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, 4 reviewsParadise 4BR w/ Pool & Games
Home in Glen Ellyn
4.94 out of 5 average rating, 17 reviewsGlen Ellyn Home
Apartment in Chicago
5.0 out of 5 average rating, 4 reviewsLuxe 2-Level PH + Spa House Retreat! Pets Welcome
Yurt in Homewood
4.97 out of 5 average rating, 74 reviewsGlamping Yurt&RV Game Room Pool/Hot Tub/Sauna plus
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Apartment in Chicago
4.62 out of 5 average rating, 50 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Apartment in Chicago
5.0 out of 5 average rating, 3 reviewsCloud9 | Up to 15 ppl Millenium Park | The Jordan
Luxury mansion rentals
Condo in Chicago
4.95 out of 5 average rating, 132 reviewsThe Grand Kimball Lodge, Logan Square, Sleeps 14
Condo in Chicago
4.98 out of 5 average rating, 126 reviewsLuxury 4 bedroom steps from Wrigley
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
Condo in Chicago
4.94 out of 5 average rating, 125 reviews711 The Penthouse
Home in Chicago
4.9 out of 5 average rating, 162 reviewsSoaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP
Townhouse in Chicago
4.84 out of 5 average rating, 150 reviewsDowntown Elegance ✨ Private Yard Parking
Townhouse in Chicago
4.97 out of 5 average rating, 123 reviews*SPACIOUS 4 Bedroom Townhouse with FREE PARKING!*
Pet-friendly mansion rentals
Apartment in Chicago
4.83 out of 5 average rating, 254 reviews4BDRM Gorgeous Apt Pilsen Private Parking avail
Apartment in Chicago
4.82 out of 5 average rating, 277 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 Lombard
4.93 out of 5 average rating, 61 reviewsImagine… 5 Brs/ Game Room
Townhouse in Chicago
4.84 out of 5 average rating, 44 reviewsLarge Executive Row house in Historic Pullman
Home in Chicago
5.0 out of 5 average rating, 22 reviews4BD/4BTH - Entire Building+Garage - Wicker Park!
Home in Schaumburg
5.0 out of 5 average rating, 5 reviewsNifty Game Rm, King, 4 BR, 2.5 Ba Schaumburg
Home in Chicago
5.0 out of 5 average rating, 9 reviewsThe Full House
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Saugatuck Vacation rentals
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- Holland Vacation rentals
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