5 Actually Cool Chicago Tourist Activities —Plus 5 Touristy Things To Skip

I love hosting guests in my home. I always have, and it has been even more fun for me to host since moving to an attractive city like Chicago. We regularly have visitors hoping to explore the Windy City with us, which means that I have done lots of the touristy activities in Chicago over… and over… and over.

While some of those famous Chicago activities are cool, many of them aren’t. I have a visitor’s playbook at this point because I want people to love Chicago as much as I do, which means that you’ve got to be honest about what is worth visiting. While the iconic activities are great for crossing off items on your bucket list, lots of those experiences aren’t the things that I love most about living in Chicago.

I’m sharing my local tips with you today, so get your Malort shot ready as I reveal the 5 Chicago tourist activities that are actually cool, and then warn you against the 5 touristy activities that aren’t worth it.

What You'll Find In This Post

5 Touristy Things in Chicago That Are Actually Cool

Chicago Architecture Tour

If you are planning a trip to Chicago, there is no doubt that you have heard about the city’s river architecture tours. They are one of the most popular tourist activities to do in Chicago, and I am happy to report that even as a local resident, I love these tours!

Chicago’s robust architectural history is one of the best in the world, dating back to the late 1800s with Daniel Burham during the World’s Columbian Exposition. There are turn-of-the-century buildings still standing today, along with plenty of buildings from the 20th and 21st century, all of which can be admired from the Chicago river. The Chicago Architecture Center runs an excellent 90-minute river cruise staffed by volunteer architectural enthusiasts who talk in detail about the styles, landmarks, and new developments that shape Chicago’s riverfront.

Eating Garrett’s Popcorn

Garrett’s Popcorn is the famed Chicago popcorn brand which has been dishing out the city’s best flavored popcorn since 1949. Some of their shops still run out-the-door lines! I love Garrett’s so much that we even served it as a snack at our wedding! They seriously have the best flavored popcorn — the cheese is my favorite, but the caramel is exceptional too. There are several locations around the city, especially downtown, so you can swing by whichever shop is closest to pick up a bag of the Chicago mix or the Garrett’s Mix. They offer free samples for you to discover your favorite flavor!

Art Institute of Chicago

Chicago is home to lots of museums, many of which are… not noteworthy. But the Art Institute of Chicago is the one museum that I regularly recommend and have visited multiple times. The impressionist collection here is unparalleled in the US with pieces by Monet, Manet and Renoir, and the rotating modern art collections are always interesting. The sprawling museum offers adult-only night events on Thursdays, which is my favorite time to visit because you can get wine!

Seeing the Cubs at Wrigley Field

My mom is a die-hard Cubs fan, and our family has had season tickets since I was born. Going to Wrigley Field is in my blood but it wasn’t until I moved to Chicago that I realized how popular it was with visitors. Even if you aren’t a baseball fan, Wrigley Field is worth a visit, because it is the second oldest stadium in the MLB dating back to 1916. Most recently, the Cubs’ owners have expanded the exterior features of the park to offer an outdoor beer garden and patio area on Clark Street.

Because the Cubs are playing much better recently, ticket prices have gone up. This is not a budget friendly activity, but you can typically find more affordable ticket options if you attend a weekday game or if you buy tickets on the same day at the ticket office. Before heading into the stadium, make sure to snap a picture of the bright red marquee on the corner of Clark and Addison.

Live Comedy or Jazz

Live entertainment is a big business in Chicago that draws thousands of visitors every year. But this isn’t just for tourists — locals love late night entertainment too!

Sparking the careers of comedians like Tina Fey, Amy Poehler and Bill Murray, Chicago’s stand-up comedy scene is world-renowned and Second City is the most famous comedy venue in the city. Their higher ticket prices might scare people off, but thankfully there are plenty of other places to have a laugh such as The Cornservatory, Lincoln Lodge or Improvised Shakespeare.

If you are more of a live music fan, Chicago’s Jazz scene is also incredibly popular. Chicago is sometimes coined as the home of live jazz and the legendary Green Mill is the most storied place to experience live music. It is one of the oldest bars in Chicago and is rumored to have been a favorite of Al Capone back in the 1920s! Their delicious cocktails and regularly bustling scene makes you feel cool even if you don’t know anything about jazz.

5 Touristy Chicago Things That Aren’t Actually Cool

Sears/Willis Tower Skydeck

Chicago’s skyline is stunning and the Sears/Willis Tower really is one of the best ways to see it, thanks to the 103 story vantage point at the Skydeck. The now infamous glass ledges hang off the top of the building, but at a ticket cost of $25/person, it can be a pricey choice and is packed with tourists. Opt instead for a visit to the Signature Lounge at the top of the Hancock Building. The bar and restaurant offers equally awesome views but you get to drink while you admire the views! It is the most popular at sunset (understandably) so make reservations in advance.

Eating Chicago Deep-Dish Pizza

Yeah yeah, Chicago is famous for deep-dish pizza, but ask a local resident and they have probably eaten another style of pizza more recently than deep dish. While we have certainly perfected the art of deep-dish pizza, it often isn’t the pizza that Chicagoans actually crave. We have LOTS of other amazing pizza joints around the city that are worth exploring before devouring deep-dish, plus these pizzas won’t put you in a food coma.

Navy Pier

It is a mall for kids. Seriously. That’s it. It’s hard to get to, it’s overpriced, and it’s just not cool. Skip it.

The Bean

Look, I get it. The Bean is the most iconic piece of public art in all of Chicago, so many people come with aspirations of seeing it. And yes, Cloud Gate is a beautiful, funhouse-like experience that lots of people do. But it takes a maximum of 10 minutes to see it and you’ll be there with a massive crowd of people unless you go at 6am. Don’t make the Bean your destination, but rather, stop there on the way to something else in the downtown area like the Art Institute, Cindy’s Rooftop or Buckingham Fountain.

The Magnificent Mile

Do you like chain stores, huge crowds and overpriced merchandise? Well that’s what you’ll find along the Magnificent Mile. Running along Michigan Ave, the Mag Mile is Chicago’s most famous shopping district with high-end and casual brands alike. It is always crowded with tourists and quite overpriced (especially parking) but my biggest issue with the Mag Mile is that it doesn’t feel like Chicago. Nearly all of the shops are big box brands and it feels like any other city, devoid of the local pride and spirit that I love about Chicago.

If you’re looking for great shopping, try the neighborhoods instead! Armitage Avenue in Lincoln Park or Milwaukee Ave in Wicker Park are good options. Both neighborhoods offer a similar assortment of trendy shops to the Mag Mile, but with far more locally-owned and thrift options to shop ‘til you drop. Are you as obsessed with vintage shopping as I am? I wrote a whole guide about where to find the best vintage + secondhand clothing stores in Chicago!