How to get there: Metra UP-N line from Ogilvie Station, 51 minutes
Why you should visit: With former resident Michael Jordan and current resident Billy Corgan (who operates a tea shop/art studio in town called Madame ZuZu’s), Highland Park is packed with beautiful lakeside homes and filming locations that have made their way into many classic ‘80s films from Ferris Bueller’s Day Off to Sixteen Candles to Risky Business. These days the town offers a lively Downtown scene, two beaches, several golf courses, and plenty of bars in nearby Highwood. But one of the best things to do here is take a leisurely drive down scenic Sheridan Rd (which winds through several posh North Shore suburbs) before stopping off for an outdoor summer concert at iconic venue Ravinia.
While you’re here: Just across the border from Highland Park is the town of Glencoe, home to the utterly beautiful, date-worthy, and, somehow, free) Chicago Botanic Garden.