Mansion vacation 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.

United Center Compound w/Rooftop, Hot Tub, Sauna

Welcome to the Chicago Mid-Century Gem, an extraordinary urban retreat. With easy access to the CTA Green Line and Madison 20 bus stop, explore the United Center, West Loop, Fulton Market, and downtown with ease, then return to a home designed for gathering and entertaining. Featuring 4 spacious bedrooms, a chef's kitchen, a rooftop deck with a bar, a game-ready lower level, a luxurious primary suite, and a rare heated 3 car garage, this home is the perfect place to relax after every adventure.

Large Home | Free Parking | Near Downtown

• HUGE Single Family Home | 3 Floors • Parking Garage | 2 Cars! • Chef's Kitchen | Cookware | Utensils • Basement | Two Living Rooms • 4 Bedrooms | 5 Beds | Sleeps 10 • Downtown | McCormick Place: 10min(drive) • Soldier Field | Sox Stadium: 10min(drive) • Chinatown | Pilsen Nightlife: 5min(drive) • Lakefront | Beach | Museums: 10min(drive) • Outdoor Surveillance | Noise Monitoring • Washer | Dryer | Dishwasher in unit (free) • Rideshare(Uber/Lyft) | Bikeshares(Divvy) • Working Class Neighborhood

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.

Large Remodeled Home in Lincoln Park, Sleeps 12!

Stay in this thoughtfully remodeled home in Lincoln Park. Sleeps 12 w/ complimentary access to 3 parking spots! Enjoy the spacious layout, massive bedrooms, 2 private decks, and front yard w/ a grill. You will be steps from the North & Clybourn Red Line station, Divvy stations, Binny's, Whole Foods, Trader Joe's, Steppenwolf Theatre, so many incredible restaurants! Our home is (conveniently!) located next to train tracks. If you are a light sleeper, this urban location might not be for you.

Live Logan Square The Globally Loved Neighborhood

Discover your serene Logan Square oasis on a quiet cul-de-sac, just steps from Milwaukee Ave’s top restaurants, bars, Maplewood Brewery, Stan Mansion, Rosa’s Blues Lounge & The Whale. Explore the 606 Trail, hop the Blue Line to airports & downtown, Fullerton bus to Lincoln Park Zoo, and Lakefront or stroll to Bucktown, Wicker Park & the public library a block away. Enjoy self-check-in, free street parking, a fully equipped kitchen, 4 BR, 2 BA, washer/dryer & yard. (No parties per Chicago regs.)

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!

Beautiful 4 BR Family Home near Wrigley

This 4-bedroom, 3.5-bathroom home is the perfect spot for a comfortable and relaxing stay. Designed with families in mind, the house includes a play area, toys, and a high chair for younger guests. It’s also in a great location, just a short walk to local playgrounds, coffee shops, restaurants, grocery stores, the train and only 1.5 miles from Wrigley Field. Key Features: Fireplace and firepit for evening relaxation Rooftop deck with comfortable seating Gas grill for outdoor cooking

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.