Chicago is renowned for its distinguished museums, historical architecture, and world-class dining. If you’re new to Chicago, it may feel difficult to decide what not to do each weekend — spring and summer usher in street festivals, open-air markets, outdoor concerts, and more. While the colder fall and winter months welcome plenty of indoor activities with countless theaters, music venues, bars, and restaurants. There’s plenty to do in the Windy City, so we put together a quick summary of some of our favorites below to help you tour Chicago like a local.
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How to Tour Chicago Like a Local
Live Music
Winner: Empty Bottle
For almost 30 years, this tiny music hall has occupied the corner of Cortez and Western Ave. What started as a 90s-era dive bar with cheap beers, good music, and a laissez-faire attitude towards most everything, remains to this day, more or less, the same. Nestled in the quaint Ukrainian Village, come for the music, stay because it’s the funkiest scene in Chicago. The Empty Bottle is where artists like the Smashing Pumpkins, Smith Westerns, and OKGo played Chicago before they “made it.”
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Movie Theater
Winner: Music Box Theater
This historic theater stands tribute to Chicago’s colorful past and its unique architecture. Opened in 1929, Music Box Theater is best known for showing a variety of films, from cult classics to repertory films to first-run flicks. Midnight showings of “The Room” are a regular occurrence.
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Cocktail Bar
Winner: The Aviary
The Aviary takes the term “craft cocktail” to new heights. Way more than just beautiful and delicious, each cocktail is an event. These highly trained bartenders are true artists and masters of their craft. From the thoughtfully delightful recipes, to the rare spirits and the spectacular presentation, drinks at The Aviary are much more than drinks, they are works of art.
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Related: The Best South Loop Bars
Dive Bar
Winner: Richard’s Bar
Cheap beer, tin ceilings, and the best conversations in town. This quirky bar has the charming ability to make anyone feel right at home. No beers on tap though — cans and bottles only. However, the fact that you can order a boiled egg served in a shot glass for only 75 cents more than makes up for it (we think?). At any rate, the great hours, convenient location, and “come-as-you-are” attitude will surely make Richard’s Bar your new favorite spot.
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In addition to dive bars, check out our list of the top 5 Chicago breweries.
Cheap Eats
Winner: Jim’s Original
Feeding hot dog fans since 1939, this Chicago eatery satisfies your junk food cravings during late nights on the town, midday walking tours, or winter snow storms. If imitation is the sincerest form of flattery, then Jim’s Original has certainly inspired plenty of others. However, none of the others are hailed as “the best dog in Chicago” as frequently as Jim’s.
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Fancy Eats
Winner: Alinea
To call Alinea a restaurant would be an understatement. Alinea is a culinary experience: equal parts cuisine, performance, art, and emotion. This three-Michelin-starred restaurant represents the pinnacle of fine dining and remains a must for any food enthusiast.
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Coffee
Winner: Groundswell
This welcoming coffee shop greets guests with a smile and a perfect cup of coffee. Groundswell‘s coffee is single origin and expertly roasted, but remains affordable, drinkable, and approachable.
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Chicago-Style Pizza
Winner: Pequod’s
Few things in Chicago are more hotly debated than where to get the most authentic Chicago pie. So, in order to avoid a riot, we’ll just say that our favorite is Pequod’s. Perhaps it’s the caramelized crust, or maybe it’s the extra-cheese-extra-sauce mentality. Whatever it is, the food is so good that no one seems to mind (or even notice) a long wait.
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Brunch
Winner: m.henry
Everyone needs a go-to brunch spot, and m.henry will surely become yours. Stop by this Andersonville eatery for prompt service, a casual atmosphere (patio seating, too!), and a menu with options for everyone. Fluffy “blisscakes” (must order), savory sandwiches, and all-around delicious food will make this spot a new favorite.
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Daytime Activities
Winner: Garfield Park Conservatory
One of the largest botanical gardens in the nation, this conservatory is a perfect escape from the bustle of the city. Home to thousands of plant species, the Conservatory consists of eight indoor gardens. Next time you find yourself asking, “What should we do this weekend?,” stop by Garfield Park Conservatory.
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Tour Chicago Like a Local Every Day
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* The original version of this article was first published on March 19, 2019.
