The Perfect Summer in Chicago

I’ve lived in Chicago and the suburbs my whole life (aside from a few years away at college), so I like to think I know this city through and through — especially in the summer, when it really shows off. There’s nothing better than summer in Chicago, so here’s my official guide to soaking up every bit of the good weather while it’s here.

There’s nothing better than summer in Chicago — and if you do it right, it’s all about the lake, patio season, and getting out on the water. Start with a walk. One of my favorite summer rituals is heading out from the Gold Coast, starting at Oak Street Beach and wandering up the lakefront trail. The city feels different by the water — the breeze, the skyline peeking through the trees, the little moments where you remember why we all stick out those long winters.

On Wednesdays and Saturdays, I always find my way to Green City Market in Lincoln Park — coffee in hand, lake breeze in my face, and the best local produce waiting at the end. It’s the kind of morning that makes you fall in love with the city all over again.

Then, grab a seat. You can’t beat the RL patio for people-watching and classic charm, or NoMi Garden for its tucked-away elegance and city views. Shanghai Terrace is always a favorite — sleek, sophisticated, and somehow still a hidden gem. And of course, nothing feels more Chicago than the outdoor seating trifecta at Gibsons, Bellevue, or Tavern on Rush. That’s where the city comes alive: the laughter, the clinking glasses, the hum of conversations spilling out onto the street.

In between all that walking and patio hopping, carve out time to pop into a few favorite shops — it’s part of the ritual. P45 always has the best edit for something unexpected, SPACE519 is perfect for a mix of fashion and home (and don’t miss their café while you’re there — a quick lunch or glass of wine never hurts), and Dana Rebecca Designs, obviously, for a little sparkle to take home with you.

And don’t forget the water. An architecture boat tour is a must — it never gets old, even for locals. If you’re craving something more personal, grab a couple of friends and rent a tiny boat to cruise the river at your own pace. Bring snacks, your favorite playlist, and see the skyline from a whole new perspective. It makes for the best afternoon — and an even better date night.

Chicago summers are short — make them count.

Til next time
xx

Dana