Visiting Chicago for the First Time? Here’s What You Should Try

Chicago is one of the biggest and most populated cities in the United States, so there’s no shortage of things to do. However, if you’re new to visiting the area, you might feel overwhelmed with the possibilities—after all, there’s no way to do everything in a single trip. If you want to make the most of your first visit, you’ll need to find all the best things to do in Chicago and prioritize them.

Photo by Alex Powell from Pexels

Millennium Park

First up is Millennium Park, one of the defining features of Chicago in the modern era. It’s a small section of Grant Park that’s known for its massive art installations and open space. Covering more than 25 acres, it’s free to explore, and is especially beautiful in fall and spring. It’s also home to the Jay Pritzker Pavilion, an outdoor theater capable of holding more than 7,000 people—and if you’re lucky, you might time your trip to align with a free concert.

The Bean

Cloud Gate is the official name for the mirror-coated “bean” sculpture that has become synonymous with Chicago. Made of more than 168 steel plates welded together in a highly polished, seamless finish, the sculpture reflects the beautiful skyline of Chicago with slight distortion—and you can see your own distorted face in it if you get up close.

Navy Pier

Another common (and mostly free) attraction in Chicago is Navy Pier, covering 50 acres of space over Lake Michigan. You can think of it as a miniature amusement park, with thrilling rides, event spaces, beautiful gardens, and lots of unique restaurants and shops. These days, it’s considered a cultural center, and is home to a wide variety of different events.

The Field Museum

The Chicago Field Museum is one of the biggest natural history museums in the world, and features specimens and exhibits from a wide range of eras and areas of study. Notably, you’ll find the most complete T-Rex skeleton in the world, nicknamed “Sue,” and a rotating selection of exhibits you can learn about on the Field Museum website.


Skydeck, a part of Willis Tower (which remains one of the tallest buildings in the world), is an innovative experience that allows you to test your fear of heights while getting an extraordinary look at the city. This glass balcony juts out over the 103rd floor of Willis Tower, allowing you to look straight down while you feel the rest of the building sway (as it’s designed to do to accommodate the wind). It’s an absolute must if you’ve never done it before.

Shedd Aquarium

If you’ve ever been interested in marine biology or the diversity of life that lives underwater, you should visit Shedd Aquarium. It’s one of the biggest aquariums in the world, with more than 32,000 animals and a collected 5 million gallons of water. In it, you’ll find a massive “Wild Reef” exhibit that hosts sharks, rays, and other diverse creatures, and even interactive animal encounters.

Magnificent Mile

If you love to shop, you need to hit up Magnificent Mile, a stretch of Michigan Avenue that features some of the most prominent and impressive stores in the entire city. It’s commonly compared to the likes of Rodeo Drive and 5th Avenue, so if you’re traveling on a budget, this may not be for you. Still, you might enjoy the street performers who typically gather here.

Lincoln Park Zoo (and the Rest of Lincoln Park)

Lincoln Park is a free, open park you can explore with your family, and part of it is the Lincoln Park Zoo. With more than 1,100 and an extended history of development, you’ll likely find at least one exhibit that blows your mind. Lincoln Park also features a conservatory, where you can see dozens of beautiful sculptures, rare plants, and flowers.

Bars and Restaurants

Of course, you can’t visit Chicago without spending some time exploring its bars, restaurants, and nightlife. With hundreds of delicious and exciting places to try all over the city, there’s something for everyone—but the city’s claim to fame is its signature “deep dish” pizza. Dozens of establishments claim to have the best deep dish pizza in Chicago, but Giordano’s is one of the most notable.

Bonus Tips

These attractions should keep you busy on your first trip to Chicago, and possibly a few trips after it. While you’re enjoying the city, make sure you make use of Chicago’s public transportation system. The Chicago Transit Authority is robust, with buses and trains that are easy to navigate, which run throughout the city. It’s also important to dress appropriately—Chicago is known for its harsh winters, so if you’re traveling from a typically sunny area, you don’t want to be taken off guard!

Keep being AllDayChic!

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