Chicago is the Midwest’s biggest city. With its famously tall skyscrapers, notorious mob history, and decadent takes on everything from pizza to hot dogs to popcorn, it’s packed with personality as well. Whether you’re sticking to the Magnificent Mile for high-end shopping, going to Wrigleyville to immerse yourself in the thrill of a Cubs game, or heading out to Logan Square and Wicker Park, there are many sides to Chicago that are all worth exploring.
When is the best time of year to have an adventure in Chicago? Aim to visit during the warm months, if possible. Winters—even early spring and late fall—can be brutally cold and windy, and it snows quite often. Keep in mind, you’ll be using public transportation and walking a lot, so dress appropriately.
Mr. Beef on Orleans
One of Chicago’s signature dishes is the Italian beef sandwich, topped with peppers and onions and doused in au jus. Mr. Beef on Orleans has an interesting take on both customer service and the sandwich. Be prepared for a flavorful, yet messy, experience.
When you’re ready to work off that sandwich, head to Millennium Park. It’s home to several Chicago icons. You can’t stop by the Windy City without taking a selfie by The Bean—also known as Cloud Gate—or visiting the classic Crown Fountain. This park almost always has something going on, so plan to spend some time here.
If you’re afraid of heights, then you may want to pass on a trip to the Skydeck, located on the 103rd floor of the Willis Tower—formerly known as the Sears Tower. This is the tallest building in Chicago and the third tallest in the Western Hemisphere. Skydeck offers views stretching 50 miles into four states. If you aren’t afraid of heights, then you’ll want to step onto The Ledge, a glass-floored box that lets you look straight down.
Hopefully you’ve worked up a big appetite, because you can’t visit the city without trying the famous Chicago-style deep dish pizza. Gino’s East makes some of the best in the city. Nosh on thick slices of pizza with a rich, buttery cornmeal crust that’s filled to the brim with gooey cheese, tomato sauce, and savory toppings.
Billy Goat Tavern
The Billy Goat curse is a huge part of the Chicago Cubs baseball team history, which makes it an important part of Chicago history.
The Billy Goat Tavern was opened by a Chicago local named William “Billy Goat” Sianis, so called because he kept a pet goat. During the 1945 World Series, the Cubs were up on the Detroit Tigers, two games to one. They needed to win two more games at Wrigley Field to nab the title—but during game four, Sianis tried to bring his goat into the stadium as a good luck charm and was told he couldn’t. Words were exchanged, and Sianis grew so frustrated that he exclaimed that the Cubs weren’t going to win as long as the goat wasn’t allowed into Wrigley. The Cubs lost that game and were swept by the Tigers in the rest of the series, losing the championship that they very nearly won.
Sadly—for Cubs fans, at least—Sianis’ curse held true until 2016, when the Cubs finally won the World Series. Even though their tradition of losing has been broken, the Cubs fans’ tradition of celebrating wins and mourning losses in a pint of Old Style at Billy Goat Tavern will probably always be a tradition.
The Violet Hour
Pay tribute to Chicago’s gangster past at The Violet Hour, a modern-day speakeasy-inspired bar. Tell the bartender a few words describing your dream drink, and they’ll mix a custom cocktail just for you.
To enjoy some Windy City nightlife, head to the Slippery Slope. This dive serves cocktails and beer in bottles and cans, which makes it easier to hit the dance floor or play Skee-Ball. Take a breather in the lounge upstairs.
Green Mill Jazz Club
Take a trip uptown to the Green Mill, rumored to be the oldest continuously running jazz club in the country. Where else in the world can you sit in Al Capone’s favorite booth while listening to live jazz , big band music, or a quirky poetry slam?
Revolution Brewery, Chicago’s best-known and biggest craft brewery, serves up beers ranging from porters to pilsners. Sample the selection at the stunning mahogany bar at this Logan Square brewpub.
The Wieners Circle
The Wieners Circle is perfect for night owls who are a little bit hungry—that is, if you can handle a side of verbal abuse with your hot dog and fries. The service is quick, the dogs are tasty, and the people-watching is incredible, with sassy servers and tipsy patrons.
John Hancock Observatory
If you thought the view from the Skydeck was terrifyingly amazing, wait until you see what Chicago’s other iconic tall skyscraper, 360 Chicago—better known as the John Hancock Observatory—has to offer. The attraction Tilt leans tourists out at an angle 1,000 feet above the Magnificent Mile. If that’s too much, enjoy the panoramic views of the city from other spots on the 94th floor.
With a variety of brunch-themed drinks and one of the most refined brunch menus around, The Publican is guaranteed to impress. Red wine poached eggs, smoked pork shoulder over grits, and Meyer lemon donuts are just a sample of delicious delicacies you’ll find here.
Oak Street Beach
Beaches are one of the reasons Chicago is the greatest city in the Midwest. The Oak Street Beach, on the shores of Lake Michigan, offers amazing views of both the city skyline and the endless waters. Plus, it is free.
Yes, Navy Pier is touristy—but it’s still fun. The massive Ferris wheel is worth a ride, and you can stroll past the vendors hawking tchotchkes while enjoying the lakeside views. Fun fact: The world’s first-ever Ferris wheel debuted at the 1893 Chicago World’s Fair.
Just as Harry Caray was a beloved Chicago icon as an announcer for the Chicago Cubs, Harry Caray’s Italian Steakhouse is a classically Chicago institution. It doesn’t get any more old-school Midwest than a classic steak dinner in a restaurant done up in sports memorabilia.