From one Second City to another; seeking out comedy in Chicago & why we won’t be having Deep Dish pizza again

Other than being the home of skyscrapers, the deep dish pizza (more on this later) and wind, we didn’t know much about Chicago.

But James is an avid Tina Fey fan, and read about her training ground at Chicago’s Second City comedy and improv school in her autobiography Bossy Pants. TINA FEY

He knew that when we got to the Windy City, a trip to the famous venue was at the top of the list.

After the craziness of Las Vegas, landing in Chicago felt immediately real.

We were staying with friends again; we’d met the awesome (and awesomely named) Suzie Shoemaker in Argentina and she kindly offered a room in her amazing penthouse apartment in the beautiful suburb of Lincoln Park.

IMG_9612Shout out as well to her brilliant other half Brent, who was so welcoming to a couple of hobos he’d never met!

Armed with local knowledge, we blitzed the city’s main attractions. First up was the famous Bean, the giant silver sculpture by London artist Anish Kapoor (he of the London Olympics Orbit sculpture), which was a perfect muse for Chris’s photography skills.


It’s smack bang in the middle of town in Millennium Park, where there happened to be a weekend Blues festival on as well. We’re not huge fans of the genre (“all sounds the same!”) but it was fun to feel the buzz of the city on a sunny summer afternoon.

Rooftop bars are much more our scene, so we headed to Cindy’s on Suzie’s recommendation.


No rooftop worth its salt doesn’t come with a queue, so after waiting 10 minutes for the lift, we ordered an overpriced “craft” beer and surveyed the amazing views of Downtown (called The Loop in Chicago after the elevated “L” train which loops around the city centre) and the vastness of Lake Michigan beyond it.

No trip to the home of skyscrapers would have been complete without a visit to the one-time tallest building in the world, Sears Tower (now Willis Tower).

It held the title from 1973 until 1998 when Malaysia’s Petronas Towers took over. It may not be as iconic at the Empire State or Chrysler buildings, but the viewing platform was a great way of checking out some of the more beautiful Art Deco skyscrapers surrounding it. Chris was in his element! We also couldn’t resist the glass floor selfie!


Walking around the Loop, we were amazed by how intricate and beautiful many of the buildings were, so we decided on a walking tour to learn more about them.

Our favourites were the Wrigley Building, early home of the chewing gum giants, which for many resembles a giant birthday cake, and the Chicago Tribune headquarters, a stunning neo-gothic masterpiece.

It has fragments of famous buildings from around the world embedded into it at street level, from the Berlin Wall to the Taj Mahal, and even part of the World Trade Center.

We’d recommend a walking tour over the ubiquitous architectural boat tours, which limits you to the buildings in the eye line of the Chicago river.


Chicago’s other famous creation is the Deep Dish Pizza. And other than a microwaveable version called Chicago Town that we devoured in our youths, we had no idea what to expect.

Most people agreed that Giordano’s is the original deep dish to order, so we went for their classic recipe with pepperoni, onion and green peppers and waited. Then waited some more. Apparently each deep dish is hand made to order and can take 45 minutes to arrive!


Sadly, it wasn’t worth the wait. A thin crust New York or Napoli pizza is the perfect mix of crispy base, melted cheese and rich tomato sauce.

A deep dish is the opposite; the topping goes on the bottom, the cheese on top and the tomato sauce above all of it. It meant neither the cheese nor the meat was properly cooked, and the dough on the base wasn’t crispy.

It also contained probably 4,000 calories and felt more like a challenge than a pleasure. It’s likely to be our first and last deep dish experience, but we’re glad we gave it a try!


Our final night in Chicago was Second City night. The place has become a large complex with various venues, bars and teaching spaces, with caricatures of its biggest stars emblazoned on its walls. James was as excited by the place itself as the show we’d come to see!


There are at least 10 shows on sale at Second City, so we opted for a “Best Of” show which features classic sketches from its near-60 year history, new sketches and improvisation.

We immediately encountered any comedy fan’s worst nightmare; being sat within spitting distance of the stage! Thankfully the stars didn’t pick on us, and we ended up with a great vantage point.

Most of the sketches were spot on, including this quickfire one about abortion…

“So what do you think about this latest abortion bill?
“Just pay it”

The improv took weird and wonderful turns, and at least three of the stars of the show look primed for Saturday Night Live stardom. Watch Tina Fey & Rachel Dratch in action here when they were learning their craft!

It was rough around the edges in parts, but these performers are basically students, raw and new. If they’re this talented now, who knows what they’ll come up with in the future.

Our Chicago checklist well and truly ticked off, we spent our Saturday night on Suzie and Brent’s rooftop, eating amazing barbecued steak and drinking bourbon cocktails. Life doesn’t get much better.


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