Chicago is renowned for its distinguished museums, varied architecture, and world-class dining. If you’re new to Chicago, it may be more 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, 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.

(If you’re moving to Chicago, you can get a free personal assistant to help with your move! Learn more here.) We’ve also curated a list of the top apartments near the Chicago Blue Line so you don’t have to worry about traffic and parking in this bustling city.


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 Ukranian Village, come for the music, stay because it’s the funkiest scene in Chicago. This 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 it’s 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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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— cans and bottles only— however, the fact that you can get 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 this your new favorite spot.

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Check out our list of the top 5 Chicago breweries that are a must-do for touring Chicago like a local!


Cheap Eats

Winner: Jim’s Hot Dogs

Feeding hot dog fans since the 80’s, this Chicago eatery is a must during late nights on the town, mid-day walking tours, or winter snow storms. If imitation is the sincerest form of flattery, then Jim’s 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-star restaurant is the pinnacle of fine dining and 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. Their 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 something for everyone. Fluffy ‘blisscakes’ (must order), savory sandwiches, and all-around delicious food will make this spot a new favorite.

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Day-time Activities

Winner: Garfield Park Conservatory

One of the largest botanic 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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Whether you’re new to Chicago or have lived here your entire life, we can all agree that it’s a great place to call home. With so many vibrant and varying locales, there’s certainly no shortage of things to do or new spots to uncover. We hope you added a few things to your Chicago Bucket List! Let us know in the comment section if you tried anything new after reading.

Reach out to AptAmigo anytime if you’re moving to/within Chicago and want to know how we can help make your move an absolute breeze.