Whether you’re visiting Chicago for the first time or are a regular, you can’t say you’ve truly experienced Chicago unless you’ve ticked off the foundational bucket list of the city. Sure, some of these experiences locals will scoff at for being touristy — but they’re popular with tourists for a reason, and skipping out on any of them will yield an insufficient trip to the Windy City. Only once you’ve tackled these six must-dos can you claim to have really visited Chicago.
1. Rise atop the Willis Tower.
Located in the heart of downtown, Willis Tower is the tallest building in Chicago. Formerly known as the Sears Tower, this iconic 110-story skyscraper was the world’s tallest building until 1998. Take the elevator and enjoy one of the fastest rides in the world to reach the Skydeck on the 106th floor. The Skydeck displays different facts and figures on Chicago’s history through the use of beautiful visuals and receives over 1.7 million visitors every year. Step on one of the glass boxes to look down and afar. On a clear day, you might see Michigan, Indiana, and Wisconsin across Lake Michigan. This ‘top of the world’ experience will give you an unobstructed view of everything in miniature: streets, taxis, buses, bridges, and Chicagoans. If you’re really feeling brave, you can taking some photos on the glass-bottomed ledge.
2. Spend a few hours at Millennium Park and the Bean.
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If Chicago had a front yard, Millennium Park would be it. This urban spot is a local favorite. Hosting various festivals and events back to back throughout the year, this is a perfect hangout for friends and families. The park hosts theChicago’s Blues Festival, Jazz Festival, Grant Park Music Festival, and ice skating in the winter, as well as countless others. If you visit in the afternoon, you’ll hear an orchestra rehearsing on the stage free of charge. Take the pedestrian bridge leading to the Art Institute and Maggie Daley Park, which permanently hosts one of the largest climbing walls in the world. This park is likely Chicago’s most important public project since 1893.
As you walk around the park and approach Michigan Avenue, you’ll find the Crown Fountain. Designed by Spanish artist Jaume Plensa, during the summer, this tower-like structure features two LCD screens with changing faces of locals spewing water every five minutes. It’s weird, it’s funny, and you definitely won’t forget it. You can even lather up under its waterfall if you wish.
No visit to this park is complete without seeing the Cloud Gate, or “The Bean,” as it’s locally dubbed. The result of a design competition won by British artist Anish Kapoor, this stainless-steel sculpture has become a Chicago icon in the past decade. It’s massive, shiny, and reflects the gorgeous architecture of the buildings around it. No matter what the weather is, visiting the Bean will uplift your spirits.
3. Walk along the Magnificent Mile.
Paris’s Champs-Élysées, London’s Regent Street, and New York’s Times Square have one thing in common with the Magnificent Mile: they all represent a melting pot of consumerism, art, colors, and over-the-top affluence. The mile-long stretch offers a mix of high-end retailers, shopping malls, luxury hotels, and residential buildings. If you’re not into shopping, you won’t be bored, as this area melds both old and new architecture. You’ll see modern structures right next to old brown buildings built after the Great Chicago Fire. Often busy with both tourists and locals, this is also a place that showcases the diversity in Chicago and the friendliness of its residents.
4. Experience the Tilt.
The Tilt — a 45-degree slant on a glass chamber that overlooks the city along Lake Michigan from the 96th floor — is treated like a rollercoaster, and you’ll enjoy every second of the adrenaline rush. Formerly John Hancock Observatory, 360Chicago added the Tilt to its attractions in 2014. There is an extra $7 fee to experience this, but it’s worth every cent. On Thursday nights, 360 Happy Hour specials are offered by Illinois’ largest independently-owned brewery, Revolution Brewing. At Bar 94, relax and sip on some delicious local beers, including IPAs, porters, pilsners, Belgian-style ales, pale ales, barrel-aged beers, and take in the stunning views, all while a live DJ entertains.
5. Take a bite of the Deep Dish.
Invented at Pizzeria Uno in Chicago in 1943, the deep-dish pizza has since become a Chicago icon when it comes to local delicacies. This thick, pie-like crust pizza with brown edges stuffed with layers of meat, cheese, and quality tomatoes is indulgent in every sense of the word. Served hot with a heavy spatula, pre-cut weighty slices are placed onto your plate. The sight of the melting cheese and the aroma-filled ambiance will make you want to immediately grab your knife and fork. Remember, it’s a tradition that you don’t want to skip, and Chicagoans take pride in every signature craft of their state. Today, you can find some of the best deep-dish menus at Lou Malnati’s, Giordano’s, Pizano, and Gino’s East.
6. But be sure to explore the rest of the city’s food scene too.
Chicagoans love food, and they have loved, created, and recreated classic recipes since the birth of the city. Much like deep dish, you can’t leave without eating at least one Chicago hot dog. Originating in 1939 at Maxwell Street Market, the kielbasa (polish sausage) is served on a bun and topped with grilled onions, yellow mustard, and spicy sport peppers. It’s a local favorite that’s widely regarded as a creation of a Macedonian immigrant, Jimmy Stefanovic, whose business is still a thriving at 1250 S Union Ave.
Another must try in Chicago is the Italian beef sandwich. Created by Italian workers in the early 1900s, this sandwich, served on a long Italian roll, contains seasoned roast beef simmered in au jus. The beef is roasted in a broth of oregano, garlic, and spices until it’s evenly cooked, which gives the sandwich a distinct and flavorful taste. Some restaurants offer a combo, adding grilled Italian sausage to the order, so that people can experience the best of both worlds.
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