What are the top rated Pet Friendly Vacation 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 Pet Friendly Vacation Rentals in Chicago: <a href="/property/trendy-2br-apartment-in-logan-square/HA-3211952396" class="class="static-page-link"">Trendy 2BR Apartment in Logan Square!</a> <a href="/property/family-friendly-2bd-2ba-near-wrigley-lincoln-square/HA-121974965" class="class="static-page-link"">Family Friendly 2BD/2BA Near Wrigley, Lincoln Square</a> <a href="/property/spacious-and-airy-apartment-with-parking-on-site/HA-3211952379" class="class="static-page-link"">❤️ Spacious and Airy Apartment With Parking On Site!</a> <a href="/property/entertain-on-the-chain-waterfront-sauna-free-water-sports/HA-3211667677" class="class="static-page-link"">Entertain on the chain! Waterfront, sauna,FREE water sports!</a> <a href="/property/spacious-2-br-condo-free-on-site-parking/HA-3211948808" class="class="static-page-link"">Spacious 2-BR Condo + Free On-Site Parking</a> <a href="/property/stylish-and-cute-2br-apartment-near-wrigley/HA-3211952398" class="class="static-page-link"">Stylish and Cute 2BR Apartment Near Wrigley!</a> <a href="/property/tudor-house-stay-in-town-location/HA-3212131164" class="class="static-page-link"">Tudor house stay-In Town Location!</a> <a href="/property/in-town-apartment-in-downtown-geneva/HA-3211916471" class="class="static-page-link"">In Town Apartment in downtown Geneva!</a> <a href="/property/chicago-bootlegger-house-sleeps-11-22-with-3-parking-spots/HA-3212779421" class="class="static-page-link"">Chicago Bootlegger House Sleeps 11-22 with 3 parking spots</a> <a href="/property/king-bed-suite-spacious-newly-remodeled-house/HA-3213160138" class="class="static-page-link"">King Bed Suite, *Spacious Newly Remodeled House*</a>

How many pet-friendly vacation rentals are available in Chicago on Smartours?

There are more than 4958 pet-friendly rentals available on Smartours. Check prices and availability in Chicago and last updated on January 2026. Check an individual property if they have restrictions on the size or numbers of pets.

Do you have any luxury vacation homes that allow pets in or near Chicago?

Most definitely! There are many luxury places to stay in Chicago. Use our search filter to discover all of our luxury accommodations where pets are welcome, then choose the one that matches your taste. Sorting by price is another way to find the most expensive dog-friendly home in Chicago. Though note, more expensive is not always better.