Neighborhood: Near North Side
Address11 E. Ohio St.
Website: acmehotelcompany.com 

The Berkshire Room is a swanky lounge in the ACME Hotel, and the perfect spot for gin-fueled canoodling. Typically, hotel bars have a shady connotation that you wouldn't associate with a first date, but this place is as amiable a spot as you'll find downtown. Go for the Dealer's Choice—a DIY drink option that puts a cocktail's spirit, flavor profile, and glassware in your hands—because it's the perfect opportunity to kittenishly debate your new plus-one.