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The Chicago Good Life’s Top Picks for May 2025

Chicago Good Life 4/23 9:34A thechicagogoodlife
Hey Chicago! May 2025 is starting to get busy again. Start with the AAPI Food Crawl in Wicker Park, then enjoy Mexico Fest at Navy Pier and the Lincoln Square Ravenswood Wine Stroll. Don’t forget Kids...

FORE! It’s par-tee time.

Once Upon a Dollhouse 4/18 9:09A Dollhouse
With a natural swing and a love for the game that bloomed before he could even walk, Teddy Freddy brings joy to everyone he encounters. But watch out—you might just get caught in his contagious giggle...

Where to Shop Local for Mother’s Day Gifts

Chicago Good Life 4/16 6:15A thechicagogoodlife
FourSided ENJOY, an Urban General Store As Mother s Day gets closer, we wanted to highlight the plethora of unique boutiques Chicago offers! Beyond the usual retail giants, Chicago s diverse...

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Surf Ocean-Like Waves

Chicago Magazine 4/29 1:00A Chicago Magazine
St. Joseph, MichiganDrive time: 1 hour 35 minutes While Sheboygan is often billed as the Malibu of the Midwest, you’ll find equally good waves more consistently on the other...

Shred Sand Dunes

Chicago Magazine 4/29 1:00A Chicago Magazine
Mears, MichiganDrive time: 3 hours 30 minutes The Silver Lake Sand Dunes straddle 2,000 acres of mesmerizing slopes between Lake Michigan and Silver Lake, with 450 of those...

Mountain-Bike Some of the World’s Best Trails

Chicago Magazine 4/29 1:00A Chicago Magazine
Duluth, MinnesotaDrive time: 7 hours Nestled on Lake Superior’s coastline, Duluth offers more than 90 miles of bike trails. That’s impressive enough, but what really sets it...

Camp Under the Stars

Chicago Magazine 4/29 1:00A Chicago Magazine
PENFIELD, ILLINOISDrive time: 2 hours About 45 minutes northeast of Champaign lies the Middle Fork River Forest Preserve, the only designated International Dark Sky Park in...

Nail Your Whitewater Rolls

Chicago Magazine 4/29 1:00A Chicago Magazine
Wausau, WisconsinDrive time: 4 hours 15 minutes There are few better places to learn to kayak rapids than Wausau Whitewater Park. It spans a third of a mile of the Wisconsin...

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