Mansion vacation rentals in Chicago
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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
Luxury mansion rentals
Condo in Chicago
4.95 out of 5 average rating, 129 reviewsThe Grand Kimball Lodge, Logan Square, Sleeps 14
Apartment in Chicago
4.93 out of 5 average rating, 134 reviews❤️ Lowest Rates! Spacious Duplex with Parking!
Condo in Chicago
4.94 out of 5 average rating, 125 reviews711 The Penthouse
Apartment in Chicago
4.86 out of 5 average rating, 169 reviewsImpeccable 5-Bed Wrigleville Beauty
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!*
Home in Chicago
4.9 out of 5 average rating, 161 reviewsSoaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP
Townhouse in Chicago
4.84 out of 5 average rating, 150 reviewsDowntown Elegance ✨ Private Yard Parking
Pet-friendly mansion rentals
Apartment in Chicago
4.82 out of 5 average rating, 277 reviewsStylish Comfy Flat by Wrigley Field+CTA for Groups
Home in Chicago
4.82 out of 5 average rating, 139 reviewsHistoric Old Town, Fabulous 4 Bedroom Home
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
Home in Chicago
4.93 out of 5 average rating, 104 reviewsLuxury House 6BED/2.5BATH/4PARKING close to lake
Apartment in Chicago
4.98 out of 5 average rating, 52 reviews4 BR Mayfair flat
Townhouse in Chicago
4.86 out of 5 average rating, 43 reviewsLarge Executive Row house in Historic Pullman
Home in Chicago
5.0 out of 5 average rating, 13 reviewsModern Family Townhouse
Mansion rentals with a pool
Home in Schaumburg
5.0 out of 5 average rating, 3 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
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
Apartment in Chicago
4.62 out of 5 average rating, 50 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Apartment in Chicago
New place to stayCloud9|Near Millenium Park|The Poppy
Destinations to explore
- Downtown Chicago Vacation rentals
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