Vacation rentals with a home theater in North Side

Jacuzzi|Movie Theater|Games|Arcade|Gym|Kid's Space

Welcome to Portage Park! This beautifully remodeled 5-bedroom, 3-bathroom luxury style home is spacious 2,200 sq ft retreat designed for families, friends, and large groups of up to 16 guests. With 2 levels of living space, hot tub backyard, fun games, gym and a one of a kind entertainment basement inluding a home theater, game station for kids, game table & arcade machine, King Master with a private string light filled outdoor deck, we have everything you need for a memorable Chicago vacation!

Highrise Hideout (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.

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!

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

3 Luxury Master Suites by Gardens, Lake & Chicago

Welcome to your elegant Glencoe retreat on Chicago’s North Shore. This bright & beautifully finished home offers the perfect mix of comfort and sophistication with its 3-bedroom, 3-bathroom + queen sleeper sofa & 2 living rooms. Each bedroom has its own full bathroom, giving every guest privacy and convenience — a rare luxury in a vacation rental. Minutes from Chicago Botanic Gardens & Glencoe Beach. Perfect getaway to spend sunny days enjoying the charm of the North Shore. Family amenities

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

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.

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.

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

NEW Spacious 2-Story Designer Home • Yard • Garage

Stylish 2 story home with elegant touches throughout. Every room offers an experience, with thoughtful details incorporated across the unit. From the moody living room with eye popping wall finishes, to the sleek modern kitchen and dining area, every space is designed to impress. Each bedroom has its own cozy theme and comfortable beds. Relax on the huge couch with the 75” TV, play foosball with friends, or unwind by the fire pit on the back patio. Free garage parking included.

Coach House•Theater•Parking•6 minute Walk to FLW

Welcome to our fully stocked 2BR Coach House in Oak Park! This thoughtfully designed home offers free parking, central AC/heat, in-unit laundry, fast Wi-Fi, a private backyard, and more. Unwind in the board game and arcade room or relax in the theater room equipped with a 75” TV with complementary snacks and drinks. Perfect for families, couples, remote workers, or friends seeking a private, comfortable home base with easy access to downtown Chicago and all Oak Park offers.

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.