Vacation rentals with a home theater in Chicago River

4.97 out of 5 average rating, 30 reviews

A gray wooden house is shown with a front staircase leading to the entrance. Several windows allow natural light to fill the interior. The surrounding lawn is well-maintained, and mature trees offer shade, creating a serene environment close to neighboring properties.

Apartment in Forest Park

Comfy & Cute-Oak Park Area - Parking +Public Trans

Centrally located near downtown Forest Park, walk to the many restaurants, shops, and tourist attractions. Minutes from the Green Line and Metra to get you downtown to museums, restaurants and shopping. Beautiful 1 bedroom apartment in a 4 flat building on a quiet block. Great fit for short and long-term rentals. The kitchen is fully equipped for home cooking. Radiant heat. Laundry available in the building WIFI. Streaming HD TV. Free parking. This unique place has a style all its own.

A bright and airy living area is filled with natural light from floor-to-ceiling windows, offering expansive city views. A plush sectional sofa is positioned on a soft area rug. Potted plants and a console with a television add to the inviting ambiance.

4.97 out of 5 average rating, 33 reviews

Skyline Oasis: City & Lake Views

Welcome to our breathtaking one bedroom penthouse-like corner apartment! With stunning city, lake, and river views, this high-floor oasis offers an unforgettable stay. Stylish and luxurious designer furniture, spacious balcony, full kitchen stainless steel appliances, work area, fast wifi, immaculate cleanliness, rain shower, king-size bed, TVs, fan, AC. Building amenities: pool, jacuzzi, fitness room, plus more. Cleanliness is our top priority, ensuring an immaculate space for your stay. Enjoy!

An outdoor pool is surrounded by lounge chairs in various colors, creating a bright and inviting atmosphere. Tall buildings are visible in the background, and the pool reflects the clear blue sky overhead.

4.9 out of 5 average rating, 113 reviews

The Executive's Escape (2BD / 2BA)

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

A spacious dining area features a large wooden table set for a meal, surrounded by green chairs. Natural light fills the room through multiple large windows, offering views of the greenery outside. A vase with flowers and decorative items add subtle charm to the setting.

5 out of 5 average rating, 9 reviews

Explore•Relax | Family/Pets | 10m O’Hare | 30m DT

• 10 minutes to O’Hare • Sleeps 19 comfortably–7 bedrooms and 4 baths • Close to CTA & Metra–easy access to all Chicago attractions • 30 minutes to Downtown Chicago • Near Rosemont nightlife/casino–endless entertainment nearby • Full kitchen & spacious dining • Dedicated Workspace • Free on-site parking • Pet friendly upon approval (limit 2) • Peaceful community vibes only! Keep outdoor fun within fenced area, not driveway or front • Please help us keep noise respectful for our great neighbors.

The exterior of the home features a warm brick façade, large front windows allowing natural light to fill the interior, and inviting steps leading to a decorative front door. Lush greenery and potted plants enhance the welcoming atmosphere of the entrance.

4.97 out of 5 average rating, 92 reviews

H&H 1896 - Spacious, Fully Stocked, & Free Parking

Built in 1896, modern restoration, & featured on HermosaChi blog “Homes built before 1900”. The exterior of this private compound includes free driveway parking for up to 6 cars, beautiful backyard garden, pergola, fire pit, basketball court, & children’s swing set. The interior sleeps up to 21 guests, consists of modern aesthetics, moody hues, home theatre, exercise room & also a kids jungle gym. Located just 20 minutes from the heart of downtown Chicago, your private urban retreat awaits!

A comfortable seating area features a plush sectional sofa adorned with soft throw pillows. Light beige cushions contrast against the deep green walls. A large television is mounted opposite the seating, while sheer curtains frame the window beside a door that leads outside.

4.95 out of 5 average rating, 38 reviews

Designer Garden Unit in Bridgeport

Welcome to Bridgeport! You're a short walk from the best coffee shops, vintage stores, cocktail bars, art galleries, parks, restaurants, and Rate Field, the home of the White Sox! The neighborhood has so much to offer! Just minutes from Chinatown, McCormick Place, and 10 minutes to downtown Chicago! Be sure to check out my guidebook for recs! I look forward to hosting you! -Free street parking -easy Uber/Lyft 24/7 -easy access to public transit -15-25 mins from Midway -30-45 mins from O'Hare

4.98 out of 5 average rating, 215 reviews

A modern kitchen features sleek gray cabinetry and stainless steel appliances, including a refrigerator and oven. A neutral area rug complements the wood flooring. Natural light is provided by large windows, and stylish wall decor adds a contemporary touch to the space.

Condo in Chicago

RockStar Pad W3A BoysTown/Wrigley Field/Parking

HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $10/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

A modern two-story home features large glass windows that reflect surrounding greenery. The entrance, adorned with a light fixture, is accessed by a set of stairs leading up from the black iron gate and fence that encloses the property.

4.94 out of 5 average rating, 34 reviews

Bucktown Home - Great Location!

Modern, single-family home in the heart of Bucktown. Completely renovated! Close to shops & restaurants on Damen Avenue as well as the 606 trail and Wicker Park. Two living areas that include a drop down theater screen and wet bar in the lower level. There is an outdoor patio attached to the house as well. Perfect for business travelers, families, or couples. Especially suited for a family trip to the city! We do require reservation inquiries supply us with details about their trip.

A cozy seating area features two brown leather chairs positioned near a contemporary electric fireplace. The wall is adorned with a large painting and a mural resembling a library, creating an inviting atmosphere. Warm lighting enhances the elegance of the space.

4.9 out of 5 average rating, 42 reviews

The Grand Vic: Large 5BD/3BA Home (+Garage)

Welcome to the Grand Vic, an extraordinary Airbnb nestled in the heart of the city’s historic North Center neighborhood. This one-of-a-kind property has been meticulously designed to be more than just a place to stay—it's a journey through the very best of the Windy City’s culture, history, and charm. * 5 min drive/20 min walk to Wrigley Field * Short walk to many restaurants, bars, and cafes * Sleeps 12 comfortably, 5 bedrooms and 3 full baths * 24 min drive from O'hare Airport

4.89 out of 5 average rating, 111 reviews

The sitting room features various seating options, including a floral-patterned sofa and orange lounge chairs. Soft lighting illuminates the space, which is accented by thatch palm leaf wall coverings and tropical decor. An exercise area is visible in the background, enhancing the room's versatility.

Guest suite in Chicago

Tropical Bungalow Getaway in Quiet Neighborhood

Located on a quiet tree lined street, the bungalow's garden level design was influenced by the rumpus rooms of the 1950's. A private side entry, a few steps down from the rear courtyard, leads into your tropical get away. Heywood Wakefield furniture and thatch palm leaf wall covering enhance the Tiki vibe of the sitting room. An exercise area, private bedroom and bath are all accessed from this main space. While the suite is at garden level, it is always bright and airy.

Superhost

A spacious living room is displayed, featuring a large sectional sofa adorned with decorative pillows. A glass coffee table rests on a patterned rug, while creative wall art and a wooden sculpture enhance the atmosphere. Soft lighting from a ceiling fan provides a warm ambiance.

4.98 out of 5 average rating, 51 reviews

Private Duplex w/ Games + Theater | Near UChicago

Enjoy our spacious 2-level home this fall and winter, perfect for families and groups. The lower level is your entertainment hub with a 120" projector, retro arcade, ping pong, board games, reclining sectional, 1 bedroom, and 1 bath. Upstairs features two bedrooms, a full bath, an electric fireplace for cozy nights, a fully stocked kitchen with coffee, and a furnished patio. Kids and young adults especially love the fun setup, making it a memorable Chicago stay for all.

The game room features a red-themed layout filled with arcade machines, a pool table, and foosball. A variety of classic games are showcased, providing a fun atmosphere for guests. Bright lighting illuminates the room, inviting enjoyable gaming experiences.