Holiday rentals in Oakwood Beach

Sunny Penthouse - Oakwood Beach

Bright top-floor 2-bedroom, 2-bath condo in the heart of Bronzeville with soaring ceilings and abundant natural light. Relax in the in-unit jacuzzi jetted tub after a day exploring Chicago. The fully equipped kitchen has everything you need to cook at home, or enjoy nearby restaurants. 🌊 Just a 18-minute walk to Oakwood Beach & the lakefront. Within a 20-minute drive of Downtown, Soldier Field, Guaranteed Rate Field, the Field Museum, the Art Institute, Chinatown, Hyde Park, Pilsen & more!

Large Minimalist Garden Studio: Centrally Located

Need a cozy, unique, convenient, & affordable place to stay? Look no further, this may 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 ideal escape. Relax, recharge, and leave your worries behind in a space thoughtfully designed for your comfort and convenience.

Oakwood Beach Lake & SkylineViews+CuldeSac+Parking

Modern luxury awaits you in this Urban Oasis in North Kenwood/ McCormick area. 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 many attractions that the Windy City has to offer. A few minutes from Obama Presidential Center, Navy Pier, Downtown, White Sox Stadium, Museum Campus, University of Chicago, 31st and Oakwood Beach Perfect for photos and filming!

Cozy Coach House Apartment-Near Downtown Chicago

Relax at this peaceful private entrance stay in the historic North Kenwood neighborhood right next to Hyde Park! Centrally located, blocks from the lake front, next to pickle ball park, 7 min drive to UChicago campus, and 8 mins drive to the world renowned, Museum of Science and Industry! A short walk to the Metra Train/buses to downtown, 12 min drive to downtown Chicago (6 miles), 10 min drive to McCormick Place (3.5 miles), and 9 min drive to the new Obama Presidential Center (2 miles)!

Lux Home Chicago 7mins Downtown

Come stay at our luxurious 2-story newer construction home in Chicago. This centrally located, gated, 4 Bedroom, 5Beds, 3 1/2 bath home is ideal for family vacation, work or leisure trips. It comes with a full upscale gourmet kitchen and a spacious fully furnished basement with gym equipment. It is just a 7mins drive to the best attractions in Chicago, including the beach and museums; close to numerous restaurants, nightlife, and major highways for easy travel and access around the city.

La Casita Norte

Modern Bronzeville 1-Bedroom Apartment in quiet centrally-located neighborhood close to McCormick Place, Wintrust Arena, and White Sox Park, IIT, and 31st Street Beach. Sleeps 4 with a full bed and queen living room sofa sleeper. Comfortable dedicated workspace with reliable Wi-Fi connection and morning coffee. Huge bath w/ separate shower and endless hot water, wet bar, living room, washer/dryer. Fitness room with a Bowflex machine, treadmill, Pilates reformer, yoga mats, trampoline.

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.

Lovely 1-bedroom serviced apartment near Museums!

Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

Blake’s Place

Welcome to our charming Air BnB! Nestled in a prime location, this cozy and stylish space is perfect for your getaway. With its tastefully designed interiors, and comfortable furnishings, you'll feel right at home. Our place features plush double queen size bunk beds for a restful sleep, while the fully equipped kitchen allows you to prepare delicious meals. Relax in the inviting living area or step out and enjoy a nice walk along Lake Michigan just 10 mins away.

Peaceful Hyde Park Studio Near UofChi & Nightlife

Stay in the heart of Hyde Park! This cozy 400 sq. ft. studio features a queen bed, 65" Roku TV, full kitchen, and private bath. Walk to the University of Chicago, the Museum of Science & Industry, and 53rd Street’s cafés, shops, and restaurants. Easy access to Metra, CTA buses, and the lakefront make exploring Chicago simple and convenient. Perfect for solo travelers, couples, or weekend getaways seeking comfort and style in a vibrant, historic neighborhood.

Stylish Hyde Park/Kenwood Brownstone Garden Apt

Enjoy a stylish experience in Chicago's historic Hyde Park/Kenwood neighborhood in this updated brownstone garden apartment. You'll have an entire tastefully designed speakeasy chic 2-bedroom/1.5-bathroom unit with a separate entrance to yourself. Great location off South DuSable Lakeshore Drive- you're minutes away from Lake Michigan's scenic lakefront, the University of Chicago, McCormick Place and downtown Chicago.

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!