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I’m dangling over the edge of the Willis Tower, Chicago’s tallest building, strapped into my seat next to a dozen other adventure seekers. Suddenly, we swoop upwards, turn, and then plunge 101 storeys to street level where we zoom across lanes of traffic and tag along on the back of a rushing elevated train. For someone with a fear of heights, this is a screaming good time. This ride called Flyover Chicago on Navy Pier was suggested to me as a “must-see” by members of the r/Ask Chicago community on Reddit.
When I first started travelling decades ago, I’d always pack one, or even two guidebooks depending on my destination. Now, of course, all the information we need is literally at our fingertips on our phones, leaving our suitcases a lot lighter. For my most recent trip to Chicago, I did most of my research on Reddit and relied on the kindness of Internet strangers to help me find the best of Chicago.
There are many other sites for research of course, and I had to beware of Internet rabbit holes but I started with the r/AskChicago, r/chicagofood, and r/chicago Reddit communities. And what helpful people Chicagoans turned out to be. Before long, I had a long list of suggestions for the best attractions, restaurants and museums for my husband and I to visit. And an unexpected way to get over my fear of heights.
Back on the ground, so to speak, we were amazed by the amount of trees that line the streets and the many parks of this city of 2.7 million people. The third largest city in the U.S. truly lives up to its motto “City in a Garden.” Although it’s primarily known as the birthplace of the skyscraper, Chicago has the largest amount of green space of any municipality, with over 600 parks. It also has a busy 29-km lakeside bike and running trail, plus, as the city advertises, “24 beaches and no sharks.” There’s a free zoo, free fireworks at Navy Pier twice a week, and 77 unique neighbourhoods to explore. We had a lot of ground to cover.
First up, where should we eat? Chicago is well-known for great food and thanks to the r/chicagofood community on Reddit we discovered that there’s much more to Chicago than deep dish pizza and hot dogs. There are so many excellent restaurants to choose from but here are a few recommendations we’d like to pass along.
For breakfast, we loved Batter & Berries in Lincoln Park. Their signature French toast flight with strawberry, lemon, blueberry and caramel syrups and fresh fruit are served with love and a side of Chicago House music.
We rode the Brown Line to the last station at Kimball to walk over to Dulce de Leche in Albany Park. This family-owned business began with all hands on deck during the pandemic. They proudly present a Latin American fusion menu featuring delicate crepes and 22 different coffees including horchata and cortado. Everything is made fresh in a tiny kitchen, from the goat’s milk cajeta cream cheese to the granola. Bonus: the Brown Line is the hands-down suggestion for the best scenic transit line according to r/AskChicago. The elevated train line (a.k.a. the L) takes you over the river and through the heart of several Chicago neighbourhoods before returning to The Loop downtown.
Do you love The Bear? Then you’ll love Publican Quality Meats in West Loop. Chef Rob appears in the series as a master butcher and he knows his way around every cut of meat. This is the place to go for a casual lunch on a patio. Try a huge, tender Italian beef sandwich, a Chicago specialty, loaded with Caruso’s Giardiniera, a mix of pickled peppers, celery, cauliflower and carrots in a bath of premium olive oil that soaks into the hefty sesame bun. Redditors recommend the crunchy homemade pickles as a side and the porchetta sandwich, too.
More about dinner later, but first, we visited the Art Institute of Chicago. Home to the largest collection of Impressionist Art outside of Europe, the AIC also has a modern wing where you’ll be welcomed with a cheery electronic “Hello” as you enter. The collection includes masterpieces like Grant Wood’s American Gothic and Van Gogh’s The Bedroom, but Redditors tipped me off to The Thorne Miniature Rooms, an out-of-the-way collection of historic rooms reproduced at 1:12 scale. Each of the 68 rooms is made of the same materials as full-sized rooms with silverware, crystal chandeliers and furniture made by top American craftsmen and designers and perfect for kids and adults to enjoy together.
Alas, the river was beckoning. It was time for a boat ride through the glittering spires of Chicago’s stunning architecture on a Chicago Architecture Center River Cruise. There are several river cruise companies, but the CAC was the choice of r/AskChicago. The_deserted_island reports that “CAC docents have 30-40 required buildings to talk about…. some of them build in their passions and thread a story. I was on one recently and the docent built in a bunch of food history.” We took the last cruise of the day to watch the lights flicker on in the buildings at sunset and the huge neon Centennial Ferris Wheel light up on Navy Pier.
Now for dinner. Chicago has many excellent pizza joints, but we were hungry for fine dining. Redditor u/conqu287 suggested Gibson’s Italia where they “had an absolutely exquisite meal, start to finish… The staff is super attentive … we felt really well taken care of. And don’t even get me started on that view!” We can agree. Gibson’s was a wonderful experience. The steak was seared to perfection and the carbonara was exceptional. It’s definitely a place to see and be seen so the people watching was excellent, too. We also enjoyed a meal at Eataly. “Honestly”, writes If-By-Whiskey on r/chicagofood, “I realize this is a chain, but Eataly is where I have gotten dishes that taste the most similar to what I have eaten in Italy”. A big thumbs up for their tiramisu, the best we’ve ever had.
Having tried the simulated ride at Flyover Chicago, I was ready to see Chicago at altitude one more time. Skydeck was recommended on r/AskChicago. It’s included in the Chicago CityPASS so you can pick a clear day anytime over nine consecutive days to visit. The Shedd Aquarium, the fascinating Field Museum and the excellent Griffin Museum of Science and Industry with its multiple scientific displays, are also part of the pass.
The ride up to Skydeck on the 103rd floor of the Willis Tower (formerly the Sears Tower), was swift and fun. A wraparound digital display introduced us to the tower and Chicago. New multimillion-dollar interactive displays touch on every aspect of the city from its history to music to how the flow of the Chicago River was reversed. Once we reached the highest observation deck in the U.S., we could find landmarks easily with the interactive panels. Finally, I was ready to try stepping out on The Ledge, a 1.3-metre-wide clear glass box that hangs out 412 metres above the ground. And I was surprised to see that Chicago and Reddit had helped me lose my fear of heights.
Where to Stay
Culture lovers will love The LaSalle Chicago, Autograph Collection, Chicago’s only true luxury boutique hotel in the Loop. Located on the top three floors of a Daniel Burham-designed historic property, The LaSalle will pamper you with luxurious decor and amenities like Frette linens, 24-hour room service, and an outstanding restaurant, Grill On 21. Their goal is to help you save your most valuable resource – your time. The location is within walking distance of Cloud Gate, (lovingly known as The Bean), the Art Institute of Chicago, the Chicago Architecture Center, and Willis Tower.
Chicago Marriott Downtown Magnificent Mile is a large, modern, family-friendly hotel just north of the river close to The Children’s Museum, Flyover Chicago and the Centennial Wheel on Navy Pier, the Chicago Zoo, and the beaches. Just outside the door, you’ll find a shopper’s paradise along Michigan Avenue. Harvest, their scratch kitchen, uses produce from their rooftop garden and honey from their apiary. Lou Malnati’s famous deep-dish pizza is a five-minute walk away.