Vacation rentals in Oakwood Beach

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Top-rated vacation rentals in Oakwood Beach

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Top guest favorite
A well-lit bedroom features a spacious bed with a soft, green blanket and burgundy pillows. A wooden desk and chair sit near a closet with sliding doors. Two vibrant artworks adorn the wall, and a cozy area rug adds comfort to the floor.
Guest suite in Chicago
4.92 out of 5 average rating, 106 reviews

Cozy 2BD Lake Apt Near Downtown, McCormick & More

Enjoy your getaway in this cozy solar powered and eco-sustainable garden apartment 5 minutes walking to Lake Michigan where you can access beaches, bike paths, prairies, parks & more! We are less that 8 min away from downtown, the University of Chicago, Soldier Field, the Field Museum and more. Our home is located in the historic Oakland neighborhood, central to so much of what Chicago has to offer. We love welcoming guests to our garden apartment where making your stay relaxing is our pleasure

Guest favorite
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
4.92 out of 5 average rating, 146 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.

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, 290 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.

Guest favorite
A modern kitchen area features white cabinetry and stainless steel appliances, including a refrigerator and stove. A small wooden dining table is positioned against the wall, complementing the neutral tile floor and the soft lighting from recessed ceiling fixtures.
Apartment in Chicago
4.97 out of 5 average rating, 35 reviews

Cozy newly renovated apartment in Bridgeport

Welcome to your perfect home away from home in Bridgeport, Chicago 🏡 This newly renovated cozy 1-bedroom, 1-bathroom apartment offers a comfortable, inviting space just 10 mins to downtown Chicago. Located couple minutes from Chinatown Whether you're here to catch a White Sox game or immerse yourself in the vibrant local food scene and culture, this location is ideal for exploring the best of Chicago. FREE PARKING 🅿️ NO PARTIES.

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 cozy sleeping area features a queen bed adorned with plush yellow pillows atop crisp white linens. A vibrant mural in earthy tones of green, pink, and orange adds a modern touch to the room, complemented by natural light from the nearby window.
Apartment in Chicago
5 out of 5 average rating, 32 reviews

2BR Brownstone 7-min to Events, Downtown, & Beach

Welcome to The Garden Oasis — a cozy, winter-ready Chicago retreat just 5 minutes from Soldier Field and McCormick Place. Perfect for Bears games, conventions, and stay-in nights, this historic brownstone features a warm living space for movies, board games, and hot chocolate with marshmallows. Close to great food and downtown, yet ideal for relaxing indoors after a day out.

Guest favorite
A modern living area features a light green sectional sofa adorned with dark blue accent pillows. A decorative area rug with a subtle pattern is positioned beneath a glass coffee table. Natural light filters through sheer curtains, and a plant adds a touch of greenery.
Apartment in Chicago
4.83 out of 5 average rating, 180 reviews

The Posh Apt. Mins to Downtown & Hyde Park

This spacious garden apt in a 12 yrs old building is sitting in the heart of a historical Bronzeville neighborhood. The unit is setup with all necessary amenities/supplies that will make you comfortable and a memorable trip for you. It is modern, contemporary and a most stay place for a guest like you! I bet you will like it.....

Guest favorite
Apartment in Chicago
4.79 out of 5 average rating, 29 reviews

Elegant 2BR/2BA Retreat

Experience the perfect blend of classic charm and modern comfort in this spacious 2-bedroom, 2-bathroom apartment nestled in the heart of Hyde Park. Located on the picturesque E 56th St, this residence offers an inviting atmosphere for families, academics, or travelers seeking a serene urban escape.

Popular amenities for Oakwood Beach vacation rentals

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