“It could only happen in a town like this,” swing legend Frank Sinatra croons in the 1964 Rat Pack hit, My Kind of Town (Chicago Is). But for the casual visitor or the new resident recently arrived in the Windy City, there’s almost too much happening in Chicago to take it all in. So, what are the famous sites or popular activities that you shouldn’t miss, no matter if you are now living your new life in Chicago or if you are just passing through?
Start out with this somewhat eclectic top five list for a glimpse of Chicago’s top attractions.
1) Appreciate Art
There’s a reason why the Art Institute of Chicago shows up in every travel guide to Chicago. It’s worth every dime of its $23 admission fee – and then some. Founded in 1866, the world-famous museum is now the second largest art collection in the United States, right after the MOMA in New York City.
Most tourists come to gawk at the impressive Impressionist galleries and its masterpieces by such household names as Monet, Renoir, and Van Gogh. The iconic American artworks on display attract lots of attention, too – from Edward Hopper’s melancholy Nighthawks to the organic abstractions of Georgia O’Keeffe’s flower paintings.
However, don’t hesitate to get off the beaten track. If you plan in a bit more time for your visit, you can explore exhibits as diverse as African American sculpture, sumptuous kimonos, Renaissance suits of armor, Navajo blankets, Ming dish bowls, and Byzantine gold coins.
2) Shop Thrifty
While Chicago obviously provides ample opportunity to max out your credit card in the designer boutiques along the “Mag Mile”, there are more fun ways to shop in town. Every Sunday, Maxwell Street Market in University Village transforms the former “home of the blues” into a big open-air garage sale. While snacking on inexpensive street food, you can leisurely shop for a flea-market bargain. Just remember that one man’s trash is another man’s treasure!
A similar motto applies to Randolph Street Market, a mixture of indoor and outdoor sales event, where you have to pay a $10 entrance fee at the gate. Among heaps of cheap costume jewelry, you’ll find the occasional vintage treasure.
For the true antiques, however, browse the 80,000 square feet show room of Architectural Artifacts on North Ravenwood Avenue. There you can easily spend a fortune on all sorts of valuables and curiosities.
3) Time Travel
Maxwell Street used to be nicknamed “the Ellis Island of the Midwest” – a play on the colorful history of immigration that has shaped Chicago’s diverse demographics. The Chicago History Museum on North Clark Street is a good starting point for your journey through the city’s past. The “Crossroads of America” exhibition features the “Sweet Home Chicago” video gallery, where members of various communities talk about their personal history of Chicago. There are plenty of smaller museums scattered about town, each dedicated to another group of “hyphenated” residents. A special highlight is the DuSable Museum of African-American History in Bronzeville, the historical heart of Black Chicago.
If you prefer the culinary to the cerebral, though, head into Chinatown for upscale Szechuan cuisine at Lao’s. There are also numerous Irish pubs around, but for an authentic Irish-American pint, make a detour to the Far Southwest Side.
4) Get the Blues
Chicago is a major stop on the Jazz Track, an unofficial itinerary / pilgrimage route for those interested in the history of jazz and blues. Some local sights are more suited to true aficionados, like the graves of sax player Eddie Harris, harmonica virtuoso Junior Wells, and blues pianist Little Brother Montgomery, who are all interred on Chicago’s Oak Woods Cemetery. Another living legend of Chicago’s blues scene passed away fairly recently: In 2012, Earle Lavon “Von” Freeman – a true master on the tenor saxophone – died in his beloved hometown at the ripe old age of 88.
While you can no longer hear “Vonski” play live at The Apartment Lounge, as he was wont to do every Tuesday night till 2011, you can still head to The Green Mill – the venue where he had some of his last gigs. The cocktail lounge in Uptown Chicago is among the few surviving locations that combine the vibrant history of music and the seedy history of crime: You might either listen to a future candidate for the Jazz Hall of Fame – or if the live act hits the wrong note, you can at least admire Al Capone’s favorite booth.
5) Cheer for the home team.
The days of Michael Jordan as the Chicago Bulls’ star player may be long over, but this doesn’t mean that sports buffs will run out of things to do in Chicago. The Bulls have been plagued by injuries for the last couple of seasons, but maybe they’ll have better luck in 2013/14.
If basketball isn’t your thing, you still have two local baseball teams to root for: U.S. Cellular Field is home to the White Sox, the World Series champions of 2005, while the Cubs – the league’s perennial “lovable losers” – play on Wrigley Field.
If You Go
www.artic.edu (The Art Institute of Chicago)
www.cityofchicago.org/city/en/depts/dca/supp_info/maxwell_street_market.html (Maxwell Street Market)
www.randolphstreetmarket.com (Randolph Street Market)
www.architecturalartifacts.com (Architectural Artifacts, Inc.)
www.chicagohistory.org (Chicago History Museum)
www.dusablemuseum.org (DuSable Museum of African-American History)
www.tonygourmetgroup.com (Lao Sze Chuan Restaurant)
www.dignitymemorial.com/oak-woods-cemetery/en-us/index.page (Oak Woods Cemetary)
www.greenmilljazz.com (The Green Mill)
www.nba.com/bulls/ (Chicago Bulls)
https://chicago.whitesox.mlb.com/cws/ballpark/index.jsp (U.S. Cellular Field)
https://chicago.cubs.mlb.com/chc/ballpark/index.jsp (Wrigley Field)