Book Dog Friendly Accommodation in Chicago

We selected the 21 homes worth renting in this location

Home spotlights in Chicago

Skyscraper

Skyscraper

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Arriving at this home in downtown Chicago, you’re sure to be charmed by the typically Chicagoan high rise. Gaze down on the city above, and delight in the central location in the North River district – it's famous for its abundance of galleries and arty culture.

On Cloud Nine

On Cloud Nine

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Chicago isn't just known for its lively music scene and deep-dish pizza, but also for its larger-than-life architecture – after all, those skyscrapers speak for themselves. The best way to make the most of the magnificent metropolis?

Running Loops

Running Loops

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

This stylish home-from-home is in Chicago’s artistic and culinary zeitgeist – South Loop. A cool and creative neighbourhood, known for its lively music scene, bold architecture and history, you’re within walking distance from the Museum Campus and Art Institute – perfect for city-breakers and culture vultures alike.

Work & Play

Work & Play

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Work from home with ease at this stylish apartment in Chicago’s trendy River North neighbourhood. You’ll have plenty of options from where to set up shop – from the breakfast bar in the kitchen, to the bright blue armchair in the living room with sprawling city views.


We selected the top 3% holiday homes in Chicago Dog Friendly Accommodation

Explore the 21 most perfect homes in our collection

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Most popular homes in Chicago

Bluegill

Bluegill

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Checking Account

Checking Account

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Easel And Brush

Easel And Brush

  • 5 guests

  • 2 bedrooms

Near North, Chicago

Designed For Life

Designed For Life

  • 5 guests

  • 2 bedrooms

Near North, Chicago

Savings Account

Savings Account

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Modern Dream

Modern Dream

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Slice Of Sky

Slice Of Sky

  • 3 guests

  • 1 bedrooms

Rush & Division, Chicago

Solo Breeze

Solo Breeze

  • 2 guests

  • 1 bedrooms

Near North, Chicago

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Frequently asked questions

If you're planning a holiday and hoping to take your canine companion along for the ride, then you've certainly come to the right place. Here at Plum Guide, our collection of luxury Dog Friendly Accommodation in Chicago, Cook County, Illinois, United States consists of only the top 3% of homes. Each home is put through a vigorous vetting process, culminating in a visit from an independent Home Critic, so there is no danger of anything slipping through the cracks. Every rental in our collection comes fully furnished, with a fully-equipped kitchen, essential bathroom toiletries, and all linen included. Book a stay in Dog Friendly Homes To Rent in Chicago now, and secure a trip to remember for all parties. To ensure the home you choose is perfect for you, seek the help of our friendly team, who are ready to assist you at any time of day.

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