Local Confessions: Fun Places in Chicago

fun places in chicago

I had a feeling about the city of Chicago from the moment I booked my flight. The feeling was hard to unpack, but it’s a feeling I hadn’t yet had about any other place I’d traveled. Maybe it was the whisper of Al Capone calling my name, the classic photo taken with the Bean, or the thought of eating a hotdog at a Cubs game. These were all things that have long been on my bucket list—until now. 

Our trip to Chicago showed me what true Midwest culture is like, through food, cocktails, and experiences galore. This article is a hotlist of places that were all recommended to me by locals and friends alike, and I got to experience quite a few of these fun places in Chicago for myself. So without further adieu, keep reading to see what makes this city so great.

Chicago’s Restaurant Scene

fun places in chicago
Glazed duck wings, served with soul at Wood in Boystown.

From restaurants on the water to rooftop extraordinaires, you’re sure to find any cuisine in an atmosphere that piques your curiosity. Choosing between neighborhoods like West Loop, Pilsen, and River North—to name a few—you can keep things simple with Mediterranean shared plates, or go more elaborate with meat dishes carved tableside. Regardless of which restaurant you choose, you can always find a delicious meal with an equally captivating ambiance.

UPSCALE RESTAURANTS:

CASUAL CUISINE:

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Chicago Coffee Shops

fun places in chicago
Starbucks gets creative: coffee & cocktails combined.

In a windy city like Chicago, you’ll want a hot coffee to keep you warm while you explore. The coffee scene is anything but shy here, boasting more hole-in-the-wall joints than one can fathom. But the king contender who will forever leave a lasting impression on me during my trip to Chicago was none other than the three-story Starbucks Reserve Roastery!

COFFEE SHOPS:

P.S. If you’re not a fan of the cold, don’t forget to snag one of these fuzzy coats for women or men.

Chicago Nightlife

fun places in chicago
Pretend like the Prohibition never existed—only at Al Capone’s old hangout spot, the Green Mill.

Don’t underestimate how much excitement a city’s nightlife can bring to a place. Once I realized bars don’t close until 4 a.m. and beyond, let’s just say Chicago felt like my oyster. If you’re a night owl, this city offers more karaoke bars, Irish pubs, and picturesque cocktail bars than you could try to drink in a single bar crawl. If you’re looking for fun places in Chicago, the list below is like seeing the city from a bartender’s POV.

LOCAL’S FAVORITE BARS:

Chicago Experiences

fun places in chicago
Soak up every minute of Chicago’s stunning skyline on this local River Boat Architecture Tour.

What would a city be without fabulous outdoor activities, tours, and culture for days? If this is top of mind, you won’t be disappointed when it comes to experiencing fun places in Chicago. The River Boat Architecture Tour was one of my favorite attractions in the city. Why? It was fascinating to hear the stories of how the city’s skyline came to be. 

FUN THINGS TO DO:

Bonus: Halloween in Chicago

When we decided to book our trip to Chicago on a Halloween weekend, that’s when I knew we were in for a treat. The city was packed full of locals, ready to mingle and hang out. Just the energy alone was enough to make our Airbnb stay in Boystown feel like the mecca of Chicago. The neighborhoods listed below are a few that we explored on Halloween weekend—recommended to us by the locals as great spots for nightlife.

HALLOWEEN HANGOUT NEIGHBORHOODS:

  • Wicker Park (Personal favorite!)
  • Bucktown 
  • River North
  • Boystown
  • Wrigleyville
  • Humble Park 

Check out this interactive map of Chicago’s neighborhoods 📍

As you can see, there’s more to Chicago than any traveler could have imagined in a single trip. More spontaneity, class, culture, and history than a Midwesterner would like to admit—seeing that their city has been and always will be a hot destination. While it was my first trip to Chicago, this just goes to show that each time you visit can be a different experience. From deep dish to prohibition-style jazz clubs—this city has it all.

Ciao, 

Sydney

P.S. For more tips on how to travel like a boss when visiting fun places in Chicago—hit this link.