Checking Out Chicago

My travel research and wishlist looks pretty similar for every trip. I’m always on the hunt for fun, fabulous, pretty, delicious, and interesting. Architecture, art museums, magical meals, discovering local favorites, and finding iconic pop culture/film/tv locations are my favorite ingredients for a successful city visit. NYC, Seattle, San Francisco, and Chicago are hard to top in this arena. Alaska was a HUGE departure from my normal itinerary, and it took a little adjusting when I arrived in the last frontier and when I left for the lower 48. Chicago was literally culture shock, but I enjoyed every second soaking up the abundance of accessible culture there and exploring with my sister.

It’s funny, nature inspired much of the beauty in the art I so passionately pursue, but being outside isn’t something I naturally gravitate towards. I’m a girl that needs to feel prepared for an adventure, and no matter what I do, I never feel sufficiently prepped to be out in the wild. Especially if I have to rely upon my wits and not the technology I’ve become so dependent on. Alaska was wild for me in a multitude of ways, but being outside without a thoroughly researched and very carefully planned list was refreshing and rewarding. I am surer of my capabilities and no longer paralyzed by fear of all the things that might go wrong, but switching gears from trying not to get eaten by bears to being in Cubs Country was a bit harder for my brain than I anticipated.

Nature was one of the key inspirations for the impressionists I love so much. It doesn’t take an art enthusiast to know how much nature inspired Van Gogh and Monet, but it’s one of Frank Lloyd Wright’s Five Inspirations too. Lucky for me, Chicago is rich in the work of my favorite artists, and architects. I even get a bonus Frank with the gorgeous Gehry designed Pritzker Pavilion.)

Last summer, my sister, Kyra, and I made a quick trip to Chicago for a Monet exhibit at the AIC, and an architecture boat tour, which I’ve wanted to do for decades. Whether you explore by boat or on foot, time on the riverwalk is never wasted. It is part of what makes Chicago so special. The guides are knowledgeable and the tour is fun. The scenery is lovely, and we sat spaced out on an open air deck. I recommend booking a sunset cruise as the sunset over the lake and the lights of the city are an added bonus to your tour. If you time it right, you’ll catch Art on the Mart at 9 or 9:30. I also snuck in some sites from my favorite John Hughes films, which I shared in my suburban highlights.

I didn’t do much planning or research before I arrived in Chicago, I just knew I was delivering my dog, helping my sister get settled into her new temporary home, revisiting a favorite place with people I loved, and it was full of things you’d usually find on a Lyssa Itinerary. I sang Run Run Rudolph to myself as I rolled through O’Hare, like any good Home Alone fan would do, and prepared to have an AMAZING time crossing cool things off my list. Even if it all seemed a little weird after the wilderness.

One of my favorite places in the country, and top of my list for Chicago, is the Art Institute. I have loved it immensely since I was a very little girl. My dad once drove me 3 hours each way to the AIC just so I could write an art history paper on Seurat’s A Sunday on La Grande Jatte, a longtime favorite of mine. The iconic image of Cameron standing in front of it in Ferris Bueller is only part of the appeal, I promise. Both sides of my family used to play a (now defunct) board game called Masterpiece, it is pretty much Monopoly with art instead of real estate. Each painting is assigned a random value and goes up for auction- you can get anything from a worthless forgery to a multi-million dollar acquisition. All of the art used is part of the permanent collection at The Art Institute of Chicago. I passed my love of art (and the game) to Kyra, and we had a wonderful time hunting down every piece we could remember while we waited for our turn to see the Monet. The Monet Exhibit was spectacular, as expected, and I was surprised by the quantity of pieces I’d never even seen in books before. We also made sure to hunt down the Chagall windows, tucked in a corner by the greek antiques. After a dozen trips to the museum, I finally found them and added them to my “must repeat with every visit” list.

I wasn’t going to prioritize going back again this year, but my sweet friend Stephanie is a member, and we popped in for a few minutes on our art and architecture adventure. She shared some of her favorite pieces while I visited mine, and we serendipitously discovered the freshly installed Tiffany Window.

I fully endorse Penny Lane’s maxim that if you ever get lonely, just go to the record store and visit your friends; but I think favorite art museums work just as well. Sometimes it is lonely marveling at masterpieces solo. It is so refreshing to visit with a fellow enthusiast, and reconnecting with an old friend about life, love, and art was beyond wonderful.

Stephanie has been a Chicago resident for several years, but we went to middle and high school together in Austin. We had the same group of friends, went to the same church, were in marching band together, but we weren’t particularly close. We reconnected on social media after college and were thrilled to discover how many shared interests we had as adults. I had Van Go on the brain after my VanGOgh adventure with Letters to Theo. I was thrilled that she joined us for the Van Gogh For All experience. We somehow had the entire exhibit to ourselves. Kyra, her roommate Madelyn, Stephanie, and I had so much fun playing with the interactive displays, laughing, chatting, and unlocking our inner artists.

Having heard that I had never seen the Louis Comfort Tiffany Dome at the Chicago Cultural Center, Stephanie planned an AMAZING field trip for us. It was a novel experience having someone else take the lead and share treasures I didn’t even know existed. The Cultural Center is one such treasure, and it blew me away. Housed in the former public library, the building itself is worth a wander, plus it is FREE. The visiting exhibit on comics was delightful, but nothing could have prepared me for the wonder of that dome. The Tiffany Window at the Art Institute was beautiful, but the dome defies description. I would have gladly sprawled on the floor looking at that leaded glass for an entire afternoon.

We also checked out the Chicago Athletic Hotel. Aside from the architectural marvel of this gorgeous old venetian inspired hotel, the coffee shop and sports lounge are excellent places to hang out and escape winter blues and the wind. I could have grabbed a coffee at Fairgrounds, or a cocktail in the lounge and sat there for days. But alas, I had a Yom Kippur dinner to get home to. I told Kyra to put this on the top of her list for prime first date spots and I suggest the same for you.

Stephanie took me on one last pilgrimage before we parted ways. I have no idea how I missed so much Chagall in Chicago, but his The Four Seasons mosaic also completely escaped my notice. I had never happened upon this huge treasure tucked between the skyscrapers, and I am so grateful she changed that for me! It is truly remarkable, and right near some of Chicago’s best shopping. I hope you’ll take a few minutes to see it.

Frankly, I dont think there are better architectural field trips than visiting ones built by Frank Lloyd Wright or Frank Gehry. Vastly different in style, and not particularly my personal aesthetic, but I find their perspectives fascinating. Frank Gehry designed the Disney Concert Hall in LA, the Guggenheim Museum in Bilbao, Spain, and the Pritzker Pavilion , which has been a favorite stop for decades. I’ve always wanted to see a performance under the canopy of arches and architectural details. My wish came true this year when my sister and I went to see the free showing of The Rocky Horror Picture Show with live action accompaniment. It was everything I wanted it to be. We had a wonderful view of the skyline, the cloud gate “bean,” and that enchanting Gehry architecture. I don’t care if it is a terrible tourist trap, I love Millenium Park. They have miniature golf, rock climbing, crown fountain, lots of free concerts and performances, and the people watching is pretty great too. It’s not a very sexy tip, but if you pre-pay for Millenium Garage parking online, it’s considerably cheaper than just driving into a garage and paying on arrival.

Frank Lloyd Wright got his start in Chicago. He worked for the famed Adler & Sullivan Architectural Firm before being fired by his mentor Louis Sullivan for his bootlegged (unsanctioned side-hustle) projects. You can visit Frank’s home, studio, and 25 of his early works in nearby Oak Park, which I cover here. The Frank Lloyd Wright Trust is housed in The Rookery Building, where Frank renovated the most unbelievably beautiful Light Court.

I’m a goodie two shoes rule following planner, but apparently I’m willing to bend some rules for Frank Lloyd Wright and spiral staircases. I couldn’t make the times work for a guided tour, and the building was closed when I arrived, but I followed some wedding vendors into an open service entrance. The ground floor was breathtaking, but I really wanted to see the spiral of the staircase rather than the split. For the first time in my life, I decided to ask for forgiveness instead of permission and I ducked around a few “no entry beyond this point” type signs in search of the famous stairs. I went after what I wanted and was handsomely rewarded. I had a few minutes to snap some photos of my new favorite #wrightsite before security asked me to leave. Sorry Guggenheim NYC, these sexy spirals are now #1 on my list of loveliest places. If you can make it to a tour, you will have no regrets.

There is so much to see and do in Chicago. Catch a Cubs or Bears game, Shedd Aquarium, The Field Museum, ride the ferris wheel at Navy Pier, check out the sky deck at Willis Tower, shop the Magnificent Mile, or eat at the very long list of fancy five star dining. There’s a massive list of iconic food I’m dying to try like The Aviary, Alinea, Girl & The Goat; but you’re never going to convince me that deep dish is pizza. Please be sure to leave some time to explore some of the treasures outside the city limits. While I rarely request that you plan suburban field trips, there are some things film and architecture fans just cant miss just outside the city. Either way, Chicago is one of those places that requires a return visit. I’m already scheming how to get back before Kyra’s student teaching assignment ends.