8 Things to Do in Chicago, IL

This past fall, my work travels took me to Chicago for a conference and I decided to add a few extra days to explore the windy city. Chicago is a city I’ve never heard anyone say a bad word about (with the exception of the cold weather or rival remarks from my sports fan friends) so I felt intrigued to see what it was all about. I had some pretty high expectations…and am happy to say, Chi-Town lived up to the hype. Chicago is a rare mix of small town heart with a big city feel that made me feel instantly right at home.

1. The Green Mill

When I think of the great music cities across the country, Chicago is not one that comes to mind. But with Chicago’s rich culture of art and history, I shouldn’t have been as surprised as I was when I discovered The Green Mill. The Green Mill is somewhere that struck a chord with me for many reasons. Besides the obvious that it had great live music, its rich history dating back to the Capone days and hole-in-the-wall feel captivated me. From the outside, it doesn’t look like much. But once you’re inside, it feels like you’ve been transported back in time to the Prohibition era. The booth that Al Capone used to sit in is even still there – the spot that allowed him to keep both the front and back entrances in sight.

From the Road I'm On - Green Mill

2. Chicago Cultural Center

This building is worth a visit for many reasons, but my favorite and definitely a do-not-miss is the Tiffany Dome. Here in Chicago, it is the largest Tiffany glass dome in the world – measuring 38 ft in diameter. With over 30,000 pieces of glass reflecting light in its magnificent glory, no pictures can do it justice.

From the Road I'm On - Chicago Cultural Center

3. Girl & the Goat

The other thing that did not disappoint in Chicago was the food. Truth be told, I didn’t know much about Chicago cuisine past the deep-dish pizza spots at first. But with a little digging and a little luck, I came across Girl & the Goat.

I was able to snag a reservation on Open Table, but realized I must have lucked out when the next available table was over a few weeks out. The restaurant is owned by Top Chef winner, Stephanie Izard. As we were being seated, I overheard the table next to us tell the waiters “we’ve been waiting for over a year to try this place!”. :-0 If you’re able to plan ahead, I definitely suggest trying to see if you’re able to snag a reservation in advance. Also, they have adorable takeout bags as seen below..

From the Road I'm On - Girl & The Goat

4. Millennium Park

No trip to Chicago would be complete with getting an obligatory pic with “The Bean” (formally referred to as “Cloud Gate”) in Millennium Park. Not gonna lie, I found the Bean to be pretty fun to see in person and worth the hype. The park itself is a cute area of green space in downtown Chicago to walk around too.

From the Road I'm On - Millenium Park

5. John Hancock Observatory (360 Chicago)

Located directly above Miracle Mile, the John Hancock Observatory offers stunning views of the city skyline and Lake Michigan. I recommend going in the evening to enjoy cocktails while you’re high up in the sky looking down on the city below. I’m not even kidding – even the view from the bathroom is this stunning.

From the Road I'm On - John Hancock Observatory

6. Firecakes Donuts

One of my favorite treats in Chicago came as a surprise I stumbled upon while walking down the street. I’m a sucker for small-batch donuts and apple cider, and Firecakes delivered on both of these. I savored the apple cider as long as I could, both for its taste and a little extra warmth walking down the blustery blocks.

From the Road I'm On - Firecakes

7. The Berghoff

The Berghoff came highly-recommended from some local friends and family, so I was pretty excited when I got the chance to experience it. The Berghoff Restaurant opened in 1898, beginning as a men-only saloon that served free corned beef sandwiches with the purchase of a Berghoff Beer. I’d recommend stopping in for any beer fans or history buffs – pretty cool place!

From the Road I'm On - Berghoff

8. Gino’s East of Chicago

Last but not least, pizza. A trip to Chicago wouldn’t count without some iconic-deep dish pizza. Dating back to 1966, Gino’s East has been popular with locals, celebrities, and tourists alike. You can glance pictures of some of their most famous visitors’ pictures hanging on the walls, and the names of millions more etched into the walls of the restaurant that make for a very fun atmosphere.

From the Road I'm On - Gino's East

Published by From the Road I'm On

Hi friends, I'm Kim. I started writing at an early age, mailing short stories and song lyrics cross country to my favorite penpal, my grandfather. As a journalist and editor by profession, he didn't go easy on me and equipped me with revisions well beyond my years. I credit him with both giving me the writing bug, and challenging me to push my work. Since then, I've written anything and everything I can get my hands on. Articles, social media posts, songs, short stories, academic reports, to-do lists, journal entries, and everything in between. In addition to my own travel blog, From The Road I'm On, I am a regularly featured contributor for Visit Pittsburgh.

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