A recently imported Seattleite offers one final testament to America’s second city.
Do the small stuff. So much of what makes Chicago incredible is not in any pamphlet or guide book, and much of it is free. You simply need to look for it. Talk to the locals! Go vintage shopping on 18th Street in Pilsen or barhopping in Wrigleyville. Have lunch in Chinatown. Take the Shorelight Sights architecture tour along the Chicago River. Scale all nine floors of the Gotham-esque Harold Washington Library. Ride the L. Seen an improv comedy show at Second City. Spend a day biking the entire lakefront trail. Have a picnic in Oz Park. See the Tiffany dome at the Chicago Cultural Center free of charge!
Do the big stuff too. Don’t skip the Shedd Aquarium,
Willis Sears Tower, John Hancock Center, Art Institute of Chicago, Field Museum, Buckingham Fountain, Navy Pier, The Bean, The Magnificent Mile, etc. just because you don’t want to look like a tourist. They’re the city’s best attractions for a reason. I avoided these sites for years until I finally realized that I had missed something that I, as a local, was supposed to be an authority on. Do the big stuff and the small stuff. Or better yet, find the small stuff inside the big stuff. Tons of people go to the Art Institute and walk right past the South Garden—a stunningly picturesque, easy-to-miss terrace with a water fountain that looks like something straight out of Versailles. This is where my husband and I took our engagement pictures. The Chicago Theater is another great example. Lots of tourists take pictures in front of the theater, but you could stop and see a show!
Spend a day in Pilsen. Start at La Catrina Cafe with an egg croissant and a cinnamon latte. Just three blocks away from La Catrina, you’ll find Open Books Pilsen, which is like Barnes & Noble on crack; it will take you half the morning to get your fill. If reading isn’t your thing (shame on you), try the greenhouse-retail shop hybrid of my cactus-loving dreams, the Shudio, or the free National Museum of Mexican Art. Pilsen is also home to some of the best vintage shopping in the city. On the second Friday of every month, shops and galleries in Pilsen extend their hours. You’ll find wine, music, art and discounts all night long. I recommend starting at Knee Deep Vintage and working your way down 18th Street. I recommend a pre-thrifting dinner at Honky Tonk Barbecue and post-thrifting drinks at Skylark. Pilsen is home to some amazing Chicago artists and start-ups, including CIRCUS magazine.
See the Chicago skyline from the water. If you can’t find your way onto a boat, see it from Navy Pier. Chicago’s Navy Pier hosts firework shows throughout the summer on Wednesdays at 9:30 p.m. and Saturdays at 10:15 p.m. If you can handle the crowds, you can see the sparkling city skyline at night against an explosive rainbow sky while you enjoy an overpriced Chicago-style hot dog.
Taking public transportation? You go, Glen Coco! Your L train/CTA bus is always 15 minutes further away than your transit app tells you.
Utilize parking apps like ParkWhiz or SpotHero to find inexpensive parking in the city. Save yourself the time and money, and book your spot in advance. Just last month, I paid $7 through ParkWhiz to park for nine hours in a downtown lot that charges your average Joe $80 by the day. Apps like SpotHero and ParkWhiz find vacant spaces in great lots near your destination and offer them to you for a discounted rate. Utilize transit apps like Lyft and Uber for longer trips.
Chicago in December really is the best time of year. I’m serious. No, really! It gets as cold as everyone says, and the wind WILL hurt your face, but Chicago during the holiday season is a one-of-a-kind experience. Keep warm by a delicious cup of spiced wine as you peruse the eclectic holiday shop windows of Chicago’s open-air Christkindlmarkt, inspired by one of the first holiday markets of its kind in 16th century Nuremberg, Germany. See a performance of The Nutcracker by the Joffrey Ballet at the Roosevelt Theater. Experience ZooLights at the Lincoln Park Zoo with a steaming cup of hot chocolate! Just make sure you’re prepared for circumstances like this, okay?
Did you know Route 66 starts in Chicago? I know, right?!
Explore Chicago’s coolest neighborhoods and suburbs. You’ll find the best tacos in Chicagoland at La Principal in Evanston. Scouts honor. The restaurant is just off the Metra & Purple Line at 700 Main St. in Evanston, Ill. And down the street, there’s a consignment shop with the $5 racks you’ve been waiting for all your life; there’s also a City Newsstand right next to the train stop with magazines you didn’t even know existed. You’ll also want to explore Naperville, Lincoln Park, Wicker Park, Logan Square, River North, Greek Town, the South Loop and Pilsen.
Visit Wrigleyville for a Cubs Game. Then, go barhopping down Clark and Addison. Even if you’re not a baseball person, you should do this. It’s an experience, okay? I’m a die-hard St. Louis Cardinal fan, and even I enjoyed my visit to Wrigley. The atmosphere is so fun, and the nightlife is stellar.
Stop by the Disney Store on Michigan Avenue and ask for a sticker! It’s a flagship store, which means the creators put far more thought into the design than your average mall store. I worked at the Disney Store for three years in college, and I still love re-visiting the magic. If you’re a die-hard Disney fan like me, this is an absolute must.
You must try Chicago-style hot dogs and deep dish. People get into actual arguments over the best spots to check this one off the bucket list. I can only speak to my experience, so please nobody fight me. My husband and I both prefer Lou Malnati’s to Giordano’s and Gino’s East. We’re also huge fans of Chicago Pizza and Oven Grinder Company, which isn’t strictly deep dish. They make pot pie pizzas, which is a whole other brand of deliciousness unique to Chicago that you simply have to experience. The wait is always long, but always worth it. As for the hot dogs: the Chicago-style hot dog recipe is very specific. I tend to be picky about my food, so I’ll admit I’ve only ever had one official Chicago-style hot dog, and that was just to say I tried it. So, I’ll leave the hot dog reviewing to other more qualified foodies. I’m told, however, that Superdawg Drive-In on Milwaukee Ave. is a great place to start. If you’re so inclined, you can check out a history of the Chicago-style dog here.
While you’re at it, try any number of the city’s internationally-renowned eateries. Chicago’s restaurant scene is made up of far more than quality comfort food. Chicago is home to some of the top restaurants in the world. It’s also home to a slew of celebrity chefs. You can find the Chicago Tribune’s top restaurant picks here. My favorite dining spots are Stephanie Izard’s Little Goat Diner in the West Loop and Art Smith’s Blue Door Kitchen & Garden in the Gold Coast. My husband and I hosted our rehearsal dinner at Blue Door, and believe me: people were raving about Smith’s buttermilk fried chicken longer than they were raving about our actual wedding.
Bring your reusable bags with you, and help protect Chicago’s largest freshwater supply. Did you know that nearly 22 million pounds of plastic end up into Great Lakes every year, according to researchers at New York’s Rochester Institute of Technology? About 50 percent of that plastic occupies Lake Michigan, per wiscontext.org. Here’s the thing: plastic bags don’t biodegrade. They take anywhere from 15 to 1,000 years to breakdown into tiny toxic pieces; this pollution has been proven to impact humans and marine life around the world. You can become part of the solution to this problem by refusing to use single-use plastics. Hang your reusable shopping bags on your doorknob, or stuff them in your purse. Hell, hang them next to your favorite pair of jeans! Whatever you have to do to avoid asking for yet another plastic shopping bag, do it. Want to take it a step further? Join me in refusing plastic water bottles! Bring a canteen with you everywhere you go, and fill up at the tap or water fountain.
Speaking of beaches, Chicago offers 25 FREE beaches along Lake Michigan for your enjoyment. Oak Street Beach and North Avenue Beach are by far the best for getting beach-side shots of the skyline, but they are also the most popular, so keep the crowds in mind.
If you plan on visiting/living in Chicago at any time during the months of September-April, buy a parka. Immediately.
Feature image by Danielle Molnar