The lake isn’t the only waterfront in Chicago, though.If you’re in the Loop anyway, pick a spot along the quickly-developing Chicago Riverwalk to grab a drink and a bite with your date.Hit up Geneva for some gorgeous waterfront drinking, New Glarus to enjoy “America’s Little Switzerland” (and lots of yummy beer), or any of a slew of other options.
There is perhaps no easier summer date than at one of Chicago's fine tiki bars: immediately fun and tropical, the only way you can screw this up is to start talking politics.
But is there anything more romantic than the 100-year-old theaters in the Loop Theater District, like the CIBC for you high-roller Show off how cool you are with your in-depth knowledge of Chicago’s secret bars.
Since knowing that the mural on Damen in Wicker Park opens up to Violet Hour is no longer considered insider information, Booze Box is a sexy bet, The Office is uber-swank, and East Room is not technically secret but does lack proper signage.
Chicago may not be known as a gambling mecca per se, but the city is surrounded by a variety of casinos that can make for a fun alternative to the standard dinner-and-a-movie routine.
Hit up suburban casinos like Rivers Casino, Harrah’s, and Grand Victoria, or ride the shuttle to places like Horseshoe Hammond and try to get lucky in more ways than one.