Views and Theatre Cues // The Perfect Day in Chicago

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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!

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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 down at Lake Michigan from the John Hancock Tower Observatory in Chicago

A cityscape of 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

Addie is a social media manager, avid traveler, and the voice behind Addie Abroad. She founded the blog to share her journey of exploring the world on a budget, offering practical tips, honest guides, and personal stories from her adventures. From backpacking through Europe to uncovering hidden gems closer to home, Addie’s passion for meaningful travel inspires readers to explore new cultures and create unforgettable memories—all without breaking the bank.

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About addie abroad

Hi, I’m Addie—a social media manager, avid traveler, and storyteller who turned a move from Illinois to Scotland into a lifelong love for exploring new cultures. Since 2016, I’ve been sharing budget-friendly tips, honest guides, and personal travel experiences to help you create unforgettable adventures while sticking to your budget.

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