Chicago: Surviving & Thriving in the Windy City

Words by Nick Lipton
Photos by Nick Lipton

A lot can be, and has been said about Chicago. It’s big, towering, old and new. It burned down once, only to be rebuilt bigger and better. The winter sucks and the summer rules. In short, the Windy City is America’s last great urban hope. A hotbed of true grit, style, freedom and big city living. It’s got the best food, bars and devil-may-care attitude of any American city. And for a field trip, you’ll never get the full picture or have a real clear picture of what’s going on, so here’s a guide to getting the goods quick and easy.

First and foremost, drinking in Chicago is important. I don’t know if you’ve heard of Al Capone but the man built an empire on getting people tanked. Add that to the roughest winter on Earth and you’ve got a garden of hardened livers and shot/beer combos. From speakeasies to big fancy cocktail spots, sports bars, neighborhood haunts, dive bars and of course the beloved liquor store full-bar combos, this city sets you up. So, here’s a few pointers: Want to get hammered with the hip? Head to Division street between Damen and Ashland. Start at Rainbo Club and work your east past some of the cities best dives until you land at Rite Liqours. You’ll never remember it, but you’ll never forget it.

For the thrill-seeking-good-times-guy, Chicago will never disappoint. We stay open until 4AM, and 5AM if it’s Saturday. Why? Because it’s better that way. So, for something off the beaten path, try the L&L Tavern in Lakeview. Multiple serial killers have called it home, and they’ve got a great cheap beer special. Other good ones include Old Town Ale House, home of some of comedies greatest joke tellers and a whole lot of weird art, Danny’s, the dance club dive bar that’s just in some random house, and Maria’s Packaged Goods down in Bridgeport.

The good people of Chicago do more than drink – they also celebrate and hold onto a good thing. From the greatest sports teams to the best food and classic shops, here’s a cheat sheet to having a good time fast. Start at the Green Mill. It was Capone’s hangout, but also where slam poetry was invented, and still has a shrine in honor of both. Check out Central Camera – , it’s older than your grandpa and just as incredible. Any food joint with an old neon sign out front is going to be good, but great cooks from around the world have been pouring into the city for years, making it a culinary dream. More on that later though, because you’ve got work to do. Get yourself to a ball game, or just go stand in front of Wrigley Field and feel the power of a true American legend. Oh, and if you just want to get rowdy, walk down the street where people party like it’s Y2K every night of the week.

Food. We eat it. With no shame. Fat people come here to feel good about themselves. And you know what that means? We cook it up right. Google up one of these spots for a mind blowing good time: Bari for subs, Kaizan for Japanese, High Five Ramen, the soup speakeasy, Longman & Eagle, an old man bar with a Michelin Star, Crisp Chicken for a Korean mother’s touch, Fatso’s Last Stand to taste a burger built to take down In ‘n’ Out, and Twin Anchors to eat the ribs Frank Sinatra ordered on the regular. Finally, if you’re feeling swanky, check out Randolph street in the West Loop. High Five is right there, along with a bunch of other fancy stuff, and my personal spots – Chicken Shop and Fox Bar – are hiding on the very public second story of a private members club. This list will kick you all over the city, and yet is only scratching the surface.

Don’t be a dork. Chicago was built for tourists and you should take advantage of it. Acting too cool to see The Bean, to check out the Art Institute of Chicago or to wander around downtown isn’t just a waste of your time, it’s a waste of mine for writing this. For a little out of the ordinary adventure, check out the free Lincoln Park Zoo on your way to our giant beach, head to the Garfield Park Conservatory or head south to the Space & Industry Museum. All awesome – all worth it. If you’re with Mom, take the Architectural Boat Tour. It sounds boring, but it’s one of those freak in the sheets situations. You’ll love it, that’s a promise.

Finally, just go have some fun. This city is vibrant, loud, and unlike New York, it actually never sleeps. For great music, start at The Empty Bottle or Thalia Hall, or check out Fireside for some bowling and punk rock history. Head underground for a “Cheezborger” at the Billy Goat Tavern. Go be a dirt-bag the right way at Coles in Logan Square, or hit any of the other bars on the block. And finally, take the EL everywhere. It’s cheap, dirty and you’ll see some stuff to tell your friends about.

So come, hang, visit, move here. This city isn’t going to be swallowed by the ocean anytime soon, the summer is honestly the best in the country and it’ll take you at least a decade to feel like you’ve got any real idea of the rhythm and vibe that makes this place go ‘round and ‘round.

Oh, and don’t visit in the winter.

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