Mansion vacation rentals in Chicago

Find and book unique mansions on Airbnb

Top-rated mansion rentals in Chicago

Guests agree: these mansions are highly rated for location, cleanliness, and more.

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Guest favorite

A spacious kitchen features modern cabinetry and stainless steel appliances. An island with bar seating for eight is complemented by sleek blue chairs. Natural light fills the area from large windows, illuminating the open layout that transitions into a cozy dining space.

Home in South Loop

Large Home | Free Parking | Near Downtown

FamilyValueTV

4.89 out of 5 average rating, 129 reviews

Top guest favorite

A comfortable living room is showcased with a grey sofa adorned with decorative pillows. A round coffee table sits on a patterned rug, and a green vintage cabinet adds a pop of color. Bright light enters through open doorways, leading to a dining area beyond.

Condo in Downtown Chicago

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.

ValueFamilyLayout

4.97 out of 5 average rating, 150 reviews

Top guest favorite

An expansive rooftop patio is showcased, featuring woven outdoor couches with blue cushions arranged around a glass-top table. The city skyline is prominently visible, with notable buildings punctuating the clear blue sky, complemented by touches of lush greenery.

Home in Downtown Chicago

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.

ValueLocationGrill

4.95 out of 5 average rating, 131 reviews

Top guest favorite

A comfortable living area showcases a modern design with a large flat-screen TV mounted on a stone feature wall. Soft lighting highlights a cozy seating arrangement, including a plush sofa and two armchairs. A decorative coffee table sits in the center, contributing to a welcoming atmosphere.

Apartment in Albany Park

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!

ValueLocationHeating

4.97 out of 5 average rating, 217 reviews

Guest favorite

Condo in West Side

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.

LocationFamilyWalkability

4.93 out of 5 average rating, 178 reviews

Top guest favorite

An aerial view displays a modern building featuring a vibrant green rooftop adorned with real grass. Below, the ground level showcases a Starbucks coffee shop framed by large windows. The surrounding urban environment is identifiable by tree-lined streets and nearby structures.

Home in The Loop

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.

LocationValueDecor

5.0 out of 5 average rating, 132 reviews

Guest favorite

A spacious living room features large windows allowing natural light. A modular sectional sofa is arranged invitingly in front of a sleek fireplace. A modern coffee table sits atop an area rug with geometric patterns, and an expansive wall-mounted TV awaits entertainment.

Home in Chicago

Gorgeous 5 BR Gem Sleeps 18 with Tons of Games!

No cleaning fees! Gorgeous gem 10 miles from Downtown, Airport, Lake Michigan, and United Center! 15 miles from Wrigley Field and the Zoo. Next to CTA! 6 bedrooms 2 bathrooms, 10 beds. Sleeps 18 comfortably. Perfect for large groups! Modern smart home with air hockey, pool table, video games, 2 ping pong tables, foosball, 9 big screen TVs including 85" Samsung QLED with surround sound, outdoor dining, charcoal grill, cornhole, dining room, game room, 2 living rooms, and full kitchen.

LocationValueTV

4.91 out of 5 average rating, 136 reviews

Top guest favorite

A dining area features a round wooden table surrounded by six chairs, enhanced by soft lighting. Exposed stone walls and large windows contribute to a cozy ambiance, while potted plants add a touch of greenery.

Apartment in Lake View

Inspiring Stone Grotto Sleeps 10-20 & Free Parking

Imagine a stone castle, medieval style; except this one has an 85" HDTV, Wifi, 16' long granite bar with full kitchen and appliances. The warm glow of recessed lighting and polished concrete floors of this basement unit create a comfortable atmosphere. Lots of space with over 2,000 square feet; fully rehabbed with all newly appointed features. A secure building with a private entrance, free parking. Perfect for large groups of up to 20 friends and family; located in East Lakeview.

ValueLocationAir conditioning

4.94 out of 5 average rating, 232 reviews

Superhost

A modern living area showcases a coffered ceiling and stylish furnishings. Plush sofas and accent chairs are arranged around a coffee table, with a large wall-mounted television and a decorative painting enhancing the aesthetic. Natural light enters through multiple windows, illuminating the space.

Condo in West Town

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.

FamilyLocationNearby

4.95 out of 5 average rating, 219 reviews

Top guest favorite

A cozy living area features comfortable seating with a dark blue sofa, two armchairs, and a wooden coffee table. Natural light streams through large windows adorned with decorative frames. A small decorative tree and artwork add warmth to the space, complemented by a soft area rug.

Home in Lincoln Park

Historic Old Town, Fabulous 4 Bedroom Home

Lovely Historic 4 Bedroom, 3 bathroom home in Old Town, walking distance of restaurants, boutiques, coffee shops, the lake front and excellent public transportation. 2nd Fl. Master Bedroom has a King size bed and Twin plus private bath with bathtub, walk in shower, w/d; 2nd Fl. two room "suite" with a Queen size bed in each room and private bathroom. 1st Fl. bedroom with Queen bed and private bathroom. Off Street Parking and Private Deck! License Pending.

FamilyLocationBiking

4.87 out of 5 average rating, 212 reviews

Top guest favorite

A spacious living area is furnished with two comfortable sofas and an armchair. A central coffee table rests on polished wooden floors. A built-in bookshelf displays decorative items, and a fireplace adds character, complemented by a wall-mounted television above.

Apartment in Hyde Park

Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!

This will likely be the largest condo you have ever seen. This condo is 5 mins from the University of Chicago and the University of Chicago hospital. You will be a quick 10-15 min uber ride from downtown and 5 mins from beautiful Lake Michigan. We are currently only booking out of town travelers. We are not doing parties or events. I live in the building so if you are trying to have a party I will have it shut down and you will be asked to leave within an hour.

FamilyValueIndoor spaces

4.94 out of 5 average rating, 588 reviews

Top guest favorite

The brick exterior of the three-story home features large windows that provide natural light, framed by dark accents. A set of stairs leads to the black front door, showcasing a modern design. The surrounding area includes concrete walkways and mature trees.

Home in Wrigleyville

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.

LocationFamilyLaundry

4.99 out of 5 average rating, 121 reviews