Apartment vacation rentals in Woodlawn

4.92 out of 5 average rating, 131 reviews

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 Chicago

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.

Superhost

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 Chicago

4.89 out of 5 average rating, 190 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.

5 out of 5 average rating, 11 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.

4.8 out of 5 average rating, 260 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

Superhost

A plush teal velvet sofa is positioned in a well-lit living area, accompanied by decorative pillows in orange and mustard. A vibrant area rug adds color to the space, while wall art featuring abstract designs hangs above. The open kitchen is visible in the background.

4.82 out of 5 average rating, 65 reviews

Quaint Apt near UChicago, Wifi + Parking + Laundry

Unwind at our stylish and cozy 3-bedroom, 2-bathroom apartment located just steps from the University of Chicago in the vibrant Woodlawn neighborhood. The space features, an open-floor plan, hardwood floors, a fully equipped kitchen, plenty of natural light. It's the perfect place for a family or a group of friends who want a quiet place to relax while still being close to food, fun and tourism in Chicago. Ideal for family vacations, group trips, traveling professionals or students.

Superhost

A serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.

Apartment in Near North Side

4.82 out of 5 average rating, 772 reviews

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

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.

4.93 out of 5 average rating, 118 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 well-appointed bedroom features a cozy bed with a dark patterned blanket, complemented by decorative pillows. Natural light enters through a window, creating a bright ambiance. A stylish bedside lamp and a small nightstand add functionality to the space, alongside a decorative wall art piece.

4.79 out of 5 average rating, 118 reviews

Best Location in Hyde Park apartment

Lovely 2 bedroom apartment in Hyde Park location. Within one block of the U of Chicago. The lake is within a 10min walk. Close to the science museum, Metra, restaurants, parks, and famous Japanese garden. Updated unit was remodeled last year for you to enjoy. Separate living/dining rooms. The dinning room has a large table for you to enjoy a meal or get some work done. Great view to the park and tennis courts and porch on the kitchen to enjoy breakfast outside. Parking available.

Top guest favorite

A cozy living area features a sectional sofa with a yellow throw blanket draped over it. Two round tables, one wooden and one light, are positioned nearby. A ceiling fan with a light fixture is visible, along with an artwork displaying an elephant and botanical prints on the wall.

Apartment in South Shore

5 out of 5 average rating, 16 reviews

Comfy 3Bdrm near LSD,Obama Center, UIC, Sci Museum

South Shore located along Chicago’s shoreline, with stunning views of Lake Michigan. This location is a perfect stay. Guest will enjoy easy access to everything from this centrally located apartment. Minutes to University of Chicago or nearby beaches. One block from Metra Train Station to downtown or the north suburbs. Less than a mile from Obama Library or the Science Museum. Or travel the Nearby Lakeshore drive to downtown in just 15 minutes. Jewel Osco grocery located nearby.

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.

4.92 out of 5 average rating, 83 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!

A spacious living area is furnished with two comfortable sofas and an armchair. A central coffee table rests on polished wooden floors. A built-in bookshelf displays decorative items, and a fireplace adds character, complemented by a wall-mounted television above.

4.94 out of 5 average rating, 536 reviews

Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!

This will likely be the largest condo you have ever seen. This condo is 5 mins from the University of Chicago and the University of Chicago hospital. You will be a quick 10-15 min uber ride from downtown and 5 mins from beautiful Lake Michigan. We are currently only booking out of town travelers. We are not doing parties or events. I live in the building so if you are trying to have a party I will have it shut down and you will be asked to leave within an hour.

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.