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 up: our hotel. We picked The Wade, and it turned out to be just the right mix of city energy and all the little dog-friendly touches that make traveling with Luna easy.
As soon as we walked in, I could tell we’d made a good choice. The Wade is super welcoming to pups, and its spot on Lakeshore Drive, right across from Navy Pier, couldn’t be better. We even got to watch the Navy Pier Summer Fireworks from our room, which felt like having our own private show.
One of my favorite things? There were grassy spots close by for Luna’s potty breaks, always at the top of my list when we travel together. And just steps from the hotel, there’s a pedestrian tunnel that leads straight to Jane Addams Memorial Park, the Lakefront Trail, and Ohio Street Beach. It honestly felt like we’d found a hidden shortcut under the city.
Of course, no hotel is perfect, so here are a couple of things to keep in mind if you’re thinking about staying at The Wade:
- The restaurant and bar are closed at lunchtime, so you’ll want to plan ahead for midday snacks.
- The elevators can get pretty slow when it’s busy. Luna and I had a few moments where we looked at each other like, are we ever getting to our room?
Still, for the views, the location, and all the dog-friendly perks, The Wade was a fantastic home base for our 4th of July adventure.
Lakeside Meals at Caffè Oliva
A girl and her dog have to eat, right? Luna and I strolled down the Lakefront Trail and found ourselves at Caffè Oliva, a laid-back spot right on Ohio Street Beach.
It honestly felt like a mini vacation: waves rolling in, music in the background, and the smell of something delicious on the grill. The best part? It’s dog-friendly, and they even have a special menu just for pups.
Luna wasted no time ordering (okay, I ordered for her). She got 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.
Just a quick heads-up: even though Caffè Oliva is right on Ohio Street Beach, the beach itself isn’t dog-friendly. Luna had to watch the waves from the patio, but honestly, the sunset over the lake made it more than worth it.
The Highlight: Montrose Dog Beach
No dog-friendly Chicago trip is complete without a stop at Montrose Dog Beach. Luna was counting down the days for this part, and honestly, so was I.
Montrose Dog Beach was even better than I had pictured. The sand was soft and clean, the water was cool and sparkling blue, which felt incredible since it was over 90 degrees. Everywhere you looked, there were happy dogs and their owners soaking it all in.
I’ve been to dog beaches where people… let’s just say… forget to clean up after their pups. But here, everyone was so respectful, and it made the whole experience genuinely enjoyable.
Luna ran wild off-leash, made a bunch of new friends, and splashed in and out of the lake until she was soaked and sandy. When we were both ready for a break, we found Mutt Jackson, a dog wash station, right outside the beach. It was the perfect spot to rinse Luna off before heading back into the city.
If you’re thinking about visiting, here’s a quick tip: the Chicago Park District Dog Friendly Area Permit process has changed a little. When we went in July 2025, I called the Parks District, and they sent me a form for our vet to fill out, and I mailed it back with an $8 check. A few days later, Luna had her official blue tag for her collar, which meant she was all set for the beach.
We’re already planning our next trip back. I’m pretty sure Luna is still dreaming about that beach.
A Few Stops Just for Me
While Luna snoozed after her big beach day, I snuck in a couple of stops just for me.
I wandered into The Last Chapter Book Shop Chicago, and let’s just say I may have gone a little overboard on romance and fantasy novels, candles, and the cutest bookish accessories. Zero regrets.
Even though it’s not dog-friendly, I had to check out the Harry Potter Shop Chicago. As someone who grew up hoping for a Hogwarts letter, this place was pure magic. I browsed wands and house scarves, and treated myself to a Frozen Butterbeer at the Butterbeer Bar. It was happiness in a cup.
By the time the fireworks started over Navy Pier, Luna and I were both happily worn out. She curled up next to me on the hotel couch while the sky outside our window lit up with color, and I couldn’t imagine being anywhere else.
If you’re dreaming of a dog-friendly 4th of July getaway, lake breezes, great food, and sandy paws included, Chicago might just win your heart like it did ours.
Until the next adventure,
🐾 Lauren & Luna
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