What are the top rated Villa Rentals in Chicago?

There are a lot of options in Chicago. If you plan on staying in the Chicago area, consider making a reservation for a few nights at one of these properties as these have been rated the top Villa Rentals in Chicago: <a href="/property/the-sono-chicago/EP-12913775" class="class="static-page-link"">The Sono Chicago</a> <a href="/property/52nd-floor-magmile-penthouse-views-fireplace-pool/HA-32165673" class="class="static-page-link"">52nd Floor MagMile Penthouse Views Fireplace Pool</a> <a href="/property/bella-villa-on-taylor-street-chicagos-little-italy-1-mile-west-the-loop-uic/HA-1217399612" class="class="static-page-link"">Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop &amp; UIC</a> <a href="/property/55th-floor-penthouse-with-award-winning-views/HA-3217757" class="class="static-page-link"">55th Floor Penthouse with Award-Winning Views</a> <a href="/property/3f-vintage-graystone-in-little-italy-near-loop-uic-united-ct-mccormick-place/HA-3212331854" class="class="static-page-link"">3F Vintage Graystone in Little Italy near loop UIC United Ct &amp; McCormick Place</a> <a href="/property/53-floor-magmile-penthouse-views-balcony-pool/HA-32172685" class="class="static-page-link"">53 Floor MagMile Penthouse Views, Balcony, Pool</a> <a href="/property/luxury-loyola-3-bedroom-2-bath-near-subway-and-beach/HA-321963119" class="class="static-page-link"">Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach</a> <a href="/property/51st-floor-magmile-penthouse-views-balcony-pool/HA-321411255" class="class="static-page-link"">51st Floor MagMile Penthouse Views Balcony Pool</a> <a href="/property/2-story-penthouse-views-fireplace-pool-gym/HA-321275170" class="class="static-page-link"">2-Story Penthouse Views, Fireplace, Pool, Gym</a> <a href="/property/new-luxury-penthouse-condo/HA-3212177560" class="class="static-page-link"">NEW LUXURY PENTHOUSE CONDO</a>

What is the rate per night for renting a villa near Chicago?

At Holidayinthehamptons, the average rental fee for standard villas in Chicago is $808 per night. Holidayinthehamptons has a large database of quality villas near Chicago that are suitable for families, a romantic getaway, or a solo trip with single or multiple bedrooms.

Do you have a villa in Chicago that allows pets?

Yes, here are the top villas rentals in Chicago that are pet friendly: HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12 Hamaline Luxury Guest House Luxury 9 BR, Villa Mins from Downtown and the Lake. Villa D' Citta Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach Homan Square The Sono Chicago Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood See all pet-friendly vacation rentals in Chicago on Holidayinthehamptons

Are there any rental villas in Chicago that are suitable for families?

Most of our listed villas are suitable for families. The number of rooms varies, and you can check out the complete list of villas in Chicago to find what works for you.

Do your rental villas in Chicago have indoor swimming pools?

Based on the 2026 data from our Holidayinthehamptons site, there are more than 9 private swimming pools or villas with indoor pools in or near Chicago.

Chicago Villa Rentals【 LUXURY 】

HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12

From US $493

9.6 (14 Reviews)

Villa

HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12

Air Conditioner
Parking
Pet Friendly

Chicago Villa Rentals & Homes

Find villas near Chicago - We found 9 exact matches

When do you want to travel?