Mansion holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago mansion rentals
Luxury mansion rentals
Home in Gold Coast
5 out of 5 average rating, 4 reviewsGold Coast Pristine 4BR/4.5BA Home | Free Parking.
Home in Logan Square
4.93 out of 5 average rating, 15 reviewsBucktown Home - Great Location!
Apartment in Lake View
4.8 out of 5 average rating, 123 reviewsSpacious Home, Incredible Lakeview Location
Home in Near North Side
4.96 out of 5 average rating, 23 reviewsPrivate Downtown Retreat with Rooftop Oasis
Home in Logan Square
5 out of 5 average rating, 35 reviewsLux LoganHouse w/garage, Sleeps 12, & rooftop deck
Home in Lake View
4.94 out of 5 average rating, 53 reviewsEntire house w/ free parking, close to Wrigley!
Townhouse in West Town
4.91 out of 5 average rating, 117 reviewsUpscale 4-Bedroom Townhouse w/Garage - LOCATION
Home in The Loop
5 out of 5 average rating, 72 reviewsArchitect's Urban Oasis | 4bd/3ba I Luxe
Pet-friendly mansion rentals
Home in North Center
4.98 out of 5 average rating, 52 reviewsBeautiful Family Home in North Center near Wrigley
Home in Schaumburg
4.85 out of 5 average rating, 71 reviewsSpacious 5 Bedroom 1 Level Renovated Modern House
Rental unit in Lake View
4.82 out of 5 average rating, 304 reviewsSophisticated, Historic & Comfy Flat near Wrigley!
Home in Elmhurst
4.93 out of 5 average rating, 158 reviewsThe Ultimate Escape|Unpack|Relax|Enjoy!Sleeps10-14
Home in Logan Square
4.92 out of 5 average rating, 26 reviewsEntire Home in Historic Logan Square
Home in Chicago
4.92 out of 5 average rating, 84 reviewsBeautiful Chicago Greystone
Home in Oakbrook Terrace
4.78 out of 5 average rating, 54 reviewsDesirable chic home in a Prime Location!
Home in Chicago
4.98 out of 5 average rating, 44 reviewsHyde Park Haven: Exquisite Airbnb
Mansion rentals with a pool
Rental unit in The Loop
4.85 out of 5 average rating, 13 reviewsDTown Penthouse - 4bd/4ba (+Parking + Gym + Pool)
Rental unit in Magnificent Mile
Luxury Designer Penthouse Combo |South| Gold Coast
Home in Munster
5 out of 5 average rating, 7 reviewsMunster hide away
Home in Bloomingdale
4.94 out of 5 average rating, 34 reviewsGiant Swimming Pool with Whole House!
Home in Bensenville
5 out of 5 average rating, 14 reviewsNew! Arcade+Sauna+Slots+Karaoke+more by O’Hare
Home in Lake Forest
4.9 out of 5 average rating, 63 reviewsBeautiful 137 Year Old Farm Home (3night min)
Rental unit in The Loop
4.63 out of 5 average rating, 56 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Rental unit in Logan Square
4.89 out of 5 average rating, 9 reviews2-level PH w/ 2 Luxe Suites Combined; Spa Access
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Saugatuck Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Bend Holiday rentals
- South Side Holiday rentals
- Schaumburg Holiday rentals
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