertops is visible on the left.

4.96 out of 5 average rating, 526 reviews

Unique Lincoln Park Duplex Apt

Unique apartment duplex in the heart of Lincoln Park on a quiet residential street; jus a few blocks away from Lincoln Park Zoo and DePaul University, walking distance to the lakefront and easily accessible public transportation.

Popular amenities for Woodlawn apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.7 out of 5 average rating, 70 reviews

The image displays views across the street from the property. Lush green trees line the sidewalk, providing shade. A spacious walking path is visible, alongside a well-maintained street with parked vehicles. The surrounding area suggests a welcoming and well-kept neighborhood.

Apartment in Woodlawn

Bright Vintage University Center Condo

4.94 out of 5 average rating, 36 reviews

A cozy living area features a large, brown leather sofa adorned with patterned pillows. A round table sits in front of it, complemented by a pair of armchairs. Artwork adorns the walls, and soft lighting highlights the space, while a fireplace adds warmth.

Apartment in Chicago

Spacious two bedroom condo with a cozy feel!

4.86 out of 5 average rating, 22 reviews

The living area features hardwood flooring and blue upholstered sofas with cushions. A light, modern coffee table sits in front of the seating area. The space is illuminated by natural light through nearby windows, enhancing its airy feel.

Apartment in South Shore

South Shore Dr Retreat

A spacious living area features a large sectional sofa arranged around a coffee table. A dining table is positioned nearby, complemented by four chairs. Natural light enters through multiple windows, illuminating the hardwood floors. A ceiling fan and decorative artwork enhance the casual setting.

4.97 out of 5 average rating, 63 reviews

Beautiful Condo in North Kenwood with Parking

Apartment in North Kenwood

A spacious living area features two comfortable seating arrangements, including a light-colored sofa and a dark armchair. Large windows are dressed with navy curtains, allowing natural light to fill the room. A circular coffee table is centered on a decorative area rug, complementing the modern decor.

4.89 out of 5 average rating, 55 reviews

Condo off the lake

A comfortable living area is highlighted by a light-colored sofa adorned with decorative pillows. A coffee table sits centrally on a patterned rug, with a television mounted nearby. Bright natural light fills the space through large windows, accented by sheer white curtains.

4.93 out of 5 average rating, 58 reviews

Cozy 3 Bedroom Condo near University of Chicago

Apartment in North Kenwood

A modern living room is presented, featuring a brown leather sofa and two armchairs with light upholstery. A round wooden coffee table sits at the center, accompanied by two textured stools. Two mirrors adorn the wall above the sofa, while large windows allow natural light to fill the space.

4.96 out of 5 average rating, 45 reviews

The ModernFarmhouse Chicago-Near Downtown Chicago

An open concept living area features a modern sofa with a textured throw, paired with a round side table. Two computers are positioned at a sleek desk beside a decorative plant. A television sits on a media console, under a striking lighting fixture and an elegant wall clock.

4.93 out of 5 average rating, 75 reviews

Modern Apt Near U of Chicago!

Pet-friendly apartment rentals

Apartment in Ukrainian Village

The living area features a spacious couch accompanied by two armchairs, all positioned around a circular dining table. A large window allows natural light to illuminate the space, adorned with potted plants and modern artwork that adds a touch of style.

4.98 out of 5 average rating, 106 reviews

Spacious 3BR/3BA Condo in Trendy Ukrainian Village

Apartment in Logan Square

A comfortable living area features an orange sofa and a variety of artwork on the walls. A round coffee table sits in the center of a patterned area rug. Natural light filters through the window shades, enhancing the welcoming vibe of the space.

4.95 out of 5 average rating, 109 reviews

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

4.8 out of 5 average rating, 197 reviews

A modern living area is presented with a dark gray sofa adorned with neutral pillows and a cozy throw. A round mirror reflects light, while a white coffee table with a decorative plant sits centered on a plush area rug, enhancing the room's inviting atmosphere.

Apartment in East Pilsen

Charming Condo near U.C./Loop/McCormick Place

4.9 out of 5 average rating, 139 reviews

A modern living area features a light-colored sectional sofa adorned with blue accent pillows. A round black coffee table is positioned in the center, resting on a decorative rug. Two lamps and a piece of coastal-themed artwork complement the bright, airy atmosphere.

Apartment in Bridgeport

Convenient & Spacious 3BR Condo w/Free Parking

4.93 out of 5 average rating, 310 reviews

A bedroom features a spacious bed dressed in deep blue linens, complemented by decorative pillows. The walls are painted in a rich blue, accented by round mirrors. Two bedside lamps illuminate the space, while a patterned area rug lies on the hardwood floor.

Apartment in Oak Park

Picture Perfect 3Bed Steps from Train and FLW

Apartment in Lincoln Square

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.

4.97 out of 5 average rating, 465 reviews

Lincoln Square Gem!

4.91 out of 5 average rating, 106 reviews

A spacious living area is shown, featuring a large sectional sofa with decorative pillows. A glass coffee table occupies the center of the room, while a television sits on a wooden stand. The kitchen is visible in the background, with modern appliances and a dining area.

Apartment in Chicago

Spacious 5-BR Apt next to transit Free Parking