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
Oct. 18 – 25
Condo in Chicago
4.94 out of 5 average rating, 124 reviews711 The Penthouse
Oct. 21 – 28
Apartment in Chicago
4.92 out of 5 average rating, 133 reviews❤️ Lowest Rates! Spacious Duplex with Parking!
Jul. 12 – 19
Apartment in Chicago
4.86 out of 5 average rating, 166 reviewsImpeccable 5-Bed Wrigleville Beauty
Oct. 9 – 16
Condo in Chicago
4.82 out of 5 average rating, 187 reviewsChicago River West 4 Bedroom / 3 Bathroom
Jul. 14 – 21
Condo in Chicago
4.98 out of 5 average rating, 123 reviewsLuxury 4 bedroom steps from Wrigley
Dec. 12 – 19
Home in Chicago
4.9 out of 5 average rating, 160 reviewsSoaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP
Jul. 23 – 30
Townhouse in Chicago
4.97 out of 5 average rating, 122 reviews*SPACIOUS 4 Bedroom Townhouse with FREE PARKING!*
Sep. 25 – Oct. 2
Pet-friendly mansion rentals
Apartment in Chicago
4.82 out of 5 average rating, 275 reviewsStylish Comfy Flat by Wrigley Field+CTA for Groups
Nov. 19 – 26
Apartment in Chicago
4.86 out of 5 average rating, 154 reviews*Comfortable & Spacious Home Close to Downtown*
Feb. 7 – 14
Home in Chicago
4.84 out of 5 average rating, 150 reviewsDowntown Elegance ✨ Private Yard Parking
Feb. 9 – 16
Home in Chicago
4.93 out of 5 average rating, 101 reviewsLuxury House 6BED/2.5BATH/4PARKING close to lake
Dec. 10 – 17
Home in Mokena
4.85 out of 5 average rating, 13 reviewsMarvel - 4BRs, 2 BA & Game Rm
May 9 – 16
Home in Chicago
5.0 out of 5 average rating, 20 reviews4BD/4BTH - Entire Building+Garage - Wicker Park!
Dec. 17 – 24
Home in Elmhurst
4.89 out of 5 average rating, 9 reviewsElegant Haven: 4BR/3BA Retreat
May 11 – 18
Home in Skokie
5.0 out of 5 average rating, 24 reviewsLuxury Home - Pool Tbl/Bar/Patio
Jan. 10 – 17
Mansion rentals with a pool
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Nov. 12 – 19
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
Jul. 23 – 30
Yurt in Homewood
4.97 out of 5 average rating, 74 reviewsGlamping Yurt&RV Game Room Pool/Hot Tub/Sauna plus
Jan. 28 – Feb. 4
Apartment in Chicago
5.0 out of 5 average rating, 4 reviewsLuxe 2-Level PH + Spa House Retreat! Pets Welcome
Oct. 23 – 30
Apartment in Chicago
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Mar. 11 – 18
Apartment in Chicago
5.0 out of 5 average rating, 3 reviewsCloud9 | Up to 15 ppl Millenium Park | The Jordan
Dec. 12 – 19
Home in Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
Aug. 13 – 20
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Aug. 17 – 24
Destinations to explore
- Downtown Chicago Vacation rentals
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