Eight Reasons to Get Outdoors This Summer

Regardless, it’s time to break out the shorts and sunnies and take to the great wide open.

Hence: eight outdoor adventures every Chicagoan should partake of this summer.

Included: getting lost in the country’s biggest cave system, a 100-foot-long party barge on Lake Michigan and riding the biggest, baddest Ferris wheel the Windy City’s ever hosted.

Party on Lake Michigan at the America’s Cup World Series
Your summer won’t be complete without witnessing multimillion-dollar wing-sailed yachts swapping paint at death-defying speeds. That’s what’s on deck when the world’s most legendary and oldest sailing competition comes to Chicago for the first time ever, bringing with it freshwater events like the Boater’s Bash, where you’ll get three sheets to the wind on a 100-foot-long party barge in the middle of Lake Michigan. You’ll wanna brush up on your sailing lingo here. All the good stuff is going down at Navy Pier. (June 10-12)

Navy Pier’s old Ferris wheel
Ride the Centennial Wheel at Navy Pier
Speaking of Navy Pier: while you’ve been staying a tourist arm’s-length away for years, our city’s biggest attraction has been making moves, and this summer’s a nice time to see what’s new. First: a bigger, better Ferris wheel. It opens Memorial Day weekend. Second: the food. In short, it’s respectable, some may argue destination-worthy. In addition to DMK Burger and Fish Bar serving up to-go booze, you’ve also got the Beverly’s legendary Original Rainbow Cone moving in. Bring the kids. (All summer long)

Pledge your allegiance at the Crosstown Classic
If there was any a time to catch the Crosstown Classic, it’s this year. Our beloved Cubs and Sox are only meeting four times this year, and if things continue to go as they’re going, we’re in for a helluva showdown. Because let’s be real: the whole city is dreaming of a Cubs-White Sox World Series. (July 25-28)

Picnic and chill at the Millennium Park Summer Film Series
Ferris Bueller’s Day Off turns 30 this year. You must see that. Other flicks of note: A League of Their Own, a full-moon double feature with Moonstruck and Silence of the Lambs, and Purple Rain presented by Sound Opinions at the Movies. (Tuesdays, all summer long)

Celebrate the Bard at Chicago Shakespeare in the Park
It’s been 400 years since Shakespeare’s death, and world is celebrating in a big way. So, too, Chicago, and there’s nothing better than catching a Shakespeare play en plein air. This summer, the Chicago Shakespeare Theatre company is performing Twelfth Night, and will be rolling to a park near you. Cost: zero dollars. Hit the Shakespeare 400 Chicago website for other ways to celebrate history’s greatest playwright. (All summer long)

Run, bike and utilize The 606
New bike repair stations on the 606 give you more reason to bike it. But you should run it. Walk it. Take advantage of it. The neighborhood-friendly elevated park is celebrating its one-year anniversary in June, and there’s perhaps no better way to experience its splendor than a massive three-mile-long block party. (All summer long)

View art and drink in Downtown alleys at Activate
Presented by the Chicago Loop Alliance, Activate returns with full-blown art-centric pop-up alley parties you don’t wanna miss. When else can you drink in Loop alleyways for free, and legally? Goes down once a month until October and kicks off on May 13th. (All summer long)

Salute our National Parks by spelunking Mammoth Cave
The National Park Service turns 100 this year, and what better way to celebrate than road tripping to the closest one to Chicago? That’d be Mammoth Cave, right outside of Louisville, Kentucky. It’s the world’s largest known cave system, with over 400 miles explored. (All summer long)

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This is but only one installment of 37 Things a Man’s Gotta Do This Summer, our annual compendium of everything worth seeing, doing, eating, drinking and generally making time for in your neck of the woods between now and September