Spring has sprung across the country, meaning slightly warmer temperatures on the East coast and sunny skies with little rain out West. With summer just around the corner, we’re already dreaming about our next vacation. Each week, we’ll pick our favorite dog-friendly Airbnb vacation rental in a city we’d love to visit – so you can pack your suitcase, grab the leash and get out of town.

Sunny & Spacious Vintage 2 BR Gem in Chicago

Apartment in Chicago, United States. Sparkling Art Nouveau Gem in Wicker Park 10 minute walk to Damen-Blue Line 10 second walk to Damen Bus Line 1 block from Division St. Scene Quiet Edith Wharton Residential Neighborhood 10ft Ceilings-Hardwood Floors W&D LGBT Encouraging SIX Privat… View all listings in Chicago

Where you’ll stay:
Vintage décor and modern furnishings make this sunny and spacious apartment the ultimate Chicago getaway. With two bedrooms, one and a half bathrooms and two living areas, there’s plenty of space for your crew. The apartment also has a spacious patio, so you and your dog can relax outside after a long day of playing tourist. Necessities like a washer and dryer and fully stocked kitchen will make it feel like you never left home. Did we mention the apartment has hardwood floors, 10-foot ceilings and an awesome view?

Why we love it:
This apartment is nestled in Wicker Park, a neighborhood home to up and coming artists, eclectic culture and fantastic restaurants. Named one of “America’s Best Hipster Neighborhoods,” by Forbes, Wicker Park is known for its galleries, music venues, shopping and food. If you’re in the area, you’ll want to check out West Division Street for everything from boutiques to bars. Plan your trip in late May, and you’ll catch the city’s Do Division 2015 Street Fest, where you can bring your dog to watch live music and shop the sidewalk sales.

What you need to know:
Renting this apartment will cost you $320 per night, plus an additional $75 per night if you have more than two guests. There’s free WiFi and two TVs available for guests, but no cable. If you’re planning on driving, keep in mind the street is permit parking only, so you may need to search around the corner to find a permit-free zone.

Editor’s Note: As always, we recommend that you check with the homeowner for specific restrictions on breed, size or number of dogs allowed in the residence.


A group of dog lovers that enjoy a good game of fetch in the park, a cold drink at a sidewalk patio, and Instagramming dog selfies with the best of them. We're working hard to find the best stories about our shared dog culture for you and your best friend.