Embrace the summer at a tiki bar
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. Three Dots and a Dash and Lost Lake are among the most famous in the city, but alarmingly fun times can also be had outside city limits at popular suburban hangs like Hala Kahiki and Chef Shangri-La.
Get smart at a boozy bookstore
A bookstore may not sound like the most exciting date in the world, but places like Lincoln Park’s Kibbitznest are tailor-made for summer. With a front room stacked with newspapers and magazines, a bar stocked with everything from Chicago dogs to Irish coffee, and a back game room, a quick stop in from the heat here can quickly turn into three hours gone by in a flash.
Road trip to New Glarus or Geneva
Remember how nice it was when you didn’t have to spend 20 minutes brushing and scraping snow and ice off your car and shoveling a pathway out of your parking spot? Of course you do, because the time is now! Enjoy the great open highway with the windows down and show your date a change of scenery. 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.