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/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/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/modern-corner-2br-in-streeterville-roof-deck-lake-views/HA-1219588184" class="class="static-page-link"">Modern Corner 2BR in Streeterville | Roof Deck | Lake Views</a> <a href="/property/lowest-rates-fun-stylish-3br-in-logan-square/HA-3213993999" class="class="static-page-link"">❤️ Lowest Rates! Fun &amp; Stylish 3BR in Logan Square</a> <a href="/property/adorable-single-family-home-in-logan-square/HA-3211664685" class="class="static-page-link"">Adorable single family home in Logan Square</a> <a href="/property/mich-ave-5-safe-dtown-grant-park-museums-2bd-2ba/HA-3212036872" class="class="static-page-link"">MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba</a> <a href="/property/chicago-gold-coast-luxury-home-best-location-walking-distance-to-anywhere/HA-3212133270" class="class="static-page-link"">Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!</a>

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

There are more than 3056 pet-friendly rentals available on Rentthecottages. Check prices and availability in Chicago and last updated on December 2025. 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.