25N’s (Unofficial & Possibly Superior) Local Guide to Chicago
So… you’ve come to our lovely home city for that coworking conference. Between crucial hallway catch-ups, networking over hotel breakfast, and trying to outsmart the Whova app, you’re going to need ways to wind down. (Or—for our fellow introverts—a back booth where you can stare blankly into the mid-distance with headphones on.)
These are the Chicago spots our team loves when we’re not debating which space has the best natural light. It’s your field guide to the good stuff.
Eat / Drink
For incredible skyline views, Cindy’s is the spot. Go for the cocktails, stay for a sunset selfie that could be your best LinkedIn performer all month. (Or honestly better: make you forget LinkedIn exists).
We respect Lou’s. We really do. But Milly’s is the Chicago deep dish that has r/chicagofood all aflutter. Gooey, messy, glorious. Don’t wear white.
When you’ve hit your deep-dish limit, grab sushi that hits reset. Affordable omakase, crispy tempura, and a lunch special that makes you late to the 1:15 session start.
Arguably (fight us, we can handle it) the best burger in Chicago. Possibly the Midwest. Add patio weather and start scrolling Zillow for real estate 1 block down.
Hidden tiki bar. Ridiculous cocktails. With mood lighting to make everyone look mysterious and successful.
You could stop at one scoop, but why? Ft. flavors that sound fake but taste like pure joy.
This is what we mean by “the G.O.A.T.”. It’s the sibling of the famous Girl and The Goat Restaurant, but in brunchy comfort-food form.
Fondue that transports you to a 70s dinner party in the best possible way. Invite your speed- networking neighbor.
Filipino breakfast, elevated to art form. Order anything. Then order again.
To Do
Chicago River Architecture Cruise
Yes, it’s touristy. But yes, it’s as delightful as everyone says. You’ll leave knowing what a flying buttress is, and somehow caring. (The CAC - linked - runs the best one of these in our opinion.)
Lakefront Trail (+ a bike ride)
This stretch of Lake Michigan’s waterfront is the city’s inbuilt reset button. Rent a step-through bike and take a lil zoom around.
Emporium Arcade Bar (Fulton Market)
Pac-Man, pinball, and craft beer. Your inner child is jumping up and down.
We can’t endorse all the weirdness you’ll find here, but it is a reliable blast for vintage treasure-hunters. Last time we went we’re pretty sure we found a time machine.
Former salt warehouse, now concert venue. Best comeback story in the city since the Cubs in 2016.
Step into the glass box, tilt out over the city, and slap on your best “no…it’s chill…” face. 25N lore: one of our teammates even got engaged here.
We’re very proud of our art museum around here. It’s one of those “just for an hour” stops that turns into half a day.
Because watching penguins waddle never gets old. Trust us - we tested that theory.
Your Turn?
Check off a few, add your own, and tell us what we missed. We’re ready to gently debate you over deep dish options at our team table or the WPS booth.