Amelia Bailey

The Windy City used to be best known for three prominent residents: Al Capone, Oprah and Michael Jordan. Many Chicagoans were content with their reputation for gang violence and the occasional successful sports franchise, but in the early 2000s, Mayor Richard Daley decided the city needed a change of face. The Obama campaign and the  failed 2016 Olympic bid resulted in a massive overhaul of the city’s tourist destinations and transportation systems.  The city is most accessible by train, known as the “El,” and tourists can visit the best of the North, South, and West sides all in one day.

Start: Red Line, Belmont

See: North Halsted, a neighbourhood that never sleeps, is home to Boys’ Town. Sporty visitors should walk to Wrigley Field, where millions of Chicagoans get their hearts broken by the cursed Cubs every year.

Do: Browse the thrift stores on Belmont.

Eat: For over sixty years, Ann Sather’s on Belmont and Clark has been serving cinnamon rolls big enough to feed Jay Cutler. They’re even more delicious a la mode.

Red Line, Fullerton

See: L. Frank Baum wrote The Wonderful Wizard of Oz in Lincoln Park’s residential park, now known as Oz Park. Today the city honours the classic novel with Tin Man, Cowardly Lion, Dorothy and Toto sculptures.

Do: Hop in a paddle boat at the Lincoln Park Zoo and catch a view of some flamingos and the John Hancock building.

Eat: R. J. Grunts has been serving burgers, shakes, and rock ‘n’ roll to the stars for decades. While definitely touristy, their cookie dough milkshakes can’t be beat. For takeout, head to the original Potbelly Sandwich Works on Lincoln Avenue for the meat lover’s “wreck” and an ice cream sandwich.

Brown Line (Loop), Sedgwick

See: John Belushi, Stephen Colbert, and Tina Fey started their comedy careers on the Second City stage. Chicago’s best comedy club is still serving cheap jokes and cheaper drinks seven nights a week.

Do: Walk over to North Avenue Beach for a game of beach volleyball and a view of the skyline.

Eat: The Green City Market just south of the zoo brings local organic produce and baked goods to the city twice a week, and attracts the best local chefs.

Purple Line, Randolph and Wabash

See: The Art Institute of Chicago has always attracted tourists. The newly completed Modern Wing is a work of art in itself, and is the perfect size for an afternoon visit.

Do: Snap a photo in front of the Cloud Gate, also known as the “Bean,” which reflects the city’s diverse architecture.

Eat: Mrs. Field’s chocolate chip cookies on Randolph are filled with butter, chocolate, and more butter and chocolate. It’s impossible to buy less than a dozen. Gourmands looking to splurge should head to the Loop’s Frontera Grill, Japonais, or Tru.

End: Green Line, 63rd and Cottage Grove:

See: University of Chicago students have named the institution “Where Fun Goes to Die,” but a pleasant place to grab some coffee, walk around, and learn about the Manhattan Project. Researchers conducted the first man-made nuclear reaction underneath what is now the Regenstein Library.

Do: See how close you can get to Barack Obama’s Hyde Park home on 50th and Greenwood. See how many Hyde Parkers you can talk to before hearing about the fact that Obama still owns a house in Hyde Park.

Eat: Grab a sandwich from the Medici bakery and walk to the Point on East 57th Street to watch the sunset.

Other Worthy Stops:

China Town (Red Line, 21st and Cermack), the Hispanic Pilsen neighborhood (Pink Line, 18th Street), and anywhere on the lakefront.

Things not to do:

– Swim in Lake Michigan. Newly elected mayor Rahm Emmanuel lost a finger after swimming in the lake with a wounded hand and contracting gangrene.

– Eat deep dish pizza at Giordano’s. The restaurant is filled to the brim with tourists. Edwardo’s or Pizza Capri offer deep dish as well as traditional thin crust.

– Eat in Viagra triangle, the triangular intersection with a slew of steakhouses, and creepy rich men looking to pick up women at 11 a.m. But then again, if you’re a woman under 25 looking to get some, this might be a good hangout spot.