Vacation rentals with a home theater in The Loop

Portage Park |Jacuzzi| Movie Theater|16 Guests|Gym

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

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!

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.

New 3Bed 1 Bath Foosball+ Ping-Pong+theater room

Have fun with the whole family at this stylish place. Only 15 mins away from Midway. 3 Bedrooms and a sofa bed , enjoy our theater area or if you're feeling competitive you can always start a foosball or ping-pong tournament with your guests. Also stay in and cook in our huge kitchen or eat at any of our delicious local restaurants 5 min walking distance. Grocery store also 2 blocks away. Really responsive Host ready to accomodate. Airport Pick up also available. This unit is entirely yours

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

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, 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!

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

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

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

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.

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.