Dog Friendly Tours in Illinois

Taking the dog out for a walk takes on a new meaning when you’re on vacation in Illinois. After all, there are tons of sights to see, and smell, around every corner. Browse our dog friendly tours in Illinois below for the scoop on self-guided walks, driving tours, and group tours that both you and your dog are sure to enjoy.

Pet Friendly Gangsters and Ghosts Tours
Gangsters and Ghosts Tours 'Gangsters and Ghosts Tours' is a pet-friendly Airbnb Experience hosted by Stevie. You and Fido will venture out on a historically-based walking tour of Chicago's Loop Vice District, highlighting the gangsters, their crimes and deals, and ghost stories of the area's past. The experience lasts 2 hours and can accommodate up to 20 guests of all ages. Rates start at $27 per person. See Details
Pet Friendly Mercury's Canine Cruise
Mercury's Canine Cruise *** Call ahead to find out about any temporary restrictions due to COVID-19. *** Dogs on boats? Yes! Bring your pooch on a leash and enjoy quality time with your dog while cruising on Chicago's waterways. Sit back, relax and soak in the city as you enjoy a lively narration of Chicago’s rich history and architectural marvels with dog-friendly highlights. Keep your dog on your lap, in a seat or on the deck. The dog cruise boat offers plenty of safe outdoor seating, water bowls and a special newspaper-lined restroom for your pet. Enjoy a great day out of doors with your favorite companion. Reserve your tickets online or at the ticket office, open daily at 8:30am. Tickets available online or dockside day-of. Adults: $37; Kids 5-15: $16; Kids under 5 are free; Dogs: $8; Groups of 20 or more, call (312) 332-1368.​ See Details
The Chi-Town Showdown Scavenger Hunt 'The Chi-Town Showdown Scavenger Hunt' is a pet-friendly Airbnb Experience hosted by Kat & Alan. Discover Chicago on a scavenger hunt with your pooch. First, receive instructions and warm up for the event. Then, depart with your dog on a tour of the sights and sounds of Chi-town. Take part in fun activities and complete clues along the way. The experience lasts 2 hours and can accommodate up to 30 guests of all ages. Rates start at $22 per person. See Details
Seadog Cruises Chicago You and your pooch can see the Windy City from the water aboard a Seadog Cruises speedboat. Departing from Navy Pier, Seadog Cruises offers a variety of tours to choose from. The popular Lakefront Speedboat Tour is a fast-paced, 30-minute adventure highlighting some of Chicago's top spots. If you want a more leisurely tour, head out on the 75-minute River and Lake Architecture Tour, which extends your adventure through the Chicago River Locks. As an added bonus, humans traveling with their pups receive a discount on regularly-priced tickets! See Details
Kayak Chicago Come paddle with your best friend on a kayak at Montrose beach. We will start you out with an orientation, teaching paddle strokes, safety and rules of the water. Bring a doggie life jacket and you can enjoy the water together. The kayaks are very stable sit-on-tops, so your dog can sit or stand on the boat. See Details
Podcast Producing with a Pioneer 'Podcast Producing with a Pioneer' is a pet-friendly Airbnb Experience hosted by Jaime. Fido is welcome to join you as you learn the basics of starting your own podcast from preparation to publishing. Your host will also explain a variety of hard/software and applications, and give you hands-on experience at producing a podcast during this session. The experience lasts 3 hours and can accommodate up to 4 guests ages 18 and up. Recommended for college students and older, interested in podcasting. No prior podcasting experience is necessary. Beginners welcome! Rates start at $150 per person. See Details
Shoreline Sightseeing Bring Fido aboard one of the Shoreline Cruises boats for a trip on Lake Michigan or the Chicago River. Well-behaved, leashed pets are welcome on classic lake cruises and architecture cruises. The classic lake cruise will highlight historic lakefront sights and attractions along Lake Michigan. The architecture cruise will take you down the Chicago River to see buildings such as Tribune Tower, Wrigley Building, Trump Tower, Marina City, and more. Dogs are not permitted on special event cruises or on fireworks cruises. Shoreline Cruises depart from multiple locations depending on cruise and time. Call or visit website for exact departure location. See Details
Star in Your Own Photo Shoot Outdoors 'Star in Your Own Photo Shoot Outdoors' is a pet-friendly Airbnb Experience hosted by Carla. Create some unique memories with your pooch at this photoshoot in Chicago. You will walk along with your host in the Lake Street and train tracks area discovering graffiti and street art for unique photo backgrounds. Your host will capture photos of you along the way. The experience lasts 1.5 hours and can accommodate up to 10 guests of all ages. Please be prepared to walk 4 blocks. Rates start at $79 per person. See Details
Must Have Chicago Photos 'Must Have Chicago Photos' is a pet-friendly Airbnb Experience hosted by Carla. Create some lasting memories while with your pooch in Chicago. Explore downtown on foot while your host captures moments of you together in locations such as Millennium Park, Chicago Theater, River Walk and more. Private shoots are also available. The experience lasts 1.5 hours and can accommodate up to 10 guests ages 2 and up. Rates start at $79 per person. See Details
Private Soapmaking Class 'Private Soapmaking Class' is a pet-friendly Airbnb Experience hosted by Sarah. With prior approval, your well-behaved pooch is welcome to join you at this workshop where you will learn the history of soap making and get to create your own loaf using olive, coconut, and palm oils. You will get to personalize your soap by choosing a fragrance from a variety of scents and herbs. Your host will guide you throughout the process and you will end up with a 1.5 pound loaf of soap that will be ready for pick up and cut into bars the next day. The loaf can also be shipped to you for an additional charge. The experience lasts 2 hours and can accommodate up to 4 guests ages 10 and up. Rates start at $65 per person. See Details
Sketching Chicago with Ink & Watercolors 'Sketching Chicago with Ink & Watercolors' is a pet-friendly Airbnb Experience hosted by Monika. Contact host before booking so that a more dog friendly location can be planned. Your pup will sit beside you at this workshop while you create an urban sketch of Chicago using pencil, ink, and watercolors. Your host will provide a sketch kit, examples for inspiration, plus tips and techniques along the way. While you sketch, your host will also discuss the history of Urban Sketching. The experience lasts 2 hours and can accommodate up to 3 guests ages 18 and up. Parents may also bring children under 2 years of age. Rates start at $49 per person. See Details
Sailing Chicago's Gorgeous Lakefront 'Sailing Chicago's Gorgeous Lakefront' is a pet-friendly Airbnb Experience hosted by Dan and Jen. Sail from DuSable Harbor to favorable winds led by Captain Dan. Your host will take care of the sailing, but is happy to guide you if you want to join in. Dogs are welcome and your host has some sizes of dog life jackets. Let them know first to see if they have the right size for your pooch. The experience lasts 3 hours and can accommodate up to 10 guests ages 5 and up. Life jackets are required for non-swimmers. Rates start at $100 per person. See Details
Route 34 Drive-In Theater Drive-in theater with full snack-bar and grill, bounded by corn fields far from ambient city lights. Open on weekends. Grass surface rather than paved and dogs are welcome. See Details
Awesome Ottawa Tours Graveyards 'Awesome Ottawa Tours Graveyards' is a pet-friendly Airbnb Experience hosted by Thomas. You and Fido will explore the burial ground and pioneer graveyards of the area, while learning about those who are buried at these locations. Your hosts will also provide you with the interesting and quirky history of the town. Appropriate footwear for you and a leash for Fido is required. Boots and hiking boots are recommended depending on weather. Your host may also have their Lab along for the tour! The experience lasts 2 hours and can accommodate up to 8 guests ages 12 and up. Rates start at $30 per person. See Details
Private Lifestyle City Photo Shoot/Tour 'Private Lifestyle City Photo Shoot/Tour' is a pet-friendly Airbnb Experience hosted by Arthur. Create some lasting memories with your pooch while in Chicago. Your host will give you a tour of the city while capturing beautiful, candid and posed photos of you along the way. Your host can also teach you about modeling and photography, the editing process, rules/guides, etc. if you would like. You will receive 10 edited images and all unedited photos (usually 200+). Be sure to contact the host prior to booking to let them know that Fido will be joining the session. The experience lasts 2 hours and can accommodate up to 2 guests ages 16 and up. Rates start at $74 per person. See Details
Explore Chicago with a Photographer 'Explore Chicago with a Photographer' is a pet-friendly Airbnb Experience hosted by Emile. Create some lasting memories with your pooch at a photoshoot in Chicago. You and Fido will walk around The Bean and Buckingham Fountain while your photographer captures both candid and posed photos of you. Price per person is for a group up to 4 people -only one booking needed. You will receive 20 edited photos per session in 3 business days. The experience lasts 1 hour and can accommodate up to 4 guests ages 18 and up. Parents may also bring children under 2 years of age. Rates start at $129 per person. See Details
Overnight Paranormal Investigation 'Overnight Paranormal Investigation' is a pet-friendly Airbnb Experience hosted by Rebecca. Enjoy an overnight investigation of this haunted house and farm. You and your pooch can conduct your own paranormal investigation of the farm, as long as they are house-trained. Your host will give you a history of the home and a walk through tour of paranormal hot spots. The experience lasts 10 hours and can accommodate up to 10 guests ages 16 and up. Rates start at $150 per person. See Details
Windy City Ghosts Windy City Ghosts is a pet-friendly tour of Lake Michigan’s famed metropolis. The standard tour route is one mile. Eight different locations are included in the standard tour, including Lincoln Park and Lion House. Tours are held every night. Dogs are welcome on tours, as long as they are on a leash and well-behaved. This tour is offered by Colonial Ghosts, LLC. See Details
Movie FX/Special Effects Makeup 'Movie FX/Special Effects Makeup' is a pet-friendly Airbnb Experience hosted by Your Peeps. Your pooch is welcome to sit along with you as you learn these special makeup techniques. Be sure to bring makeup and tools along with you as only some supplies will be provided. Contact host prior to booking if bringing Fido along. The experience lasts 1.5 hours and can accommodate up to 8 guests ages 11 and up. Rates start at $60 per person. See Details
Chicago Cake Decorating 'Chicago Cake Decorating' is a pet-friendly Airbnb Experience hosted by Karen. Learn how to decorate a cake from an expert with a variety of different icing supplies. Dogs are welcome to join the fun of this yummy experience that lasts 2 hours and can accommodate up to 8 guests ages 18 and up. Rates start at $75 per person. See Details
Lincoln Park/Lakeview Photoshoot 'Lincoln Park/Lakeview Photoshoot' is a pet-friendly Airbnb Experience hosted by Katherine. Create some lasting memories with your pooch. Your host will help you pose and capture beautiful photos at the Lincoln Park Conservatory and the Lakefront of Chicago - in an area only locals know about. The experience lasts 1 hour and can accommodate up to 10 guests of all ages. Rates start at $75 per person. See Details
Magnificent Mile Walking Tour 'Magnificent Mile Walking Tour' is a pet-friendly Airbnb Experience hosted by Rachel. You and your pup will be guided down Michigan Avenue where you will get to see all of the popular and historic spots. You will also pass Fort Dearborn, get a hot chocolate at Ghiradelli, and have a chance to to window shop on the Magnificent Mile. If bringing Fido, contact host prior to booking so accommodations can be made. The experience lasts 2.5 hours and can accommodate up to 10 guests ages 14 and up. Rates start at $18 per person. See Details
Chicago Historic Financial District Tour 'Chicago Historic Financial District Tour' is a pet-friendly Airbnb Experience hosted by Rachel. You and your pooch will take a guided walking tour of the district and discover the historic buildings and architecture. See the Old Chinatown, the elegant Rookery, and the Chicago Board of Trade and the last remaining Chicago Cow Path. Please note that Fido won't be allowed inside any buildings, but if the tour stops at one, someone from your group can wait outside with the pup. The experience lasts 2 hours and can accommodate up to 8 guests ages 13 and up. Rates start at $18 per person. See Details
Windy City Street Photography Tour 'Windy City Street Photography Tour' is a pet-friendly Airbnb Experience hosted by Dorsey. A well-behaved pooch is welcome to join you at this hands-on workshop as long as you are able to keep an eye on him while learning and using your camera. You will visit various iconic sites and discuss an artistic approach to photographing each site before taking pictures. Your host will provide you with different techniques to getting unique photos and also take a photo of you at each stop that will be later emailed to you. The experience lasts 3 hours and can accommodate up to 5 guests ages 16 and up. Guest should have a general knowledge of camera functionality. Rates start at $250 per person. See Details