8. South Haven
Located on the shore of Lake Michigan at the mouth of the Black River, South Haven was once known as "the Catskills of the Midwest" and also "the Jewish Brigadoon," as the resort crowd that flocked there every summer in the first half of the 20th century was predominantly... Irish Catholic! Kidding, they were Jewish. So there you go, some history.
South Haven has seven public beaches and a great view of the South Haven South Pier Lighthouse (another lighthouse!), but before you check them out, start your day at Café Julia for a specialty coffee and homemade pastries. Later, grab a glass of wine and a cheese plate at Channel Wine Bar for lunch, then share small plates and sip on cocktails at Taste for dinner. Sure, Chicago visitors will loudly remind everyone within earshot that none of these places are AS GOOD AS CHICAGO, but that's because Chicagoans are the absolute worst.
All of the beaches in Manistee are public and they're the big, beautiful kind of beaches that are full of sugary-soft sand. Oh, and if you like impossibly charming historic buildings lining a quintessential American Main Street, or cute riverwalks (and cute bridges, and cute marinas, etc.), and if you just want to miniaturize it all and put it in your pocket to keep with you forever to make you smile when you're feeling blue, then Manistee is for you. Unfortunately, the dining and drinking culture -- and man, this pains us to say -- leaves a lot to be desired. SO CLOSE, MANISTEE.