Places to stay near Oak Street Beach

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Top-rated vacation rentals near Oak Street Beach

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Guest favorite

The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.

Condo in Chicago

4.95 out of 5 average rating, 104 reviews

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE!! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops. Free parking on Lawndale Ave.

Guest favorite

A lush garden pathway winds through vibrant flower beds and greenery, leading to a cozy seating area nestled under a tree. The stone path is framed by various plants, showcasing a tranquil outdoor setting perfect for relaxation.

Guest suite in Chicago

4.96 out of 5 average rating, 338 reviews

Secret Garden @ The Noble Farmhouse | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

Guest favorite

A bright entryway features a white shelving unit adorned with a plant and a small decorative bottle. A wooden staircase is visible in the background, leading to the upper floor. Sunlight filters through the surrounding windows, creating a welcoming atmosphere.

Apartment in Chicago

4.84 out of 5 average rating, 211 reviews

Cozy Northside Apt near Transp&Beach&Free St Prkng

PRIVATE Entrance, One Bedroom Apt w/ LVG RM near Lake Michigan in beautiful, residential & diverse neighborhood. FREE on street PARKING, OR driveway spot for Addt fee. Sleeps up to 6. *It has a Kitchenette, Full Bath, WiFi, Cable TV, in unit W/D. Close to METRA TRAIN (1 block & 18 min to loop/city center), Bus Stop 1 block & the CTA "L" (elevated) Red Line to City 7 blocks away. Enjoy our proximity to Public Transit, Beaches, Loyola & NW Universities. Great for family, friends & kids.

Guest favorite

A spacious living room features large windows allowing natural light to fill the space. A comfortable light-colored sectional sofa is situated in front of a glass coffee table, with a medium-sized rug underneath. A wooden side table and a television mounted on the wall are also visible.

Apartment in Chicago

4.94 out of 5 average rating, 179 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Guest favorite

Bungalow in Chicago

4.9 out of 5 average rating, 30 reviews

Located on Beautiful and Quite Boulevard!

Welcome to The Boulevard A spacious house recently updated located at the beginning of the beautiful quite boulevard. The house is on beautiful Wrightwood Neighborhood Greenway! This house is centrally located 5 minutes away from Metra train station ( Healy Station) that will get you downtown in 15 minutes. Check with Metra for train times. Drive Downtown in 20 minutes(no traffic), O'Hare airport, West Loop. 20 mins to Lakeview, Wrigleyville, Boystown, Logan Square, Bucktown & Wicker Park.

Guest favorite

A modern living area features a spacious blue couch and two black reclining chairs facing a wall-mounted television. A light-colored coffee table sits in front, with a decorative plant in one corner. Natural light fills the space, highlighted by hardwood flooring.

Home in Chicago

4.88 out of 5 average rating, 169 reviews

Lake View | Wrigley Designer House w/Patio

Between Wrigley Ville and Lincoln Park, our home is on a quiet street. We are surrounded by coffee shops, restaurants and nightlife. There is a Whole Foods less than a block away, a Target and other groceries stores within 5 minutes walk. The house is over 2,500 square feet spread over 3 floors, with 4 completely separate bedrooms. Extra tall ceilings in the common areas, artsy cathedral ceilings and skylights in the upstairs bedrooms and very comfortable mattresses will help you unwind.

Top guest favorite

A modern kitchen featuring a large island with seating for six, complemented by sleek cabinetry and stainless steel appliances. Natural light fills the space through a nearby window, and an adjacent dining area is visible, offering a blend of functionality and style.

Home in Chicago

5 out of 5 average rating, 12 reviews

Alluring Avondale Abode

Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

Top guest favorite

A vast sandy beach extends toward the horizon, where gentle waves meet the shoreline. A harbor pier is visible in the distance, leading to a lighthouse. Dune grass and a wooden fence mark the beach's edge, with an overcast sky providing a soft, diffused light.

Apartment in Chicago

4.95 out of 5 average rating, 80 reviews

Loyola & Lake -3br/2bth close to the Lake & Loyola

Amazing lake views from 2 outdoor spaces! This lovely 3 bedroom, 2 bath unit has a large front balcony and also a rear deck looking out to the lake. The unit has an updated kitchen & 2 baths, a dining area, in unit laundry & a spacious living room with a fireplace & lots of books and games to keep you entertained! Walking distance to restaurants and bars. Starbucks is a short walk down Sheridan. Kayak/paddle board rental available (May 1-Oct 15th), weather permitting.

Superhost

Apartment in Chicago

4.92 out of 5 average rating, 12 reviews

2-level PH w/ 2 Luxe Suites Combined; Spa Access

The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: - Uber-fast Wifi streaming, - Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches - European decor - 2 kitchens - The popular 606 Trail access is 100 ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

Guest favorite

The exterior of a charming Victorian house is showcased, featuring a white facade, large windows, and a decorative entryway. An American flag hangs from the porch, surrounded by greenery and a well-maintained pathway leading to the entrance.

Apartment in Chicago

4.9 out of 5 average rating, 184 reviews

Clean, spacious, walk to Wrigley! Self check-in!

Park your car and forget it- or just leave it at home! Charming 3 BR first floor apartment in a Victorian building in the ultimate location, perfectly situated between Wrigleyville and Lincoln Park in the beautiful, vibrant Lakeview neighborhood. Guys seriously… this is the ideal neighborhood for a Chicago getaway or visit with family.

Top guest favorite

The exterior of a three-story residential building is depicted, featuring a wooden porch with steps leading to the front door. Large windows allow natural light to enter, and greenery surrounds the entrance, complementing the light-colored siding and red brick foundation.

Apartment in Chicago

4.96 out of 5 average rating, 281 reviews

Spacious 1BR apartment in a central location

Private 1BR in Avondale neighborhood of Chicago. Right off the Expressway, it's 20 mins from O'Hare, 20 mins from Downtown (both by Blue Line) 20 mins from Wrigley Field (bus). Comfortable and spacious attic apartment in a residential area. Lots of street parking.