Everything You Should Do With Two Days In Chicago

Published on October 9, 2022
Any first timers in Chicago might feel overwhelmed since the city has so much to offer visitors, especially if the trip is a quick weekend. However, you can pack so much into two days without feeling like you’ve sacrificed the Chicago experience. Here are some of the must see and do’s while you’re in the Windy City.
Chicago, Illinois

Chicago, Illinois

The Magnificent Mile

The Magnificent Mile is one of the city’s upscale areas that’s well known for its high end shopping. Here you can also find some of Chicago’s most iconic buildings including the Chicago Water Tower, Wrigley Building, and the John Hancock Center. It’s no surprise really that this area is one of the most expensive places to live in the US, just behind Fifth Avenue in New York City and Rodeo Drive in Beverly Hills, California.

The Magnificent Mile

The Magnificent Mile

Art Institute of Chicago

Inside of Millennium Park, you’ll find the Art Institute of Chicago, which is one of the oldest art museums in the US and is home to some of the most famous pieces of art in the world. Some iconic works located here include A Sunday Afternoon on the Island of La Grande Jatte by Goerges Suerat, American Gothic by Grant Wood, Nighthawks by Edward Hopper, The Old Guitarist by Pablo Picasso, The Bedroom by Van Gogh, and many many more.

Art Institute Of Chicago

Art Institute Of Chicago

3 Arts Club Cafe

If you take a stroll around Old Town, you might feel like you’ve been transported to somewhere in England, as you’ll be surrounded by Victorian style buildings all around. When you’re here, be sure to head to 3 Arts Cafe, which is located inside of Restoration Hardware. It might sound odd to go to a cafe inside of a home furnishing company, but trust us, it’s very much worth it.

3 Arts Club Cafe

3 Arts Club Cafe

Skydeck

Chicago is known for its towering skyscrapers, and at Skydeck, you can visit the top of the Willis Tower, which was the tallest building in the world for nearly 25 years after it was built in 1973. Located on the 103rd floor, the Skydeck can be reached by elevator, which only takes on minute to whisk you all the way up! There you’ll be see stunning views as well as be able to city the city quite literally underneath you thanks to the glass floors.

Skydeck

Skydeck

Wrigley Field

Even if you’re not a baseball fan at all, it’s still fun to visit Wrigley Field, as it is not only beautiful but also quite historical. You can see if you can get tickets for a game where you can enjoy the classic hot dog, popcorn, and America’s favorite pastime, or you can just visit around the field if you prefer. Of course, there are plenty of bars located all around so you can grab a drink nearby.

Wrigley Field

Wrigley Field

Navy Pier

The Navy Pier is a wonderful place to visit during your trip to Chicago since it is packed full of restaurants, gardens, parks, and shops to explore. In fact, there’s more than 50 acres of attractions to explore, so you can really make a whole day of it if you want. There’s a reason why it’s one of the most visited attractions both in Chicago and the entire midwest.

Navy Pier

Navy Pier