11 essential activities to experience in Chicago

Chicago is a treasure in the Midwest with endless offerings. While the city is famous for its delicious deep-dish pizza, there’s a wealth of other experiences waiting to be uncovered.

Chicago caters to everyone with its wonderful blend of nature, art, and culture. With two major airports, easily reachable via public transport and served by all leading airlines, you'll find plenty of flight choices. Additionally, points hotels are plentiful.

Here’s a roundup of 11 must-experience activities when exploring the Windy City.

Indulge in a deep-dish pizza

Upon arrival, deep-dish pizza is probably at the forefront of your mind, and for good reason. Lou Malnati's Pizzeria serves up some of the best, but if you're in search of hidden gems, don’t miss Art of Pizza or Pequod's. Just be ready for a serious food coma afterward—these pizzas are no joke!

Stroll along the Chicago Riverwalk

The riverwalk is a 1.25-mile scenic path running alongside the Chicago River, featuring murals, statues, and other artistic installations developed over the last decade. You'll discover plenty of excellent restaurants and bars offering outdoor seating right by the water. If you happen to be there in March during St. Patrick's Day, don’t miss the river dyed bright green!

Wander the lakeside trail along Lake Michigan

Lake Michigan ranks among the largest lakes globally, featuring an 18-mile paved trail along the city's eastern shoreline. This path is ideal for walking, biking, and offers easy access to swimming spots like Montrose Beach, Oak Street Beach, and North Ave Beach. You can rent bikes at various points along the trail or join a guided Segway tour through the South Loop area. Plus, the lakeside trail connects seamlessly to the Riverwalk and multiple downtown entrances for convenient access to your favorite hotels.

Discover Chicago's waterways

Exploring the river or lake is even more enjoyable than walking beside them. Rent kayaks or paddle boards if you're seeking adventure, or experience the water from a larger boat. Boats can be rented by the hour in the summer, or you can book a tour. Numerous providers offer architecture tours that provide insights into the city's history while you relax on the river. If you love kayaking and want to learn more about the city, be sure to try the architectural kayaking tours.

Visit the Art Institute of Chicago

This renowned museum is a must-visit for anyone interested in history and culture. Located adjacent to the famous Cloud Gate sculpture, also known as "The Bean," in Millennium Park, the Art Institute of Chicago is one of the oldest and largest art museums in the nation, boasting nearly 300,000 pieces in its collection. The museum features both indoor and outdoor exhibits, along with rotating special displays, such as the Obama portraits, ensuring that even frequent visitors find something new to enjoy.

Stroll through the parks

If you're looking to save some money during your visit, Chicago offers a wealth of free attractions. With 570 parks in the area, you're likely to discover a fair or festival while you wander. Notable parks include Lincoln Park, Grant Park, Millennium Park, and Garfield Park. The 606, a recent addition completed in 2015, transforms a previously abandoned elevated railway into a 2.7-mile trail linking various parks and public art pieces.

Visit a local farmers' market

Chicago is famous for its culinary scene, and visiting a farmers' market is a great way to savor the local flavors. Throughout the summer, there's nearly a farmers' market happening every day. The Logan Square, Lincoln Park, and Green City markets are the most popular weekend spots, offering an array of fresh produce, meats, and artisanal crafts. For an indoor option open during the week, the Chicago French Market in River North operates year-round.

Explore the Maxwell Street Market

For those seeking a great deal, the historic Maxwell Street Market near the West Loop is a must-visit. This long-standing Chicago tradition showcases a variety of handmade crafts, delicious food, and live entertainment. Established in 1912, it has evolved into a vibrant cultural hub. The market operates from 9 am to 3 pm on the 1st and 3rd Sundays of each month, weather permitting, from June to December.

Catch a Cubs game

Chicago is famous for its sports, and if you're in town during baseball season, don't miss a chance to see a game at Wrigley Field. Attending a ball game is a classic Chicago experience. Before entering, take a moment to admire the statues of legendary Chicago Cubs players at Addison and Clark streets. If you have a young fan attending their first game, stop by the fan services desk to obtain a first-time attendance certificate. Just be sure to arrive before the National Anthem for your certificate!

Enjoy an evening at a speakeasy

In a city steeped in history, it's no wonder that Chicago boasts a number of must-visit speakeasies. While the entrances are now easier to locate, they still offer a distinctive taste of the city’s nightlife. Popular spots like Violet Hour and the Chicago Music Lounge are well-deserved favorites. However, for a truly historic experience, check out The Drifter inside the Green Door Tavern, which has roots as an actual speakeasy from the prohibition era.

Join one of the city's vibrant music festivals

Chicago is renowned for its lively music scene and exceptional concerts. Events like Lollapalooza, the Windy City Smokeout, and the Pitchfork Music Festival are just a few annual highlights catering to diverse musical preferences. The city also hosts numerous smaller downtown music festivals celebrating blues, jazz, gospel, and house music. Plus, various neighborhood festivals, especially in areas like Wicker Park East, bring even more musical enjoyment throughout the city.

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