Vacation rentals in Oakwood Beach

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Top-rated vacation rentals in Oakwood Beach

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Superhost
Private room in Chicago
4.7 out of 5 average rating, 33 reviews

Private living room with a Divider and sofa bed.

The apartment will be shared with other guests. Dispite being in the living room, it similar to being in a large room, The divider can be adjust as shown. There is a Full sofa bed, night desk and work desk with chair, Keep in mind there is no doors just divider, its exactly as show hence the discount so book accordingly. Your items are secure with us as we have a strict no entry to the guest personal space. There is also storage for your items and hangers and a bean bag cushion for you to relax.

Guest favorite
A spacious living area is depicted, featuring a comfortable seating arrangement with two sofas facing a mounted TV. A wooden coffee table is centered amidst the seating. The light-filled space leads into the dining area and kitchen visible in the background.
Private room in Chicago
4.85 out of 5 average rating, 105 reviews

Private room close to IIT, McCormick free parking2

Private bedroom, share bathroom with one other guest. Queen size bed, mini fridge and 32in Smart TV. Located at historical Douglas area, Chicago landmark . Close to subway station, bus, IIT, McCormick place (25 min walk, or bus #3 , or Uber<$10), loop, museum campus, white socks station. Area is quiet and safe, near restaurants and super markets. Free street parking. The bed room is located on 2nd fl of the house, it has a lock key Roof top patio with downtown view. Washer dryer in basement.

Top guest favorite
Private room in Chicago
5 out of 5 average rating, 142 reviews

Urban Oasis Pilsen - guest room in townhouse

Experience the charm of Pilsen, one of Chicago's trendiest neighborhoods. Your private bedroom features a queen-size bed and an en-suite bathroom with a tub/shower. The room includes a small desk, ample storage space, and a TV with streaming services. Triple-paned windows provide plenty of natural light while minimizing noise from the nearby I-90/94 freeway. The room is located on the third floor (40 steps)! The second floor offers access to the kitchen, living room, TV den, and balcony.

A modern living area features a comfortable dark sofa positioned in front of a sleek TV stand with a television. A low coffee table sits on a soft rug, while wall-mounted planters add greenery. Natural light filters through the window covered with blinds.
Apartment in Chicago
4.76 out of 5 average rating, 21 reviews

Charming 1BR/1BA Apt in Chicago

Welcome to this charming 1-bedroom, 1-bath apartment nestled in one of Chicago’s most desirable neighborhoods. This cozy unit blends classic character with modern updates, featuring hardwood floors, large windows, and a bright, functional layout. The kitchen offers updated appliances and plenty of cabinet space, while the bedroom provides a quiet, comfortable retreat. Enjoy easy access to local cafes, parks, shopping, and public transit—perfect for city living with a touch of charm.

Guest favorite
A cozy bedroom features a spacious bed with a soft white comforter. A modern television is mounted on the wall opposite the bed. A circular mirror and small table add to the decor, while a vintage-style refrigerator and a bathroom door are visible in the background.
Private room in Chicago
4.98 out of 5 average rating, 186 reviews

McCormick332, Chinatown, SOX, GrantPark, UC

Feel free to check us other listings: https://www.airbnb.com/h/zengarden001 https://www.airbnb.com/h/zengarden221 https://www.airbnb.com/h/zengarden331 https://www.airbnb.com/h/zengarden333 A new renovated luxury zen garden step to Chicago loop, McCormick Place, Millennium Park, Navy Pier, SOX, Art Institute, UIC, IIT, UCHICAGO, Chinatown(hundreds of delicious food), Midway Airport. Perfect place for everyone in Chicago! Super easy free street parking!

Guest favorite
A private room features a spacious bed with crisp white bedding. A wall-mounted television is situated opposite, with a small table and chair nearby. A fan is positioned to the side, and a compact refrigerator is visible next to the table. Natural light filters through sheer curtains.
Private room in Chicago
4.92 out of 5 average rating, 289 reviews

HydePark002, UC, NavyPier, Chinatown, freeparking

Feel free to check us other listings: https://www.airbnb.com/h/hydepark001 https://www.airbnb.com/h/zengarden333 https://www.airbnb.com/h/zengarden332 https://www.airbnb.com/h/zengarden001 Hyde Park luxury private room with a keypad lock on each room door. Shared full bathroom only for 2 rooms. Step to UChicago, Chicago loop, McCormick, Chinatown(hundreds of delicious food). Perfect for everyone in Chicago! Free street parking.

Superhost
Apartment in Chicago
4.76 out of 5 average rating, 21 reviews

Bright & Cozy Studio in the Heart of Hyde Park

Cozy, sunlit Hyde Park studio just blocks from UChicago. Enjoy a comfy queen bed, private bath, fast Wi-Fi, and a fully stocked kitchen with all essentials. Nestled on a quiet, tree-lined street in a safe, walkable neighborhood near cafés, restaurants, parks, and museums. Easy CTA and Metra access for downtown trips. Perfect for solo travelers, couples, and visiting academics seeking comfort, convenience, and a welcoming, homey atmosphere.

A spacious sleeping area features a large bed adorned with a geometric patterned blanket. Black and white artwork decorates the walls, complemented by a standing lamp. A cozy seating area is included, showcasing patterned cushions and throws for added comfort.
Guest suite in Chicago
4.81 out of 5 average rating, 331 reviews

Comfy/Private Entry & Bath/Free Parking - Win Win!

A Hidden GEM on a private block in Bronzeville, ranked one of the hottest neighborhoods in Chicago. Great for those looking to travel the city from Downtown (4 miles), to the lake (1 mile) to Hyde Park (walking distance) or those simply looking to stay in and rest in a peaceful place. Welcoming guests from near and far in this comfy studio designed specifically to host those for a great Chicago experience!

Guest favorite
A cozy front room features a light gray sofa adorned with decorative cushions. A sleek glass table is positioned beside the sofa, while a large wall-mounted TV is visible above. Natural light enters through a small window with blinds, and a colorful area rug adds warmth to the space.
Apartment in Chicago
4.93 out of 5 average rating, 41 reviews

Comfy Near Downtown Chicago

Keep it simple at this peaceful and centrally-located place. Near the University of Chicago and only ten minutes from Downtown Chicago. Located in the Bronzeville neighborhood on a cute and quiet block. Spacious one bedroom unit with a newly remodeled bathroom and Jacuzzi tub. Big screen TV in the cozy and comfy front room. And nice kitchen with the setup ready for meals and entertainment.

Condo in Chicago
5 out of 5 average rating, 3 reviews

Entire Home in Bronzeville

Modern 2-story condo in the heart of Bronzeville! Enjoy 2 bedrooms, 2 baths, and an open living space with a fully stocked kitchen. Upstairs, relax or play a round of pool in the loft game area. Minutes from Downtown, McCormick Place, and Lake Michigan. Perfect for families, friends, or business travelers looking for comfort, style, and fun in one of Chicago’s most historic neighborhoods!

Top guest favorite
A welcoming living room features a large wooden table surrounded by plants and comfortable seating. Natural light floods the space through expansive windows, enhancing the earthy tones of the decor. A cozy sofa and a vintage armchair create an inviting atmosphere for relaxation.
Private room in Chicago
4.96 out of 5 average rating, 527 reviews

Private room w/bath in urban canopy

Private bedroom w/attached private bath in a gorgeous 3-bedroom/2-bath apt on the only curvy street in Hyde Park. Common entrance and living spaces, shared with an artist who uses two bedrooms - one as studio. Enjoy the lush light-infused top floor of a turn-of-the-century urban tree house.

Guest favorite
Private room in Chicago
4.83 out of 5 average rating, 564 reviews

The Blue Room

A spacious single-family home; minutes away from Midway Airport (train station), within walking distance from gorgeous and dog-friendly parks, and walking distance of plentiful of supermarkets and convenience stores. Downtown Chicago is just about 40 minutes away from a train ride.

Popular amenities for Oakwood Beach vacation rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. Oakwood Beach