9 Touristy Things to do in Chicago

Chicago is the quintessential Mid-Western city. Having been born and raised in central Wisconsin, Chicago was often the place my family would take off to when we wanted a weekend full of shopping, delicious food and touristy things to do in the “big city”.

I’m not the type of traveler who sticks my nose up at tourist areas or attractions. More times than not tourist attractions are heavily visited because they’e pretty impressive and worth seeing at least once. Chicago is by no means in the same category as New York City when it comes to tourist attractions but there definitely is a handful of things I think every person should do at least once when visiting The Windy City.

Take a picture by The Bean

Located in Millennium Park, Cloud Gate, or “The Bean” as it’s most commonly known as, is one of Chicago’s most photographed landmarks. The Bean is a relatively new tourist attraction to Chicago and is only 10 years old. Never the less, at all hours of the day you will find people hovered around this shiny display of art looking to snap the perfect picture.


Visit the Skydeck at the Willis Tower

The Skydeck at The Willis Tower (formerly the Sears Tower) is one of the best ways to get an all encompassing view of the entire city from 103 floors up. The Skydeck officially opened to the public in 1974, but in 2009 the Tower debuted a brand new attraction called The Ledge, glass boxes that hang out 4.3 feet over the Skydeck to give you a truly unique (and somewhat terrifying) view of the city.


Eat deep-dish Chicago style pizza

Chicagoan’s have a fierce love for their iconic deep-dish Chicago style pizza. Many pizza joints in the city claim to have “the best” or be “the first” to make the incredible culinary creation. Luckily for you I know exactly where to find the best deep-dish pizza in Chicago.


Shop the Magnificent Mile on Michigan Ave.

Every big city in America has that one road famed for having the best shopping in the entire city. New York City has 5th Ave, LA has Rodeo Drive, and Chicago has Michigan Ave., or the Magnificent Mile. Not only does this 13-block stretch of road contain some of the best shopping in the mid-west but it’s also home to some of the best hotels, best dining, and best entertainment as well.

Take a picture by the famous Chicago sign

Did you even go to Chicago if you didn’t take a picture of the sign? No, definitely not. Located in the heart of the city’s theatre district, The Chicago Theatre is one of the city’s most iconic buildings. The outside of this building is beautiful by itself, but the inside is really where the building comes alive. If you have time, buy tickets to see a show there, or even schedule a tour of this iconic building.


Explore the Chicago Riverwalk

I know what you’re thinking, you’ve seen one riverwalk, you’ve seen them all. You couldn’t be more wrong. Chicago’s Riverwalk is one of my favorite things about the city. Some of the best views of Chicago can be found on the city’s riverwalk. Not only that, but in the summertime, it’s a great place to hop on a river cruise and see the city from a different vantage point. The Riverwalk is currently in the process of being expanded 9 blocks, which is scheduled for completion later this year.

Go Museum crazy

Chicago nearly gives NYC a run for its money in the Museum department. The Museum of Science and IndustryField Museum of Natural HistoryArt Institute of Chicago, and the Museum of Contemporary Art are just the beginning. Add in the Shedd Aquarium, and the Adler Planetarium and you’ve got something for everyone. The best part about the museums in Chicago is that nearly every one has set days that are “free days” where admission to the museum is free. This site had a great line-up of all the free days for Chicago Museums.


See the sights at Navy Pier

Navy Pier is a 3,300-foot-long pier on the Chicago shoreline of Lake Michigan. Since its construction in 1916, the pier has had many uses including being a Navy Training Center and then a college classroom for the University of Illinois. Nowadays the pier is home to the Chicago Children’s Museum, Pier Park, an IMAX theatre, and hosts some of Chicago’s biggest events including the city’s 4th of July and New Years fireworks displays.

Take in a Cubs game at Wrigley Field

Nothing says, Chicago quite like the Cubs. At 102 years old, Wrigley Field is one of the oldest fields in Major League Baseball, second only to Boston’s Fenway Park (104 years old). If baseball history is something you’re interested in, book a tour of the field. If just taking in a game is more what you’re looking for, head to Wrigleyville well in advance of game time. Grab yourself a sandwich from Lucky’s and explore the area. One of the best ways to get to know a city is to become a fan of their most loved sports team for a day.


Chicago is the quintessential midwest city with tons of awesome food, amazing architecture, and great things to see and do. These are the best touristy things to do in Chicago.

What’s your favorite touristy thing to do in Chicago?


  • fabulous post! i’ve been to chicago once, but several years ago and i didn’t take a photo with the sign so clearly i didn’t even go. i don’t even remember the bean, to be honest. i’m sure it was there when i went, but i didn’t see it. i was there on my own as well, so hardly any pictures. anyway! it’s actually fairly close to us so I’d love to go back for a weekend trip and i’ll be saving this for then! thanks for sharing 🙂

    • Glad it was helpful for you, Kristen! It really is a great city. Big enough to be touristy but not overwhelmingly huge like NYC.

  • THAT PIZZA: OMG. I had no idea “deep dish” actually meant it was stuffed with even more things underneath the toppings! I can’t wait to do Chicago one day; hoping for a friends’ weekend there someday! Great post, and fun to find you on #TravelTuesday!

    • Glad you stopped by, Christy! Chicago would be the perfect place for a friends weekend getaway! It’s worth a visit for the pizza alone in my opinion 😉

  • Woo I’ve done a few of these! I can still remember how good that pizza was, if only we could get some good authentic deep dish pizza in the UK!

  • I haven’t been to Chicago (yet), so, I want to do all of these (doesn’t matter if they are touristy). I think I can skip the Wrigley Field since I am not a sports (or baseball) fanatic.

    • haha, yeah not everyone finds baseball to be the most entertaining of sports. The area where the field is, Wrigleyville, has a great energy to it so even if you did skip the game you could still get a good feel for it just being in the neighborhood. 🙂

  • We had a chance to do a few of things when we were in Chicago last year, but it sounds like we still have a few more to do! I loved visiting Willis Tower, but I totally got freaked out going on the Sky Deck! It didn’t help that my husband kept on acting like he was going to jump when we standing on the ledge!

    • hahaha! I went out on the ledge and took some pictures, but I didn’t spend a lot of time just hanging out there. It is kind of a trippy experience for someone who’s not a fan of heights.

  • It seems like I know a lot of (OK, well maybe not KNOW them, but am at least Facebook friends with) people who have been to Chicago recently!

    And all of them seem to have done most of these things! Being in Ireland, I feel like every time I’ve talked to an Irish person who has visited the US, they’ve always made a stop in Chicago. I feel like I’m missing out on something!

    Saving this list for when I finally do make it there!

    • haha, I completely get what you mean by saying “know” AKA-facebook friends. I’m glad to hear Europeans seem to be well-traveled in Chicago! I’m biased because I grew up around it, but it truly is one of my favorite cities and I think it has a lot to offer for many different types of people.

  • Chicago is somewhere that’s always tempted me – great list of tips for when I finally get there. Love the look of the Bean particularly. #citytripping

    • Glad to hear you enjoyed reading! Thanks for hosting a great link-up! 🙂

  • I just completed an internship in Chicago and I agree with all of these things to see and do in the city! In addition to Willis Towers there is also 360 Chicago and I’ve also heard the Architectural Boat Tour is something to see (I opted out because of motion sickness concerns).

    • Ahh yes! I’ve heard some great things about some summer time boat tours on the river! I’ve never personally taken one so I didn’t want to recommend one, but maybe that’s something I’ll look into for my next visit.

  • Oh my goodness, I DIDN’T get a picture by the Chicago sign!! Did I actually visit Chicago? I did get several by the bean though – so must have gone. After spending an extended amount of time there last year, I ticked off most of those…didn’t see the Cubs tho (out of season). The museums are excellent but I really didn’t love the deep dish pizza – sorry!! Thanks for linking to #citytripping x

    • I agree, the museums are fabulous! The Shedd Aquarium was one of my personal favorite attractions. Sorry to hear you weren’t a deep dish pizza fan! I’ve heard some people say it’s too much cheese and too many toppings.

  • Chicago is such a beautiful city. You’ve hit some great highlights. Also, I’d forgotten how deep dish Chicago pizza pie could be!

    • The pizza can’t be missed in my opinion! I get some every time I’m in Chicago.

  • Yes to all of these! Although I have to admit that we’ve lived here for six years now and we’re still checking things off the list. There is just so much to do. I actually didn’t care much about Chicago while we were living in it. But now that we live in the suburbs but go down there often to do things, I have completely fallen in love with it.