Whether it’s your first date or fifth, making a lasting impression is key to building a strong and healthy relationship. When all you crave is something fun to break the ice – or you just want to bond over a new shared experience – a fun date in Chicago is just what you need!
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!
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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’.
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6. Grab a Deep-Dish Together
We all know well that a Deep-Dish Pizza will easily feed an average family of five for a week. That said, bonding over your favorite food is a ritual that every lasting couple must go through, and since the waiting time for a quality pie is around 45 minutes, you’ll be afforded plenty of time to get to know each other better. Don’t underestimate the power of the pizzeria when researching romantic things to do in Chicago. We’re big fans of the pizza at Chicago institution Gino’s East, where hundreds of couples have found love over pizza before, scribbling their names on its walls as a sign of their lasting devotion – to pizza, and each other!
7. Spend the Day at Lincoln Park Zoo
A great daytime activity, spending time together at Lincoln Park Zoo is easily one of our best fun date ideas in Chicago. Arguably the most popular zoo in the mid-west – and free to the public – Lincoln Park Zoo prides itself on the high quality of care given to all of its inhabitants. You’re sure to spot your favorite animal here, and whether you share a love of Lemurs or a passion for the Pygmy Hippopotamus (who doesn’t?) a date at the zoo is sure to be a memory that lasts a lifetime.
Need to find the right person to take on one of our top date ideas? Chicago is full of singles! Join EliteSingles today and discover your matches.