Finding Leisure on Business: Chicago

Ferris Bueller. Pizza. Oprah. Hot dogs. Barack Obama.

Ok, that’s the list. That’s all I knew about Chicago before I landed at Midway. Terrible, isn’t it? Food, a fictional character, and someone who wields more power than most countries combined (I’m talking Oprah, not Barack).

I’ve flown via Chicago many times, but for all the landings and take-offs made at O’Hare and Midway, I never stuck around to explore the city itself. Up until June, my only views of Chi-Town were through the eyes of Steve Urkel in Family Matters or through the eyes of an E.R. in well, E.R..

Cue the Internet Retailer Conference & Exhibition.

Earlier this month, my company sent me to Chicago for the IRCE—a gathering of about 7,000 nerdy internet-lovers who sell random stuff online (from scuba gear to underground swimming pools, wrestling shoes to jewelry). Though I spent most of my time in an overly air conditioned McCormick Place convention center, I did manage to escape at night and do my duty as a travel blogger.

Our hotel, the illustrious Downtown Travelodge, was about a 20 minute/$30 cab ride from the airport. Not to say I highly recommend it. Reading reviews the night before proved to be a mistake, as they lamented the place for the bedbugs and rude staff. I was on edge all night, wondering if the mysterious little bed monsters would attack, but luckily, there were neither bedbugs nor discourtesy. But keep in mind, the place isn’t exactly Shangri-La.Its one saving grace was the excellent location—smack dab in the middle of the Columbia College scene, the area was brimming with youth. With a Starbucks around every corner and a group of twentysomethings carrying lattes around every other corner, it was a fun vibe. Restaurants were everywhere and the Hilton up the street had a shuttle to the convention center (I lusted after the glorious Hilton, clean and lavish and out of price range).

Though you’re surrounded by brilliant architecture and honking cars, you’re also not far away from nature with Lake Michigan splashing up on the shores of downtown. Leafy green parks abound and there’s an odd sense of calm throughout the third busiest city in America. Until, of course, the Blackhawks win the Stanley Cup and all hell breaks loose.

I started to fall in love with Chi-Town as soon as I took to the streets—they were clean and seemingly familiar, with interesting storefronts lined up along the broad avenues. Even abandoned spaces for lease were interesting, as they became makeshift art galleries for local artists. And the people? Couldn’t be more pleasant. It seems like a half-hearted, lackluster statement, but honestly, Chicagoans were incredibly nice. But before I fell completely head over heels, I had to sample the food. …and it passed with flavorful flying colors.

From deep-dish pizza at Lou Malnati’s to a pub-style dinner at Miller’s, from heaping bowls of pasta at Oprah’s favorite downtown haunt Pizano’s, to delicious green curry at Tamarind, the food scene was delectable and affordable. Every meal tallied under $20, including beer or wine, and nothing fell short of the high expectations I assigned.

Chicago is also home to a few eminent entities: the Cubs, the White Sox, and my friend Anna of blogging fame—we might be the only two people from our senior capstone class to keep up with our assignments; see her awesome music blog at http://popapocalypse.blogspot.com/.

Anna and I met up at the overpriced, over-the-top, over-hyped BIG Bar in the Hyatt Regency hotel. The view was spectacular, the inappropriately named “big” drinks were not. We risked looking like the sorority-type girls we disdained in college and ordered cosmos. At $13 a pop, you’d expect a bucket of booze, but when the rinky-dinky martini glasses arrived, it was a reality check that we were in the middle of a city. Of course they were $13 a pop. Of course they were tiny. It was downtown Chicago and happy hour isn’t in a hotel bar’s vocabulary. We switched to beer and I was grateful for my per diem.

I always appreciate being in a place where you can hail a cab the minute you step onto the sidewalk (especially after a martini or two, no matter how small they are). Chicago was chock full of cabbies, but had several alternatives to the typical taxi route. Downtown was certainly manageable to walk, and even though the CTA trains had a knack for waking me up every hour on the hour, the benefits of such an extensive public transportation system didn’t escape me.

You could rack up dozens of culture points in Chicago, with the Museum of Contemporary Art, the Museum of Science and Industry, and here in Chi-Town, even improv comedy troupes could ramp up your cultural score. The Second City comedy enterprise originated in Chicago, and churned out the likes of Steve Carell, Chris Farley and my personal hero, Stephen Colbert.


Going on a trip without any prior knowledge of the city you’re landing in (beyond the fictional and celebrity-fused tidbits you pick up throughout a lifetime), is actually a refreshing concept. I’m so used to rigorously searching Wikipedia and planning details from beginning to end online, that doing it the old-fashioned way was fun and invigorating. Perhaps, that’s just the “Old Chicago” way.