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
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
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, 74 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
Apartment in Chicago
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Apartment in Chicago
New place to stayCloud9|Golf,Gym,CoWorking@LincolnPark|The Ash
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Luxury mansion rentals
Condo in Chicago
4.95 out of 5 average rating, 129 reviewsThe Grand Kimball Lodge, Logan Square, Sleeps 14
Home in Chicago
4.93 out of 5 average rating, 211 reviewsLuxe 6BR House *Trendy Logan Square *Garage Access
Condo in Chicago
4.94 out of 5 average rating, 124 reviews711 The Penthouse
Apartment in Chicago
4.92 out of 5 average rating, 133 reviews❤️ Lowest Rates! Spacious Duplex with Parking!
Condo in Chicago
4.98 out of 5 average rating, 125 reviewsLuxury 4 bedroom steps from Wrigley
Townhouse in Chicago
4.97 out of 5 average rating, 122 reviews*SPACIOUS 4 Bedroom Townhouse with FREE PARKING!*
Apartment in Chicago
4.92 out of 5 average rating, 61 reviewsThe Waveland Room 4 Bed/4bath Private Roof-Deck!
Home in Chicago
5.0 out of 5 average rating, 33 reviewsBright & Spacious 4BR Home in Heart of Logan Sq!
Pet-friendly mansion rentals
Home in Chicago
4.82 out of 5 average rating, 140 reviewsHistoric Old Town, Fabulous 4 Bedroom Home
Condo in Chicago
4.79 out of 5 average rating, 107 reviewsSpacious Home, Incredible Lakeview Location
Apartment in Chicago
4.82 out of 5 average rating, 276 reviewsStylish Comfy Flat by Wrigley Field+CTA for Groups
Apartment in Chicago
4.86 out of 5 average rating, 155 reviews*Comfortable & Spacious Home Close to Downtown*
Home in Chicago
4.85 out of 5 average rating, 115 reviewsHuge Home *Prime Spot *Yard *Parking *Fireplace
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, 103 reviewsLuxury House 6BED/2.5BATH/4PARKING close to lake
Apartment in Chicago
4.83 out of 5 average rating, 252 reviews4BDRM Gorgeous Apt Pilsen Private Parking avail
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
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