Most Amazing Things to Do in Chicago

This is just a fantastic place with plenty of sights to enjoy and things to observe. We know that it may be overwhelming when first visiting as to what destinations to add to your itinerary. Check out the list of the best local attractions, including:


Love it or loathe it, deep-dish pizza is where it’s at in Chicago. There’s much debate over where the best pizza in the city can be found, though it’s generally agreed that the original was invented at Pizzeria Uno. With dozens of lists of “best” pizza restaurants, fiercely fought online battles amongst various loyalists. And, more choice than you can shake a gorgeous piece of golden crust at, there’s no real option here.

Beer Tasting Tour

Would you like to have a drink to go with your pizza? Chicago takes beer almost as seriously as the deep dish and many of the local breweries run visits where you can sample the product as you see how it’s made. 

Get festive

Lollapalooza, Blues Fest, Chicago Jazz Festival, Windy City LakeShake…the list goes on! Chicago has more than 200 festivals, events, and celebrations this year alone, so you’re bound to catch at least one.

Millennium Park

No list of Chicago highlights would be complete without a tour of this popular park and, crucially, it’s “Cloud Gate” sculpture, more commonly known as “The Bean.” You’ll recognize it from almost any film set in Chicago, any picture of Chicago and even the odd video game. So guess, how exciting this could be!

Hit the beach

Situated as it is on the bank of Lake Michigan, Chicago has over 26 miles of public beaches to explore. Illinois Beach State Park is just excellent for camping and hiking, Kathy Osterman Beach is very popular for its clear water and North Ave. Beach is the place to be seen as the most famous stretch of sand in the city.

Adler Planetarium

This is an observatory that also functions as a museum, theater, and research center. Situated right near the Shedd Aquarium in the Museum Campus along the lakefront and offers an unblocked view of the skies above.

With an All-Access admission pass, you’ll be able to enjoy unlimited shows, special exhibits, and all that the planetarium has to offer.

If you are hungry, you should probably head to Chicago! Take your best friends and family and enjoy a few days in the Windy City. We went with our co-investors who helped us start up our painting company 10 years ago ( It was a nice treat for us all and well worth the effort to save and plan well.

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