7 Fun Date Ideas in Chicago for you to try together...
While ours is not an exhaustive list of romantic things to do in Chicago, we think we’ve cherry-picked the best of the best! With a little something to suit every taste, time and weather, here are our top 7 fun date ideas, Chicago style...
1. Go Boating on Lake Michigan
Nothing beats a classic walk along the Lakeshore - or does it? For a fun date that's a little more active, hire a yacht or a powerboat and set sail on Lake Michigan. Countless boat hire companies offer you the chance to be the captain of your own ship for the day, though if you'd prefer something a little more relaxed, you can both take it easy on a scenic canal cruise through central Chicago instead.
2. Become Big Kids at Navy Pier
Don't dare think that you're too old for the good, clean fun of Navy Pier. There's so much to enjoy here; start off on the 150ft Ferris Wheel for fabulous views of the city and Lake Michigan, before taking a whirl on the carousel or putting your way to glory on the mini-golf course. Round off a jam-packed day in front of the big screen - Chicago's largest in fact - at Navy Pier's IMAX Cinema. See someone you know on the way? You could always claim you're off to see a play at the Chicago Shakespeare Theater. Better still, embrace the goofiness of this ever-popular Chicago fun date idea!
Looking to meet Chicago Singles? Check out our dedicated page
3. Follow in Capone's Footsteps at the Green Mill
This Uptown Jazz and Cocktail joint was reputedly Al Capone's favorite, and thought to be one of the oldest continuously running Jazz clubs in the States. An iconic venue for a date, soak up the history - and a couple of Martinis - together any night of the week; the Mill is home to world-class Trad, Contemporary and Improv Jazz throughout the year. With the bands often playing long into the early hours of the morning, there's every chance you'll catch the sunrise over the city together come dawn. To our mind, it's one of the best date spots in Chicago.
4. Get Your (Ice) Skates on
Of all the romantic things to do in Chicago during Winter, skating in Millennium Park is top of our list - and you don't have to be very good at it either! The family friendly rink welcomes all abilities, from seasoned professional to absolute beginner. The charming indoor rinks at Irving Park, Wilmette and Glenview give you the chance to Skate/Date year-round too. Either way, wear clothes you don't mind getting wet and treat yourselves with a warming, well-earned coffee afterwards.
5. Laugh it up at The Second City
There's no denying that of all our fun date ideas in Chicago, this may be the riskiest. While a night of fun and laughter sounds like a great idea in principle, there's always the chance that you won't have the same sense of humor at all. For many people this is a deal-breaker. That said, often it's those that share a sense of humor that stay together longest. Our recent study of America's funniest singles prompted our resident psychologist Salama Marine to say "Laughing together is probably the best sign of a healthy relationship". Find common ground here and you may just have found 'The One'.
Want qualified dating tips? Meet our resident psychologist Salama Marine