
Vacation rentals in Oakwood Beach
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Top-rated vacation rentals in Oakwood Beach
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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

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.

Executive Contemporary Duplex
Discover a newly remodeled, stylish, & spacious 2-bedroom garden home with a separated basement apartment nestled in the historic Bronzeville neighborhood. This beautiful residence boasts enchanting décor and well-appointed living spaces that promise a memorable stay. Its minimalist charm and comfortable setup reflect a contemporary/modern aesthetic, making it an irresistible choice for guest. Just 6 mints from the downtown, 20 mints from Midway Airport, and 4 mints from McCormick Place & UOC.

Royal Coach House Cottage
Royal Coach House Cottage- Nestled in Bronzeville community and nearby Historic Hyde Park neighborhood that is safe and family oriented. Our space is quite cozy, quaint and ideal for relaxation, peace & quiet. Flower and vegetation garden landscape. Centrally located 1.5 miles from lake front, nearby shopping, movie theater, and restaurants. Seconds from park, walking track and playground. Minutes from downtown and Magnificent Mile. Local transportation accessible including bicycle rental.

Guesthouse | Near public transit and Lake front
A unique 400 sqft loft with bright open concept multipurpose space, large windows, full kitchen, and private access located in the historic Kenwood/Hyde Park area. Public Transportation - 5 minute walk Lakefront - 10 minute walk University of Chicago - 2 miles Museum of Science and Industry - 2.8 miles Mccormick Place 3.4 miles Millennium Park - 6 miles Navy Pier - 6.7 miles Hyde Park restaurants! Perfect for individuals or couples, great access to expressways to get anywhere in the city.

Cozy Uneek Space - Centrally Located Garden Unit
Need a cozy, unique, convenient, & affordable place to stay? Look no further! This might just be the perfect spot for you. Located in the heart of Historic Bronzeville, just minutes from downtown Chicago, McCormick Place Convention Center, Illinois Institute of Technology, Sox Stadium, & only 1.2 miles from the University of Chicago, this spacious & serene retreat offers the perfect escape. Relax, rejuvenate, & leave your worries behind in this space designed for your comfort & convenience.

Sunny Penthouse - Oakwood Beach
Gorgeous top-floor 2-bedroom, 2-bathroom condo in the heart of Bronzeville! With high ceilings and tons of natural light. The fully equipped kitchen has everything you need to cook a delicious meal, or you can enjoy one of the many great dining options nearby. 🌊Take a 15-minute walk to the lakefront and Oakwood Beach. Centrally located near: • Downtown Chicago • Soldier Field & Guaranteed Rate Field • Field Museum & Art Institute • Chinatown, Hyde Park & Pilsen • And much more!

2BR Brownstone 7-min to Events, Downtown, & Beach
Welcome to The Garden Oasis! Stay here if you want to live like a local in a historic Chicago Brownstone just minutes from the heart of the city. Thoughtfully designed with modern touches, a cozy living space, and plenty of natural light, it's the perfect place to relax after exploring. Walk to the beach, lakefront trail, and local eateries, or take a quick ride downtown to visit Chicago’s top attractions. Experience the best of the city from your own private retreat!

Lovely Garden Studio in Chicago
Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

NEW! Lake & Skyline Views Kenwood CuldeSac+Parking
Modern luxury awaits you in this Urban Oasis. New construction with all new finishes and stylish decor. Great natural light, free parking, views of Lake Michigan and the Chicago Skyline, nestled on a culdesac. Take advantage of countless attractions that the Windy City has to offer. A few minutes from Navy Pier, Downtown, White Sox Stadium, Museum Campus, University of Chicago, 31st Street and Oakwood Beach Perfect for photos and filming!

Large Studio Apartment with no cleaning fee
Large studio garden unit located in the lowest level of a 3 level home. Space is private with no shared interior common area. Great location. Minutes from Lake Michigan trails and beaches. City bus is close and El (train) 1 mile to west. 8 Minutes to Grant Park and all the city has to offer. Mccormick Place and University of Chicago are about 5 Minutes. Always plenty of street parking. Uber and Lyft serves.

Garden Retreat in Historic Bronzeville
Welcome to your home away from home in historic Bronzeville! This private basement unit sleeps 3 with one queen bed and a fold-out couch. Enjoy a full bathroom, private entrance, and everything you need for a comfortable stay. Located near McCormick Place, Chinatown, museums, the lakefront, public transit, and just minutes from downtown. Whether you're here for work or relaxation, we'd be happy to host you!
Popular amenities for Oakwood Beach vacation rentals
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Destinations to explore
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- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- 875 North Michigan Avenue
- Humboldt Park
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Washington Park Zoo
- Willis Tower
- The Beverly Country Club
- Raging Waves Waterpark
- The 606