A Dog-Friendly Chicago Weekend: Bookstores, Wrigley & Way Too Much Cake

Some weekends have a theme. This one had several: Independent Bookstore Day, a very long to-do list of dog-friendly Chicago stops, and a custom cake waiting patiently back at the hotel. Luna approved of all of it, and honestly, so did I.

We based ourselves at The Talbott Hotel in the Gold Coast for the weekend, and worked our way across the city from there. Here’s how it went.

Friday Night: We Made It

We pulled into the city Friday evening and checked into The Talbott, a boutique Marriott Autograph Collection property right in the Gold Coast. It’s one of those hotels that genuinely means it when they say dog-friendly, no awkward side-eye at check-in, and no complicated pet paperwork. Luna walked through that lobby like she owned the place.

Dinner at Laural’s

After settling in, we headed downstairs to Laural’s on the first floor for dinner. We started with the Crispy Cauliflower with preserved lemon and pickled vegetable aioli, which was pretty good. I had the Gourmet Burger with taleggio cheese, spinach, caramelized onions, tomato, black pepper, and Dijon mayo with fries. Not my personal style of cheese, but that’s a me problem. Service was on the slower side, though it helped that there was another dog at the table next to us and their very lovely owners to chat with.

She did not walk back out under her own power. But we’ll get to that.

Saturday: The Full Dog-Friendly Chicago Sweep

Stop 1: Tails in the City

First stop Saturday morning was Tails in the City on East Delaware, a proper dog boutique with a curated selection that makes you immediately forget your budget. We picked up a few fresh-baked dog treats and a toy (the Chewy Vuitton bone, obviously), and stood on the Gold Coast sidewalk feeling very much like people who have their lives together.

Stop 2: The Last Chapter — Independent Bookstore Day

I had specifically planned this trip around Independent Bookstore Day, and The Last Chapter on West Roscoe was first on the list. It’s a romance-only bookshop, the perfect niche, the kind where you immediately feel like you’ve found your people. When we arrived, there was already a crowd gathered out front, the vibe was festive, and Luna sat across the street surveying the whole scene like a very patient general. We went in together and found some great bookish merch, and, as it turned out, cake.

Inside, there’s a booth installation completely covered in pink and red cut paper hearts, floor to ceiling. Luna needed a photo in it immediately, and the other customers were more than happy to help make that happen. She was a hit.

The real discovery was The Cake Bar pop-up happening inside the shop for IBD. The concept: choose your base (vanilla, chocolate, funfetti, red velvet), pick an icing, load up on toppings, and finish with a drizzle. It was so much fun. I built mine, tucked it into my bag, and carried it around the city for the rest of the day, saving it for that night.

Stop 3: Wrigley Field

We were already in Lakeview, so a Wrigley Field pitstop was non-negotiable. Luna sat in front of the marquee and looked very much like someone who was born for this moment. We took approximately four hundred photos. These are the ones that made the cut.

Stop 4: Budweiser Brickhouse Tavern

Lunch was at Brickhouse Tavern, right in the Wrigleyville neighborhood, conveniently close to the stadium, so it practically plans itself. The patio faces the field, the food is exactly what you want after a full morning of walking, and Luna was welcome to join. She immediately identified the best seat and sat down to supervise. We also put her Cubs bandana on here, which, in hindsight, is the correct order of operations.

Stop 5: Pup Social

After lunch, we made our way to Pup Social, Chicago’s first private off-leash bar and dog park, located in Bucktown. They were hosting an Open House Pup-Up event this weekend, which meant the space was open to non-members to experience. The setup is genuinely impressive: a fully fenced outdoor play area with pet-grade turf, a giant tennis ball, string lights overhead, and a full bar for the humans. Luna socialized with other dogs, which, honestly, she doesn’t always do, while I watched and felt so proud of her.

She also posed beautifully in front of their sign, which is really all I asked of her.

Barnes & Noble at the Noel State Bank Building

Since we were already on the north side, we made one more stop: the Barnes & Noble in the former Noel State Bank building at the six-corners intersection of Milwaukee, Damen, and North in Wicker Park. The building dates to 1918, and the rounded facade and ornate stonework are all original. The interior is even better, with a coffered ceiling, a stained glass skylight, and enough architectural detail to make browsing feel like a museum visit.

Luna was welcome inside, though by this point, she had approximately zero interest in more walking. We took the exterior photos and called it good.

The Journey Back

By the time we made it back to The Talbott, Luna had fully depleted her energy reserves. My dad, who had graciously come along for the entire day, carried her through the lobby in his arms. The hotel staff took it completely in stride. The marble floors reflected everything beautifully. It was a moment.

Saturday Night: Dinner and the Cake, Finally

Luna stayed back at the hotel while my dad and I walked over to Pizano’s Pizza & Pasta for dinner. I had the Anne Marie’s Tortellini, pasta stuffed with chicken and prosciutto in a creamy meat sauce, and my dad had the Chicken Parmesan. Both were exactly right for the end of a very full day.

We ordered room service for dessert. I paired mine with a scoop of vanilla ice cream and finally — FINALLY — cracked open the Cake Bar creation I’d been carrying around since morning. My dad ordered the hotel’s chocolate cake. Luna may or may not have had a bite of the vanilla ice cream. She gave us the puppy eyes. We are only human.

It was, by any measure, a very good Saturday in the windy city.

The Full Dog-Friendly Itinerary at a Glance