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Best Impromptu Activities in Chicago

Chicago offers a myriad of exciting last-minute activities, ensuring that spontaneous plans can be just as memorable as meticulously planned ones. Here's an overview of ten of the best last-minute activities to enjoy in the Windy City.


a person with a red shirt

OFF-SPRING: New Generations

Take advantage of our OFF-SPRING exhibit before it closes on February 27th! This thematic group exhibition of 100 multi-media artworks by 60 artists from around the world highlights how religious, cultural, familial, and personal rituals shape who we are and how and where we live, love, and learn.

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a person getting on a yellow truck

Street Food Exploration:

Dive into Chicago's diverse street food scene. Head to neighborhoods like Wicker Park or Logan Square to discover food trucks, pop-up stands, and local vendors serving up delicious bites.

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a large room with a large crowd

Comedy Club Night:

Check out one of Chicago's renowned comedy clubs for a night of laughter. Many venues offer last-minute tickets, providing a spontaneous and entertaining evening.

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a group of people playing instruments

Late-Night Jazz Session:

Immerse yourself in the city's rich musical heritage by catching a late-night jazz performance. Many jazz clubs, such as the Green Mill, offer impromptu shows.

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a city skyline with a sunset

Sunset River Cruise:

Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise. Hop aboard a climate-controlled vessel in the heart of the Magnificent Mile, and cruise along the river where your guide will point out architectural highlights.

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a person standing in front of a wall with graffiti

Pop-Up Art Installations:

Keep an eye out for pop-up art installations or gallery events happening around the city. Chicago's art scene is dynamic, and spontaneous displays can be found in various neighborhoods.

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a woman drinking from a glass

Bar Hopping:

Looking for a night on the town? We can’t blame you! Chicago has some of the Midwest’s greatest craft scenes. Enjoy a laid-back evening exploring Chicago's vibrant neighborhoods through casual bar hopping, where you can unwind with refreshing drinks and soak in the city's chill nightlife vibes. Start at Lure Fishbar in the lobby of the 21c Chicago and see where the evening takes you.

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a group of bicycles parked by a body of water with buildings in the background

Lakefront Bike Ride:

Catching a day of rays? Rent a bike and take an impromptu ride along Lake Michigan's shoreline. The lakefront path is beautifully illuminated at night, offering a refreshing and spontaneous outdoor experience.

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a statue of a lion with Art Institute of Chicago in the background

Chicago Museums:

Did our exhibitions spark museum mania? Chicago's museum scene is a diverse and vibrant tapestry, weaving together world-class institutions such as the Art Institute, the Field Museum, and the Museum of Science and Industry, offering visitors an enriching journey through art, history, and science in the heart of the city.

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a city skyline at night

Riverwalk Stroll:

Take a walk along the Chicago Riverwalk, enjoying the scenic views, public art installations, and the lively atmosphere of the waterfront.

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Whether you're in the mood for culture, entertainment, or outdoor adventures, Chicago's dynamic offerings ensure that there's always something exciting to do, even at the last minute.