
Places to stay near Oak Street Beach
Book unique holiday rentals, homes and more on Airbnb
Top-rated holiday rentals near Oak Street Beach
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

LIVN Millennium Park Downtown Chicago 1 BR
Experience the best of Chicago from this stylish, newly renovated 1-bedroom at 19 S Wabash Ave. Perfectly located in the heart of downtown, you'll be steps away from iconic Millennium Park, the vibrant shops of Michigan Avenue, and a world of dining options. This 1 bedroom offers modern comfort with a fully equipped kitchen, including a refrigerator, dishwasher, and coffee maker, plus the convenience of an in-unit washer and dryer, making it ideal for both short getaways and extended stays. Enjo

Charming 3-BED in Lincoln Park/ Old Town & Parking
Welcome to our charming retreat in the historic Old Town Triangle/Lincoln Park district of Chicago. This conveniently located 3-bedroom apt, including office space, is nestled in the heart of a safe residential neighborhood with a 5-min walk to Brown Line and 10-min to Red Line. Within a 20-min walk, you'll find yourself at Lincoln Park Zoo, Beach, Second City, and Wells Street, immersing yourself in the vibrance of the old town. Book now to experience the best of Chicago. Parking+EV charging.

Fulton House #1 (2bd/ 1ba)
Unique & stylishly designed by Chicago's own Outline Interiors, this highly sought after location is for those that want to stay on a calm side street around the corner from city's best, award-winning restaurants and trendiest shopping. The fully-serviced apartment has the business-travel amenities you want: ultra speed wifi, work stations, top tier dining options within steps of the front door, Nespresso coffee, bottled water, washer/dryer. First-come parking next door: $20/nt or $200/mo.

Gold Coast Pristine 3BD|2BR| Patio |Parking| Beach
FREE GARAGE PARKING! Garage Clearance 6ft. Step into luxury in this modern loft with 3 bedrooms, 2 bathrooms and a private patio with breathtaking views. Experience the feeling of being at home in a bright and spacious haven amidst Chicago's most sought-after neighborhood "Gold Coast" This centrally located gem is situated within walking distance of much of Chicago Downtown's exquisite dining, upscale boutiques, popular tourist destinations, and just a stone throw away from Oak Beach.

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.

Penthouse Corner 3BR in Streeterville | Roof Deck
Stunning 1,500+ square foot corner penthouse with oversize windows, an open layout, and dramatic city and lake views from every room. This bright and modern three bedroom, two bathroom apartment 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° views of the skyline and the lake. This is the best location in the city!

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).

Chic Home! Walk to Nightlife-Comedy-Restaurants!
Stay in the heart of Chicago Old Town! This bright, cool and comfortable one bedroom, one bath is decked out in mid century modern furniture, exposed brick, new appliances and has a true city feeling! It comfortably sleeps two (3rd person can sleep on the couch), just 2 blocks to Lincoln Park, and 3 blocks to the famous Second City & stellar Old Town bars. Not to mention a quick 5 minute Uber ride to river north district (downtown Chicago)!

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.

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.***

Old Town Condo: Private Terrace & Garage Parking
Experience vibrant Chicago from this modern 2-bed, 2-bath Old Town condo. Perfect for families or professionals, it features a private terrace, gourmet kitchen, dedicated workspace, and a rare dedicated parking spot. Soaring 13-ft ceilings and stylish design create a light-filled urban retreat just steps from Lincoln Park, Second City, and North Avenue Beach. Comfortably sleeps 4.
Popular amenities for holiday rentals near Oak Street Beach
Apartment rentals with wifi

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

Modern Izakaya Studio in Wicker Park

Studio flat in the heart of Chicago's Gold Coast

Your perfect place looks like?

NEW luxury Old Town 1-Bedroom condo

Chicago Oasis | Spa Bath, Patio & Fireplace

Two Bedroom w Porch in Wicker Park

Lincoln Park Hideaway - 5 Min Walk to the Park!
Family-friendly house rentals

Flat in Lincoln Park 2-Flat Central to Everything

NEW! 3BR/2.5B Duplex in Noble Sq

The Ashlin House.

Entire first floor in Lincoln Square!

Wrigleyville Southport Studio

3 bed/2 bath by United Center w/ private parking

Private Downtown Retreat with Rooftop Oasis

Large Home | Free Parking | Near Downtown
Apartment rentals with air conditioning

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Archways at the Lincoln Park Zoo 2bed/2ba

The Lakefront Lookout (Rooftop Deck • Gym)

Spectacular Pilsen Studio for 2!

Spacious 1-bedroom South Loop Loft I Sleep 5

Coach House in Historic Old Town Chicago

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt

Urban Chic Apartment by the Magnificent Mile
Other great holiday rentals near Oak Street Beach

The Dunhill - Designer Gold Coast Flat by Mag Mile

Level Junior Two Bedroom Suite | Fulton Market

Elegant Gold Coast Duplex, Walk to Downtown

Gold Coast 1BR – Easy Downtown Access

Hancock Lookout|Steps to Beach&Transit, CHI Views

2BR w/ Huge Rooftop & Chicago Skyline Views

Luxury Designer Penthouse|Private Deck|Gold Coast

A Sunny, Well-Kept & Comfy Studio in Gold Coast
Destinations to explore
- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- Chicago River Walk
- The Field Museum
- Shedd Aquarium
- University of Chicago
- Humboldt Park
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Union Park
- Frank Lloyd Wright Home and Studio
- Donald E Stephens Convention Center
- Beachwalk Vacation Rentals
- Washington Park Zoo





