Chicago is Illinois’ third most populated city in the United States. This large city sits on Lake Michigan, and it is famed for its architecture. Visitors flock to see architectural landmarks like the Willis Tower (formerly the Sears Tower). But it’s got more than great buildings. Art lovers can check out the masterpieces on display at the Art Institute of Chicago, theatre-goers can watch a play at the Goodman Theatre, and those who love to shop can spend some time on the Magnificent Mile. There’s so much to see in the city, so to help you plan your trip, we’ve listed some of the best things Chicago is famous for. Once you know where to go, it’s then high time to select where to stay among the best affordable Airbnbs and Vrbo vacation rentals in the city.
With one of the best skylines in the States, Chicago serves as the home of over 1,300 high-rise buildings, with more than 50 of which go beyond 600 feet (183 meters). Willis Tower, the 110-level building formerly known as the Sears Tower, is the tallest structure in the city. Chicago is where skyscrapers originated, with the Home Insurance Building completed in 1885 being the first one. The steel-frame method for building skyscrapers started in Chicago. Skyscrapers did not use to be how we know them now, early skyscraper structures in the 19th century are defined as steel-framed construction of at least 10 levels. Modern skyscrapers are currently defined as being at least 492 feet (150 meters) in height.
2. Windy City
Here’s the long-story-short if you’ve ever wondered how Chicago got its popular nickname of Windy City. The city isn’t the windiest one in the States, so many have wondered where the moniker came from. According to history.com, the chilly breeze that comes from Lake Michigan and into the streets of Chicago is the most obvious source of the nickname, although there is no concrete resource for this detail. Another prominent example of Windy City is the citations of the nickname in the newspapers Chicago Tribune and The Cincinnati Enquirer during the rivalry of Chicago and Cincinnati between the 1860s and the 1870s. To this day, no one knows the exact origin of the nickname, but Chicago does wear it loud and proud!
3. Deep-dish pizza
Perhaps one of the best things to ever come from Chicago that we can all agree to love is the heavenly gift of deep-dish pizza. This particular type of pizza is baked in a high-edge pan, giving more space for cheese and chunky tomatoes. It may look and feel messy, but it is one of the most delicious things you will ever feast on. Cultural historians note that there are not enough sources on who and where did the deep-dish pizza in Chicago come from, although there have been reports that Pizzeria Uno pioneered the dish in 1943. We can all agree, though, that whoever made this top-tier pizza is someone we should endlessly give thanks to!
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4. Taste of Chicago food festival
Let’s start our list off with one for the foodies. The Taste of Chicago food festival is the largest food festival in the world. Taking place for five days each July in Grant Park, the festival showcases Chicago’s food with a multitude of vendors. It has been running since 1980, and it offers visitors a chance to sample regional and international dishes. Try a classic Chicago deep-dish pizza, or go for a unique ethnic dish. And there’s more to do than just eat. You’ll find free live music, art performances, and cooking demonstrations. The only trouble will be trying to fit everything in your stomach!
Taste of Chicago food festival
Address: Grant Park, Chicago, Illinois, USA
Website: Taste of Chicago
5. Outdoor concert at Jay Pritzker Pavilion
The Jay Pritzker Pavilion is a bandshell situated in Chicago’s famous Millennium Park. The bandshell was designed by renowned architect Frank Gehry, and it opened to the public in 2004. The Pavilion is home to the Grant Park Symphony Orchestra and Chorus, and it also hosts the Grant Park Music Festival, America’s last remaining free outdoor classical music program. But more than classical music is played there. Mainstream musicians have taken the stage, from Tori Amos to the Decemberists. Most performances are free, and all rehearsals are open to the public. If you’re a music lover, it’s the perfect place to hear some tunes.
Outdoor concert at Jay Pritzker Pavilion
Address: 201 E Randolph St, Chicago, IL 60601, USA
Website: Jay Pritzker Pavilion
6. Cloud Gate at Millennium Park
Let’s add this iconic sculpture if we’re talking about what is Chicago known for. Next up we have another famous piece of Millennium Park: the Cloud Gate sculpture. This artwork was created by artist Sir Anish Kapoor, and it was completed in 2006. It’s perhaps better known by its nickname, the bean, due of course to its bean-like shape. It’s one of Chicago’s most famous landmarks these days. Visitors crowd around the sculpture, in large part due to its shiny, reflective surface. It’s the perfect place to snap a selfie and commemorate your trip to Chicago. The artist likes to create visually striking items in an urban environment, which gives viewers a transformative experience.
Address: 201 E. Randolph St., between Michigan Ave & Columbus Ave Chicago, IL 60602
Website: Cloud Gate
Opening hours: 6am - 11pm (daily)
7. Navy Pier
Navy Pier is one of Chicago’s most famous landmarks, and a popular tourist destination. Built in 1916, this pier sits on Lake Michigan in the Streeterville neighbourhood. With plenty of activities to do, it makes for a fun day out. If you like theme parks, there are rides to enjoy including a carousel and a funhouse maze. The Chicago Shakespeare Theatre is located on the pier, as is an IMAX theatre, so you can catch a play or movie. The pier is also home to art shows, shops, restaurants, and the Chicago Children’s Museum. And one of its most famous attractions is the Ferris wheel, which has recently been replaced with a brand new model. With plenty to keep you occupied and great views of Lake Michigan, Navy Pier makes for an excellent day out.
Address: 600 E Grand Ave, Chicago, IL 60611, USA
Website: Navy Pier
Tip from our local expert
Walking out onto Navy Pier offers a variety of attractions, shopping, and the opportunity to walk above Lake Michigan. One of my favorite activities on Navy Pier is walking to the end and looking out across Lake Michigan. With beautiful views across the water during any season, going during winter can be bone-chilling, but you might be offered beautiful views of floating ice chunks on the lake.
8. Wrigley Field
Sports fans are likely to be familiar with Wrigley Field. This baseball park dates back to 1914, and it is home to the Chicago Cubs, one of Chicago’s two Major League Baseball teams. One of the oldest baseball parks in the nation, this famous thing in Chicago is notable for its ivy-covered walls, its Art Deco marquee, and its hand-turned scoreboard. Of course, it’s the place to go if you want the great American experience of watching a baseball game. But the park is also home to live concerts, so music fans can enjoy this destination as well. Wrigley Park, and it’s surrounding neighborhood Wrigleyville, certainly come alive during a ball game, so if you like sports, you don’t want to miss a game while you’re in the city.
Address: 1060 W Addison St, Chicago, IL 60613, USA
Website: Wrigley Field
9. Lincoln Park
Lincoln Park is a vibrant neighborhood location on Chicago’s north side. Lincoln Park is home to, well, Lincoln Park, Chicago’s largest park which sits on Lake Michigan. This tree-lined neighborhood is also home to great bars and restaurants, live music venues, the Lincoln Park Zoo, and the Chicago History Museum. Foodies will want to try Alinea: hailed as Chicago’s best restaurant, it has an ever-changing menu. There’s plenty of shopping to be done in the neighborhood, so head into cool shops like Dave’s Records where you can pick up some vinyl or Bluemercury where you can buy high-end beauty products. Lincoln Park is the perfect place to wander at your leisure, stopping at wherever takes your fancy.
10. Chicago Loop
The Loop is a vibrant business district located centrally in downtown Chicago. It’s home to high rises, shops, restaurants, and parks. If you’re looking to enjoy some culture, you could take in the art at the Art Institute of Chicago or see a live gig at the Chicago Theatre. If it’s a nice day and you want to stretch your legs, head to Grant Park or Millennium Park. There’s plenty to enjoy if you’re a foodie; go for high-end French food at Everest or enjoy the comfort of pub food at The Gage. There’s so much to keep you entertained in The Loop, so enjoy walking around and exploring the area.
11. Garfield Park Conservatory
The Garfield Park Conservatory is one of the largest conservatories in the United States. Located in Garfield Park on Chicago’s West Side, it features plants from across the globe. Built in the early 1900s, its construction was a collaboration between architects, engineers, and sculptors, and its design is meant to mimic the haystacks found in the Midwest. There’s plenty of foliage to explore here, including the Palm House, the Fern Room, and the Desert House. There are also outdoor gardens to explore. This famous Chicago thing is the perfect spot for plant lovers to visit and allows everyone to enjoy the beauty of nature.
Garfield Park Conservatory
Address: 300 N Central Park Ave, Chicago, IL 60624, USA
Website: Garfield Park Conservatory
Opening hours: Thurs - Tues: 9am - 5pm; Wed: 9am - 8pm
Tip from our local expert
One of the best places to visit in Chicago when you are wanting to get out of the cold, the Garfield Park Conservancy is a must-visit location. Offering hundreds of species of plants and several semi-tropical environments, you can find yourself surrounded by greenery even when there is snow on the ground. If you are in Chicago in the winter, this is a must-visit free botanical garden that will whisk you away to another world!
12. Chicago Riverwalk
Let’s finish our list off with the Chicago Riverwalk, a pedestrianized area in downtown Chicago along the Chicago River. The area features plenty of restaurants, rest spots, and places to enjoy the river. Head to Urban Kayaks to rent a kayak and view Chicago from the river. If you like to fish, make your way to the fishing pier and cast your line- just be sure to get a fishing license first. There’s lots of public art on display, so as you stroll along the Riverwalk, do keep your eyes open. And when you’ve worked up an appetite, there are lots of restaurants to choose from. Head to Island Party Hut for tropical-themed fare or enjoy a steak at Chicago Cut Steakhouse.
Tip from our local expert
Make sure to slow your roll as you walk along Chicago's River Walk to take in the beautiful architecture along this path. From the many different bridges to the towering skyscrapers, you can admire the historic and new architecture that makes this city beautiful! Make sure to bring a windbreaker, as sometimes the wind along the River Walk will remind you why Chicago is referred to as the windy city.
13. Chicago (from USD 33.0)
360 Chicago is an observation deck located on the 94th floor of the John Hancock Building. It’s an excellent spot to take in the city, as it provides 360-degree views over the skyline and Lake Michigan. The observation deck also provides opportunities to learn about the city’s history, including its neighborhoods and architecture. If the observation deck isn’t thrilling enough, you can ride TILT, a moving platform which tilts you over Michigan Avenue from 94 floors up. Not for the faint of heart! If you’re torn between visiting 360 Chicago during the day or as the sun sets, don’t fret: there’s a ticket which allows you to visit twice. So you can see the city with the clarity of day time and also enjoy its twinkling lights at night.
Chicago 360 Observation Deck, Combo Day and Night Admission
Duration: 1 to 2 hours
Chicago has so much to offer, from food festivals to public art and sports parks to conservatories. It’s hard to narrow the city’s offerings down to just a few, but we hope you enjoyed learning a bit more about Chicago’s most famous attractions. Now pick your favorite and start planning that trip to the Windy City.
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