Seeing Chicago for the First Time

The Elephant & Castle is an English-themed restaurant located in Chicago’s Business District.

I’ve often driven by Chicago on the way to another destination and admired its towering buildings, but I had never actually visited the city until this past April. I spent a couple of quick days taking in the art and architecture before heading out on a Route 66 cross-country road trip, and my one takeaway from the Windy City? I’ve got to go back as soon as possible.

There is so much to see in this welcoming Midwestern metropolis that it’s impossible to spend just a weekend wandering the sights. While I tried to fit in as much as I could, I was left wanting more.

Those familiar with the city will, of course, recognize “The Bean,” an affectionate nickname for the 12-foot-high sculpture located in Millennium Park, made of 168 massive stainless-steel plates. A huge attraction to tourists and locals alike, Cloud Gate (its actual name) mirrors the buildings and people that surround it, making it not only an encapsulation of the city but also an interactive art experience. Thousands of people visit the park each day to take pictures both of The Bean and “in” The Bean, making it the perfect place to kick off an art tour of Chicago.

The concept of selfies has been taken to a new level at The Faces of Chicago display in the park, where two identical 50-foot towers project video images of Chicago citizens. These massive faces, taken from a cross-section of 1,000 residents, represent Chicago’s vast demographics in terms of age, gender, and ethnicity, reflecting the diverse makeup of this melting-pot city.

The Millennium Monument, a nearly full-sized replica of a peristyle that originally stood on the same site at the corner of Michigan Avenue and Randolph Street between 1917 and 1953, pays tribute to the park’s 122 founders. Featuring 40-foot-high columns set in a semi-circle, the monument stands as a tie between the city’s past and present.

There are numerous Chicago River cruises, including an art and architecture cruise that offers views of Marina Way and the Wrigley Building.

Of course, not all of Chicago’s art is outdoors. The world-renowned Art Institute of Chicago is a must-see and is considered one of TripAdvisor’s “Best of the Best” U.S. attractions. While tickets are a little steep at $32, it’s well worth it to see Georges Seurat’s A Sunday on La Grande Jatte, Vincent van Gogh’s self-portrait, and Grant Wood’s American Gothic in person. Free tours are offered daily, and numerous exhibitions—including Frida Kahlo’s Month in Paris: A Friendship with Mary Reynolds (which runs through July 13)—provide even more reasons to spend a day enjoying art.

How to See the City

While Chicago is quite drivable, it’s a lot easier to just park where you’re staying and enjoy the views through a variety of transit options. Note: If you are going to park downtown, be aware that you won’t be paying Pittsburgh prices—a half-day’s parking at a city garage cost $74!

One of the most popular ways to see the city is from the Chicago River on an art and architecture cruise. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit. The 90-minute tour, which costs roughly $45, includes views of Marina City, the Wrigley Building, and other historic highlights.

Lou Mitchell’s Diner is known for being the first stop for road trippers taking on the legendary Route 66.

You can also take a hop-on, hop-off tour covering the city’s must-see sights by open-top bus. The tour includes strategically located stops where you can hop off to explore the city on foot before returning to the tour at your leisure. While on the bus, you can enjoy learning about the city and its rich history, and you don’t have to do it all in one day! You can choose from 24-, 48-, or 72-hour tour tickets to suit your schedule.

You can’t help but see the ’L’ when you’re in the city; just look up and you’ll spot the Chicago Transit Authority (CTA) trains running overhead. The name, short for “elevated,” refers to a system that serves over 140 stations located throughout the city and nearby suburbs—on elevated tracks, in subways, or at ground level.

I found it surprisingly easy to use the ’L’, despite never being very good at figuring out how to travel by train or subway. Instructional boards showing the routes are posted prominently at each station, and it’s easy to buy a Ventra card at a kiosk to pay for your trip. We were pleasantly surprised by how eager to help the CTA employee was when we had a question—that rumored Midwestern hospitality is for real!

Where to Eat

This is actually kind of a silly question in Chicago; what you should be wondering is how many places you can nosh at and still be able to waddle back to your hotel. The choices range from famous Chicago deep-dish pizza and Chicago-style Italian beef sandwiches to high-end, elegant restaurants like the James Beard-awarded Alinea and Michelin-starred Smyth.

Cloud Gate, otherwise known as “The Bean,” is a huge tourist attraction.

We grabbed a quick lunch at Elephant & Castle, an English-themed restaurant located in the Business District near the legendary Chicago Theatre, which gave us the perfect starting point for our walking tour of the city. We also had breakfast the next morning at Mitchell’s Diner, a renowned Chicago tradition where most Route 66 travelers begin their journey. Don’t be concerned about the line at the door—tables turn fast and the food is served quickly, so you can get your day (or your drive) started early.

To really enjoy all the delicacies the city has to offer, sign up for a food tour. There are so many options, including Chinatown food tours, iconic foods of Chicago tours, pizza, donut, and craft brewery tours—even one dedicated to the restaurants that inspired the TV show The Bear. Not only will you enjoy an amazing array of dishes, but you’ll also walk off at least some of those calories as you travel to different destinations.

To learn more about all there is to do in Chicago, check out www.VisitChicago.com.