What to do in Chicago: More than just deep dish pizza, hot dogs and architecture

What to do in Chicago?

It’s highly likely you probably think of their amazing deep dish pizza, the famous Chicago Dog and of course the world class architecture when you picture Chicago. But here’s the thing, it’s freaking beautiful and full of things to see and do too!

We had no idea what to expect when visiting this city. 

We visited for 6 weeks, enough time to really fall in love with the Windy City. Obviously 6 weeks is way more than enough time to visit Chicago as we do tend to spend longer periods of time in each place we visit as we need to get work done as well. In our opinion, 2-3 full days here will give you the chance to see and experience everything. 

We would highly recommend you visit if you get the opportunity! 

Heads up though, don’t expect to stick to a diet while you’re here; due to said pizza and hot dogs haha! 


An iconic building that I’m sure you’ve already heard of if you’ve visited or planned a trip to Chicago, this ledge on the 103rd floor of Willis Tower provides the best view points of the city and you will even have the opportunity to step out onto a glass box and see the city below you. 

Lincoln Park Zoo 

Hey, it’s free. Anything free is good! 

Situated smack dab in the middle of the city, once you enter the zoo you can no longer tell you are in one of the largest US cities. There is a ton of different animals and species and even though we visited during a cold time of the year, got to see plenty of outdoor animals even with snow on the ground. Bonus if you have kids with you! 

Navy Pier

This is another gem located on Lake Michigan. Can be really rough during cold times of the year with the breeze off the lake, but has a really neat Ferris wheel for great views and has some shopping and dining options as well. 

During warmer times of the year it is a water sport haven so a must if you enjoy SUP or boating!  

Wander The City 

Chicago’s beauty far exceeded our expectations. The awe-inspiring skyscrapers and liveliness really make up this cities character. We found a lot of entertainment from just walking the streets and exploring the downtown area. 

Make sure to have a stop at Giordano’s for their famous Chicago deep dish pizza or a locals favorite, Chicago’s Dog House for a Chicago style dog! 

River Tour

There are quite a few options for river tours in Chicago, but our personal favorite was Wendella Boats. The tour itself lasted a little over an hour and a half and takes you through the river and lake and has some of the best views of the city. 

There’s snacks and restrooms as well as heating during the colder months and air during the summer months and even a bar on board so the hour and a half isn’t bad. They are very informative but keep it interesting and laid back so the guide definitely made it a fun experience. 

Millennium Park


This one is an obvious must if you are seeing Chicago for the first time! Basically it’s a huge park located next to the city and the Lake Michigan shoreline full of different art, views and even entertainment if you’re lucky enough to visit during the warmer times of the year. 

Here you’ll find the Crown Fountain, Cloud Gate (The giant bean pictured above) beautiful sky line views and a ton more. 

Tip: If you travel with your kids like us, there’s a huge playground for them in the park as well! 

Magnificent Mile 

Magnificent Mile is just that… Magnificent. This is basically the more luxurious side of town with a mile long strip of upscale shops, cool restaurants and luxury hotels. Some of our favorites were the Chicago Water Tower and 360 Chicago Observatory. 

Come to the Magnificent Mile to admire the luxurious buildings and grab a coffee at the Corner Baker Cafe. 

Check out our guide here on things to consider before planning your trip to Chicago! 

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