Mansion holiday 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.
Holiday rentals for every style
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Popular amenities for Chicago mansion rentals
Luxury mansion rentals
Apartment in Chicago
4.95 out of 5 average rating, 128 reviewsThe Grand Kimball Lodge, Logan Square, Sleeps 14
11–18 Jan
Flat in Chicago
4.96 out of 5 average rating, 235 reviewsSpacious 5-BR home next to transit! Great area!
10–17 Jul
Flat in Chicago
4.92 out of 5 average rating, 133 reviews❤️ Lowest Rates! Spacious Duplex with Parking!
2–9 Jul
Apartment in Chicago
4.98 out of 5 average rating, 123 reviewsLuxury 4 bedroom steps from Wrigley
20–27 Dec
Apartment in Chicago
4.82 out of 5 average rating, 187 reviewsChicago River West 4 Bedroom / 3 Bathroom
8–15 Jul
Flat in Chicago
4.86 out of 5 average rating, 166 reviewsImpeccable 5-Bed Wrigleville Beauty
14–21 Oct
Home in Chicago
4.9 out of 5 average rating, 160 reviewsSoaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP
21–28 Jul
Home in Chicago
4.84 out of 5 average rating, 150 reviewsDowntown Elegance ✨ Private Yard Parking
27 Mar – 3 Apr
Pet-friendly mansion rentals
Home in Highland Park
4.91 out of 5 average rating, 109 reviewsRejuvenate and Relax in the North Shore
16–23 Oct
Flat in Chicago
4.86 out of 5 average rating, 154 reviews*Comfortable & Spacious Home Close to Downtown*
7–14 Nov
Flat in Lake View
4.82 out of 5 average rating, 273 reviewsStylish Comfy Flat by Wrigley Field+CTA for Groups
14–21 Mar
Apartment in Chicago
4.79 out of 5 average rating, 107 reviewsSpacious Home, Incredible Lakeview Location
15–22 Jul
Home in Des Plaines
4.83 out of 5 average rating, 167 reviewsExotic House - Few minutes from O'Hare and Chicago
19–26 Jan
Home in Elmhurst
4.88 out of 5 average rating, 8 reviewsElegant Haven: 4BR/3BA Retreat
5–12 May
Home in Chicago
5.0 out of 5 average rating, 20 reviews4BD/4BTH - Entire Building+Garage - Wicker Park!
18–25 Oct
Home in Schaumburg
5.0 out of 5 average rating, 4 reviewsNifty King Bed Home, 4 BR, 2.5 Ba Game room
5–12 Dec
Mansion rentals with a pool
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
18–25 Apr
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
6–13 May
Yurt in Homewood
4.97 out of 5 average rating, 74 reviewsGlamping Yurt&RV Game Room Pool/Hot Tub/Sauna plus
18–25 Jan
Flat in Chicago
5.0 out of 5 average rating, 4 reviewsLuxe 2-Level PH + Spa House Retreat! Pets Welcome
23–30 Oct
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
12–19 Jan
Flat in The Loop
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
24–31 Mar
Flat in The Loop
5.0 out of 5 average rating, 3 reviewsCloud9 | Up to 15 ppl Millenium Park | The Jordan
22–29 Jan
Home in Schaumburg
New place to stayParadise 4BR w/ Pool & Games
31 Aug – 7 Sep
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
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