Chicago: Exploring the City by the Lake

Several years ago I had a brief layover at Chicago’s O’Hare Airport. It was one of those layovers just short enough that I couldn’t leave the airport, but just long enough that I wished I could’ve escaped the bright fluorescent lights and mob of travelers. I remember flying out that night, catching a glimpse of the city nestled by the lake, and telling myself that I’d be back to explore another day.

Last week, I found myself again in the swarming terminal at O’Hare, but this time, I was visiting Chicago for real! The plan was to hang out with my friend Josh, who had just started law school, and to explore the city for the first time, checking out everything it had to offer.

This post is a recap and rundown of the activities, sights & sounds, and food & drinks I enjoyed in Chi City. I included a handy map of the spots I explored in case any readers plan to visit in the near future!

Day 1

After landing from my red-eye flight, I made it to Josh’s apartment in the Gold Coast, a nice and quiet part of the city with lots of upscale restaurants and shopping. It was still 6am on the West Coast, so I fought the tiredness by eating a giant omelette breakfast complete with hot cakes at The Original Pancake House. Unsurprisingly, I took a comfy nap right after to recover.

Street tacos at Big Star

Street tacos at Big Star

After my nap, we walked over to the Museum of Contemporary Art, a smaller modern art museum next to Josh’s law school campus. The museum was the perfect size, with just enough artwork to keep us interested. There were cool exhibits like the room full of sand dunes (representing the number of stars in the galaxy) or the light up art pieces created by Alfredo Jaar, electronic producer Nicolas Jaar’s dad.

After the museum we stopped by the Northwestern Pritzker Law School campus, also known as Josh’s second home. We checked out the library where all the magic happened and I stopped to admire a Lichtenstein art print on the way out. Next we headed to Wicker Park, Chicago’s version of the Mission in SF. After enjoying an afternoon snack at Big Star (street tacos and beer), we walked around the neighborhood, trying out some amazing donuts from Stan’s Donuts and delicious third-wave coffee at 80s-themed cafe The Wormhole Coffee. Before heading out, I had to try Jeni’s Splendid Ice Creams. The scoops of brown butter almond brittle and churro ice cream were incredible indeed.

Super-hip Wicker Park

Super-hip Wicker Park

For dinner we walked to The Halal Guys Chicago, which was only 5 minutes from the apartment. I was so full from the previous meals, snacks, and desserts that I had to settle for the small bowl. That night I met up with another friend (and Josh’s law student classmate) Jared, and we went to a housewarming party hosted by the incoming class of law students.

Day 2

The second day started with one of my most-anticipated activities – the Chicago Architecture Foundation River Cruise. Josh and I walked over to River North and caught the 11am tour, headed by a wonderful volunteer guide who spent 90 minutes sharing the history and architecture of almost all the major buildings along our route on the Chicago River. The high rise buildings surrounded us on both sides as we sat on the open deck with our necks craning up to admire the huge structures.

Chicago Architecture Foundation River Cruise

Chicago Architecture Foundation River Cruise

We finished the tour just in time for lunch, so we walked over to Portillo’s, a famous Chicago hot dog chain, to sample a Chicago-style hot dog (fresh tomatoes, pickles, relish, no ketchup) and Italian beef sandwich. The food was very oily and predictably delicious, exactly how I imagined it to be. I topped off the meal with a huge serving of frozen custard.

To fight off the post-lunch food coma, we walked to Millennium Park to see the famous Cloud Gate sculpture, better known as the Bean. It was pretty cool getting up close and seeing our reflections and other optical effects, but the area was pretty crowded so we took off after snapping a few pictures. We spent the afternoon resting in anticipation of steak night.

Chicago-style hot dog, Italian beef, & onion rings at Portillo's

Chicago-style hot dog, Italian beef, & onion rings at Portillo’s

Several weeks before traveling to Chicago, I made a reservation at Benny’s Chop House because I’d heard Chicago had many great steakhouses serving incredible steak. We weren’t disappointed. The 18-oz dry-aged rib eye was out of this world. The aging process made the flavors even more concentrated and the texture was perfect. I slept very well that night.

Day 3

Since Josh had class again starting Monday, I spent the next couple days exploring the city largely on my own. The third day was art day, so I went to the Loop to grab a quick breakfast and pour-over coffee at Intelligentsia Coffee before entering The Art Institute of Chicago.

Entrance to the Chicago Institute of Art

Entrance to the Chicago Institute of Art

This art museum trip ranks as one of the most pleasant I’ve been on. Thanks to the weekday timing, the crowds were few and I was able to enjoy even the must-sees by Monet, Seurat, Matisse, Hopper, Picasso, and Warhol. Hours went by without my noticing as I enjoyed one exhibit after another. I finally took a lunch break, walking over to Al’s Beef for a dipped Italian beef sandwich, one of the messiest sandwiches I’ve ever eaten. With my hunger satisfied I headed right back to the Art Institute to enjoy a couple more hours of art.

Bacon & pineapple donut at Firecakes

Bacon & pineapple donut at Firecakes

By the time I left it was late afternoon, but I still had some time to kill before Josh finished his classes for the day. I walked around the Loop and stopped by Alexander Calder’s Flamingo Sculpture, as seen in Ferris Bueller’s Day Off. I enjoyed a bacon & pineapple maple donut at Firecakes. Then I met up with Josh, took a much-needed nap, and ate dinner with another friend, Albert, who was back in town, along with the law school crew. We chose Nando’s Peri Peri, apparently a group favorite, and I enjoyed the South African/Portuguese-style flame-grilled chicken along with mashed peas. Later that night I met up with Albert to catch up over drinks at a cool rooftop bar called Drumbar.

Day 4

My final day in Chicago also ended up being the most memorable. I was determined to try out different forms of transportation for the trip, so that morning I bought a 24-hour pass for Divvy Bikes, Chicago’s bike share program. I picked up a bike from a station in the Gold Coast and biked to Lincoln Park, a trendy neighborhood next to a huge park (which gave off an Inner Sunset vibe, another neighborhood next to a huge park).

Rhino at Lincoln Park Zoo

Rhino at Lincoln Park Zoo

I enjoyed a sausage and eggs breakfast at Frances’ Deli and walked over to Lincoln Park Zoo, which offered free admission year-round. I watched gorillas, monkeys, rhinos, giraffes, and other animals in the midst of screaming kids from the various school groups on field trips. The zoo had modern facilities but gave off a really classic vibe, since a lot of the exhibits were housed in older buildings dating back to the early 1900s.

After the zoo visit I made a quick detour to Lincoln Park Conservatory, a cool Victorian-era glass house built in the 19th century with a diverse collection of plants from around the world. It was nearing lunchtime so I took another route to bike back downtown – this time along the Lake Michigan shore on Lakefront Trail. It was an absolutely beautiful day. The sun shined overhead as the city highrises in the background grew taller and taller. Other folks, from joggers to bicyclists to tourists, were also enjoying the view along the trail.

View of Chicago from Willis Tower

View of Chicago from Willis Tower

The day just kept on getting better. I entered the restaurant Gino’s East and found out they had a 50-cent customer-appreciation deal on personal deep dish pizzas, so I got to check off deep dish on my Chicago tourist list as well. After lunch I took the elevator up 108 floors to the Skydeck on top of Willis Tower, the second-tallest building in the US. Apart from the amazing view, another highlight was standing on The Ledge, several all-glass balconies that extended outside the building.

I made it down to Earth and biked back to meet up with Josh after his last class of the day. It was nearing my time to head out to the airport so we enjoyed the $1 oysters happy hour at Hugo’s Frog Bar before I packed my stuff, loaded up a final Divvy bike, and biked to a station for Chicago’s elevated train, dubbed the “L” or “El.” The train ride to the airport was picturesque, and as golden hour came and went, I knew this wouldn’t be my last time in this amazing city.


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