A 20-Something’s Guide to Chicago

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 20-something to another.

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The Chicago River in the city center

Contrary to popular belief, there are, in fact, some delicious restaurants beyond the stereotypical fare 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. Located on North Clark Street in River North, it’s situated right near Chicago’s most bustling strips with shopping, attractions, nightlife and more. Stop by for breakfast (I hear they have an awesome brunch menu), 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. Plus, it’s another spot to catch a great view of Lake Michigan.

shedd aquarium
My boyfriend and me outside of Shedd Aquarium

When traveling to Chicago during the summer months, my number one spot is always the beach. Wait, Chicago has a beach?! While it’s not a secret to everyone, I’ve noticed many visitors are surprised to find there are East Coast-esque beaches right smack dab in the Midwest. Located along beautiful (but chilly) Lake Michigan, Chicago is home to quite a few beautiful sandy beaches that are perfect for sunbathing and taking cool dips in the freshwater lake. Oak Street Beach is a favorite among both tourists and locals, and even has an outdoor bar and restaurant with standard bar fare. My only advice: Don’t drink too many margaritas on an empty stomach. You’ll probably fall asleep on the beach and wake up cranky with a hangover from hell. (Not speaking from personal experience or anything. Hehe.)

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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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Beautiful view of the city at sunset 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 of mine.) 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.

What are your favorite spots to visit in Chicago? Share in the comments below!

Also, keep an eye out for my upcoming Chicago restaurant guide for yummy dining suggestions for your next trip!

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