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

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.

Luxury Condo | Spa Bath | Full Kitchen | FREE PRKG

Enjoy a luxurious escape in this modern Bronzeville home where style meets comfort. Designed with contemporary finishes, cozy textures, and a serene vibe, it’s perfect for couples, families, friends, or business travelers. Easily accessible to UChicago, McCormick Place, Soldier Field, Shedd Aquarium. With quick freeway access to I-90 & Lakeshore Drive, Downtown Chicago is just minutes away! Relax, unwind, and enjoy free street parking plus all the essentials for a premium Chicago stay.

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.

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.

Modern Haven in Little Village

Step into The Artistic Brick Loft, featuring modern amenities and artistic flair. The bedroom includes ample storage and unique décor. The living area boasts an exposed brick wall, chic furniture, and captivating artwork. The kitchen offers modern appliances and a dining area. The bathroom features a sleek design with a walk-in shower. In-unit laundry and easy street parking compared to other city locations ensure a hassle-free stay. Enjoy comfort and style.

Long Stay,The Jewels,2bd/2ba,UC 2mi,Pkg,DTWN 15mi

Welcome to ABODE6535: The Jewels Suite. This apartment is named after Chicago's popular grocery store chain and its residents' unique way of saying it. :) This vibrantly curated apartment is designed for comfortable extended stays that may make you consider making Chicago home, or at least make sure you feel at home while you're here. You will be welcomed into a well-appointed space with cozy linens, sparkling clean bathrooms and warm touches at every turn.

Comfy suite w/ steam shower near McCormick Place

Welcome to the landmark! Our well appointed studio space is situated in the historic Calumet-Giles-Prairie District; minutes from McCormick Place, Sox Park, Wintrust Arena, IIT, and downtown. Walk to 31st St Beach, bike to Museum Campus. Perfect for business or leisure; enjoy steam shower, Wi-Fi, smart TV, and full kitchen. Easy access to major highways and public transit. We also offer a Honda Accord rental car on Turo for your convenience upon inquiry.

Bright & Cozy Studio in the Heart of Hyde Park

Cozy, sunlit Hyde Park studio just blocks from UChicago. Enjoy a comfy queen bed, private bath, fast Wi-Fi, and a fully stocked kitchen with all essentials. Nestled on a quiet, tree-lined street in a safe, walkable neighborhood near cafés, restaurants, parks, and museums. Easy CTA and Metra access for downtown trips. Perfect for solo travelers, couples, and visiting academics seeking comfort, convenience, and a welcoming, homey atmosphere.

Comfy/Private Entry & Bath/Free Parking - Win Win!

A Hidden GEM on a private block in Bronzeville, ranked one of the hottest neighborhoods in Chicago. Great for those looking to travel the city from Downtown (4 miles), to the lake (1 mile) to Hyde Park (walking distance) or those simply looking to stay in and rest in a peaceful place. Welcoming guests from near and far in this comfy studio designed specifically to host those for a great Chicago experience!