Driving time from Chicago: One and half hours
Getting to the Cream City requires a painless drive, but if you plan to fully indulge, ditch the car and hop on the BYOB-friendly Amtrak, which will deposit you in the heart of the city in an hour and a half. Start your day with a stack of pancakes and a round of mimosas at Sweetdiner. Meander around the Historic Third Ward and hop into home decor shops like The Home Market or fun specialty shops like MOD GEN. Seek refuge and treats at the Milwaukee Public Market, where you’ll find a hodgepodge of the city’s best vendors, including blends from The Spice House, seafood from St. Paul Fish Company, hand-dipped chocolate from Kehr’s Candies and vino from Thief Wine Shop & Bar. Before catching a train home, walk off the day with a trek along to Lakeshore State Park, a unique 22-acre urban oasis that juts out from the shoreline.