Holiday rentals with a home cinema in Downtown Chicago

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.

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

2-Story Unit | Theater+Arcade | PS5 | UChicago

Relax with family and friends this summer in our spacious 2-level home, equipped with central air! The lower level is your private fun zone—featuring a 120" projector for movies, a retro arcade game, ping pong, board games, a bedroom and bath, and a reclining sectional for movie nights! Upstairs, you'll find two bedrooms, a full bathroom, an outdoor patio, and a fully stocked kitchen with an air fryer, Keurig, and complimentary coffee. Everything you need for a fun, comfortable stay together.

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.

Luxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |

20 mins from popping downtown Chicago and tucked within one of the Northside’s finest tree-line streets—The Haus of Love: A modern wood burning fireplace, new hardwood floors, and a bright airy space greets you in this newly renovated Kosher inspired design Spacious Eat-In Kitchen w/ double everything. Separate Formal Dining. Wetbar. High End Quartz Countertops 3Bd 3.5Bath Master BD w/Heated Floors, 10-ft ceiling, skylights, and a huge 8-ft tub.

Modern Oasis | McCormick - Theatre - Radius

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.

Urban Oasis | Kid Friendly | Quiet Street

Spacious rooms, cool design house, and peaceful location, ... are some of the things you can expect when staying at the property :). We also have tons of amenities: + 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