How to Spend Labor Day Weekend in Chicago

Making the most of the last long weekend of summer looks a little different this year. But that doesn’t mean it can’t still be a memorable one. Savor the last days of late sunsets, long daylight hours, shorter workweeks, and bearable temperatures in the Windy City with these fun, seasonal activities available to Chicago’s residents and local visitors. We know that many of these activities have been altered to ensure safety guidelines and measures are taken but note that keeping a safe distance from individuals and groups as well as wearing a mask at all times is an added measure that you can control! We’ve aimed to select activities that are conducive to these precautions. 

Drive-in movie

Swim in the lake


Rent a boat, paddle board, or kayak


Rent bikes or scooters and do a neighborhood tour

Visit a museum 

Visit the nation’s largest rooftop patio bar


Take a hike at one of these nearby trails


Go on a boat tour

Picnic in Millennium Park, or sip sitting along Chicago’s River Walk

Visit a greenhouse, conservatory, or botanic garden

See bees in action in Pullman and score local honey

Movie in the park

Take a cocktail class


Attend Jazzfest virtually

Visit an outdoor beer garden

Visit a massive sunflower field


Inddulge at Lobster Fest



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