Vacation rentals in Oakwood Beach

A large, reflective sculpture sits in an open area, surrounded by towering buildings that showcase various architectural styles. The sky displays a soft blend of colors, hinting at dusk. Lush greenery is visible at the base of the sculpture, adding contrast to the urban landscape.

4.92 out of 5 average rating, 121 reviews

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.

A large, polished sculpture known as Cloud Gate reflects the skyline of Chicago's buildings, creating a mirrored effect. People are seen congregating around the structure, enjoying the park surroundings and taking photos, while green grass and urban landscaping are visible in the area.

4.89 out of 5 average rating, 28 reviews

Executive Contemporary Duplex

Discover a newly remodeled, stylish, & spacious 2-bedroom garden home 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, it's perfect for any length of stay.

A cozy bedroom features a spacious bed with patterned bedding, complemented by decorative pillows. A mirror and a wooden dresser are positioned against the wall. Natural light filters in through the two window coverings. A comfortable chair sits in the corner, and a small rug is placed underfoot.

4.94 out of 5 average rating, 149 reviews

Cozy 2 bdrm near McCormick Place & Wintrust Arena

Come enjoy Chicago via our cozy apartment in the quiet yet friendly Historical Bronzeville community. We are nestled between Hyde Park and South Loop, where you will find plenty of restaurants, theaters, and nightlife. Only minutes away from McCormick Place, 10-15 min drive from downtown and 3-12 miles from all the sports arenas and airports. You can bike or walk to the nearest grocery store, park, gym, and beach. The nearest bus and/or train is 2-3 blocks away for your convenience as well.

An aerial view captures the Royal Coach House Cottage, highlighted by a red wooden deck extending from the second floor. Surrounding homes and lush green trees provide a shaded environment. A well-maintained lawn and neatly arranged outdoor spaces are visible, offering a peaceful setting.

4.89 out of 5 average rating, 182 reviews

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.

4.85 out of 5 average rating, 149 reviews

A map displaying the route from Hyde Park to a nearby location, showing a distance of 2.9 miles with an estimated travel time of 9 minutes. Various streets and landmarks are outlined, with clear indicators for directions and distances.

Condo in Chicago

Quiet, Modern, Convenient 2 bedroom condo

PLEASE READ DESCRIPTION PRIOR TO BOOKING* Stay at this quiet, charming, Chicago-themed garden unit, sitting in the heart of Chicago's historic Bronzeville neighborhood. This convenient location with 1000 sq feet of space is perfect for young professionals, student, small groups, families, and people traveling with children. Easy access to public transportation, downtown Chicago, the Museum of Science and Industry, the University of Chicago, downtown Hyde Park, and etc. Hotel style, no kitchen

4.92 out of 5 average rating, 71 reviews

A compact workspace is situated near a fully equipped kitchenette. The desk, affixed to the wall, is complemented by a black office chair. An oven is integrated into the cabinetry, while a coffee maker is positioned on the countertop beside a sleek trash can.

Guesthouse in Chicago

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.

A serene garden area features a variety of flowering plants and lush greenery, bordered by a stone wall. A circular seating arrangement with four chairs surrounds a fire pit, creating a tranquil outdoor space. Decorative elements, including a birdbath, add charm to this peaceful setting.

4.92 out of 5 average rating, 36 reviews

Garden Apartment in Gated Home

This large 1300 sq ft professionally decorated, modern apartment has high 14 ft high ceilins and windows that create a bright living atmosphere. It features a fully stocked kitchen with stainless steel appliances. There's lots of entertainment space. It is within 3 miles to downtown, the Convention Center, Solider Field, and White Sox Stadium. Also, Chicago's universities and hospital districts are close by. Walk 2 blocks to enjoy the lakefront and parks. FREE ON SITE PARKING JANUARY- MARCH

Top guest favorite

An open-concept living area is visible from an elevated viewpoint, showcasing a blend of modern design and comfort. A warm-toned sofa and armchair are positioned around a low coffee table, with a fireplace adding a focal point. Natural light floods the space, highlighting the hardwood flooring.

5 out of 5 average rating, 23 reviews

Villa Noir Chicago Victorian 7 min to downtown

Welcome to Villa Noir - an expertly designed vacation HOME fully equipped with everything you need for a most enjoyable stay! Our home features 4 spacious bedrooms, 2.5 bathrooms, dedicated workspaces and a chef’s dream kitchen…not to mention an entire level of entertainment space! Complimentary amenities throughout…high-speed Internet, smart TVs, and coffee station. We are centrally located…a 7 minute drive to downtown dining / shopping, museums, the beach, McCormick Place and more!

4.93 out of 5 average rating, 27 reviews

An aerial view captures a bustling Chicago skyline with iconic skyscrapers by Lake Michigan. The expansive stadium is shown alongside green spaces and waterfront activities, illustrating the city's vibrant urban life.

Condo in Chicago

Lakeside Retreat: Charming Greystone Near Downtown

Immerse yourself in the vibrant energy of Chicago while enjoying the elegance of our greystone apartment. Located within a 10- 15 minute drive to downtown, you can effortlessly walk or bike to the scenic trails along Lake Michigan/ Lake Shore Drive. This urban oasis offers a perfect blend of city living, providing a comfortable haven after a day of exploring the dynamic surroundings. This location is close to Museums, Aquarium, Planetarium, U of Chicago as well as McCormick Place.

An outdoor hot tub is positioned on a wooden deck, featuring a secure cover along one edge. Relaxing seating is provided by a nearby chair. The hot tub is equipped with jets and clear water, creating a serene environment for use at an additional charge.

4.88 out of 5 average rating, 16 reviews

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 is 5 Minutes. Always plenty of street parking. Uber and Lyft available. Note:The caption under my picture is inaccurate. We have been hosting since 2019.

A large 75-inch television mounted on a wall displays a home screen featuring various streaming options. Below it, a sleek black media console holds items such as gaming controllers and DVDs. The plush carpet adds a soft texture to the area.

4.94 out of 5 average rating, 17 reviews

Stay & Play: Sox, Bears & Lake!

This spacious 1 bed 1 bath Garden unit is perfect for exploring Chicago! Located in a family-friendly historic Chicago neighborhood next to White Sox Stadium, Soldier Field, and a 15-minute walk to Lake Michigan. It's also just a 10-minute drive to the Magnificent Mile for Chicago's best shopping and dining. The unit features a 75-inch TV, darts, mini fridge, microwave, and complimentary snacks and coffee. A cozy spot for sports fans and city explorers, alike!

Top guest favorite

A modern living space is illuminated by natural light from large windows, showcasing a stylish dining table accompanied by upholstered chairs. A comfortable seating area features a sectional sofa and decorative accents. A classic game table adds an engaging element to the room's design.

5 out of 5 average rating, 74 reviews

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!

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Popular amenities for Oakwood Beach vacation rentals

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Other great vacation rentals in Oakwood Beach

A hallway showcases an arched entryway leading into a shared living space. Light grey walls provide a soft backdrop for the hardwood flooring. A white door stands ajar, revealing additional areas such as the dining table and kitchen, enhancing a sense of openness.

4.72 out of 5 average rating, 39 reviews

Bees Knees - Room 3

MikaylahRating, 5 stars3 weeks ago

I really enjoyed my stay here . Genova place is very affordable, well kept for a shared space . I like that everything was organized . Toiletries such as body soap , hair conditioner was provided as well as towels and linens . Genova was able to accommodate me as well with some plans that didn’t quite work out with my airfare . I was very grateful and appreciative of that as well . Very good and timely with communication on whatever I needed . I’m sure a future stay here will be planned out . Maybe sooner than later . Great host . Until next time …

The kitchen features modern cabinetry with light wood finishes, complemented by stainless steel appliances. A gas stove and oven are positioned beneath a sleek hood. Lighting is provided by recessed fixtures, and the space includes a double sink, coffee maker, and a door leading to the hallway.

5 out of 5 average rating, 17 reviews

Private bath Hyde Park UChicago x2

MichaelaRating, 5 stars3 days ago

The room was clean, instructions to get in the apartment are very easy to follow. Great communication with the owner. The apartment is located very close to the public transportation.

A modern kitchen is featured with white cabinetry and stainless steel appliances. A round wooden dining table is complemented by orange chairs. A bouquet of flowers adds a splash of color, while natural light brightens the space through the window.

4.85 out of 5 average rating, 119 reviews

Hyde Park/UC Newly Renovated Private Room #1

MarcianoRating, 5 stars2 weeks ago

Great stay at Andy's place. Listing is accurate to the description. Place is clean, private room and shared bathroom has all the essentials. Roommates were very private so I felt like I was free to stay in the common areas without much disturbances. Andy himself was very professional and responsive to my messages. Check in was very easy. I would recommend Andy's place and would definitely stay here if I am in town again for a conference. Thank you for a very peaceful and pleasant stay, Andy!

4.92 out of 5 average rating, 273 reviews

A bowl of salad features succulent grilled shrimp atop a bed of greens. Slices of avocado and crispy tortilla strips add texture. The dish is presented in a white bowl with a blue rim, placed on a rustic wooden table beside a blue and white striped cloth and fork.

Hotel room in Rosemont

Relaxing Standard Room l Free Airport Shuttle

AlexeiRating, 5 stars2 weeks ago

easy check-in, super clean, friendly staff. parking is easy and affordable. will definitely be staying again!

A spacious balcony features wooden flooring and a railing, providing an outdoor space overlooking a green area. Nearby buildings can be seen in the background, along with unobstructed views of the surroundings, creating a serene setting.

4.8 out of 5 average rating, 5 reviews

room with Queen bed, work desk and dresser

ElsieRating, 5 stars3 weeks ago

We had a lovely time at Aminata’s place, who was always so helpful and responsive. The area is near a train station into the centre of the city, and the neighbourhood is quiet. We would come back and stay again.

4.84 out of 5 average rating, 31 reviews

A modern kitchen is showcased with white cabinetry and stainless steel appliances. Ample counter space is complemented by a large kitchen island, featuring elegant pendant lighting. Bar stools provide seating, and plants adorn the countertop, enhancing the functional and inviting layout.

Condo in Chicago

Condo off the lake

GabeRating, 5 stars1 week ago

This was the best property we've ever stayed at. Everything was as advertised or better. Darryl answered all our questions in a timely fashion and even had the place ready a little before our scheduled check-in to accomodate our flight schedule. The neighborhood is excellent, very safe and quiet. We never had to park more than 50 feet from the front door. Everyone's first impression was "This place is huge" and it was actually even better than the pictures indicated--and the pictures indicated it would be great. Absolutely would look to stay here any time we are in Chicago and looking for something south of downtown. Would recommend to anyone looking for a place in the area. Easy commutes to downtown or Hyde Park and ride shares always arrived within 10 minutes.

A modern bathroom features a tub with a showerhead and sleek white tiles. A patterned curtain provides privacy, while a mirror enhances the sense of space. Two bath mats are positioned on the floor, and toiletries are neatly arranged on the wall.

4.88 out of 5 average rating, 78 reviews

HydeParkC, UC, Chinatown, NavyPier, freeparking

SophiaRating, 5 stars2 weeks ago

My fiancé and I were in Chicago for the weekend for a short getaway. John’s place was perfect! It was quiet, extremely pristine, and offered free parking. The neighborhood was walkable and beautiful. The only thing I wish they offered was flexible check in. There was a time difference from Cincinnati to Chicago so we arrived earlier than expected. Overall, the stay is definitely worth the price!

A modern kitchen is equipped with stainless steel appliances, including a refrigerator, microwave, and stove. White cabinets provide ample storage, while a countertop offers space for food preparation. A washer and dryer are located beside the door, complemented by light tile flooring.