There’s nothing quite like the sparkle of fireworks over Lake Michigan – and sharing it all with your furry best friend makes it even better. This year, Luna and I packed our bags and headed to Chicago for the 4th of July, ready for a few days of city lights, good eats, and lots of tail wags.
I’d been to Chicago before, but never with a dog, and I wasn’t sure how dog-friendly the city would really feel during a big holiday weekend. Spoiler alert: it turned out to be one of the best trips we’ve ever taken.
Checking In at The Wade
First things first: our hotel. We stayed at The Wade, which felt like the perfect blend of city vibes and dog-friendly convenience.
The moment we arrived, I knew we’d picked the right spot. Not only does The Wade welcome pups, but it’s also planted right on Lakeshore Drive, directly across from Navy Pier. That meant we could see the Navy Pier Summer Fireworks right from our hotel room window – talk about front-row seats!
Another huge win? There were grassy patches nearby for Luna’s potty breaks, which is always one of my top priorities when traveling with her. Even better, there’s a handy pedestrian tunnel right by the hotel that pops you out at Jane Addams Memorial Park, the Lakefront Trail, and Ohio Street Beach. It felt like we’d discovered a secret passageway under the city.
Now, I’d be lying if I said everything was perfect. A couple of things to note if you’re thinking of booking The Wade:
- Their restaurant and bar aren’t open for lunch, so you’ll need to make other plans for midday meals.
- The elevators can be painfully slow during busy times. Luna and I definitely had a few “why is this line so long?” moments waiting to get to our room.
But all in all, for views, location, and dog-friendly perks, The Wade made a great home base for our holiday weekend.
Lakeside Meals at Caffè Oliva
Of course, a girl (and her dog) has to eat. So Luna and I wandered down the Lakefront Trail and ended up at Caffè Oliva, a breezy spot right on Ohio Street Beach.
I’m not exaggerating when I say it felt like a little slice of vacation paradise: waves rolling in, music playing, the smell of grilled food drifting through the air. Best of all, it’s dog-friendly, and they even have a menu just for pups.
Luna wasted no time ordering (okay, I ordered for her) the Gracie Burger off the dog menu, which she inhaled in record time. I went with the Hummus & Pita Platter, which was fresh and delicious. The staff were absolutely lovely and brought Luna her own water bowl, treating her like the true VIP that she is.
One heads-up if you go: while Caffè Oliva sits on Ohio Street Beach, the beach itself isn’t dog-friendly. So Luna had to admire the sand and waves from the patio instead. Still, the sunset views over the lake were totally worth it.
The Main Event: Montrose Dog Beach
Of course, no dog-friendly Chicago adventure would be complete without a visit to Montrose Dog Beach. This was the part of the trip Luna was most excited about – and honestly, same.
Montrose Dog Beach turned out to be even better than I imagined. The sand was soft and clean, the water was cool and a beautiful, clear blue (which felt amazing since it was over 90 degrees outside), and the whole place was buzzing with happy dogs and their humans.
I’ve been to dog beaches where people… let’s just say… forget to clean up after their pups. Not the case here. Everyone was extremely respectful, and it made for a truly pleasant experience.
Luna zoomed around off-leash, making new friends and splashing in and out of the lake. And when we were all worn out and sandy, there was Mutt Jackson, a dog wash station right outside the beach. It was so convenient to rinse Luna off before heading back into the city.
If you’re planning a visit, just a quick note: the Chicago Park District Dog Friendly Area Permit process has changed a bit. When we visited in July 2025, I called the Parks District, and they sent me a form for our vet to fill out. I mailed it back with an $8 check. A few days later, Luna had her official blue tag for her collar, giving her beach privileges.
We’re already talking about when we can go back. I think Luna’s still dreaming about that beach.
A Few Non-Dog Stops
While Luna napped off her beach adventures, I squeezed in a couple of stops for myself.
I stumbled into The Last Chapter Book Shop Chicago, and oh my goodness, I might have spent slightly too much money on romance and fantasy novels, candles, and the cutest bookish accessories. No regrets.
And even though it’s not dog-friendly, I couldn’t resist visiting the Harry Potter Shop Chicago. As someone who grew up waiting for her Hogwarts letter, this place was pure magic. I wandered through wands and house scarves, and treated myself to a Frozen Butterbeer at the Butterbeer Bar. It was basically happiness in a cup.
By the time the fireworks exploded over Navy Pier, Luna and I were both blissfully exhausted. She curled up beside me on the hotel bed while colorful bursts lit up the sky outside our window, and I couldn’t help thinking there’s nowhere else I’d rather be.
If you’re dreaming of a dog-friendly 4th of July getaway, complete with lake breezes, delicious food, and sandy paws, Chicago might just steal your heart the way it did ours.
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