Holiday rentals with a home cinema in Downtown Chicago

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 Professional's Playground (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.

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!

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

Urban Oasis | Kid Friendly | Quiet Street

(SEND INQUIRY FOR JAN 2026 SPECIAL) 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

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.

Exquisite 4-Bedroom Retreat in Chicago

Welcome to our exquisite 4-bedroom, 4-bathroom haven! - Modern elegance meets unparalleled comfort - Spacious living area with chic furnishings - Upscale kitchen with high-end appliances - State-of-the-art theater for movie nights - Two rooftop deck areas for relaxation - Located in a prime neighborhood Experience the pinnacle of comfort and sophistication – book your stay now and elevate your getaway to new heights in this extraordinary residence. Your dream retreat awaits!

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

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.