7 Things To Do In Chicago

7 Unmissable Things To Do In Chicago

Whether you’re a Chicago native or simply spending a few days in the Windy City, you sure as heck won’t be bored. From tropical cocktail bars and world famed architecture to outdoor concerts and the Cubs, there’s plenty to do here.

But how to choose which things to add to your list and which ones to skip? Fear not, we’ll save you the hours of scrolling with these seven essential things to do in Chicago.

1. See a concert in Millennium Park

Chicago’s best-known green space, Millenium Park is home to Cloud Gate (a.k.a. “The Bean”), outdoor concerts, film screenings, outdoor workouts and tours. During summer, spread out on the Great Lawn for a series of outdoor music performances from local, national and international acts. You can also catch cult films on the big screen, too.

Millennium Park in Chicago

2. Check out the city’s cocktail circuit

One of America’s greatest drinking cities, Chicago has lively dive bars, hidden Speakeasies, rooftop patios, brewpubs and so much more.

Looking to have a night out on the town in the Windy City? Follow our top spots for a drink – or two – and you’ll find yourself in only the very best Chicago bars…

cocktail circuit in Chicago

3. Support the Cubbies at Wrigley Field

Wrigley Field is the second-oldest ballpark in the major leagues. The ivy-lined outfield walls, historic man-operated scoreboard and the bleacher bums rallying the team to victory, makes catching a game at Wrigley a must stop for any sports fan.

4. Eat some famous deep dish pizza

Deep-dish pizza is a Chicago specialty, so it’s basically a requirement that you eat at least one while you’re here. The thick crust and ultra gooey cheese pizza cooked to perfection in a pan will have you addicted on the first bite.

Check out the best pizza spots in Chicago and the rest of Illinois here.

deep dish pizza in Chicago

5. Hike the 606

The 606 is an elevated former railroad track that runs along the Bloomingdale Trail for 2.7 miles between Ashland Avenue and Ridgeway Street, across four different neighborhoods of Chicago. Whether you choose to bike it or hike it, you’ll see a different side of the city.

606 in Chicago

6. Go to a Jazz Night at the legendary Green Mill Cocktail Lounge

In business since 1907, this historical jazz venue is still doing live jazz every night in a prohibition-era speakeasy atmosphere. Plus, every Sunday at 7 pm, the Green Mill hosts the Uptown Poetry Slam, hosted by the father of slam poetry Marc Smith.

Green Mill Cocktail Lounge

7. Brave the glass floor ledge at the SkyDeck

After only a 40-second ride in North America’s fastest elevators to the observation deck, you’ll be on the 94th floor of the John Hancock centre for a seriously incredible view. The legendary TILT feature will let you literally lean out over the skyline below.


Sarah Clayton-Lea

Co-founder of Big 7 Travel, Sarah created the company through her passion for championing the world's best food and travel experiences. Before her career in digital media, where she previously held roles such as Editor of Food&Wine Ireland, Sarah worked in the hospitality industry in Dublin and New York.

Contact [email protected]

View stories