Holiday rentals with a home theatre in The Loop

Highrise Hideout (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.

2BR Downtown Elmhurst | Pool, Gym, Kings, Garage

A professionally managed 2-bed 2-bath apartment in downtown Elmhurst, providing the perfect balance of luxury and comfort for business travelers and families. Walk to the cafes, restaurants, and shops of downtown Elmhurst, nearby classy Oakbrook (8 mins), O'Hare airport (12 mins), and blocks to the Metra train station with easy access to downtown Chicago! Enjoy the pool, fitness center, garage parking, courtyard with firepits, pool table, and movie theater - convenience is at your fingertips!

Private Duplex w/ Games + Theater |15 min 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

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 lot

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.

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.

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.

Loop 1BR | Steps to Millennium Park & Bean

Steps from Millennium Park in downtown Chicago. Modern 1BR with queen bed, full kitchen, in-unit washer/dryer, WiFi, and workspace. Building offers heated pool, gym, and 24-hour concierge. Walk to The Bean (3min), Riverwalk (2min), Art Institute (5min). CTA Red Line across the street connects you everywhere. Perfect for couples or solo travelers seeking an unbeatable Loop location.

Wicker Park 4BD Home: Parking, Theater, & Rooftop

Welcome to TheDreamRentals, an opulent 4-bedroom sanctuary in the city! - Grand foyer and spacious living areas - Chef's kitchen with top-of-the-line appliances - Five luxurious bedrooms with private retreats - State-of-the-art home theater for cinematic experiences - Two rooftop patio decks with panoramic city views Book your stay with TheDreamRentals today!