How to Visit Chicago for the First Time

On the surface, Chicago may seem like a city with two sides: north and south, Cubs and White Sox, winter and summer. First-time visitors may not get to see Chicago for its progressive attitudes, diverse neighborhoods and politically-mind communities. It’s the kind of place that demands a return trip even before you’ve arrived. To help get you started, check out how to visit Chicago for the first time.

Incorporated in 1837, Chicago is an American boomtown. Its population of roughly 30,000 residents in 1850 grew to more than 2 million by 1910. This influx of people brought with them a diverse mix of cultures, religions and beliefs. Illinois’ largest city sits on the southern shores of Lake Michigan, one of North America’s Great Lakes. Similar to Manhattan, many of Chicago’s early skyscrapers date back to the 1890s, which gives the city a rich architectural skyline. The financial district and its looming towers can be seen from great distances when approaching the city by car. In addition to having big buildings, Chicago has been home to some of America’s biggest icons, including Oprah, Michael Jordan, Harry Caray and the Obamas, just to name a few.

Additionally, Chicago has a satisfying culinary scene. Hearty meals and strong drinks are served in generous portions. With European, Asian and African influences, Chicago’s food options are as diverse as its people. From live music to professional sporting events, there are plenty of interesting things to experience in the Windy City.

How to Visit Chicago for the First Time | Top 10 Things to Do in Chicago

Enjoy a few laughs

Courtesy of Second City

Chicago’s Second City, located in Oldtown, offers nightly performances and seasonal shows featuring some of the most talented comedians in the business. The comedy club has been operating as a theatre and improv school since 1959. Throughout the years, company alumni have included many of comedy’s greatest heroes, including Bill Murray, John Candy, Chris Farley, Amy Poehler and Aidy Bryant. After the show, grab a drink at 1959 Kitchen & Bar, the club’s on-site restaurant, or the neighboring Old Town Ale House.

Experience baseball history

City of Chicago Photo Courtesy of Choose Chicago

Chicagoans are crazy about baseball. In a city with two Major League teams, visitors will need to pick a side. If you choose the Cubs, you will not be disappointed with a visit to the historic Wrigley Field on the North Side of Chicago. Built in 1914, the stadium is the second-oldest ballpark in Major League Baseball, just behind Boston’s Fenway Park (1912). Baseball memorabilia is on full view throughout the stadium, including the original scoreboard from 1937. Depending on the location of your seat, you might just get lucky with a game ball souvenir. To increase your chances of catching a game ball, sit along the first and third base lines for foul balls and in the bleachers for home-run balls. Don’t forget to try a Chicago-style hotdog, which is typically topped with mustard, relish, onion, tomato, pickle, peppers and celery salt. Stadium tours are available during the offseason.

Cruise on the Chicago River

The architecture boat tour is a great introduction to the Chicago skyline. Many of the city’s most stunning buildings can be enjoyed from the top deck of the First Lady. The tour highlights many important architectural styles, including Chicago School, neoclassical, art deco and modern. The 90-minute excursions are expertly hosted by docents from the Chicago Architecture Center, and tours operate from mid-May to mid-October. For an unforgettable experience, check out the twilight tours, which offer beautiful sunset views from the Chicago River. The vessels can carry up to 250 passengers and feature open-air upper decks, full-service bars, climate-controlled lower cabins and upscale marble and granite restrooms. It is advised to purchase tickets in advance.

Satisfy your pizza craving

Photo by Manvi Mathur

Pizza might not seem like a memorable holiday experience, but it can be in Chicago. For starters, “Chicago-style” typically implies that the pizza is made using thick or deep dish crust. There is also a thick layer of cheese under toppings and tomato sauce. It seems backward, but in the best possible way. Cornmeal is used to give the buttery crust a bit of a crunch. This deliciously filling style of pie can be found throughout the city. For classic versions, check out Pizano’s Pizza or Gino’s East.

Explore an unforgettable art collection

Photo Courtesy of Choose Chicago

The Art Institute of Chicago is one of the world’s leading art museums. Centrally located in Grant Park, the Art Institute offers visitors notable works from around the world. Its permanent collection features more than 300,000 pieces, including Seurat’s A Sunday on La Grande Jatte (1884/86), Van Gogh’s The Bedroom (1889), Wood’s American Gothic (1930), Hopper’s Nighthawks (1942) and Motley’s Nightlife (1943), among many others. In 2009, the museum opened a modern wing designed by Renzo Piano, which features prominent artists like Jasper Johns, Takashi Murakami, Robert Rauschenberg, Cindy Sherman and Andy Warhol. Don’t miss the Thorne Miniature Rooms located on the museum’s lower level.

Unwind to the sound of live jazz

Abel Arciniega Photo Courtesy of Choose Chicago

Chicago has jazz roots that date back to the 1920s when Jelly Roll Morton and Louis Armstrong were drawing large crowds. Today, music fans can visit Green Mill in Uptown for live jazz every night until 4am, except for Saturdays when it’s open until 5am. Known as one of the oldest continuously running jazz clubs in the country, Green Mill has welcomed jazz legends like Von Freeman, Franz Jackson and Wilbur Campbell. Seating is first-come, first-serve, and entrance fees vary depending on the band.

Celebrate St. Patrick’s Day

Green river in Chicago

Given the large Irish-American population, Chicago is the best place to be for celebrating St. Patrick’s Day. Each year, revelers take to the streets and flood neighborhood Irish bars wearing their best green-colored outfits. For five hours, typically starting at 9am on the Saturday prior to St. Patrick’s Day in March, the Chicago River is dyed emerald green. Thousands of spectators gather along the scenic Riverwalk to see green water flowing through the city’s center. Chicago also hosts one of the largest St. Patrick’s Day parades in the country, which includes a three-hour procession with colorful floats, troops of Irish step dancers, marching bands and bagpipers.

Become one with nature

City of Chicago Photo Courtesy of Choose Chicago

Lincoln Park is a great way to spend an afternoon in Chicago, especially during the warmer summer months. This 1,200+ acre park is situated on the North Side of Chicago along Lake Michigan. Visitors can explore the Chicago History Museum, Lincoln Park Zoo, Theatre on the Lake, Peggy Notebaert Nature Museum and Lincoln Park Conservatory. There is something for everyone in this urban oasis, and many activities can be enjoyed for free. After the park, take advantage of the good weather with a stroll along the neighboring beach for beautiful views of Lake Michigan.

Go to the theatre

Abel Arciniega Photo Courtesy of Choose Chicago

Chicago’s flourishing Theatre District, located in the Loop, features more than 200 theatres, including five Tony Award-Winning companies. Visitors can choose from a selection of world-class productions. Check out the district’s three Broadway In Chicago theatres: CIBC Theatre, James M. Nederlander Theatre and Cadillac Palace Theatre. Also, don’t miss the Goodman Theatre, Chicago’s oldest and largest not-for-profit theatre.

Get a little tipsy

Adam Alexander Photography Photo Courtesy of Choose Chicago

With more than 100 breweries, Chicago is the perfect place to sample interesting craft beers. First-time visitors should check out Goose Island, a well-known Chicago-born brewery. Learn about the brewing process at Goose Island’s Fulton Street brewery and taproom, located in West Loop. Tours operate Thursday through Sunday, and advanced booking is recommended. Beer samples and a custom beer glass are included in the tour ticket price.

If you’re still thirsty, check out Lagunitas Brewing Company’s 300-seat taproom located in Douglas Park. Offering excellent beer, live music, food and tours Wednesday through Sunday, Lagunitas is the largest brewery in Illinois.

Coming Soon!
Obama Presidential Center is located in Jackson Park on Chicago’s South Side near the University of Chicago. Once completed, the facilities will honor the legacy of President Barrack Obama and First Lady Michelle Obama. The museum, and its public meeting space, library and plaza, will provide visitors with a space to reflect, engage and learn.

If you enjoyed How to Visit Chicago for the First Time, check out other travel articles about the United States.