Holiday rentals in Oakwood Beach

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

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.

Bronzehaus - near McCormick, UChicago & Downtown

Welcome to Bronzehaus – a chic retreat in the heart of historic Bronzeville. Bronzehaus is a newly renovated, thoughtfully designed 2-bedroom, 1-bath garden-level apartment blending comfort and class. Inspired by the rich jazz legacy and artistic soul of the area, this stylish space features modern amenities and a cozy layout. Whether exploring nearby galleries, museums, a day at the beach, or heading downtown - Bronzehaus offers a comforting stay. Come stay where heritage meets hospitality.

Modern 2BRD apartment| 5min to McCormick Place

Stay in a newly remodeled, spacious 2-bedroom apartment in Chicago. FREE STREET PARKING (a rare gem in Chicago!) Just blocks from Illinois Institute of Tech, a 7-8 min walk to Green/Red lines, 15 min walk to White Sox stadium, 20 min walk to 31st St Beach, and a 5 min drive to McCormick. Sleeps up to 4 with 2 private bedrooms, full kitchen, workspace, TVs & WiFi. Please note: This is a multi-unit building with long-term tenants, so occasional noise from neighbors may be heard.

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 Belmont 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.

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).

A Family Rowhouse by UChicago

Our three level rowhouse includes a main floor with an open concept living space and kitchen making it the perfect gathering space. Basement in-law suite with kitchenette allows for max privacy for a large group. Located on University Ave. steps from UChicago and easy access to the lakefront trail and beaches as well as to downtown via Metra or express bus. A short walk to downtown Hyde Park. NOTE: Registered guests only. No parties. Thanks!

Bronzeville Beauty: Modern Style + Historic Charm

Come relax and take in Chicago's historic Bronzeville neighborhood. Stay in the bright and sunny garden unit of a fully renovated landmarked home built in 1887. We are located across from a neighborhood park with excellent access to CTA transit. Walkable to Lake Michigan, Lakefront Trail, White Sox stadium, IIT. Very close to McCormick Place, Hyde Park, and Chinatown. If you drive, free street parking is readily available in front of our home.

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.

CasaNova Modern City Living

Sprawling 4 Bedroom, 2.5 Bath 3 story house nestled on private cul de sac in a residential area. Chicago’s North Kenwood/Bronzeville neighborhood walking distance to the lakefront and 10min drive to city’s loop. Features open floor plan with hardwood floors, fireplace in living room, washer dryer, with outdoor space on each floor. Large patio available to enjoy Chicago's city and lake views!

2BR Brownstone 7-min to Events, Downtown, & Lake

Welcome to The Garden Oasis — a cozy, winter-ready Chicago retreat just 5 minutes from Soldier Field and McCormick Place. Perfect for Bears games, conventions, and stay-in nights, this historic brownstone features a warm living space for movies, board games, and hot chocolate with marshmallows. Close to great food and downtown, yet ideal for relaxing indoors after a day out.

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 May 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours***