Journey To Chicago: What to Do in the Windy City

Downtown Chicago, Illinois

Journey To Chicago What to See and do
An iconic view of Chicago


What do you picture when you hear that word? I hear Polish truck drivers in a Mamet play delivering groceries, spectacular wind chills blowing off Lake Michigan, Cubs and White Sox, Bauhaus and Contemporary structures sitting side by side, Al Capone and speakeasies, Second City, Windy City, White City, Home Alone, Chicago the Musical, deep dish pizza, Sears Tower, loudness, and the eternal rumble of the “L” trains.

We visited Chicago for only two full days and a morning, so we only saw downtown Chicago, for the most part.  Still, we saw Chicago as it woke up in the morning and how it went to sleep (or didn’t go to sleep), how it breathed and lived, and with the advantage of beautiful fall weather, we explored quite a bit.

The Magnificent Mile

A View of The Magnificent Mile - Michigan Avenue
A View of The Magnificent Mile – Michigan Avenue

Wild garlic.  That’s what Chicago really means.  Chicago’s recorded history began with its discovery by the French and the name Chicago came from the Algonquin word shikaakwa, which is a wild garlic plant that was abundant in the area.  It was interesting to hear this piece of history during one of our tours, to be reminded that the roots of American cities, large and small, all came from Native Americans who roamed the entire continent.  Today, when you walk through The Magnificent Mile, located on Michigan Avenue, you’re walking through a commercialized paradise of shopping and entertainment, gawking at hyper-tall steel and glass structures.  People bemoan the Southside gang violence that seems to plague Chicago more so than other big cities, but you go back 80 years and Chicago’s streets were bloodied by Al Capone and the North Side Gang.  You go back 300 years, and the very land upon which Chicago sits was used as a bloody, violent battlefield between the Iroquois and the Algonquin for control of the fur trade.  The insignias have changed, but the violence hasn’t.

The MM is well preserved, mostly clean, and is kind of like a less opulent version of Times Square.  In fact, that’s how I’d generally describe Chicago compared to New York City.  Doesn’t sound terribly exciting, but it’s not a put-down.  Chicago has all the high/low elements of NYC, but it’s a bit toned down and, as a result, dare I say it’s more enjoyable to walk around the Loop than 5th Avenue.

The Loop

Ruby in front of The Bean
Ruby in front of The Bean

History, of course, is more than just birth and evolution.  The Great Chicago Fire destroyed much of the Business District and left 100,000+ homeless, but Chicagoans persevered and rebuilt not only what was lost, but also created opportunities for expansion.  The Loop is the cool name given to Chicago’s Business District.  No one wanted to call it “The Business District”, so they gave it a nicer name.  It’s a very walkable, enjoyable piece of real estate.  Shops and restaurants galore, attractions and historical buildings everywhere, the wind blowing in from Lake Michigan, more tourists than locals.

The Loop houses about 30K people, most of which have the money to live in expensive condos scattered across 1.5 square miles.  With that amount of money, it can either be spent on glitz (Vegas) or culture, and Chicago seems to have decided for culture.  It’s got some tremendous stage theaters, including the Chicago Theatre, Steppenwolf Theatre, Oriental Theatre, Goodman Theatre (Mike Nichols, David Mamet), Victory Gardens Theatre, Broadway Playhouse, and, of course, the great comic factory Second City.  Many great plays have been performed in these theatres.

The Bean (officially called Cloud Gate, but The Bean just sounds better) is a towering, gorgeous steel sculpture which sits right in the middle of Millennium Park.  Millennium Park is a grandiose name, but the park itself isn’t really that long.  It’s about 3% the size of Central Park, but it does have an outdoor pavilion, the aforementioned Bean, and nice walking paths near the water.  The Bean is the most popular attraction in the park, always swarmed with people taking pictures from various angles.  It might be touristy, but it is fun to play with the different angles and poses, and it is doubly fun to see grown adults giggle and frown and smile at this large toy in the middle of a large city.

Of course, while the name Millennium Park sounds both futuristic and antiquated, it was actually built in 2004.  A purely modern-day invention.  The most famous park in Chicago is Jackson Park, which was the site of the famous event in Chicago’s history, the 1893 Columbian Exposition (also known as the World’s Fair).  Sadly, after the fair ended, the park burned, and never retained the promise of the original plans created by the great designer of Central Park himself, Frederick Olmsted.  It’s still around, however, and recent restoration efforts have helped improve its features and make it more enjoyable to locals.

The Food

Hillary Vs. Trump, Sandwich Wars
Hillary Vs. Trump, Sandwich Wars

Ask people what food to try in Chicago, and the answer is usually, 8/10, deep-dish pizza.  Might be cliche, but people do seem to be protective of their deep dish pizza, and you better not even suggest that they do it better anywhere else (like New York; just don’t mention New York in anything, Chicago and New York have a professional city rivalry).  The deep dish pizza variety stuffs the crust with cheese, so that your arteries don’t know what hit them!  It is a marvelous invention, I must say, and even a small, 6-inch portion is quite enough to fill you up.

During our first day, our first full meal in Chicago, we went to Giordano’s for a taste of this famous pizza.  They were very busy, overflowing with a mass of people, but service was pretty crisp, and we had our pizzas in about 20 minutes from the time we ordered.  We did a lunch special with a small pizza and a side, so all in all it was a satisfying and budget friendly ($10 per person) meal.

For dinner, we went to a fancy pants Chinese place because we had a craving for Xiao Long Bao, steamed soup dumplings.  The place was called Imperial Lamian, so right off the bat, you feel grand just stepping inside.  The bao came in various colors, and various flavors, such as gruyere cheese, szechuan spice, duck, or pork.  They were all great, but the best one was probably the szechuan, it had a great kick.

The food highlight of our trip was Quartino on State Street.  We had just finished biking by the lake and through downtown for a couple of hours, so we were hungry and saw a lot of people crowding this Italian place, so we decided to give it a try.  The place is basically Italian-style tapas, but it has an old-school Italian feel.  Luckily, were were given a spot on the 2nd-floor balcony, so we had nice views of downtown, and the great weather meant was just a cherry on top.

High Line and Goodbye

We finished off our trip with a bike trip through the recently reclaimed High Line in the Logan Square neighborhood, which was a pleasant trip.  Two days is not nearly enough to explore Chicago, but we were fortunate to spend most of our Saturday visiting historic buildings that are usually closed to the public (it’s a once-a-year event, called Open House Chicago).  We saw old banks, churches, hotels, and got to see a part of Chicago that most tourists miss.

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