Holiday rentals with a home cinema in Near North Side

The Metropolitan Retreat (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.

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!

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!

Private Theater Duplex • 15 Min to Downtown

Enjoy our spacious 2-level home this spring and summer, 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 2 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!

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

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 Unit Highlights: - Stunning views of the city - Black-out curtains & roller shades - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modern design

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.

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 $20/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.

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.

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.

Luxury 4BR w/ Theater, Near Downtown & McCormick

Immerse yourself in East Pilsen, Chicago's most artistic neighborhood, where culture meets convenience. This modern 4 bed 2 bath home is just minutes from downtown, Chinatown, McCormick, and a 7-minute walk to Radius Chicago. Surrounded by vibrant restaurants, breweries, bars, and art galleries, it's perfect for travelers seeking a stylish retreat with free and easy street parking. Enjoy the best of the city next door to downtown—without the noise.