Curated City Guides by Your Favorite Designers and Tastemakers.
Chicago:
Mig Reyes
of 37 Signals
Bars & Restaurants
Piece Pizza
Heading to Piece with a group of friends is quite possibly one of the best ways to end a weekend. Forget that “Chicago deep dish” mindset for just a minute. Sitting near the heart of Wicker Park, they craft all of their own brews and whip up some downright good thin-crust pizza. Also, invite me when you go. It’s truly one of my favorites. 1927 W North Ave
Flo
This is a must-do on your breakfast and brunch list. Have some fresh coffee while you wait, and enjoy the American Southwest-infused flavors to fuel you for the day. I’ll be sad if you don’t eat here. 1434 W Chicago Ave
DMK Burger
A slightly swanky (but incredibly delicious) burger bar at a reasonable price. Quite honestly, I’d go here every day just for their assortment of fries alone. 2954 N Sheffield Ave
Five Star Bar
A short ride from downtown will bring you to this West Town neighborhood bar. A punk-rock vibe with a huge selection of beer and bourbon, this is the bar I frequent the most—especially on weeknights! 1424 W Chicago Ave
Longman & Eagle
You should only head to this Logan Square spot if you like incredible food and great drink selections. Brunch, dinner or drinks—they’re all just too good. They’re quite the hot spot, so bring a small to mid-sized group as they don’t take reservations. 2657 N Kedzie Ave
Violet Hour
This is a great spot for a low-key, speakeasy vibe for smaller groups. Tucked away in Wicker Park, you can expect some truly fantastic hand-crafted cocktails from some of Chicago’s most passionate mixologists. 1520 N Damen Ave
Shops
Quimby's Bookstore
Since we’re all creative types here, one shop to make a stop at is Quimby’s. They’re chock full of indie zines, comics, graphic novels and out-of-nowhere art and ephemera. Everything is unusual, in the best way possible. Bring some tote bags, you’re bound to find some gems. 1854 W North Ave
The Boring Store
If you’re into beautiful design and typesetting—duh, of course you are—you must head to The Boring Store and find yourself some cool spy trinkets. The best part? The proceeds of this Dave Eggers brainchild go to supporting the Chicago Public Schools tutoring center tucked behind the storefront! Have fun and do some good at the same time. 1331 N Milwaukee Ave
Threadless
I’d be remiss to not include my own stomping grounds! But really, the Lakeview area is beautiful and bustling, which is why we have one of the coolest brick and mortar stores on Broadway. Check it out, sport some new tees during the conference. Summer is hot in Chicago, y’know. 3011 N Broadway St