A 20-Something’s Guide to the Windy City

The best part about a big city is the new adventure that awaits each time you visit.

Although I’m still very much a tourist in Chicago, I’ve developed a list of my own favorite things to do in the Windy City, as well as the things I’ve personally found to be underwhelming and overrated. So while my suggestions are far from an end-all-be-all guide to Chicago, here is how I enjoy those long-weekend trips to the Windy City, from one young twenty-something to another.

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The Chicago River, in the center of the city

Contrary to popular belief, there are, in fact, some delicious restaurants outside the stereotypical realm of Chicago-style deep-dish pizza and hot dogs. One must-try that you can’t go wrong with is a solid burger joint: 25 Degrees. Stop by for breakfast, lunch or dinner and I can guarantee you won’t be disappointed. They serve a full bar for every meal and are known for their milkshakes, particularly spiked ones.

Once you’ve entered a substantial food coma, it’s time to walk off that big meal and hit the town. I personally say skip the giant bean sculpture at Millennium Park and head over to Chicago’s charming museum campus. With Shedd Aquarium, Adler Planetarium and the Field Museum of Natural History all in one spot, there is something to pique everyone’s interest.

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My boyfriend and me outside Shedd Aquarium
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…and again the following summer

If you happen to travel to Chicago during the summer months, my number one spot is always the beach. Wait, Chicago has a beach?! Located along beautiful (but chilly) Lake Michigan, Chicago is home to quite a few beautiful sandy beaches. Oak Street Beach is a favorite among both tourists and locals, and even has an outdoor bar and restaurant.

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Oak Street Beach

After you’ve gotten your full intake of vitamin D, stroll alongside Lake Michigan and head over to Navy Pier, just about a 20-minute, scenic walk. The view from the pier is breathtaking. Ride the Ferris wheel or take a boat tour and snap some spectacular photos.

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Girls’ trip at Navy Pier
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View of the city from a boat tour at Navy Pier

As far as nightlife goes, Hubbard Street in River North is the place to be. Tons of bars and clubs line this strip, all with their own flair. Howl at the Moon is a super fun, unique spot with live music and dancing. The first time I went, I watched the pianist rap the entirety of The Real Slim Shady by Eminem without missing a beat — he totally killed it. The tune then switched to an Elton John cover — another personal favorite. That being said, this is a place for music lovers of all genres to enjoy. If you’re into a more upscale bar or club with a DJ, Rockit is another solid choice with two floors of music and dancing.

Like I said, I’m still very much a tourist in Chicago. Some places still at the top of my list to visit include the Museum of Contemporary Art, which is said to be Chicago’s top attraction (How have I still not been?!), and a tour of Goose Island Brewery (for all your craft beer lovers like me). With so many things to do and new places to try, Chicago is one destination that never gets old.

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Lake Michigan at Oak Street Beach
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