HOW Design Live: A Local’s Guide to Chicago

HOW Design Live makes a return trip to Chicago this June, and we couldn’t be happier about it, because it’s pretty much our favorite destination city for the conference, and the site of our biggest and most successful events. Even better, Chicago has tons to offer graphic designers and creative types after each day’s program ends. We asked designer, speaker and Chicago fan Mig Reyes to scout out some spots that HOW-goers must hit while they’re in town. After reading his list of recommended bars and restaurants, dangit, we’re already hungry.

There’s so many great places to check out, I want to pull everyone away from the downtown area. The real magic begins when you start to explore the neighborhoods—and these places are mere cab rides away. (No more than $10 a cab fare to the furthest destinations.)


Quimby’s Bookstore
1854 W. North Avenue

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.

The Boring Store
1331 N. Milwaukee

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.

3011 N. Broadway

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.

Other must-sees:

Old Time Pottery


Piece Pizza
1927 W. North Avenue

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.

1434 W. Chicago Avenue

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.

DMK Burger
2954 N. Sheffield

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.

Other must-sees:

Kuma’s Corner
Hot Doug’s


Five Star Bar
1429 W. Chicago Avenue

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!

Longman & Eagle
2657 N. Kedzie Avenue

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.

Violet Hour
1520 N. Damen Avenue

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.

Other must-sees:

The Whistler
Revolution Brewing

Mig Reyes is an interactive designer at Threadless.  He talks about awesome on Twitter. Get scoop on Mig’s session at HOW Design Live, and register today (if you haven’t already).

Have your own recommendations for Chicago hotspots (bars, shops and restaurants)? Use the Comments box to share your Windy City faves!

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