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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago mansion rentals
Mansion rentals with a pool
Home in Schaumburg
4.33 out of 5 average rating, 6 reviewsParadise 4BR w/ Pool & Games
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Glen Ellyn
4.94 out of 5 average rating, 17 reviewsGlen Ellyn Home
Yurt in Homewood
4.97 out of 5 average rating, 75 reviewsGlamping Yurt&RV Game Room Pool/Hot Tub/Sauna plus
Apartment in Chicago
5.0 out of 5 average rating, 4 reviewsLuxe 2-Level PH + Spa House Retreat! Pets Welcome
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Apartment in Chicago
5.0 out of 5 average rating, 3 reviewsCloud9 | Up to 15 ppl Millenium Park | The Jordan
Apartment in Chicago
4.62 out of 5 average rating, 50 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Luxury mansion rentals
Condo in Chicago
4.95 out of 5 average rating, 132 reviewsThe Grand Kimball Lodge, Logan Square, Sleeps 14
Townhouse in Chicago
4.95 out of 5 average rating, 196 reviewsLuxury River West Townhome with Garage
Condo in Chicago
4.94 out of 5 average rating, 126 reviews711 The Penthouse
Condo in Chicago
4.98 out of 5 average rating, 127 reviewsLuxury 4 bedroom steps from Wrigley
Home in Chicago
4.9 out of 5 average rating, 162 reviewsSoaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP
Condo in Chicago
4.82 out of 5 average rating, 188 reviewsChicago River West 4 Bedroom / 3 Bathroom
Apartment in Chicago
4.93 out of 5 average rating, 134 reviews❤️ Lowest Rates! Spacious Duplex with Parking!
Apartment in Chicago
4.86 out of 5 average rating, 169 reviewsImpeccable 5-Bed Wrigleville Beauty
Pet-friendly mansion rentals
Condo in Chicago
4.79 out of 5 average rating, 109 reviewsSpacious Home, Incredible Lakeview Location
Home in Chicago
4.82 out of 5 average rating, 139 reviewsHistoric Old Town, Fabulous 4 Bedroom Home
Townhouse in Chicago
4.84 out of 5 average rating, 150 reviewsDowntown Elegance ✨ Private Yard Parking
Home in Chicago
4.93 out of 5 average rating, 106 reviewsLuxury House 6BED/2.5BATH/4PARKING close to lake
Apartment in Chicago
4.86 out of 5 average rating, 155 reviews*Comfortable & Spacious Home Close to Downtown*
Home in Oakbrook Terrace
4.82 out of 5 average rating, 38 reviewsDesirable chic home in a Prime Location!
Apartment in Chicago
4.98 out of 5 average rating, 53 reviews4 BR Mayfair flat
Townhouse in Chicago
4.84 out of 5 average rating, 44 reviewsLarge Executive Row house in Historic Pullman
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