Places to stay near Oak Street Beach

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Top-rated vacation rentals near Oak Street Beach

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Top guest favorite
A large dining table made of wood is surrounded by minimalist lighting fixtures. Natural light enters through multiple windows, highlighting the room's mix of exposed brick and modern furnishings. A cozy seating area is visible, featuring a sectional sofa and a television mounted on the wall.
Apartment in Chicago
5 out of 5 average rating, 315 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.

Top guest favorite
A charming exterior of a historic building is framed by lush greenery. The property features a classic façade with large windows that invite natural light, along with well-maintained steps leading to the entrance, set against a backdrop of manicured trees.
Condo in Chicago
4.73 out of 5 average rating, 259 reviews

Studio flat in the heart of Chicago's Gold Coast

Come stay in our one-bedroom studio apartment with a fully equipped kitchen and bathroom. Take in the perks of our central location with easy access to the Gold Coast beach and public transportation. Gibsons and the Original Pancake House are also a stone’s throw away. The property is the perfect refuge after a long day in the Windy City or sunbathing on the beach. After working hard and playing hard, a comfy bed with high-quality linens ensures you’ll be rested and ready for the next day.

Guest favorite
A hot tub with bubbling water is illuminated by soft blue lights, surrounded by wooden fencing. String lights overhead add a warm ambiance, creating a serene outdoor space for relaxation.
Condo in Chicago
4.94 out of 5 average rating, 274 reviews

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Superhost
Apartment in Chicago
4.81 out of 5 average rating, 1,001 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.

Top guest favorite
A modern kitchen space is illuminated by large windows, showcasing a view of the building's exterior. A round dining table with four chairs is positioned beside the kitchen, which features stainless steel appliances and sleek cabinetry. A decorative plant adds a touch of green to the design.
Condo in Chicago
4.95 out of 5 average rating, 144 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 favorite
Apartment in Chicago
4.84 out of 5 average rating, 339 reviews

Cozy Lincoln Park Studio - Steps to Zoo!

This cozy studio in the heart of Lincoln Park is just steps away from some of the best experiences that Chicago has to offer! Just a block from the Lincoln Park Zoo and near the great restaurants and bars of the neighborhood, there's something here for everyone. See a show at the world-famous Second City, take a quick ride up Clark St to see the Cubs play at historic Wrigley Field, or just stay in and relax, there's no wrong way to spend your time in the Windy City!

Top guest favorite
A private porch is depicted with a small round table and two black chairs. Green shrubs and potted plants add to the natural setting, while a view of tree-lined streets and brick buildings is visible in the background.
Home in Chicago
4.96 out of 5 average rating, 285 reviews

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

Top guest favorite
A spacious rooftop deck is adorned with a large sectional sofa in blue upholstery, offering panoramic views of the surrounding skyline and Lake Michigan. Glass railings enhance the open atmosphere, providing an unobstructed sightline to the water and buildings in the distance.
Condo in Chicago
4.9 out of 5 average rating, 188 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.

Top guest favorite
A modern kitchen features a spacious island with seating for two, surrounded by sleek cabinetry and stainless steel appliances. Natural light floods in through large windows, illuminating the décor, including a vibrant green wall accent and a textured area rug on the floor.
Apartment in Chicago
4.95 out of 5 average rating, 115 reviews

Pilsen Modern Chic Retreat

Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.

Guest favorite
Apartment in Chicago
4.98 out of 5 average rating, 204 reviews

Elegant Suite in Gold Coast

Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, this generous one-bedroom apartment is perfectly situated in the middle of the action for your Chicago adventure. ***Please note that from March until the end of September 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours. Construction will not be happening on the weekends.***

Superhost
A bright and open living space is highlighted by natural light from large windows. A spacious kitchen with wooden cabinetry and stainless-steel appliances is visible, alongside a comfortable seating area featuring a light-colored couch and a glass coffee table. A dining table enhances the inviting atmosphere.
Home in Chicago
4.82 out of 5 average rating, 278 reviews

Spacious Luxury Townhouse - Old Town

Historic 3 bedroom home in Old Town! Comfortably sleeps 6, and access to 3 levels of living space. The massive rain shower in the master bath is my favorite part, but there's plenty of luxury here to enjoy. Plus, we're right in the heart of Old Town, just steps from all of the shops and restaurants on Wells Street, and a 5 minute walk to the Sedgwick Brown/Purple line stop - you can be in the Loop in 20 minutes! Book today!

Guest favorite
Apartment in Chicago
4.92 out of 5 average rating, 181 reviews

Modern 3BR with Private Rooftop & Free Parking

A beautiful and modern 2450 sq feet apartment with a private rooftop deck, a rooftop firepit, an additional private patio and yard, brand new appliances, and bright spacious interior. Free private on-premise parking (1 garage spot and one driveway spot) in the heart of Chicago and a blocks walk to the L-transit system provides easy access to both downtown, the greater Chicago area, and both major airports.

Popular amenities for vacation rentals near Oak Street Beach

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