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Your HOW Guide to Chicago

For both visitors and Chicago natives who are gathering for this week’s HOW Design Live, we’ve put together a cheat sheet of our favorite places, food, and things to do in the city.

This city is so much more than hot dogs, gangsters, and tall buildings. Chicago has the reputation as the “city that works” and we’re really proud of the title that let’s everyone know that we’re good at getting it done. Designers and firms of all stripes call the Windy City home, from well-known agencies like VSA Partners, Crosby Associates, SMBOLIC, and IDEO to trailblazing firms such as Seguara, Inc, Grip Design, 50,000 Feet, Someoddpilot, Coudal Partners (and ourselves, of course). Chicago is even home to creative collectives like Quite Strong and The Post Family. There’s so much to do in this city, so consider the suggestions below just an appetizer of what’s available to do, see and eat in the Second City.

Chicago is one of the country’s greatest public transportation cities, so almost anything you want to see or do is accessible via El train, cab, bus, or by foot. We’ve given handy locators below in distance from The Hyatt and HOW Design Live, along with Google Maps links.

Chicago Pizza


If you’ve been living under a rock for the last 10 years, you might not know that Chicago is considered a world-class dining city. We have amazing eats from foie gras to a particular style of hot dogs. So, here are a sampling of the gastronomical delights available here:

Frontera Grill
This is the casual Mexican restaurant of Rick Bayless, which he turned into an empire.
(1 mile from The Hyatt | map)


This other “Little Sister” Mexican restaurant of Bayless’ is more of a quick-service cafe that leans towards amazing versions of popular street food.
(1 mile from The Hyatt | map)

Gino’s East
, Pizzeria Uno, Chicago’s Pizza
The debate rages on about what is the best Chicago-style deep dish pizza, but these are a few of the authentic city’s best, and you can make up your own mind. (And for our money, it’s all about the dark horse small chain of Chicago’s Pizza.)
(Ginos: 1.3 miles from the Hyatt | map / Uno: .8 miles from the Hyatt | map / Chicago’s: 4.9 miles from the Hyatt | map)


This local hot dog chain has exploded into the suburbs, but still has a single location in the city. Try the shaved Italian Beef sandwich, a must-try Chicago original.
(.9 miles from The Hyatt | map)

Kuma’s Corner

A hard-rock attitude coupled with arguably the city’s best burgers.
(6.8 miles from the Hyatt | map)

Hot Doug’s

Doug is known for great Chicago style hot dogs, but those in the know line up for his homemade sausages with gourmet fixings, and duck fat fries. Amazing. (6.5 miles from The Hyatt | map)

Margie’s Candies

This candy-store/old time ice cream parlor has been providing sugar-induced comas since 1921 — and we don’t think the interior has changed since. Check it.
(4.9 miles from The Hyatt | map)

Charlie Trotter’s

Some people say this world-famous, high-end establishment is the best restaurant in America. Not sure how you follow that up other.
(3.4 miles from The Hyatt | map)

The Map Room

Lots and lots and lots of amazing beers from all over the world.
(4.7 miles from The Hyatt | map)

Half Acre Brewing

One of several great local breweries (which could easily be its own list!), these guys also give tours of their North Center facilities.
(7.1 miles from The Hyatt | map)

“The Bean” sculpture at Millenium Park

Tourist Stuff

Sure, as designers, many of us pride ourselves on not following the rank-and-file, but there are certainly a few things that are worth braving the tourist crowds for:

Picasso Statue in Daley Plaza
This amazing piece was one of the first large-scale art installations, and was unveiled in 1967. Still beautiful today.
(.6 miles from the Hyatt | map)

Millennium Park

This more recent addition to Chicago public life is beautiful and people-friendly, with the mind-bending “Bean” sculpture and the interactive video screens of the Crown Fountain. Hit up the Art Institute while you’re there.
(.7 miles from the Hyatt | map)

Chicago History Museum

If you’re interested in the Chicago Fire (the epic destruction type, not the soccer team) or the riotous era of ’60s politics under Mayor J. Daley, this is the place for you. Excellent exhibits and insights into what makes Chicago so great.
(2.3 miles from The Hyatt | map)

Architectural Boat tours

One of the best ways to take in the great architecture of the Loop in a short amount of time — some tours are only 90 minutes.
(.1 miles from the Hyatt | map)

Wrigley Field

The second oldest ballpark in the major leagues, this grand old dame is still a jewel, even if the team on the field is often less so.
(6.2 miles from the Hyatt | map)

The Historic Water Tower

One of the oldest structures in the city, it now houses a free art gallery, and is one of only a few structures to survive the Great Chicago Fire in 1871.
(.9 miles from the Hyatt | map)

Segway Lakefront Tours
A great way to check out the beautiful avenues up and down the shore of Lake Michigan, riding a goofy-looking device that was supposed to “change transportation forever.”
(1.5 miles from the Hyatt | map)

Chicago Beaches

Along with a lakefront comes some great beaches, and two of the best are the North Avenue Beach and Oak Street Beach.
(1.9, 1.1 miles from the Hyatt | North Avenue Beach map | Oak Street Beach map)

Sears (don’t call it Willis) Tower
and John Hancock Building
Two of the tallest buildings in North America reside here in Chicago, and both are amazing feats of architecture coupled with outstanding views of the city.
(Sears Tower: 1.3 miles from the Hyatt | map / John Hancock Building: .8 miles from the Hyatt | map)

Chicago Art Institute
The Art Institute of Chicago

Design Nerdiness

The Art Institute of Chicago Modern Wing
The recently-completed brand new Modern wing of the Art Institute is beautiful and well worth the short walk. Kick it Ferris Bueller style with the Lion statues out front on Michigan Ave.
(.8 miles from The Hyatt | map)

Smith Museum of Stained Glass

It’s super-cool, and closeby on Navy Pier.
(1 miles from The Hyatt | map)

Uncle Fun

Oh so much more than a toy store.
(4.7 miles from The Hyatt | map)


Supercool designer toy store. Get your vinyl on.
(4 miles from The Hyatt | map)


Another awesome indie bookstore that “favor the unusual, the aberrant, the saucy and the lowbrow.”
(3.5 miles from The Hyatt | map)

Museum of Contemporary Art Chicago (MCA)

If you’re really into modern art, the MCA is the place to be, with challenging and excellent work. While you’re there, peep The Historic Watertower across the street.
(.8 miles from The Hyatt | map)

Portage Theater
, Music Box Theater
To get an authentically classic moviegoing experience, check out either of these independent, restored movie houses, with all of the glitz and beauty of their eras.
(Portage Theater: 8.3 miles from the Hyatt | map / Music Box: 5.2 miles from The Hyatt | map)

Salvage One

A gorgeous collection of restored, vintage and midcentury modern furniture and found objects.
(2.8 miles from The Hyatt | map)

Hanger 18
Super cool artsy gift shop. Representative of a whole wave of similar shops that dot the city, but worth the trip.
(6.8 miles from The Hyatt | map)

Delicious pizza image by Eric Chan. Millennium Park image by Kelly Johnson. Art Institute image by Steve Blane. Images used with permission under Creative Commons license.

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