Mansion holiday rentals in Chicago

Private Lincoln Park Condo with 2 Parking Spots

Built in 1895 and updated in 2025, the condo provides historic charm with modern convenience. The unit is light filled with ample space to spread out and relax. The bathroom has been fully remodeled and the kitchen is updated. The unit has a private balcony deck and a landscaped common patio. The unit includes 2 free off-street parking spots. Amenities include 60" 4K Smart TV, fiber internet, Nest Thermostat & Tuft & Needle/ Casper mattresses. Enjoy living in the heart of Lincoln Park.

HUGE 4BR Townhouse FultonMarket/WestLoop!

Stay in a spacious 4-story townhouse in Chicago's vibrant West Loop/Fulton Market, just steps from Restaurant Row, award-winning restaurants, nightlife, coffee shops, parks, and grocery stores. Enjoy the excitement of the neighborhood while staying on a quiet, treelined street for a peaceful night's sleep.Features include a private rooftop terrace with skyline views, an attached garage (1 regular vehicle fits), and easy access to public transit for O'Hare, downtown, Navy Pier, Mag Mile and more.

NorthSide Chicago duplex 5-BD,2King size-free park

5-BD, 2-BR duplex; a combination of first floor and garden units. Just a 3-minute walk from the train, our property is the perfect place for your big gathering. Sleeps up to 12 guests with indoor Jacuzzi, full kitchen, free indoor parking( 1 car), and private patio. Access to grill, fire pit with big screen TV, and sound system. Keyless check-in and 24/7 active security cameras. Don't miss out on experiencing the best of Chicago from our beautiful and convenient duplex unit. Book your stay now!

Private Downtown Retreat with Rooftop Oasis

Welcome to your exclusive retreat in the heart of the city, where urban sophistication meets unparalleled comfort. Nestled in between Magnificent Mile and Gold Coast, this luxurious Airbnb offers a haven of style and tranquility amidst the hustle and bustle. The rooftop patio offers incredible views of the city skyline, with touches of lush greenery. The spacious living areas boast oversized windows that flood the space with natural light. Each bedroom is a sanctuary where luxury meets comfort.

Neon Dream in River West!

Massive 4 bedroom space in Chicago’s River West Neighborhood that sleeps large groups. Perfect for bach groups, family vacas, and corp events. Features large entertaining space with pool table, 2 arcades, fully equipped bar, record player, and massive TVs with Youtube TV and Netflix. One parking spot provided with easy street parking nearby. 5 min Uber to Fulton Market; Chicago’s hottest restaurant/bar scene. Easy access via public transit and car. Centrally located to all Chicago has to offer!

Historic luxury townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the lavish Gold Coast of Chicago—one of the most sought-after locations in the city! Located on one of Chicago’s famous streets, you’ll be a 5-minute walk from the historic Gold Coast beach and intimate views of Lake Michigan. The property is also within walking distance of the subway, where you can connect to the L trains, and the Magnificent Mile. It is the perfect place to stay for adventurous travellers and those who fancy a beach in the City!

Luxury Designer Penthouse Loft | Sleeps 20

Designer Penthouse in the heart of Wicker Park! Sleeps up to 20 people! Enjoy your own private loft in Chicago's hip and trendy Wicker Park-one of the city's centers nightlife, restaurants and cultural scene. This 4,500 square foot penthouse sits on an entire floor features 18 foot open vaulted ceilings, authentic loft feel, 4 bedrooms/3 bathrooms, and is perfect for families, professionals visiting the city on work trips, and everything in between. The cityscape views are truly unbeatable!

UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)

Escape into this Wicker Park Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertainment on bustling Division St. - Close to every popular attraction that makes Chicago so great - Luxurious interior filled with natural light - Open-floor plan for entertaining! - City skyline views from top floor! - Fast WiFi (1,000 mbps) - Large attached garage! - Beautiful custom built-ins - Next to modern park and playground! - 10 minute walk from blue line (CTA L)

The Urban Oasis | Outdoor Lounge • Sleeps 10+

Luxury 4BR/2.5BA residence featuring 3 private bedrooms and an open-concept bonus room with a queen bed and full-size bunk beds—perfect for upscale families or executive groups. The spa-inspired primary suite offers a soaking tub and rain shower with multiple settings. Enjoy a modern kitchen, stylish living room with a 76” smart TV, and a large covered patio. Located near UIC, West Loop, Chinatown, McCormick Place, the lakefront, and some of Chicago’s best dining and cultural attractions.

Architect's Urban Oasis | 4bd/3ba I Luxe

Experience our one-of-a-kind home in the heart of downtown Chicago. It has 4 bedrooms, 3 bathrooms and comfortably sleeps 8. We are offering our home to select people visiting Chicago. Perfect for families and mature groups. I am an architect, and designed this home for my family in 2005. It was published in Chicago Magazine, Playboy, and featured in several TV commercials. Chosen by CS as the most luxurious AirBnb in Chicago in 2023. STRICT NO PARTY, EVENTS or EXTRA GUESTS policy.

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

Wrigleyville Single Family

Private single family home one block from Wrigley Field! Enjoy three levels of living all to yourself. Totally gut renovated home with a chef's kitchen, central heat/air, washer/dryer, and three full bathrooms. Three bedrooms on the second level with a full basement/ bedroom with its own bathroom. Large back deck off the kitchen with a gated parking pad for one large vehicle included. Have an amazing time in the very heart of Wrigleyville.