Best Dog-Friendly Activities in Chicago: Windy City Woofers!



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dog-friendly activities in Chicago

There’s certainly no shortage of fun things people can do in the Windy City, but did you know that Chicago is also one of the most pet-friendly places in the country? 

That’s right! There are tons of things to do with your doggo in Chicago (and the surrounding suburbs). 

Taking your dog on different kinds of outings is not only a great way to bond, but it also provides the kind of brain-stimulating, energy-draining enrichment that our dogs crave. 

So grab your little guy or gal and read on! We’re sure you’ll find a fun dog-friendly activity to enjoy in Chicago below! 

9 Dog-Friendly Activities in Chicago to Enjoy with Your Pooch

Chicago Activities to Do with Your Dog

From parks to pubs to playtime activities, there are scads of things you can do in Chicago with your pet. So, whether you live here full-time or you’re just visiting, check out some of the best things to do with your dog!

1. Hit the trails and hike with your pup.

hiking with dog

Hiking offers next-level exercise to your pooch, putting his body and brain to use as he conquers new territory one paw at a time. You can also tweak your hiking trip to suit your sniffer, with more difficult trails providing obstacles and varied terrain for tiring active pups and flatter, urban paths better for seniors and puppies just starting out.  

Always respect posted rules in hiking areas, and never let your dog destroy habitat through digging, shredding, or trampling foliage that wildlife relies on. 

Speaking of wildlife – that’s a definite reason to keep your canine leashed and on the trail, as coyotes, bears, and snakes also call the Chicago area home!

Get out there and explore these three dog-friendly trails around Chicago with your pup.

Deer Grove Forest Preserve

About: This slice of paradise spans 2,000 acres and is home to many mutt-friendly trails to roam with your leashed ruffer. There are over 15 miles of paths to cover with your canine, including paved and unpaved areas, matching the needs of newbies and experienced hikers alike.

Address: N Quentin Rd, north of W Dundee Road, Cook County, IL 60074

Phone Number: (800) 870-3666


Special Notes:

  • Open daily from sunrise to sunset
  • Yellow Loop is a favorite park trail for those looking for an easier route (5 miles)

Waterfall Glen Forest Preserve

About: Looking for trails with stunning scenery for you and your floof in the Chicago area? Head to this wooded wonderland with four mapped routes for hikers, bikers, and horseback riders. The park spans over 2,500 acres and has natural limestone trails that wind through the heart of the forest.

Address: N Northgate Road, Lemont, IL 60439

Phone Number: (630) 933-7248


Special Notes:

  • Open from sunrise to sunset daily
  • Dogs must be tethered to a lead that’s 10 feet or shorter
  • Unmarked trails also cut through the park, though they should be left to more experienced natural navigators
  • Cyclists and horses that also frequent the trails (they may startle some dogs)

Lakefront Trail

About: Arguably Chicago’s most famous trail, this 18.5-mile paved pathway carves along the shoreline of Lake Michigan with unmatched views of the water. It’s a good starting point if you and your pooch are just getting started in your hiking journey, as you can focus on getting steps in rather than dodging nature.

Address: 7059 S South Shore Drive, Chicago, IL 60649


Special Notes:

  • Open 24 hours a day
  • Mixed-use, so you’ll see dog walkers, skateboarders, cyclists, and more along the trail
  • The winter wind blowing off of the water is downright brutal

2. Check out one of the city’s off-leash dog parks. 

Chicago's dog parks

Does your pet need to burn off some steam? Is Spot a social butterfly who enjoys playing with other puppers? Does your dog just need some time to explore in a safe yet off-leash fashion? 

An off-leash dog park may be just what you need! 

Chicago has tons of off-leash dog parks for you and your four-footer to visit, ranging from tiny little parks suitable for low-energy pups to huge, sprawling fields that will allow even the highest-energy husky to zoom around to his heart’s content. 

Just be sure that you follow all of the park’s rules and practice good dog-park etiquette. Among other things, that means picking up your pup’s poops, ensuring that your pooch plays nicely with other dogs, and leaving treats and food at home (it can cause jealousy and resource-guarding issues). 

Additionally, be sure to look for a park with separate play areas for large and small dogs – especially if your pup is pint-sized, old, or has mobility issues. 

3. Grab a bite to eat with your pooch. 

restaurants for dogs in Chicago

Ya gotta eat (as does your dog), so you may as well bring your floof to a pet-friendly eatery! 

Chicago is loaded with dog-friendly restaurants you and your pooch can enjoy – many even provide mutt-safe menu items your dog can nom. 

Not all dogs are a good fit for public dining (such as those who struggle with reactivity), but socialized, well-behaved puppers will often love visiting restaurants. Just be sure to keep your doggo on a short leash, prevent him from begging, and walk him beforehand – you don’t want a mid-meal mess on your hands.  

Most pet-friendly eating establishments will require you to sit outside on the patio with your pet, so make sure that you check the weather forecast before heading out. If the temps are super cold or rain is in the forecast, you should probably look for something else to do with your dog. 

4. Elbow up to a bar with your barker. 

dog-friendly Chicago bars

Fancy a drink with your floof? You’re in luck! Many Chicago-area bars welcome woofers with open arms. 

Most dog-friendly bars in Chicago require patrons with pets to sit outside on the patio, but a few also allow (leashed, well-behaved) dogs to come inside. Just be sure to check and abide by the establishment’s rules.  

Just keep your pet’s personality in mind when picking a bar. Some bars may get a bit too rowdy for your Rover (especially those with live music), so stick to calmer spots if your pooch is easily overwhelmed. 

Also, and we hope this goes without saying, don’t give your barker booze. Alcohol will sicken your pet, and many beverages also contain other ingredients toxic to dogs.  

Pet-Care Pro Tip: Whip Up Some Non-Alcoholic Beer for Your Pooch!

While dogs shouldn’t be given real beer or other alcoholic beverages, you can make a DIY dog-safe beer that’s perfectly safe to share with your pet!

5. Explore the sites with your curious canine.

sight-seeing with dog in Chicago

The best dog-friendly activities involve your doggo making discoveries, but that doesn’t mean you can’t be wowed and see new things, too. Get to know the city you adore by exploring must-see areas of Chicago.

Sightseeing is one of those leisure activities we all do and rarely think to bring our barker along for. Sure, some landmarks don’t allow doggos inside, but many have pooch-friendly grounds to explore, still allowing for epic experiences and sweet selfies with your sniffer.

Check out these must-visit stops around Chicago with your canine.

Chicago Riverwalk

About: Don’t let the seemingly small 1.25-mile span of this area fool you. A lot of awesome stuff is crammed into this space, offering something interesting for every visitor to walk away with, including shops, restaurants, and scenery. You’re more than welcome to roam the area with your leashed dog and enjoy the passing boats and stunning architecture.

Address: E Wacker Drive, Chicago, IL 60601


Special Notes:

  • Open daily from 6:00 AM to 11:00 PM
  • Please keep your canine away from the Vietnam Veterans Memorial out of respect
  • Free entry for guests

Navy Pier

About: Your leashed woof is welcome to walk the common areas of this city favorite. Home to shops, restaurants, and various attractions like the Centennial Wheel, more than 9 million people visit the pier annually, so expect crowds, especially during peak hours!

Address: 600 E. Grand Avenue, Chicago, Illinois 60611

Phone Number: 1-800-595-7437


Special Notes:

  • Opens daily at 11:00 AM, and closing time varies by season
  • There is no entry fee to visit Navy Pier
  • Only service dogs are permitted inside Navy Pier structures

6. Board a boat with your barker.

boating with dogs in Chicago

Chicago’s waterside location makes it an excellent spot to take in its beauty from a boat with your best fur friend. Thankfully, there are pooch-friendly businesses welcoming well-behaved woofers aboard boat tours, too.

Boating with your pup lets him experience a host of new sights, smells, and sensations, from the repeated dipping of the vessel to the calls of birds overhead, setting his brain (and nose!) abuzz. Most importantly, this is a great opportunity to kick back and bond with your floof.

While setting sail is fun, boating safely with your dog is critical in ensuring everyone arrives ashore happy and healthy. Keep your canine leashed at all times, and consider a dog life vest when venturing out onto Lake Michigan and other large bodies of water.

Take on new horizons with your hound with one of these boating adventures.

Mercury Cruises

About: This canine-friendly cruise departs from the Chicago Riverwalk and covers portions of Lake Michigan and the Chicago River, giving you unmatched views of the city skyline and sites with your pup at your side. Water bowls are stationed onboard to hydrate your hound, while humans are offered snacks and drinks as refreshments.

Address: 112 E. Wacker Drive, Chicago, IL 60601

Phone Number: (312) 332-1353


Special Notes:

  • Runs from July to October on Saturdays and Sundays
  • Ticket prices start at $44 for adults, $20 for kids aged 5 and older, and $10 for dogs
  • Operates rain or shine
  • Watch for special pup events, like the Howl-O-Ween cruise

Shoreline Sightseeing

About: Leashed, well-mannered doggos are permitted to come along on all tours offered by this boating business, including the Architecture River Tour, Skyline Tour, and Fireworks Tour. Each tour includes at least 150 people, and refreshments are offered for sale onboard, though they accept credit card payments only.

Address: 401 N Michigan Avenue, Chicago, IL 60611

Phone Number: (312) 222-9328 ext. 1


Special Notes:

  • Open 10:00 AM to 8:00 PM daily for calls and scheduling
  • Ticket prices vary by tour, starting around $37 for adults (dogs ride free!)
  • The Fireworks Tour is not recommended for anxious doggos
  • Rain or storms impact tour schedules

7. Set out for a shopping excursion with your pooch.

go shopping with your dog

Pamper your pup with a day of retail therapy by visiting dog-friendly stores and shopping areas around Chicago. Whether you’re looking for people products or a new dog sweater, a shopping outing is the perfect opportunity to stretch your sniffer’s legs and unwind.

While not every store will welcome a pooch, walking shopping areas with your leashed buddy still provides valuable mental and physical exercise, plus a chance to practice your pooch’s manners. Just respect the rules of each shop and prevent your pooch from pottying on merchandise.

Here are some hound-friendly shopping spots around Chicagoland.

The Magnificent Mile

About: Stretching 13 blocks, this span of retail heaven is a top-notch destination for shopping with your doggo, as you can explore a variety of spots, including pet boutiques, luxury dealers, and department stores. Not every business is barker-friendly, so remember to check in advance to ensure a smooth trip.

Address: North Michigan Avenue from the Chicago River to Oak Street


Special Notes:

  • There’s more than just shopping here; also enjoy some dog-friendly eateries, events, and tours
  • Sidewalks can be packed around the holidays, making a short lead and great leash-walking skills essential

Doggy Style Pet Shop

About: Grab your four-footer some new goodies or gear at this pooch boutique offering dog food, barkin’ good bakery eats, and toys. You can even let your pup take a sniff of approval before making a purchase. Grooming and dog walking services are also available onsite (by appointment).

Address: 2023 W. Division Street, Chicago, IL, 60622

Phone Number: (773) 235-9663


Special Notes:

  • Open Monday to Thursday from 10:30 AM to 6:30 PM, Friday and Saturday from 10:30 AM to 6:00 PM, and Sunday from 11:00 AM to 4:30 PM
  • Offer a delivery service to nearby areas for a small fee 

8. Catapult your dog’s abilities to new heights with a canine sport.

dog agility tunnel

Want to go paws to the wall with your woofer’s day in the city? Try out a new doggo sport!

Dog sports are an excellent way to flex your floof’s physical and mental prowess and teach him a new skill or two along the way. They’re also a great opportunity to bond with your best fur friend as he learns and gains confidence in his abilities, whether he’s tackling a new agility obstacle or paddling with pride for the first time.

Don’t think dog sports are just for adult pups, either. Puppies and seniors can get in on the fun, too! Just pick the right lesson!

See which of these dog sports centers in the city match your mutt.

Doggy Paddle Aquatic Center for Dogs

About: Have a water lover and nowhere for him to splash? Book your pooch for some pool time at this swim stop, offering à la carte and multi-visit swim memberships. Swimming is a gentler form of exercise on canine joints, benefiting seniors and young barkin’ athletes alike. Just be sure to book in advance!

Address: 1430 W Willow Street, Chicago, IL 60642

Phone Number: (773) 922-9282


Special Notes:

  • Open weekdays from 8:00 AM to 9:00 PM and weekends from 9:00 AM to 4:00 PM
  • Swimming sniffers must be current on rabies, distemper, and Bordetella vaccines
  • The indoor park is closed on weekdays for Splash ‘n Play Daycare

Urban Pooch

About: There is no shortage of canine sports fun options at this sniffer-friendly spot, whether you’re after nose work, agility, or obedience. They have ‘em all! Set in a climate-controlled space, it’s a wonderful place for your woof to work out, even in the dead of Chicago’s infamously bitter winters.

Address: 5400 N Damen Avenue, Chicago, IL 60625

Phone Number: (773) 961-8880


Special Notes:

  • Open Monday to Thursday from 8:00 AM to 8:30 PM, Friday from 8:00 PM to 6:00 PM, and Saturday and Sunday from 9:00 AM to 5:00 PM
  • Classes are by appointment only; always call in advance!

9. Rest with your Rover at a dog-friendly hotel.

hotels that allow dogs

Sometimes, the last thing you want to do after a long day of doggo shenanigans around the city is commute home. Why not recuperate at a city hotel with your pup instead?

If your canine is full of confidence and housetrained, spending the night at a hotel lets you enjoy more time doing dog-friendly activities into the night or in the early morning, from strolling the Riverwalk to taking a sunset cruise. It’s also a chance to switch up your ruff’s routine as he settles into new, exciting surroundings.

That said, a dog-friendly hotel stay isn’t recommended for pups still learning the housetraining ropes or those with destructive tendencies, as repair bills aren’t cheap! Dogs who bark a lot are also a poor fit.

Stay in with your pup and make lasting memories at one of these mutt-friendly Chicago hotels.

Claridge House

About: The Pampered Pup package at this hotel welcomes your woof with a pup cup, bandanna, and goodie bag at check-in, plus a special 2:00 PM check-out slot so you and your Rover don’t have to rush. Dogs up to 75 pounds are allowed, and the hotel is within walking distance of parks for exercising your pooch.

Address: 1244 N Dearborn Parkway, Chicago, IL 60610

Phone Number: (312) 787-4980


Special Notes:

  • Check-in at 3:00 PM and check-out at noon
  • There is a $100 pet fee at check-in, but it’s refunded at check-out if your room’s in good shape

Chicago Athletic Association

About: Located across from Millenium Park, this pooch-positive hotel lets your sniffer spend the night with no size or weight restrictions, so even the most massive of mastiffs are welcome. Dogs must be leashed at all times in common areas, but they’re not allowed in the hotel’s bars or restaurants.

Address: 12 S Michigan Avenue, Chicago, IL 60603

Phone Number:  (312) 940-3552


Special Notes:

  • Check-in is at 3:00 PM, and check-out is at noon
  • Limit of 2 pets per room
  • Owners must sign a pet waiver at sign-in, accepting responsibility for any doggo damage inflicted
  • Valet parking is available for $79 nightly

Talbott Hotel

About: Spent a day on the Magnificent Mile with your mutt and ready to rest? Check out this woofer-welcoming hotel that charges no extra fee for pups, provided no damage is done. There’s no size restriction, and food and water bowls are offered at check-in, making your stay more like home for your hound.

Address: 20 E Delaware Place, Chicago, IL 60611

Phone Number: (312) 944-4970


Special Notes:

  • Check-in at 3:00 PM and check-out at noon
  • Several dog parks are within a short walking distance
  • Each room has a 2-pet limit

Dog-Friendly Activity Etiquette

dog etiquette for outings

When enjoying dog-friendly activities in Chicago, it’s important to make sure your dog behaves in public. A misbehaving pet can quickly ruin the fun for everyone. Sometimes, one bad incident is all it takes for dog-friendly businesses to stop allowing four-footed visitors.

To keep your flooftivities fun and safe, keep the following pet-etiquette guidelines in mind:

  • Keep your dog’s personality in mind. Not all dogs are good fits for all four-footed activities. Excitable, reactive, or defensive dogs, for example, aren’t great for visits to people- or pooch-packed areas. Similarly, very shy dogs may not enjoy going to chaotic events. Just be mindful of the things your mutt likes (and the things he doesn’t like!).
  • Double-check the calendar. Before your fur baby waltzes into a Chicago hotspot, give ’em a ring! Even the most pet-friendly restaurants, bars, and other establishments occasionally host events that won’t be ideal for your dog.
  • Leave sick pups at home. If your dog isn’t feeling well, you’ll need to leave him home to rest and recover. Sick dogs may not only spread illness to other pets, they probably won’t feel up to the hustle and bustle of a night on the town. 
  • Don’t bring six-legged pests along. Fleas are no fun for any four-footer, and the critters crawling on your canine may spread to other pets. So, be sure that you use a good flea treatment to keep your dog free of biting bugs when heading out in public. And if you’re heading to a natural area with lots of tall grass and bushes, use a good tick preventative too!
  • Make sure your dog’s vaccinations are current. Rabies shots are a must in Chicago, and some pet-friendly establishments require other vaccinations for visitors. Just check with business to find out the specific vaccinations they require. 
  • Always leash your Lassie. Most public spots in Chicago require canines to be leashed and under your physical control at all times (off-leash parks are obviously an exception) . Heed these rules, as it not only helps keep your dog safe, but it also helps avoid the kinds of incidents that cause some restaurants to stop welcoming woofers. If you regularly take your dog to pet-friendly establishments, you may even want a multi-function leash, which will also work as a tether. 
  • Respect the personal space of others. We love a sociable pup, but not everyone wants a furry hug while sightseeing. Never allow your dog to approach other people or pets, unless you’ve checked to make sure they want the interaction. Remember: As strange as it may sound to pet parents, not everyone wants to pet your dog.  
  • Always be on poop patrol. It’s critical that pet parents pick up after their pets. This not only helps to avoid unpleasant odors, but it helps prevent the spread of bacteria and disease. If your dog “drops” something, pick it up (and always have poop bags on hand! 


Chicago may have been designed with humans in mind, but as you can see, there are plenty of reasons mutts may love it too! Just remember to keep the etiquette tips discussed above in mind when venturing out with your pupperino, and keep your specific pet’s personality, wants, and needs in mind when picking an activity. 

Have you and your pooch found any great dog-friendly activities in the city of Chicago? Let’s hear ‘em! We’d love to know what you’ve done with your dog in the Windy City. 

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