
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.

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
FamilyValueTV
4.89 out of 5 average rating, 129 reviews
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
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
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
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
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
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
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
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
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
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
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 reviewsPopular amenities for Chicago mansion rentals
Luxury mansion rentals

UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)
ValueFamilySleep quality
4.93 out of 5 average rating, 151 reviews
Chicago River West 4 Bedroom / 3 Bathroom
FamilyLocationIndoor spaces
4.81 out of 5 average rating, 264 reviews
Sensational 5 Bed beauty steps from Wrigley Field
FamilyLocationBeach
4.95 out of 5 average rating, 107 reviews
Fulton Market Townhome, 4 Levels & 4 Bedrooms
ValueFamilyLong stay
4.99 out of 5 average rating, 290 reviews
The Full House
LocationFamilyNearby
4.96 out of 5 average rating, 142 reviews
Impeccable 5-Bed Wrigleville Beauty
ValueFamilyNearby
4.87 out of 5 average rating, 252 reviews
Modern Gazebo Sleeps 17 Birthday Anniversary
LocationFamilyAmenities
4.97 out of 5 average rating, 165 reviews
Entire house w/ free parking, close to Wrigley!
LocationFamilyOutdoor spaces
4.95 out of 5 average rating, 132 reviewsPet-friendly mansion rentals

Charming 5-BR Duplex by Wrigley, Garage & Yard
LocationFamilyBathroom
4.86 out of 5 average rating, 362 reviews
Spacious 5-BR Apt next to transit Free Parking
FamilyValueSleep quality
4.86 out of 5 average rating, 121 reviews
Steps to Shops, Restaurants, Trains; 5BR, 14 Guest
LocationFamilyLong stay
4.89 out of 5 average rating, 141 reviews
Beautiful Chicago Greystone
ValueFamilyParking
4.92 out of 5 average rating, 151 reviews
Private Lincoln Park Condo with 2 Parking Spots
ValueLocationGetting around
4.97 out of 5 average rating, 152 reviews
Casa Pilsen-HOUSE| Location | Entire Home | Garage
ValueLocationKitchen
4.84 out of 5 average rating, 177 reviews
Home in Glen Ellyn
ValueFamilyPets
4.89 out of 5 average rating, 224 reviews
Chicago's Bridgeport Brownstone w/Garage Parking
LocationFamilyIndoor spaces
4.76 out of 5 average rating, 153 reviewsMansion rentals with a pool

Cozy Duplex Down in Wicker Park East w/ Parking
FamilyValueLaundry
4.93 out of 5 average rating, 131 reviews
Luxury Designer Penthouse Combo |North| Gold Coast
LocationHospitality
4.8 out of 5 average rating, 5 reviews
Luxury fenced in modern ranch
FamilyIndoor spacesHospitality
4.86 out of 5 average rating, 7 reviews
Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
LocationValueAir conditioning
4.6 out of 5 average rating, 72 reviews
Pardizes Suites
FamilyLocationHeating
4.85 out of 5 average rating, 27 reviews
Wabash 4BR | Pool, Free In/Out Parking 3
LocationComfortNearby
5.0 out of 5 average rating, 3 reviews
Rosemont 4BD2BA house with Pool
LocationFamilyCondition
5.0 out of 5 average rating, 28 reviews
Red Door
LocationHospitalityNearby
5.0 out of 5 average rating, 13 reviewsDestinations to explore
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- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
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- Navy Pier
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- 875 North Michigan Avenue
- University of Chicago
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- Loyola University Chicago
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- Lincoln Park Zoo
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