The Best of Chicago in One Weekend

The skyline of Chicago, Illinois

Chi-Town. Second City. The Windy City.

Whatever you call it, Chicago is a great place for a visit and offers a huge range of activities to the over 50 million tourists who visit each year. There is something for everyone in this lakeshore city; from visiting a museum to enjoying the LEGOLAND Discovery Center, the entire family can enjoy a weekend here!

As we have mentioned in previous posts about cities like Barcelona, we love exploring on our own, but some places are set up perfectly for using guided tours. And Chicago is definitely one of those cities! It especially makes sense if you are looking to visit multiple sites that have entry fees. For Chicago and other U.S. destinations, the go-to tourist pass site to ensure you are getting the best deals is Vacation Pass.

So, are you feeling overwhelmed with everything there is to see and do in Chicago? 

If that’s the case, here are five activities to check out on your next visit to the Windy city!

Take a Boat Tour

Chicago Architect Boat Tour

photo credit: Chose Chicago

Check out Chicago from the water!

This reminds me a lot of the movie ‘The Break-Up’ starring Vince Vaughn, where his character runs a guided tour business in Chicago. They’ll help you explore the city by air, land and water! Anyway, be sure to try this out on your visit, but make sure you are there during the summer months for the best weather.

Enjoy a Chicago Architecture Foundation Walking Tour

The Aqua Skyscraper in Chicago, Illinois

Hit the pavement and enjoy the beautiful architecture found in downtown Chicago.

After the great Chicago fire of 1871, which burned down virtually the entire city, the city began its come back with a focus on architecture and steel construction. Many famous architects, like Frank Lloyd Wright, have left their fingerprints on Chicago over the years. The buildings can be seen for their originality, which makes the experience unique and much different than taking a stroll in New York for instance.

Check Out 360° Chicago

You can’t leave Chicago without getting a birds eye view of this beautiful city. Make your way to 360° Chicago (formerly the John Hancock Observatory) and take a walk out on the observation deck, it will blow you away. Voted one of the best views in America by Travel & Leisure, this view gives you a fantastic look at the city, Lake Michigan and four bordering states!

Visit the Adler Planetarium

The Adler Planetarium in Chicago

photo credit: Smart Destinations

After an action packed day of seeing Chicago from land, water and the sky, you can relax and take in a show at the Adler Planetarium. There are exhibits to view, but the shows are really where you’ll enjoy yourself and learn some interesting things about the universe. For those interested in astronomy, this is a must see!

And Don’t Forget The Bean

The Bean Chicago

And last, but not least…

Your visit to Chicago is not complete without a visit to The Bean. Be sure to view this guy from every angle, you are sure to leave with some awesome photos of yourself and the Chicago skyline! This iconic sculpture is located in Millennium Park.

This post is sponsored by Vacation Pass. 

About Matt

Matt is one-half of Great Big Globe. He loves the Green Bay Packers, chips and salsa, a strong Americano and knows an incredible amount of useless sports trivia.


  1. You also have to either take in a Chicago Cubs game while you are in Chicago. If they are not playing, then at the very least go on the Wrigley Field tour. You don’t necessarily have to be a a diehard baseball fan to appreciate the beauty and history affiliated with Major League Baseball’s second oldest stadium.

    • Good call! I am embarrassed to say that I live 3 hours from Chicago and have never been to a Cubs game. I have been to Wrigleyville though. 😉

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