Skip to main content

Three Fun-Filled Days in Chicago

Two people hugging enjoying one of Chicago's many art pieces

Looking for a fun-filled three days in the most lively city in the American Midwest? Known as the “Windy City” and for being the third biggest city in the USA, Chicago has a huge array of vibrant and fascinating attractions. Located on the shores of Lake Michigan, few places can match Chicago for its variety of entertainment offerings. If you want to explore Chicago in 3 days, then these are some of the most fun places to visit.

Day 1 – The Arts

Chicago is famed for its love of the arts. All around the city you can find a variety of museums and exhibitions showcasing this fact. In addition, from the beginnings of jazz to producing Kanye West with so much in between, Chicago has a much admired and world-renowned music scene.

Jazz and blues clubs, as well as rock and indie bars, can easily be found so why not attend a few live gigs in Chicago at one of the many spots in the city. Always check the listings for any Chicago music festivals taking place too. Here we suggest some of the more entertaining sites covering art and music venues that you can visit.

Art Institute of Chicago

Billed by many as the top attraction in Chicago, the Art Institute is just a stone’s throw away from Millennium Park and Lake Michigan. Nearly 300,000 pieces of art sit in this museum ready for your viewing pleasure so be sure to check it out. In the Family Room, you can make your own artwork and create a customized family museum tour using the JourneyMaker.

Chicago Architecture

The Windy City has a vast array of architecturally interesting buildings and one great way to see the best of it is with Chicago’s Best 90-Minute Architecture Tour. The first-ever skyscraper, the Home Insurance Building, as well as the Willis Tower (formerly Sears Tower), which was once the tallest building in the building for 25 years, are both featured on this tour.

Chicago Street Art

Once thought of as a hindrance to a city’s appeal, graffiti and street art now plays a role in attracting art lovers to a metropolis. Chicago is no exception. With some amazing street art on display especially in the Wabash Arts Corridor that is host to 20 large-scale murals within seven blocks of each other. Districts including Pilsen, Humboldt Park, and Rogers Park are also hotspots for street art lovers in this living canvas of a city.

Chicago Jazz and Blues Clubs

Chicago’s Jazz and Blues scene is world-renowned and its clubs are one of the most authentically fun things you can do in the city. Uptown is home to a number of jazz and blues bars and clubs while Downtown Chicago has even more venues for you to enjoy.

Indie Chicago

Wicker Park is a haven for independent artists and musicians with music venues on all six corners, you are spoilt for choice especially if rock and indie music is more your thing.

Day 2 – Science

Museum of Science and Industry

This is one of Chicago’s most iconic museums with a huge range of exhibits and interactive activities on offer. The world-famous Body Worlds Chicago exhibition is located here and is a must-see attraction, providing entertainment for both children and adults alike.

The Field Museum of Natural History

This is great fun for all the family! This is a premier museum with thousands and thousands of historical, cultural, and scientific artifacts appealing to a huge scope of interests. This is also a great place to find dinosaurs in Chicago — the museum contains a permanent exhibition of a 67-million-year-old and 224 bone skeleton of a T-Rex cheerfully named Sue, which is the most complete of its kind in the world.

Shedd Aquarium

If the natural scientific world is more your thing, then the Shedd Aquarium houses over 32,000 animals and provides a great deal of family fun in Chicago. As a designated National Historic Landmark, Shedd Aquarium offers you unforgettable encounters with sharks, whales, turtles, penguins, and many many more marine creatures.

Day 3 – Sports

Chicago is one of the great sporting cities in the world and home to famous basketball, ice hockey, American football as well as two baseball franchises. Therefore touring the great Chicago sports stadiums of the city is a great way to spend a day in the city, especially for those sports enthusiasts out there.

United Center

Did you watch Netflix’s The Last Dance and you’re looking for a picture with Michael Jordan? Then the United Center is home to the Chicago Bulls basketball team and the perfect place to have your photo taken with the statue of the legendary NBA star. The MJ statue is probably the most famous basketball statue in the world. On top of that, be sure to check the fixture listings to see if any NBA or NHL matches are taking place here as this is not only the home to the Chicago Bulls, but it also houses the Chicago Blackhawks ice hockey franchise.

Wrigley Field in Wrigleyville

Despite being one of the most popular MLB franchises, the Chicago Cubs went over 100 years without winning the World Series. That drought came to a halt in 2016, finally ending the Cubs’ curse of the goat. The stadium sits in one of the most unique and iconic neighborhoods in American sports: Wrigleyville. Wrigleyville is the area around the ground that contains a plethora of sports bars and souvenir stalls dedicated to the Cubs and baseball in general — a great sight for any sports fanatic.

Chicago Sports Museum

The sports museum in Chicago is a must-see attraction for all sports fans keen on learning more about all the great sporting feats Chicago has achieved. Here you can find a huge array of sporting memorabilia including a collection from the aforementioned Chicago Cubs World Series triumph in 2016. There are fanzones, exhibits, and interactive activities for all the family. It even has something for movie fans — the Hoverboard from Back to the Future II!

Soldier Field

Home to the famous Chicago Bears NFL franchise and also a host stadium to FIFA World Cups, Soldier Field is an internationally recognized sports venue. The Soldier Field capacity stands at 61,500, making this an impressive sight so try to time your visit to the city while a game is on.

So come to Chicago, as you can see it is a fun place to visit. And if you are interested in taking Chicago’s best architecture tour or hiring your own private boat for an event, contact us now!

Chicago Bucket List Previous Article What to Do on Mother’s Day in Chicago Next Article