Vacation rentals with a home theater in West Side

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, 34 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.

4.91 out of 5 average rating, 119 reviews

The Executive's Escape (Fitness Center • Sauna)

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 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, 44 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

5 out of 5 average rating, 9 reviews

Upscale High-Rise Apt · Rooftop Pool + Views

Stay in this brand-new 2025 apartment with luxury amenities. Perfect for work or leisure, it offers everything you need for a comfortable stay. Building Amenities: - 24/7 concierge & secure entry - Rooftop pool & gym with skyline views - Rooftop lounge with a fireplace - Steps from grocery stores & restaurants - Paid parking nearby Unit Highlights: - Stunning views of the city - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modernly designed interior

Superhost

A well-appointed living room displays a comfortable sectional sofa and a leather ottoman at the center. Natural light filters through a large window, illuminating the wooden floor. A staircase ascends to one side, while decorative details enhance the inviting atmosphere.

Home in Evanston

4.74 out of 5 average rating, 19 reviews

Cozy Evanston Villa with cinema and massage sofa

Come and enjoy the beautifully decorated cozy home, perfect for family union and friends gathering. The theme of our cottage is to offer you a cozy and relaxing experience. House features Breville Espresso Latte maker, specially designed home Cinema and leather Massage chairs, a dedicated peaceful workspace with enjoyable view to the neighborhood. The central location of the house, close to the Lakeshore Beach and to Northwestern University campus gives a unique vibrant touch to this place.

4.98 out of 5 average rating, 225 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 lot

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

4.94 out of 5 average rating, 35 reviews

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.

Home in Chicago

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 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, 53 reviews

Private Duplex w/ Games + Theater | Near UChicago

Enjoy our spacious 2-level home this spring, 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, and a furnished patio. Kids and young adults especially love the fun setup, making it a memorable Chicago stay for all. We welcome last minute bookings!

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

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.

4.94 out of 5 average rating, 157 reviews

Belmont Pleasures - hot tub / arcade gaming room

Welcome home! If you’re looking for a unique experience to enjoy with your friends and family come have some fun in this beautiful luxury home, located in belmont-cragin neighborhood Chicago IL 60634 The spacious house includes 3 bedrooms, 4 full bunkbeds , 2 queen beds , 2 sofa queen beds , 2 & 1/2 bathrooms . Whether you’re looking to book for a birthday, bachelor/bachelorette gathering, or trip with family and friends, this place has something for everyone.

4.86 out of 5 average rating, 43 reviews

An inviting collage displays the exterior view of a charming house with a well-maintained lawn surrounded by lush greenery. Adjacent images highlight a game room featuring a pool table and a cozy movie room. A comfortable seating area is visible, alongside an outdoor patio space.

Home in Skokie

Urban Oasis | Kid Friendly | Quiet Street

Spacious rooms, cool design house, and peaceful location, ... are what you can expect when staying at the property :). We also have tons of amenities: + fully equipped kitchen + game room for adults and kids + movie room HD projector + poker table + king bed + private garage & easily accessible street parking + many more... Distances: _ 5 minutes drive to Dempster train station. _ 7 minutes drive to Westfield Old Orchard mall. _ 25 minutes drive to down

A modern kitchen features high-end stainless steel appliances and a spacious quartz-topped island with seating for three. A wall-mounted television displays scenic imagery, and a wood dining table is paired with black chairs, while plants add a touch of greenery to the space.