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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.

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!

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

The Private Relaxation Oasis Near the Beach

Welcome to our spacious 4 bed, 3 bath oasis perfect to relax, entertain, family gatherings, friend reunions, beach vacations or corporate retreats! Our house boasts a large living room and rec room with a 75'' flatscreen TV, a dedicated workstation, a fully-equipped kitchen, and a cozy fireplace.The entertainment enthusiasts, enjoy a theatre area, reclining seats, pool table, arcade selection, & board games. The private hot tub is perfect for unwinding at night or cooling off during the day.

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

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.

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.

Cozy Cottage with Home Theatre in Joliet

Unique home because the top is totally how we bought the home everything is original from 1920's. Now the basement we renovated hence it feels like completely two different spaces. In this listing you are getting two full kitchens, 2 living rooms, 3 bedrooms and 2 bathrooms. Since this is a 1920s home there is no central air conditioning. Upstairs, there are windows units in the bedrooms that keep those rooms very cool. Downstairs, there are wall units.

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.

Fun and Cozy Family Home Near O’hare Airport

Spacious, amenity-filled home just minutes from O’Hare Airport, perfect for families and groups. Private 2-car garage plus driveway parking included. Sleeps many with 1 king bed, 3 queen beds, a twin-over-full bunk bed, and 3 twin futons. Enjoy 4 full baths, including a master jacuzzi, closets in every bedroom, and a fully equipped kitchen with coffee bar. Entertainment includes a theater room, gym, ping pong, 4-in-1 game table, and board games.