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The Windy City. The City of Big Shoulders. The City by the Lake. Chicago looms so large in the imagination that it’s easy to think you already know it. What’s behind the legend, though, is more complicated: a vast, kaleidoscopic city as layered as LA and hard-nosed as NYC, but with its own quietly confident character — this is the Midwest, after all. Here are 9 insider tips to help you navigate this classic American city.

1. It’s a Great Town for Readers

From Saul Bellow to Sara Paretsky, Chicago’s always been a literary town. And, e-readers be damned, it’s got a vibrant bookstore scene to match. Quimby’s in Wicker Park is the world HQ for ‘zines, while its neighbor Myopic Books boasts three floors of wall-to-wall used titles. A huge LGBT selection distinguishes Unabridged in Lakeview, while beloved 57th Street Books — the consumer-oriented branch of the much-respected Seminary Co-op — rates high for local authors. Not far from the Co-op in Hyde Park, Powell’s Books has long been world-famous among bibliophiles for its used books and the collection in its Rare Books Room — the oldest title was published in Verona, Italy, in 1480. Logan Square’s City Lit, feminist indie Women and Children First and community fave Book Cellar are all treasures as well.

Chicago
Chicago’s bookstore scene is a lifelong romance. Image courtesy of Kristen Heldmann via Getty Images.

2. The Airports Have Subway Stations

Before you hail a ride or fire up your Uber or Lyft app, consider that both airports here house El stations. The Chicago Transit Authority’s Blue Line terminates inside O’Hare (ORD) and for a $5 fare, you can sail downtown in about 45 minutes. From Midway (MDW), the Orange Line makes it to the Loop in a smooth 25 minutes. For just $10, a CTA day pass will also get you unlimited access to the El and Chicago’s bus network for 24 hours. If you’ve ever endured an airport trip during rush hour, you’ll know why this option makes eminent sense.

ORD to Loop in 45 via El. Image courtesy of Gary McCabe via Flickr, used under <a href="https://creativecommons.org/licenses/by/2.0/">Creative Commons license</a>.
Go from ORD to the Loop in 45 minutes via the El. Image courtesy of Gary McCabe via Flickr.

3. Speaking of the Train, a Certain Line Offers Incredible Downtown Views

As it snakes through downtown, the El’s Brown Line gives you unmatched close-up views of spectacular Chicago architecture, along with postcard panoramas of majestic Loop landscapes. The line only services downtown and northwest Chicago, but it’s worth hopping on for the cinematic scenery.

Come for the quick commute, stay for the cityscape views. Image courtesy of player_pleasure via Flickr, used under <a href="https://creativecommons.org/licenses/by/2.0/">Creative Commons license</a>.
Come for the quick commute, stay for the cityscape views. Image courtesy of player_pleasure via Flickr.

4. You Can Caffeinate Where the Mayor Gets His Daily Brew (Hint: It’s Nowhere Near City Hall)

It’s on a blah block of Humboldt Park on the city’s west side and its mismatched furniture and chalkboard menus give it a ramshackle vibe, but don’t let that fool you: Dark Matter is serious about java. Its superior micro-batch coffees, all roasted in-house, draw fanatics like Mayor Rahm Emanuel himself. Come early enough on a weekday and you might spot Hizzoner, who stops by whenever he’s in the hood, for straight black brew. But the real star here is the superlative, complex espresso, worth a special trip in its own right. If you’re looking to linger, Dark Matter’s funky Star Lounge is a block around the corner.

What
What’s with the Jerry Garcia face, you ask? We have no idea. Image courtesy of Dark Matter Coffee.

5. Shhh… Chicago’s Got Great Hidden Bars

They’ve come a long way from the days of Al Capone. What today’s secret sipping spots lack in visibility, they make up for in over-the-top style and clever drinks. Among the best:  Three Dots and a Dash, a retro-cool Tiki bar in an alley behind a barbecue restaurant; swanky craft-cocktail temple The Violet Hour, whose house rules prohibit cell phones; and The Fifth Province, a traditional Irish pub tucked deep inside the Irish-American Heritage Center.

You can order a Hush &amp; Wonder, a mix of rum, lime, creme de violette and grapefruit bitters, at The Violet Hour in Chicago. Image courtesy of Anthony Robert La Penna/Chicago Tribune/MCT/Getty Images.
You can order a Hush & Wonder — a mix of rum, lime, creme de violette and grapefruit bitters — at The Violet Hour in Chicago. Image courtesy of Anthony Robert La Penna/Chicago Tribune/MCT via Getty Images.

6. There’s a Secret Garden Hideaway — With Wi-Fi! — Atop a City Library

There’s no more breathtaking workspace in Chicago than the ninth-floor Winter Garden of the Harold Washington Library, located in the Loop. Immense and airy, it’s an almost surreal mishmash of classical architecture, Art Deco touches and sleek modernism. It’s also quiet and free to visit. Best of all, you can bring in covered beverages.

Literature and views meet at Harold Washington Library. Image courtesy of Raymond Boyd/Getty Images.
Literature and views meet at the Harold Washington Library. Image courtesy of Raymond Boyd via Getty Images.

7. You Can See 30 Plays in 60 Minutes

If you can’t take Chicago’s staggering live-theater options, the Neo-Futurists troupe has the solution. Since 1988, the company’s performed nearly 10,000 two-minute plays. The tradition continues nightly, with 30 plays performed in an hour at its Andersonville theater. And don’t worry that you might have already seen one of them: The Neo-Futurists promise those 30 plays are different every time.

Catch a play or two... or 30. Image courtesy of the Neo-Futurists
Catch a play or two… or 30. Image courtesy of the Neo-Futurists’ Facebook page.

8. Museums Here Rival Any City’s in the World

Big boys like the Art Institute of Chicago, the Field Museum and the Chicago History Museum host blockbuster shows of world-class scope, but Chicago’s also home to quirky museums with single-minded missions. The exquisite Driehaus Museum showcases the city’s Gilded Age in a converted 19th-century home. The International Museum of Surgical Science dissects medical history with a collection unique to North America. The Holocaust Museum and Education Center keeps history and memories alive. And in a converted synagogue, the Leather Archives and Museum is dedicated to, ahem, “The compilation, preservation and maintenance of leather, kink and fetish lifestyles.” There truly is a museum for everyone in this town.

Step into yesteryear Chicago at the Driehaus. Image courtesy of Jason Raia via Flickr, used under Creative Commons license.
Step into yesteryear Chicago at the Driehaus Museum. Image courtesy of Jason Raia via Flickr.

9. The Neighborhoods Are Incredibly Diverse

Indiatown. Chinatown. Greektown. Little Italy. Germantown. Polish Village. The beauty of Chicago’s neighborhoods is how they hang on to heritage even while welcoming successive waves of newcomers. The once-Czech neighborhood of Pilsen’s now home to a huge Mexican community. Andersonville, once predominantly Swedish, has embraced its LGBT and hipster identity. Historically black Bronzeville’s becoming very Chinese. Some visitors get stuck in the Loop, but it’s worth a few short trips to discover Chicago’s true heart.

Chicago neighborhoods like once-Swedish Andersonville are breaking out of their traditional cultural stereotypes. Image courtesy of Charles Osgood/Chicago Tribune/MCT/Getty Images.
Chicago neighborhoods, like once-Swedish Andersonville, are breaking out of their traditional cultural stereotypes. Image courtesy of Charles Osgood/Chicago Tribune/MCT via Getty Images.

What are some of your favorite things to do in Chicago? Let us know in the comments, below.

Featured image courtesy of Interim Archives/Getty Images.

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