Top 5 Things to Do in Chicago

In Must Do Experiences, Travel Eats, Travel Guides by ZainLeave a Comment

The Windy city is a perfect destination for a weekend trip or a quick getaway.  Whether you are a sports fan, theater geek, wine connoisseur or something in between you are certain to find something to do in this city.  Here are our top 5 things YOU MUST DO if you visit Chicago!


Michigan Avenue is the center of much of the cities activity.  Many of Chicago’s most iconic sites are found within a block or two of this thoroughfare.  Regardless of what you are looking for you will find yourself visiting Michigan Ave multiple times on your trip.  Along Michigan Ave you will the Hancock Tower, Access to the Riverside Walkway, numerous high end stores, fine dining and Cloudgate (also known as The Bean).


Outside of Broadway, Chicago has one of the US’s most lively theater scenes.  If you are lucky enough you can catch the hit “Hamilton” at the Private Bank Theatre, even if you aren’t able to get tickets in advance you can win tickets in their lottery.  If Broadway shows aren’t your thing, you can head to the Second City, an improv theatre which was were Stephen Colbert, Tina Few, John Belushi and numerous SNL comedians launched their careers.  Be sure to book tickets in advance as the sell out – who knows you may see a future SNL actor or Late Night host during your show.


One of the top attractions in Chicago is taking a 90 min cruise down the Chicago River to see the different styles of architecture that make up the city.  The knowledgeable guides will point out different characteristics of each of the skyscrapers along the banks of the river.  We recommend going on Chicago’s First Lady Tours – this company uses guides from the Chicago Architecture Foundation so you are sure to learn a lot while seeing how the landscape of the city has evolved over time.  Be sure to bring a jacket as the wind really picks up while you are on the cruise.


A visit to Chicago isn’t complete with sampling Deep Dish Pizza.  This hearty pizza is pan cooked with dough topped with cheese, with the sauce and toppings found on top of the pizza.  We recommend going to Giodarno’s to get the most authentic pizza.   If pizza isn’t your thing – you could get Chicago style popcorn at Garretts (found off of Michigan Avenue near the River).  You could also satisfy your sweet tooth with Ghirardelli and Hershey’s at their massive stores on Michigan Avenue.


Eataly is a large marketplace where you can get the finest Italian food products direct from Italy.  They have multiple themed bars (be sure to stop by the Gelato and Nutella bars) as well as a large sit down area where you can get a full meal and a large grocery store with products you can only find in Italy.

What are your favorite places to visit in Chicago?  Leave a comment below with anything we missed!

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