Tried and tested things to do in Chicago

I read a dozen travel articles on Chicago before our trip there in October 2016. Googling “What to see in Chicago” gave way to countless articles contradicting each other’s opinions on what to try in Chicago. Is this post any different? I’m just going to tell you what we tried, and what we in turn recommend. Most of our recommendations go along the lines of “Chicago is awesome, eat everything and walk everywhere.”

Note: Apologies in advance for all the pictures not being of the best quality. We visited on business so had to snap pictures wherever and whenever we could afford to!

Do: Visit the Navy Pier

View from The Centennial Wheel

The Navy Pier is pretty awesome. Stick to the outside of the Pier – where you can take an architectural river tour of Chicago (highly recommended!) with one of the many vendors there (check out their prices for comparison before you commit to one!), take a ride on the Centennial (ferris) wheel for magnificent views of the city (the London Eye of Chicago as they call it!), and visit the Shakespeare Theater.

Cruises vary between 40 and 90 minutes. We took a 60 minute tour that was extremely informative. The quality of the tour is largely weather dependent (hello, Chicago!) but we visited in October and while there were splattered rain showers, it was still very enjoyable. Take a raincoat – try not to be that obnoxious person with an umbrella ready to poke at eye out sitting in a tour group 😉

Being a huge Shakespeare buff, I was thrilled to be able to visit the Chicago Shakespeare Theater. To my disappointment, I learned that the theater is not open to the public; you can only see it if you go for a show. The shows that weekend were around twelve hours long, in commemoration of the four hundred year anniversary of Shakespeare’s death. As much as I loved the Bard, I didn’t want to spend that length of time taking in a modern interpretation of his work in a new city waiting to be explored so I skipped out on the Shakespeare Theater. Plan a few months ahead of you’re planning on visiting the Shakespeare Theater in Chicago!

Do: Visit the Chicago Symphony Orchestra

The Chicago Symphony Orchestra

The Chicago Symphony Orchestra is a cut above the rest – it has great discounts for students, is a beautiful auditorium in and of itself, and a fantastic way to spend the evening. I was lucky enough to enjoy the work of Riccardo Mutti when I visited, who is very open to, and caters towards, younger audiences in the orchestra. Even if you don’t usually visit the symphony, this is worth a visit.

Don’t: Try to hit all the museums

From the Museum of Natural History: Field Museum to the Art Institute to the DuSable Museum of African American History, Chicago has a multitude of galleries and depositories to hit if you’re a museum buff. We however you have just a weekend or so to visit like we did, we recommend visiting places like the Dreihaus Museum and Chicago Cultural Center, and taking an architectural tour instead. They have a more authentic feel to taking in the city versus following the crowds through relics preserved in glass boxes. If however, you have ample time and museums are your thing, Chicago is a great place for you!

Do: Visit Cloud 9, Millennium Park… The Bean!

Heads up – it’s filled with tourists taking selfies (just like us ;)) but it really is a cool structure to check out. It’s also right by the museums and Chicago Symphony Orchestra so it’s a great pit-stop on your way to other attractions!

Guilty of taking selfies at the Bean
The Bean is cool

Do: Visit the Lookingglass Theatre

We highly recommend the productions at the Lookingglass Theatre. It’s worth a visit just to check out the water-works-turned-theater building. We caught “Life Sucks” at the theater and it was a highlight of our trip.

The Lookingglass Theatre
The Lookingglass Theatre

Do: Try deep dish pizza

I had deep dish pizza for the first time a few years ago when I was transiting through Chicago and instantly fell in love.

I’m pescetarian so we got a veggie pizza and it didn’t disappoint!

Yes, it is a touristy thing to do. Yes, it can be overpriced. Yes, you should still try it. If you want to try Giordano’s (which is everywhere!) call in your order for take-out – the pizza takes at least forty minutes to prepare in house. It’s also extremely pricey. We recommend trying deep dish elsewhere – Lou Malnati’s and The Art of Pizza are good options. (The manager and staff at Giordano’s on North Rush Street deserve a thumbs up though, they were extremely helpful during our visit!)

Do: Visit the Signature Room at the John Hancock Center

View from the Signature Room

Skip the Willis Tower lines and grab a drink and/or dinner at the Signature Room on the 95th floor of the John Hancock Center (now the 360). The views themselves make it worth it. Going slightly before sunset and watching the lights slowly envelope the skyscape is phenomenal.

Do: Walk around!


Chicago has numerous walking tours describing the beautiful architecture of the city. We recommend taking one of these tours; but if you’re not into that/have no time, walk around by yourself. Cross the bridges, take in the river, marvel at the beautiful architecture spanning Gothic to Modern styles. We walked everywhere, only taking the subway back and forth from the airport. It may be a windy city but the walks are extremely enjoyable! (Depending on what time of year you go of course – try to avoid Chicago in the winter!)

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Walk around to enjoy spontaneous and impressive street music!

In summary:

Do: Take an architectural tour. Take a rain jacket just in case.

Do: Try deep dish pizza, preferably not in-house at Giordano’s.

Do: Visit the Signature Room and skip the lines at the Willis Tower.

Do: Visit the Lookingglass Theater, maybe even take in a show!

Do: Visit the Bean and Millennium Park

Do: Visit the Chicago Symphony Orchestra.

Don’t: Try to visit all the museums

Don’t: Try to catch too many plays in one weekend.

Do: Walk everywhere! Even if you don’t take a walking tour (which we recommend!)

Chicago is a top-notch travel destination with a variety of unconventional attractions to offer. Whether you want to go for the pizza, the architecture, or the arts, it’s well worth the journey/I promise you it won’t suck (ode to Aaron Posner and Andrew White at the Lookingglass Theatre!)

Been to Chicago? Planning a trip there? We’d love to hear about your experiences! Share your stories with us below!

As always, be a conscious traveler: Take nothing, and leave nothing behind. Be conscious, be welcome! Read more about conscious travel here.

Dinner and drinks at the Signature Room