Chicago: My favorite (and least favorite) activities to do in Chicago

Chicago: My favorite (and least favorite) activities to do in Chicago

I spent about eight years living in Chicago. One thing that always frustrated me was that most tourists were missing out on the best Chicago has to offer. The culture, the food, the music, and so on, are all not to be missed. I’m sharing everything you should do while in Chicago (and everything not to do in Chicago).

Here are five of my favorite activities to do in Chicago:

Take an Architecture Boat Tour; see the skyline at night:

The Architecture Boat Tours are a truly excellent way to experience the city. Typically the tour will take you up and down the river, providing a history of many of Chicago’s most famous and historical buildings. However, I recommend taking a sunset cruise for the most beautiful views. Even better are the extended cruises that take you out onto Lake Michigan. Viewing the skyline from Lake Michigan is not to be missed.

What to do in Chicago, Chicago river tour

Visit the beach:

Visit the beach in the midwest? During the summer, yes! Chicago has a few great beaches, including Oak Street Beach and North Avenue Beach. If your family loves to dip their toes in the water, check out one of the beaches and then go for a stroll down the Lakeshore afterward. It’s a beautiful walk along Lake Michigan.

Go to the (free) zoo in Lincoln Park:

Located in the aptly-named Lincoln Park neighborhood, the zoo is free year-round and is also one of the best in the country. Lincoln Park has plenty else to offer as well so be sure to roam around the neighborhood a bit when you’re done.

What to do in Chicago, Lincoln Park Zoo
Yes, I’m wearing space pants



Ride the “El” train:

The “El” train is actually very efficient in getting you around the city, especially if you are traveling outside of rush hours. Whether you take it once or use it throughout your whole trip, it’s a good idea to at least check it out.

What to do in Chicago, ride the El train

Attend a sports game:

Chicagoans love their sports teams. If your family agrees, check out the Cubs, White Sox, Bears, or Blackhawks when they’re in town. They’re all very different experiences, but tons of fun.

Check out the local fare:

The best rule of thumb for choosing where to eat in Chicago is: if it’s a chain restaurant, skip it. Chicago has dozens of incredible restaurants, from hot dog stands to Michelin Star restaurants. If you visit during the spring, summer, or fall, make sure you have at least one meal on a patio or rooftop – it’s a Chicago favorite.

Here are my least favorite tourist destinations (and what to do in Chicago instead):

Navy Pier:

Sure, there is a ferris wheel, but nothing at Navy Pier really embodies the spirit of Chicago. There are plenty of other things to do in Chicago that will be more fun and give you a richer experience. Check out Cloud Gate (more commonly known as The Bean) instead and then explore Grant Park from there.

What to do in Chicago, the bean

Deep dish pizza:

For some reason, no one can visit Chicago without trying the deep dish pizza. But what they don’t know is that the locals rarely eat it themselves. Try the thin crust pizza instead, or even better, head over to Portillo’s for a hot dog or Italian beef sandwich.

Sky Deck:

Every day hundreds of people line up to stand in a clear box 103 stories up above the city. Sure, it sounds great, but it’s a long wait and there’s an entrance fee. Instead, head over to the Signature Room on the 96th floor of the John Hancock Building. Instead of paying an entrance fee, you’ll have to order a drink. The views are incredible (especially the view from the women’s restroom).



What are your favorite things to do in Chicago?


2 thoughts on “Chicago: My favorite (and least favorite) activities to do in Chicago”

Leave a Reply

Your email address will not be published.


Sign up for our bi-monthly newsletter with useful tips, travel stories, and (soon) videos!
Email address
Secure and Spam free...