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Apartment vacation rentals in Woodlawn

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Top-rated apartment rentals in Woodlawn

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Top guest favorite

A cozy living room area features a dark leather sofa facing a mounted television on a wooden media console. A round shelf displays books and plants, while a small desk and chair are positioned beside a bright window.

Apartment in Bridgeport

4.94 out of 5 average rating, 164 reviews

Blue Brick Apartment in Bridgeport - Park for Free

-600 sq.ft apartment / 2nd floor / Patio Deck -Free parking pad in rear / free street parking -Commute to Downtown: 15min (drive) / 28min (transit/train) / 22min(bike) -Walk score 93! Bike Score 92! Near Trains to Downtown!! -Gated access w/ Building video and security alarm system and noise monitoring equipment. -Kitchen is stocked w/ cookware, utensils, etc. -Washer and Dryer and Dishwasher in unit (free) -Rideshare(Uber/Lyft) / Bikeshares(Divvy) are bountiful -Safe, working class neighborhood

A vibrant living area showcases eclectic décor, featuring a colorful mural with artistic motifs on one wall. A round coffee table sits in the center, surrounded by cream-colored sofas adorned with green cushions. A wet bar with wooden stools is visible in the background.

Apartment in South Side

4.92 out of 5 average rating, 135 reviews

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TVs, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles to Mag Mile, Navy Pier, Millennium Park), Beach (1 mile), Museums, & Sports arenas.

Top guest favorite

Apartment in Edgewater

4.99 out of 5 average rating, 146 reviews

Newly Renovated, Spacious 2BR in Andersonville

Welcome to your newly renovated 2nd floor oasis! Located on a serene residential street, with a private parking space and backyard, this cozy retreat is nestled between the vibrant Edgewater and Andersonville neighborhoods. Indulge in a plethora of dining and entertainment options just steps away, or take a 15-minute stroll to the CTA Redline for easy access to downtown. With a new Metra stop at the end of the block and less than 10 miles from the heart of the city, your urban adventure awaits!

A well-maintained outside space features a neatly trimmed grassy area along a pathway, flanked by vibrant greenery and flowering plants. On one side, a wooden deck with railings enhances the exterior of the two-story building, while a fence provides privacy.

Apartment in South Side

4.9 out of 5 average rating, 195 reviews

Royal Coach House Cottage

Royal Coach House Cottage- Nestled in Bronzeville community and nearby Historic Hyde Park neighborhood that is safe and family oriented. Our space is quite cozy, quaint and ideal for relaxation, peace & quiet. Flower and vegetation garden landscape. Centrally located 1.5 miles from lake front, nearby shopping, movie theater, and restaurants. Seconds from park, walking track and playground. Minutes from downtown and Magnificent Mile. Local transportation accessible including bicycle rental.

A spacious living area features light wood flooring and contemporary furnishings. The kitchen is equipped with stainless steel appliances, including a refrigerator and gas stove. A dining table with transparent chairs is positioned near a leafy plant, with a hallway leading to a bedroom in the background.

Apartment in Woodlawn

5 out of 5 average rating, 12 reviews

Charming 2-bdrm near University of CHI Campus

Perfect for business travelers, healthcare professionals, and U of C affiliates, this newly renovated and fully furnished 2-bedroom, 1-bath apartment offers comfort and convenience. Located on a peaceful, tree-lined street in the vibrant Woodlawn/Hyde Park neighborhood, the unit features modern amenities including an in-unit washer and dryer, high-speed Wi-Fi, and a dedicated workspace. Public transportation (Metra + CTA) is just steps away and downtown Chicago in just 15 minutes by car.

A compact sitting area features a beige loveseat adorned with decorative pillows. It is positioned on a patterned area rug, adding contrast to the ceramic tiled floor. Natural light filters through a window with horizontal blinds, enhancing the cozy ambiance of the space.

Apartment in Hyde Park

4.8 out of 5 average rating, 266 reviews

Cozy Studio Apt. Home-5 Min. to U of C

A private guest suite 5 min. from UChicago campus. Full access via private entrance to cozy studio created in bsmt of our home. An open floor plan with louvered wooden doors close off bedroom w/dbl bed. A full kitchen, ceramic tile bath w/tub, hand-held shower head+vanity mirror. Studio guest: "Your place really stands out from all the landlord-managed airbnb stuff in Hyde Park!" Five min. to campus, fitness ctr, & CourtTheatre; convenient, cozy & private. Registration #R24000123950

A modern living area features a plush area rug over hardwood flooring. An arrangement of seating is complemented by a sleek ceiling fan and a large television mounted above a fireplace. Bright windows provide natural light, with greenery visible outside.

Apartment in South Side

4.76 out of 5 average rating, 50 reviews

Spacious Haven Near Green Line, 20mins to Downtown

Nestled in the charming, tree-lined streets of West Woodlawn, this cozy spot invites you to explore the best of Chicago! Just steps away from the serene Washington Park, complete with playgrounds, serene hiking trails, and a lovely pond that’s perfect for a morning walk or some quiet reflection. Craving a taste of Hyde Park’s vibrant culinary scene? You’re just minutes from its top restaurants. With the Green Line train just a quick 7-minute walk away, you can be downtown in no time!

Top guest favorite

A cozy living area features two large windows allowing natural light to fill the space. A fold-out futon sofa and a black armchair are positioned around a wooden coffee table. An adjacent kitchenette with a two-seat dining table is visible, along with various plants enhancing the atmosphere.

Apartment in Hyde Park

4.93 out of 5 average rating, 121 reviews

Spacious 1BR Garden Apt & Parking

Welcome to our tranquil garden apartment on a quiet residential street near the university and all Hyde Park attractions. Enjoy morning light through picture windows in the spacious living room and adjacent kitchenette. Breakfast on the patio or garden bench on a sunny morning. Stroll to one of 20+ eateries within four blocks. We are on-premises hosts and owners, available for whatever may arise. Access is private via back gate just off the parking lot with reserved parking space.

A vintage-style sign featuring bold red and white lettering, stating 'Bohemian Lodge no 17' against a dark brown background. Decorative elements include images of beer glasses and whimsical knot designs, creating a nostalgic atmosphere.

Apartment in Lower West Side

4.84 out of 5 average rating, 303 reviews

Teeny Tiny Bohemian Lodge - Clean & Affordable

Explore the wonderful neighborhood of Pilsen from this unique little space. Private entrance to your bedroom with an attached bathroom with shower. The entire space is for your private use- nothing is shared. NOTE the bedroom & bathroom ARE the entire space. Designed for one person as a sleeping room. We can not host 2 people. Twin size American bed is 38 x 75 inches. Please CLICK "show more " below BEFORE YOU BOOK/INQUIRE I need you to read and respond to our house rules.

The front exterior of a modern multi-level building is shown, featuring large windows and a mix of wood and grey siding. A fenced yard with green grass is visible, along with a walkway leading to the entrance. Trees offer shade in the vicinity.

Apartment in South Side

4.92 out of 5 average rating, 88 reviews

Comfy Solar & Green 2BR Near Hot Hyde Park!

Hi, traveler! We're so happy to host you in our unique, private 2-bedroom garden unit that's powered by the sun. It's all electric, uses no gas and is U.S. DOE Zero Energy and Energy Star® certified! You'll also have a full kitchen, full bathroom/shower, washer/dryer, living room, work area, generous closet space, and complete privacy. Your children are also welcome. We're centrally located on a quiet, residential street in safe and lovely Woodlawn near hot Hyde Park!

The exterior of a charming brick apartment building is shown, featuring a symmetrical facade with a welcoming entrance. Planters with greenery adorn the steps, and the surrounding area includes well-maintained grass and a sidewalk. Architectural details enhance the building's character.

Apartment in South Side

4.93 out of 5 average rating, 127 reviews

Beautiful European Apartment

Enjoy this comfortable 1600 sf European Styled 3 bedroom (Queen Beds in each room) 1 bath apartment with lots of natural light. Formal dining room,comfortable living room with attached sunroom. Quite neighborhood and 3 blocks away from Public “Elevated Train” line and “Buses” to anywhere in Chicago. The apartment is walking distance from University of Chicago and the beautiful Washington Park. The park has wonderful Walking/Running Paths and Pool (Seasonal).

Top guest favorite

Apartment in Lower West Side

4.99 out of 5 average rating, 247 reviews

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

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Popular amenities for Woodlawn apartment rentals

Free parking on premises

Air conditioning

Weekly apartment rentals

Top guest favorite

A round dining table is set with blue dishware and a floral centerpiece. Four light-colored chairs surround the table, placed on a patterned area rug. Natural light is visible through two softly shaded windows, and a tall green plant adds a touch of greenery to the room.

Apartment in Beverly

4.96 out of 5 average rating, 91 reviews

Beverly Cottage Loft

The living area showcases a neutral color palette with hardwood floors. A coffee table sits in front of a comfortable couch, with a guitar resting against the wall. A TV is mounted above a brick fireplace. A dining table with four wooden chairs is visible in the background.

Apartment in Woodlawn

4.78 out of 5 average rating, 114 reviews

The Woodlawn Grey - Large 3bd/3ba Apt by UChicago

A bright living room showcases a large TV mounted on the wall. Two sofas, one a sectional, are arranged around a coffee table on a patterned rug. Windows provide natural light and views of greenery outside, while a chandelier illuminates the space.

Apartment in South Side

4.81 out of 5 average rating, 42 reviews

3 BR in Historic Bronzeville

A modern living area features a gray sofa with black accent pillows positioned beside a sleek black coffee table. A small potted plant adds a touch of greenery, while a remote control rests on the table's surface. Natural light enters through a nearby window.

Apartment in Hyde Park

5 out of 5 average rating, 23 reviews

Stylish Studio Getaway – Close to University

The exterior of a modern brick building is displayed, featuring an inviting entrance with a covered porch. Stone steps lead to a wooden door, surrounded by a neatly landscaped area with seasonal decorations, including pumpkins and colorful flowers. Decorative wrought iron fencing lines the sidewalk.

Apartment in Bridgeport

4.96 out of 5 average rating, 23 reviews

Bridgeport Garden Studio

A modern living area features a gray couch adorned with vibrant yellow 'ICONIC' cushions. Two bright yellow chairs flank a glass coffee table central to the space, which is complemented by decorative houseplants and a minimalist wall art piece above.

Apartment in South Side

4.79 out of 5 average rating, 53 reviews

W3N NexttoUniversityTrainPark 15minsDowntown Desk

A spacious living room features soft beige seating arranged around a textured area rug. A television is positioned on a low black media console, while light gray walls create a calming atmosphere. Two doorways lead to other areas of the apartment.

Apartment in South Chicago

4.88 out of 5 average rating, 17 reviews

Château Escanaba Suite 2

The hallway features dark hardwood floors and neutral-toned walls. Several doorways lead to different rooms, while a decorative area rug adds texture. Natural light is present, and a clock is mounted on the wall, contributing to the inviting feel of the space.

Apartment in Woodlawn

4.82 out of 5 average rating, 183 reviews

University Retreat

Private apartment rentals

Apartment in Hyde Park

4.8 out of 5 average rating, 123 reviews

Best Location in Hyde Park apartment

A modern kitchen is showcased, featuring sleek cabinetry in dark tones and stainless steel appliances. An island with a light countertop provides ample space for meal preparation. Natural light enters through large windows, brightening the inviting atmosphere of the open layout.

Apartment in Lower West Side

4.93 out of 5 average rating, 72 reviews

Pilsen Modern Chic Retreat

A cozy seating area is depicted, featuring a blue couch adorned with a Chicago Blackhawks blanket and decorative pillows. A small coffee table is placed on a red patterned rug, accompanied by a light gray armchair. Natural light enters through a window, enhancing the inviting space.

Apartment in Bronzeville

4.89 out of 5 average rating, 118 reviews

Chicago Themed Garden Unit - Historic Bronzeville

Top guest favorite

A light-filled living area features a gray sectional sofa adorned with blue and yellow cushions. Two large windows provide perspectives of the outdoors. A world map hangs on the wall, complemented by a small coffee table and a patterned area rug, contributing to a cozy setting.

Apartment in Lincoln Park

5 out of 5 average rating, 283 reviews

Explore Lincoln Park from a Polished Apartment

A cozy living area is highlighted by a brown sofa adorned with decorative cushions. A warm red throw drapes over the armrest. Visible at the end of the hall is the entrance to the bedroom. Light brown carpeting covers the floor, enhancing the inviting atmosphere.

Apartment in Bridgeport

4.98 out of 5 average rating, 206 reviews

Bridgeport Garden Apartment

A spacious bedroom features a large bed with white bedding and decorative throw pillows. Two windows allow natural light to fill the room, showcasing light blue walls and hardwood flooring. A colorful area rug adds warmth, while ceiling fans enhance ventilation.

Apartment in Washington Park

4.91 out of 5 average rating, 54 reviews

The Dearborn Suite 2

A modern living area features a navy blue sectional sofa adorned with light throw pillows. A round coffee table holds a woven basket and a vase of vibrant red tulips, adding a touch of color. A piece of artwork hangs on the wall, complementing the neutral decor.

Apartment in Near Southside

4.87 out of 5 average rating, 171 reviews

Modern 2BRD apartment| 5min to McCormick Place

Top guest favorite

A modern living space is shown with a relaxation area featuring dark leather seating arranged around a media console. A workspace with a desk and chair is positioned nearby. Soft lighting highlights the dark walls, and art adds a pop of color.

Apartment in Hickory Hills

4.97 out of 5 average rating, 63 reviews

Cozy Guest Suite. Private Entry+ Turo Rental

Apartment rentals with a hot tub

Apartment in Chicago Loop

5 out of 5 average rating, 5 reviews

Elevated 2BR Retreat + Balcony with Bean Views

An open-concept living and dining area is showcased with a gray sectional sofa and a wooden coffee table. A modern ceiling fan hangs above, and natural light fills the space. A dining table with six chairs is positioned nearby, adjacent to a sleek kitchen.

Apartment in West Rogers Park

4.85 out of 5 average rating, 92 reviews

Spacious Beautiful Condo

Apartment in River West

4.88 out of 5 average rating, 17 reviews

Luxury 3BD Penthouse – Private Patio+Skyline Views

Top guest favorite

Apartment in Fulton Market

4.97 out of 5 average rating, 31 reviews

Skyline Oasis: City & Lake Views

Apartment in West Town

5 out of 5 average rating, 4 reviews

Modern 4BR Retreat in Vibrant West Town

Apartment in Wicker Park

4.96 out of 5 average rating, 23 reviews

Spacious 1 BR Garden Unit-1 FREE Garage Parking

A hot tub is positioned in a vibrant game room, surrounded by colorful murals depicting a beach and lively graphics. Water glistens in the tub, inviting relaxation and enjoyment after a day of activities.

Apartment in Dunning

4.97 out of 5 average rating, 136 reviews

Belmont Pleasures - hot tub / arcade gaming room

Apartment in Chicago Loop

4.92 out of 5 average rating, 37 reviews

City Skyline Suite (2BD / 2BA)

Quick stats about apartment rentals in Woodlawn

Total rentals
140 properties
Total number of reviews
2.1K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
100 properties have a dedicated workspace
Wifi availability
130 properties include access to wifi

Destinations to explore