Places to stay near Oak Street Beach

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Top-rated holiday rentals near Oak Street Beach

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Top guest favourite
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.
Flat in Chicago
5 out of 5 average rating, 299 reviews

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

Superhost
The townhouse stands elegantly among lush greenery, featuring a classic facade with black-framed windows and a welcoming entrance. A wrought-iron fence complements the landscaped front area, while a tree provides shade along the sidewalk.
Townhouse in Chicago
4.82 out of 5 average rating, 233 reviews

Historic luxury townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the lavish Gold Coast of Chicago—one of the most sought-after locations in the city! Located on one of Chicago’s famous streets, you’ll be a 5-minute walk from the historic Gold Coast beach and intimate views of Lake Michigan. The property is also within walking distance of the subway, where you can connect to the L trains, and the Magnificent Mile. It is the perfect place to stay for adventurous travellers and those who fancy a beach in the City!

Guest favourite
Flat in Chicago
4.83 out of 5 average rating, 181 reviews

Kasa | Walk Magnificent Mile | River North

Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand new high-rise, our modern apartments include state-of-the-art amenities as well as chic details like gourmet kitchens and high ceilings. You’re less than a mile from the Museum of Contemporary Art, The Wrigley Building, and more. Our tech-enabled apartments offer self check-in at 4 pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.

Guest favourite
A welcoming living space features a blend of modern and natural elements. A green accent wall provides a backdrop to a cozy seating area with black chairs and a sofa. Decorative plants are placed throughout, enhancing the bright and open atmosphere.
Flat in Chicago
4.98 out of 5 average rating, 215 reviews

Bright Cozy Modern-Chic Condo in Trendy West Town

Kick back & relax in your home away from home in our luxurious, spacious and peaceful abode in the heart of the West Town & Noble Square neighborhoods, close to downtown. Featuring incredible natural light, modern amenities & beautiful artwork, the house is impeccably clean and designed to ensure you have the best travel experience possible. Located near the popular Grand Avenue, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

Top guest favourite
A spacious living area features large arched windows that allow soft light to fill the room. A blue sectional sofa and a glass coffee table create a comfortable space. A television is mounted on the wall, while vibrant flowers add a touch of color on the table.
Flat in Chicago
4.96 out of 5 average rating, 468 reviews

Sophisticated Flat in Historic Building

Nestled in the charming Old Town Triangle of Chicago, this luxurious flat offers a seamless blend of historic charm and contemporary sophistication. With its soaring ceilings and elegant arched windows, this immaculate space boasts a truly captivating ambiance. Impeccably designed interiors ensure a truly indulgent stay, while the building's rich heritage adds an unforgettable sense of place. Treat yourself to the ultimate Chicago getaway and bask in the allure of this stunning residence.

Top guest favourite
The living area features a spacious gray sectional sofa complemented by a textured area rug. A sleek coffee table is adorned with decorative items, while a stylish arc floor lamp provides ambient lighting. In the background, a dining space with a round table and four chairs is visible.
Apartment in Chicago
4.95 out of 5 average rating, 128 reviews

GLORIOUS GOLD COAST GETAWAY

Welcome! 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. We look forward to hosting you!

Guest favourite
An open living area is showcased with large windows revealing views of the lake. A comfortable dark sofa and modern chairs are positioned on a patterned rug. A sleek coffee table sits in the center, accompanied by decorative plants, and a wall-mounted TV is positioned nearby.
Flat in Chicago
4.75 out of 5 average rating, 217 reviews

Stunning Corner 2BR in Streeterville | Roof Deck |

Stunning 1,200 square foot apartment with oversize windows, an open layout, and city/lake views in multiple directions. This bright and modern two bedroom, one bathroom corner unit is perfect for travelers looking for a stylish escape in the sky in downtown Chicago just off the Magnificent Mile and the lakefront. The building has great amenities including an amazing rooftop terrace with 360 degree views of the skyline and the lake. This is the best location in the city!

Guest favourite
Flat in Chicago
4.96 out of 5 average rating, 274 reviews

Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D

Private 2BR apt. in vintage 3-flat in the heart of Chicago's Michigan Ave/Gold Coast neighborhood. Fantastic locations steps from world-class shopping and restaurants, Oak St. beach, and public transportation (L trains, express bus). Includes A/C, washer-dryer, super-fast wi-fi, smart TV, and workspace. Hourly rate garage parking next door. Note: Guests must walk up one flight of stairs. Light sleepers should bring earplugs as there are noises typical of a big city.

Top guest favourite
A bright living area features large windows allowing natural light to fill the space. A mix of seating options includes a red sofa and a dark chair, complemented by plants and a piano. Bookshelves line the walls, offering a cozy and inviting atmosphere.
Flat in Chicago
4.93 out of 5 average rating, 108 reviews

2br/2ba, A+ location by Mag mile, views & spacious

Unbeatable location next to Water Tower Place, with lots of natural light and partial lake view in a quiet vintage building with lots of character. Walk to nearly any attraction in central Chicago. I'm happy to help with sightseeing advice and discounts on popular tourist attractions. (Guests love: Location, View, Comfortable room and bed, Friendly/helpful host, Flexible luggage policy) Please see Airbnb listing 12323073 for additional reviews of this apartment.

Guest favourite
A cozy living area is presented, featuring a comfortable sofa adorned with decorative pillows. A coffee table sits on a patterned rug, with a flat-screen TV mounted above a decorative fireplace. Archways lead to a dining space, enhancing the room's openness.
Serviced apartment in Chicago
4.84 out of 5 average rating, 154 reviews

Downtown Guild #3 | Mag Mile Gold Coast The Lake!

Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - Steps away from the John Hancock - Gym in the Basement - Amazing location w/ many shops & restaurants nearby - Fast WIFI - KING bed - Charming, vintage Chicago building Walk to nearly any attraction in central Chicago. Please read our FAQs to answer any questions before booking.

Guest favourite
Apartment in Chicago
4.88 out of 5 average rating, 181 reviews

Lincoln Park Hideaway - 5 Min Walk to the Park!

800 sq ft 1 Bed 1 Bath Charming garden-level apartment right in the heart of Lincoln Park. Please note that you will need to walk down a short flight of stairs to access the unit. Close to all the best that Chicago has to offer! Walking distance to restaurants, convenience stores, and public transportation. Anything you could want for a nice trip to Chicago to visit friends and family, work relocation, or just explore our gorgeous city!

Guest favourite
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 Chicago
4.9 out of 5 average rating, 176 reviews

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.

Popular amenities for holiday rentals near Oak Street Beach

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Oak Street Beach