What are some of your favorite memories of Chicago, IL?
Running along Lakeshore path and inching toward Chicago's impressive downtown skyline is my favorite hobby. During Summer, the breeze from Lake Michigan keeps you cool; during Winter, only the heartiest Midwesterners can be found jogging alongside the frozen lake. I enjoy watching them from the comfort of a heated cab on adjacent Lakeshore Drive.
How would you spend 36 hours in Chicago, IL?
I would start the day with a caffeine jolt and buttery pastry at Red Hen Bread, a local chain of coffee shops that maintains a rustic vibe. Once fueled, I’d head to The Music Box Theater in Southport, an area known as much for its yuppie residents as much as it is for this gorgeous, atmospheric 1929 movie theater. After catching a good indie flick, I’d take the El (‘Elevated train’, aka CTA – Chicago’s Public Transit Authority), down to The Art Institute of Chicago and walk among the art greats for a few hours. After sneaking lunch at the Institute’s relaxed upstairs café, I’d hide away in the Art Institute of Chicago for the next few hours, I’d squeeze in shopping on the nearby ‘Magnificent Mile’, a famed stretch of shops. On day two, I would focus on eating as much as possible – perhaps starting the day with a hearty brunch of Bacino’s Pizza near Oz Park, followed by boutique window shopping in the DePaul neighborhood, ‘re-energizing’ with a cupcake at Sweet Mandy B’s or Molly’s Cupcakes, and finally treating myself to the culinary experience of Alinea, an expensive, “French Laundry” rival that requires reservations months in advance but delivers hours of foodie delight in return.
What kind of practical information should first-time visitors know about Chicago, IL?
Chicago neighborhoods are quite walkable during the summer but difficult to navigate unless you know the city well – mostly because the city is so large. And in the winters? Forget walking outside much if you’re not a fan of the cold.
The city’s two primary modes of public transit remain buses and the ‘el’, Chicago’s subway network that becomes an elevated, above-ground train as you head farther north and west in the city. (Downtown, the subway tracks sit underground.) Most areas are accessible by both bus and el, but take the el if you’re in a hurry because it makes stops less often.
Chicagoans speak English though many born-and-raised Chicagoans possess an accent that is best described as a warm yet funny-sounding blend of Norwegian, German, Polish, and Irish, reflective of the city’s rich European immigrant history.
Unlike its coastal counterparts, New York and San Francisco, Chicago is reasonably-priced. Nice, downtown hotels will run you an average of $200 total/night, cabs are noticeably cheaper than in other major American cities, and economic food options (hello, Chicago hot dogs!) abound.
What are some precautions that people should take while exploring Chicago, IL?
I’ve never felt unsafe in Chicago though our high crime rates tell a different story. Unfortunately, most of that crime is limited to the South Side, a somewhat poorer area south of the downtown Loop district. First time visitors to Chicago should research before heading into some of the more southern and western neighborhoods.
Any other indispensable pieces of advice to share?
Bring a thick, down coat if you visit during the winter. Chicago is known as ‘The Windy City’ for a reason. Hats, gloves, scarves, and face masks (only halfway joking) are recommended for people prone to feeling cold.
To find the heart of Chicago, look no farther than Millennium Park, the undisputed local capital of free summer concerts, holiday ice skating, and the city’s best photo opportunity – “The Bean” (aka: “Cloud Gate”), a sculpture inspired by liquid mercury that serves as a disorienting photo opportunity for most visitors. During the late ‘90s, renowned architect Frank Gehry and famous Chicago Mayor Richard M. Daley joined forces with artists, architects, planners, and designers to create this park from an old railroad lot, and the result is a state-of-the-art, peaceful, spring-sprinkled park that can transport you to another world.
Located in the West Loop, this cocktail lounge is one part Tom Cruise’s “Cocktail”, one part ‘”Harry Potter”, with a splash of Betty Ford. At The Aviary, experiencing the magic of your drink is as important as tasting it, and chef-like bartenders are the main attraction – you can watch them work at their mixology station through old school wrought iron bars. The lounge’s dramatic ambiance, plush seating, and one-of-a-kind drinks makes it a favorite for wedding anniversaries, birthday celebrations, and break-up splurges. No run-of-the-mill cocktails here; sip on concoctions like the Rooibos ($18), a gin-based concoction that bubbles in a vacuum-pot brew of lavender, citrus peel, lemon balm, and crushed almonds; Blueberry ($20), a rye-based drink that arrives in a carafe stuffed with a mélange of fruit and flower petals; or the buzzworthy ‘In The Rocks’ drink, a new take on the old-fashioned and served encased in a sphere of ice that you get to break with a rubber sling.
With as many pizza restaurants in Chicago as there are coffee shops in Seattle, you’ll be hard-pressed to walk down most city streets without smelling the aroma of rising dough. But in the longstanding pizza wars, Bacino’s wins tastiest underdog. This establishment’s award-winning deep dish pizzas are made with only the freshest ingredients, and you won’t need to wait in hours-long lines like you will at the more touristy rivals, Giordano’s Famous and Lou Malnati’s Pizzeria. Plus, Bacino’s proximity to the whimsical Oz Park makes a post-lunch stroll amid “Wizard of Oz” statues an easy must.
Chicago is often referred to as ‘The Second City’ by haughty New Yorkers, but the Art Institute of Chicago is a first class art mecca that gives both the MoMa and Met runs for their monies. Drawing you in with its famous collections – more Renoirs, van Goghs, Monets, Cézannes, and Picassos than you can appreciate in a single visit – the Art Institute keeps regulars coming back with its experiential installations and groundbreaking touring exhibits. Don’t miss seeing Chagall’s America’s Windows, a set of stained-glass windows—made famous by the movie, “Ferris Bueller’s Day Off”—that the artist created specifically for Chicago to commemorate America’s bicentennial. Whether you’re in need of a quick art fix or are looking to spend winter weekends productively but indoors, make the Art Institute your first stop in The Second City.
Chicago is the city of jazz, and there’s no better jazz party than Kingston Mines in the city’s Lakeview district. This Northside blues club has served up music since 1968, and in rich jazz tradition, the tunes don’t stop until the wee hours. Sip on spiked sweet tea and dance your blues away, literally, until 4am every night of the week (5am on Saturday!). A few years ago, founder “Doc” Pellegrino passed the jazz torch onto his son, MC Frank Pellegrino, helping preserve a family vibe to this ruckus dance party.