10 Fun Things to Do With Your Dog This Summer Around Chicago (Including Reactive Dog-Friendly Activities)
Now that we’re towards the end of June and it’s officially summer, I knew I wanted to write a blog post about things to do with your dog during a Chicago summer.
This is an amazing to get out and make memories with your dog - us Chicagoans know how to make the most of these warmer months and live life to fullest before get snow on Halloween and face the harsh realities of a midwest winter.
Between lakefront adventures, forest preserve walks, dog-friendly patios, and weekend road trips, there’s no shortage of ways to enjoy the season together.
But if you have a reactive, nervous, or easily overwhelmed dog, summer outings can feel stressful or complicated.
Not every dog wants to spend their weekend at a crowded festival surrounded by barking dogs, strollers, and children dropping hot dogs on the sidewalk (okay, well that last one they would probably like, but that might be the only highlight for a dog who has big feelings like my Teddy.
And that’s okay.
As a pet photographer - and dog mom to a reactive rescue myself - I know firsthand that “fun” looks different for every dog. Sometimes the best summer adventure isn’t the busiest or trendiest one. Sometimes it’s simply finding experiences where your dog feels safe, confident, and relaxed and you can both enjoy a peaceful outing together.
Here are 20 of the best things to do with your dog around Chicago this summer, including plenty of options for reactive dogs.
1. Take a Sunrise Lakefront Walk
Chicago’s lakefront is magical early in the morning or around sunset. It’s cooler, quieter, and far less crowded.
Bonus: sunrise light is gorgeous.
Best spots:
Montrose Beach
Promontory Point
Northerly Island
Reactive dog friendly? Yes
2. Visit a Dog Beach / Try an indoor swim gym on a rainy day
If your dog loves water and enjoys social play, dog beaches can be a blast.
Top picks:
Montrose Dog Beach
Looking for official dog friendly areas to take your dog around Chicago? Check here.
Reactive dog friendly? Sadly, this beach is not recommended unless it’s nearly empty and your dog can be a long lead away from other dogs - but that’s no guarantee that they won’t be approached by the other dogs.
We’ve tried a couple of indoor swim spots and Teddy LOVES it! Perfect for a rainy day activity or better option for a reactive pup.
3. Go on a Forest Preserve Sniff Walk
Forget power walking.
Slow sniff walks are incredible enrichment.
Try:
Busse Woods
Waterfall Glen
Bemis Woods
Bring a long line and let your dog explore.
Reactive dog friendly? Yes, especially on wide trails. We have personally tried Waterfall Glen. Some trailers are quieter than others so be prepared. I personally use AllTrails when I’m looking for new walks or hikes to take Teddy on. There is a free & paid version - both have extremely helpful filters to help narrow down spots for you and your pup.
4. Plan a Dog-Friendly Picnic
Simple but underrated.
Pack:
frozen treats
water (this is the water bottle I currently use for Teddy and bring to client sessions. I like how easy it is to clean and can throw it in the side compartment of backpack with very little worry about it leaking). If you have favorite walking or outing accessories - I’d love to hear about them!
blanket
shade
Choose a quiet park and enjoy downtime together.
Reactive dog friendly? Yes. Teddy has benefited from being able to just sit and observe the world at a distance that feels comfortable to him. We always bring plenty of high value treats to practice “find it” or other games that help Teddy break eye contact with a trigger and de-stress / sniff.
5. Try Paddleboarding or Kayaking
If your dog loves water and movement, this can be a fantastic bonding experience. This is on my summer bucket list to start paddleboarding with Teddy, who loves to swim!
Reactive dog friendly? Depends on location, as well as sensitivity to motion and noise.
P.S. I don’t currently have any adventure session portraits featuring paddleboarding pups - but I love this idea! Who wants to be my first?!
6. Book a Professional Photo Session
Summer golden hour. Lakefront sunrises & sunsets. Gorgeous parks, beaches & skylines.
These moments become artwork and heirlooms.
If your dog is shy or reactive, work with a photographer who understands behavior and uses distance, patience, and management - and will also help you find the best location for your reactive pup.
Reactive dog friendly? Absolutely - with the right photographer. I might know one. 😉
Side note: As much as I LOVE summer in Chicago, the weather can often be unpredictable or too hot - especially for senior dogs, so if you’re looking for a guaranteed stress-free session with no rescheduling needed, planning for a studio session is a great option in the summer months as well.
7. Create a Backyard Enrichment Day, or Rent a Sniff Spot if you don’t have a yard
If you have a reactive dog, this may be the best summer activity on this list. Sniffspot lets you rent private fenced yards, fields, and acreage by the hour so your dog can decompress safely. There are several filters to find the spot best suited for your dog. If they can’t be off leash, it could be a good opportunity to work on some long lead recall.
Think:
off-leash freedom
zero surprise dogs
stress-free enrichment
Reactive dog friendly? Absolutely.
A few ideas:
kiddie pools
frozen treats - Here’s a watermelon recipe that we’ll definitely be trying out soon! Teddy enjoys fresh watermelon, as well as frozen mango and fresh banana - but I want to make more recipes for him to taste test.
If you try the recipe above, let me know how your pup(s) liked it!
8. Join a Confidence-Building Training Class
Look for:
confidence-building programs recommended by your personal trainer after assessment
Reactive dog friendly? Yes, if properly managed.
9. Try Nosework
This is one of the best activities for reactive dogs.
Mental enrichment builds confidence and reduces stress.
There are a few classes that I’m aware of which will cater to reactive dogs. Please check each business for their current class schedules.
Co-Pilot Dog Training https://www.copilotdogs.com/
Bosly’s Backyard https://www.boslysbackyard.com/trainingclasses
10. Escape the City
If you’re looking for dog specific activities - a personal favorite of ours is Agility on the Farm where dogs can swim, engage in nosework, and rent the agility ring for a one-on-one activity.
If your dog is anything like Teddy and eats the water as he swims (he’s a goofball), we recommend doing the pool last to avoid constant potty breaks during your agility or nosework time.
Please note: There are in fact farm animals & herding classes as the name suggests, so best to avoid letting your dog get too close to those fence lines and/or animals if that might heighten reactivity.
Bonus Activity:
Celebrate Small Wins & Enjoy the Little Things
This one honestly matters most.
For reactive dogs, success may look like:
seeing another dog and staying calm
recovering quickly after a trigger
choosing engagement over scanning
Progress doesn’t always look exciting from the outside.
But those tiny victories? They’re huge.
Not every dog needs crowded patios, dog beaches, or festivals to have a great summer.
Some dogs thrive in social environments.
Others thrive in quiet spaces, structured activities, and decompression.
The goal isn’t to force your dog into someone else’s version of fun.
It’s to build a summer full of experiences your dog actually enjoys.
And those are often the moments that strengthen your bond the most.
Whether your pup has big feelings or not, the time we have with them goes by so quickly - I truly hope you enjoy these next few months as much as possible with your dog and make the most of summer in Chicago.
~Kimberly