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Having lived less than a three hour’s drive from the city of Chicago for the whole of my life, I am more than familiar with its sights and streets. This past summer, I had to take to task the job of planning the perfect day’s itinerary for my boyfriend’s first time in the city, and I think I did a pretty good job!

Views from the top at the John Hancock Observatory

Start the morning off right with a trip to the John Hancock Observatory for stunning views over the city and Lake Michigan. Although the Sears Tower is certainly the more famous observation deck, I personally think that John Hancock offers much better views, especially considering you can see the Sears Tower from it! 

Looking out across Chicago from the John Hancock Tower Observatory

Lunch at Pizzeria Uno

Going to Chicago without eating deep dish pizza would be like going to New York and not visiting the Empire State Building. It simply is a must do. Pizzeria Uno is the place that, supposedly, it all began and the deep-dish pizza was invented, so it’s a great place to visit to get your deep dish fix! Even my boyfriend has converted from his east coast thin crust ways with a visit to Pizzeria Uno.

The terrace of Pizzeria Uno, the inventor of deep-dish pizza in Chicago
The place where Deep-Dish Pizza was born

Visit the Bean

Located in Millennium Park, Cloud Gate – affectionately nicknamed The Bean – is a quintessential Chicago landmark. Spend time taking pictures of yourself in its reflective surface and exploring the rest of the park.

The Bean backed by the Chicago skyline
You can’t visit Chicago without visiting the Bean


Afternoon at the Museum

After you spend some time at the park, make your way to one of Chicago’s many museums. My personal favorite is The Field Museum, but the Museum of Science and Industry and the Contemporary Art Museum are also great!

See a Show

After dinner, pass your evening by seeing one of the many amazing shows that Chicago’s theatre scene has to offer. Stop by a Second City performance, where many SNL stars got their start, or drink up high culture at one of a million Broadway in Chicago shows!


Addie Gray is a recent college grad and a passionate solo female traveler. Having traveled to more than 20 countries, she now shares her knowledge on budget travel, solo female travel, and travel photography.


  1. […] Since we had a bit of time before our next planned stop of the day, we decided to hop on a streetcar and spend our afternoon on the lakefront. It didn’t take very long for us to settle into our lazy habits. We found a bench to sit on and took the opportunity to rest our already sore feet (I had acquired some pretty crazy blisters from making the stupid decision to break in my new Birkenstocks while we were in Chicago). […]

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