Best & Cheap Dog Friendly Vacations in Chicago, IL

Compare dog friendly vacation accommodation, From $22/night

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ACCOMMODATION TYPES

Best & Cheap Dog Friendly Vacations in Chicago, IL: Top Deals

Kasa | Balcony Studio, Shopping & Dining Nearby | Chicago River North
Apartment · 2 Guests · 1 Bedroom
Kasa | Balcony Studio, Shopping & Dining Nearby | Chicago River North
This modern apartment is located in the vibrant River North neighborhood of Chicago, offering a comfortable balcony studio for two people. Guests can enjoy being close to great shopping and dining options such as Eataly Chicago, The Purple Pig, Bar Siena, RPM Steak, and Joe's Seafood. Other nearby attractions include the Chicago Riverwalk, Navy Pier, and Millennium Park.
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$166 /night*
Waldorf Astoria Chicago Hotel
Hotel
Waldorf Astoria Chicago Hotel
4.4 (294 reviews)
This luxurious 5-star Waldorf Astoria Chicago Hotel is located in the heart of downtown Chicago, close to popular attractions such as Millennium Park and Magnificent Mile. Popular restaurants nearby include The Purple Pig, RPM Steak, and Smith & Wollensky. Guests can also take advantage of a wide range of activities including shopping on Michigan Avenue, visiting Navy Pier, or taking a stroll along the lakefront trail. Pets are allowed at this hotel.
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$461 /night
Secret Gallery on the Park❤️River North, Best Location (+Parking)
Guest Suite · 2 Guests · 2 Bedrooms
Secret Gallery on the Park❤️River North, Best Location (+Parking)
4.0 (2 reviews)
This Guest Suite is located in the River North area of Chicago and offers convenient access to popular restaurants, activities, and trails. Nearby restaurants include Green Street Smoked Meats, Beatrix, and The Purple Pig. Popular activities in the area include visiting the Art Institute of Chicago and taking a stroll along the riverfront. There are also several nearby trails for outdoor enthusiasts, such as the Lakefront Trail and the Bloomingdale Trail.
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$276 /night*
LK3 1BR Perfect Home in the City, Close to Everything
Guest Suite · 2 Guests · 1 Bedroom
LK3 1BR Perfect Home in the City, Close to Everything
This Guest Suite is the perfect home in the city, close to everything! It can sleep 2 people and pets are allowed. Located near downtown Chicago, it's a great spot for exploring the city. Popular restaurants nearby include The Purple Pig, Girl & the Goat, and RPM Italian. Active travelers will be able to take advantage of the Lakefront Trail, Millennium Park, and the Art Institute of Chicago.
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$136 /night*
Kasa | Marvelous 1B/1BA with Fast WiFi, Full Kitchen | Chicago River North
Guest Suite · 2 Guests · 1 Bedroom
Kasa | Marvelous 1B/1BA with Fast WiFi, Full Kitchen | Chicago River North
This Guest Suite is a wonderful 1 bedroom/1 bathroom in Chicago's River North neighborhood. It features fast wifi and a full kitchen, and can accommodate up to 2 people with pet-friendly policies. Nearby popular restaurants include Beatrix, Wildfire, and Joe's Seafood Prime Steak & Stone Crab. Popular activities include taking a riverfront walk along the Chicago Riverwalk, visiting the Skydeck at Willis Tower, and shopping on the Magnificent Mile. There are also several trails nearby, such as the Lakefront Trail and the Bloomingdale Trail.
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$171 /night*
The Drake Hotel
Hotel
The Drake Hotel
The Drake Hotel is located in Chicago, Illinois and allows pets. It is conveniently close to several popular restaurants such as Giordano's Pizza, Xoco, and The Purple Pig; activities like the Navy Pier and Millennium Park; and trails like the Lakefront Trail and Riverwalk.
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$183 /night
Kasa | Lovely 2BD/2BA with In-Unit W/D + Full Kitchen | River North
Guest Suite · 2 Guests · 3 Bedrooms
Kasa | Lovely 2BD/2BA with In-Unit W/D + Full Kitchen | River North
4.8 (8 reviews)
This Guest Suite is located in River North, Chicago and offers a 2-bedroom/2-bathroom unit with an in-unit washer/dryer and a full kitchen. It can sleep up to two people and pets are allowed. Nearby attractions include the Chicago Riverwalk, The Art Institute of Chicago, Maggie Daley Park, and the Lakefront Trail for scenic strolls. Popular restaurants nearby include Beatrix, RPM Italian, The Purple Pig, and Wildberry Pancakes & Cafe.
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$249 /night*
ALBW Serene and Cozy 1BR Apt near Ravenswood
Guest Suite · 2 Guests · 1 Bedroom
ALBW Serene and Cozy 1BR Apt near Ravenswood
This Guest Suite is the perfect getaway for two in the Ravenswood neighborhood of Chicago. It features a cozy 1 bedroom apartment with all the amenities you need for a comfortable stay, and pets are welcome. Nearby attractions include the North Park Village Nature Center, Peterson Garden Project, and the River Trail at Horner Park. Popular restaurants such as The Biscuit Man, Oven Grinder Pizza Co., and Gather offer delicious dining options within walking distance.
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$109 /night*
Best Western Grant Park Hotel
Hotel
Best Western Grant Park Hotel
3.8 (2170 reviews)
This hotel, Best Western Grant Park Hotel, is located in a prime location near popular restaurants such as The Gage, Pizano's Pizza & Pasta, and Nando's Peri-Peri, as well as nearby trails like the Lakefront Trail and activities such as Navy Pier and Shedd Aquarium. It also allows pets, making it perfect for traveling with furry friends.
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$143.65 /night
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Which Price Range Is Considered As A Good Deal in Chicago, IL Area?
Vacation Apartment & House Rental Price Information in Chicago, IL
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The graph shows the percentages of vacation homes in each price bucket. Chicago has the largest percentage (27.59%) of homes in $100 - $150 price range.
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How Many Accommodations Are Pets Allowed in Chicago, IL?
Pets Allowed vs Not Allowed in Chicago, IL
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17.57% of vacation homes in Chicago are pet friendly. Make sure you select the pet friendly home filter when you are going to bring your pet(s) for the upcoming vacation.
Where are the pet-friendly restaurants in Chicago, IL?
Pet-Friendly Restaurants in Chicago, IL
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Chicago is home to many pet-friendly restaurants that welcome furry friends with open arms. From outdoor patios to dog-themed eateries, there's something for every pup and their owners to enjoy.

  • Fatso's Last Stand: This hot dog stand has an outdoor patio where dogs can join their owners for lunch.
  • The Wiener's Circle: This classic Chicago spot serves up gourmet hot dogs and burgers and allows pups to enjoy a meal on their outdoor patio.
  • Yard House: This establishment offers a wide selection of craft beers and invites canines to relax on their outdoor patio.
What activities can I do with my pet in Chicago, IL?
Pet-Friendly Activities in Chicago, IL
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There are plenty of fun activities for you and your pup to enjoy in Chicago! With its many parks, trails, and off-leash areas, there's never a shortage of things to do here.

  • Montrose Dog Beach: Let your pooch run free along this sandy beach located on Lake Michigan's shoreline!
  • Wiggly Field Dog Park: This fenced-in park contains ample space for your pup to play with other four-legged friends.
  • Grant Bark Park: This large, grassy area is perfect for letting your pup explore and roam around.
Which Airports Should I Choose To Get To Chicago, IL?
Suggested Airports in Chicago, IL
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