I’ve lived in Chicago for over a decade now and have seen so many changes take place over the past ten years. The city is constantly evolving, with new shops, restaurants, museums, and attractions that pop in and out of the city on an ongoing basis. As a local, I will say that the best experiences are better off the beaten path, but I do appreciate a consistent unhidden gem or two—and many other localsfeel the same.
In this post, I’ll provide an insider’s guide to Chicago, highlighting some of the best things that locals love most about the city. Whether you’re a first-time visitor or a seasoned Chicagoan, this guide will help you explore the city like a true insider.
Eat and Drink as a Chicago local
- Grabbing tasty cocktails and delicious bites at these cool after-work spots in the West Loop or Downtown.
- Sampling Chicago favorites like Pączki or Conchas from a famous bakery.
- Lounging at aspeakeasy or secret bar.
- Dining on rich Italian dishes from popular restaurant gems likeSapori Trattoria.
- Indulging in the quintessential summer dessert, like a frozen treat from an Italian ice spot.
- Sampling a hardy selection of dim sum and other treats in Chinatown.
- Ordering a thin-crust tavern-style pizza from Italian Fiesta or other neighborhood hot spots.
- People watching or keeping it lowkey late-night at thePeninsula Hotel.
- Sampling the best tacos in the city in the Pilsen or Little Village.
- Slurping on the best ramen bowlsin Chicago in hidden spots and easy-to-find places.
- Quenching thirst with beer from a local brewery.
- Grabbing a drink from a quaint and cozy neighborhood bar.
- Pouring endless breakfast beverages at popularbottomless and boozy brunch spots.
- Dining on dishes fromblack-owned bars and restaurants around Chicago.
- Grabbing a large group of friends and hitting up a hiproof top bar.
- Scarfing down a Chicago dog or Italian Beef—they’re not just for tourists.
- Celebrating any occasion at a colorful Chicago restaurant.
Activities and Unique Things to Do
- Grabbing the best seat in the house at an iconic movie theater during a chill date night.
- Waking up early and taking a long bike ride down Chicago’s lakefront.
- Shopping for trendy threads at alocal boutique.
- Cheering for any Chicago sports team in the stands all year long.
- Taking social media-worthy photos at an experiential museum
- Spending the afternoon exploring a new Chicago neighborhood.
- Visiting a neighborhood coffee shop and sampling the best items on the menu.
- Laughing out loud to witty jokes at a local improv or comedy show.
- Finding a new novel at a local bookstore.
- Learning something new at an immersive museum.
- Experiencing the ultimate date night experience at a Candlelight Concert.
- Grabbing a few treats and catching a free movie at one of Chicago’s many parks.
- Cruising with ease down Lake Shore Drive on a warm summer night.
- Finding unique goods from locals at a community market.
- Grabbing a group and setting sail on a boat on Lake Michigan.
- Playing mini golf at the localmini golf course.
- Experiencing something new at a street festival.
- Interpreting art while visiting local art galleries.
- Discovering new and emerging talent atneighborhood theaters.
- Elevating an outdoor run on the 606 Trail.
- Sitting in serenity at a hidden park or garden.
Experiencing Chicago As a Local
Experiencing a city like a local requires time and effort. To truly be a part of a community, you have to engage with others in real life, be willing to step out of your comfort zone, and be open to something new and different. Once you do this, you open yourself up to hidden gems and encounter people, places, and things you would’ve never dreamed of. By taking the time to explore some of the local favorites highlighted in this guide, you’ll be able to experience the city like a true insider, discovering some of the best spots that Chicago has to offer. So whether you’re a longtime resident or a first-time visitor, make sure to add some of these local favorites to your Chicago itinerary – you won’t be disappointed!
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