It’s difficult to narrow down the essentials when taking a trip to Chicago. There’s Shedd Aquarium, Willis (Sears) Tower, the Art Institute with its stately lions, and of course, deep-dish pizza! With so many fantastic options, it may never have crossed your mind what less obvious opportunities you might be missing… But that’s what we’ll be focussing on here!
Oak Park, just west of downtown Chicago, has the largest collection of Frank Lloyd Wright designed buildings in the world. It’s also where his home and studio are located. You can tour both, or take a walking or bike tour of Oak Park to see many of his Prairie Style buildings. You can purchase tickets in person, but online is recommended, especially if you’re planning to visit on a weekend.
A very popular weekend in May is the Wright Plus Housewalk, when you can actually take a look inside several of the homes designed by Wright and his contemporaries. The tickets are pricey, and you do need to get them in advance, but it’s a once a year experience.
2. Kayak the Chicago River
You’ve probably heard about the Architecture River Cruises in Chicago – they’re fabulous! But if you yearn for something different, say something closer to the water and more self-propelled, try a kayak tour. Wateriders offer guided trips focusing on Chicago’s history, architecture, ghosts, and gangsters, as well as sunset and fireworks paddles. It’s truly a unique experience!
If you haven’t kayaked before, don’t worry. All ages and experience levels are welcome. Tours range from $45 to $65 per person. Beware: You are on the water, so you’ll probably get a little wet. Beach attire is suggested. Reservations are required.
From food to clothing to tools, the Maxwell Street Market located on the city’s Near West Side has a little bit of everything. Jewish immigrants, wanting to sell their produce, started the market in the late 1800s. The market grew and eventually came to resemble a modern-day flea market, with vendors selling a little bit of everything to throngs of people who would flock there every Sunday. While the market is not nearly as busy as it was in its heyday, it is a Chicago institution worth exploring if you’re in town on a Sunday.
You’ll find some of the best Mexican and Latin street food in the city here. One unique way to experience all the flavors on offer in the Market and beyond is with Chef Driven Food Tours. Your guide will be a restaurant industry professional and a Chicago native, so you’ll be sure to hit the spots most wouldn’t find. The meals do come with wine or beer pairings, and tickets cost about $140 per person.
Chicago has a fantastic theatre district in The Loop. But northwest of downtown on Halsted, you’ll find a theatre with a rich history which has launched fantastic actors and has Tony Awards to show for their innovative work.
Actors Gary Sinise, Jeff Perry, and Terry Kinney founded The Steppenwolf Theatre Company in 1974. Their first performances were in a Highland Park church basement. Today, the theatre has three performance spaces in its building. The largest, with 515 seats and the smallest with just 80. The unique spaces make for a very intimate setting for both actors and the audience.
Steppenwolf is known internationally for its groundbreaking productions, which have included August: Osage County and Grapes of Wrath. In addition to the founders, John Malkovich, Laurie Metcalf, Martha Plimpton, John Mahoney, Gary Cole, and Kathryn Erbe are part of the theater’s 49-member ensemble.
For a truly unique theatre experience, check out the list of Steppenwolf’s shows the next time you’re in the Windy City.
Chicago’s history of organized crime is legendary. Some of the country’s most famous mobsters carried out their crimes, made their fortunes, and suffered their undoing here. Capone, Dillinger, Moran. If you’re interested in the history or just want to be entertained, check out this tour. You’ll see parts of Chicago you’ve never seen and learn what the city was like in the 1920s and 30s. And, with guides like Johnny Three Knives and Baby Face Bambino, it’s sure to be a ball.
The tour lasts about 2 hours and you will be on the bus the entire time – no stopping to take pictures – so use the restroom and grab a bottle of water before you get on. Tours cost around $40 per person and they sell out, so call ahead or book online to avoid disappointment.
6. Drink a Cocktail in a Speakeasy
Chicago actually embraces its prohibition-era history, which you probably gathered from the above tour. While it may not be too obscure, knowing where to find the secret bars takes a little effort. There are several speakeasys to choose from, but one with a great atmosphere, that doesn’t require a secret password or yearly membership, is The Library in River North.
It’s located below The Gilt Bar on Kinzie Street. You’ll need to ask to be shown to The Library when you enter Gilt, because you won’t find it on your own and there may be a wait. The Library has the same menu as The Gilt Bar in case you need something to eat while enjoying your cocktails. It’s only open on Thursdays, Fridays, and Saturdays. Try and make a reservation or get there when it opens at 6 p.m.
The popularity of the sport may ebb and flow with the Winter Olympics, but you can learn to curl if you visit Chicago between October and March. The Chicago Curling Club hosts Learn2Curl events in Northbrook, about 30 minutes north of Chicago. You’ll receive on-ice instruction, take part in a simulated game, and even enjoy pizza, beer, wine, or soda while you learn the game. The lesson lasts about 2.5 hours and costs $75 per person. If you’re still wondering what curling is, players try to get stones to a target by sliding them on ice while their teammates use brooms to help the stone along the way. While the game is played on ice, no skates are required.
8. Watch a Game at Guaranteed Rate Field
Before you ask, what is Guaranteed Rate Field, it’s the home of the White Sox. You know, that team from the Southside of Chicago? OK, so you probably knew you could see the White Sox play, but it’s nice to show them a little love. Wrigley and the Cubbies tend to get the bulk of the attention especially since they’ve kicked that World Championship curse. But Chicago is home to two Major League Baseball teams, and if you enjoy America’s pastime, check this park out.