Whether it’s your first or fifth date, making a Fun Date Ideas lasting impression is key to building a strong, healthy relationship. When all you crave is a fun icebreaker, or you just want to bond over a new shared experience, a fun date in Chicago is just what you try together need! While ours isn’t an exhaustive list of romantic things to do in Chicago, we think we’ve picked the best of the best! With something YourChristianDate.com for every taste, time, and climate, here are our top 7 fun date ideas, Chicago-style…

Take a boat ride on Lake Michigan. – Fun Date Ideas

Nothing better than a classic Lakeshore ride, right? For a fun date that’s a little more active, rent a yacht or powerboat and set sail on Lake Michigan. Countless boat charter companies offer you the chance to be the captain of your own boat for the day, but if you prefer something a little more laid back, the two of you can take it easy on a scenic canal cruise through downtown Chicago.

Become Big Kids at Navy Pier.

Don’t you dare think you’re too old for the good, clean fun of Navy Pier. There is so much to enjoy here; Start on the 150-foot Ferris wheel for fabulous views of the city and Lake Michigan, before taking a spin on the carousel or winding your way to glory on the miniature golf course. Cap off a packed day in front of the big screen—in fact, the biggest in Chicago—at Navy Pier’s IMAX theater. See someone you know on the road? You can always say you’re going to see a play at Chicago’s Shakespeare Theater. Better yet, embrace the silliness of this ever-popular Chicago fun date idea!

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Follow in Capone’s footsteps at the Green Mill. – Fun Date Ideas

This Uptown Jazz and Cocktail venue was a favorite of Al Capone and was thought to be one of the oldest jazz clubs in America. An iconic date spot, soak up the history, and a couple of martinis together any night of the week; The Mill is home to world-class traditional, contemporary and improvisational jazz throughout the year. With bands often playing into the wee hours of the morning, YourChristianDate.com there’s a chance you’ll watch the sunrise over the city at dawn together. In our opinion, it is one of the best dating spots in Chicago.

Put on your (ice) skates.

Of all the romantic things to do in Chicago during the winter, skating in Millennium Park is at the top of our list, and you don’t have to be very good at it either! The family track welcomes all levels, from seasoned pros to absolute beginners. The lovely indoor rinks at Irving Park, Wilmette and Glenview also give you the chance to skate/hang out year-round. Either way, wear clothes you don’t mind getting wet, and enjoy a well-earned coffee afterwards.

Laugh out loud at The Second City. – Fun Date Ideas

There’s no denying that of all our fun Chicago date ideas, this one may be the most risky. While a night of fun and laughter sounds like a great idea at first, there’s always the chance that you might not have the same sense of humor at all. For many people, this is a deal breaker. That said, it’s often those who share a sense of humor that stick together the longest. Our recent study of America’s Funniest Singles led 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 have found ‘The One’.

Want qualified dating tips? Meet our resident psychologist Salama Marine.

Grab a bowl together.

We all know 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 all long-term couples must go through, and since the wait time for a quality cake is around 45 minutes, they’ll have plenty of time to get to know each other better. Don’t underestimate the power of the pizzeria when looking for romantic things to do in Chicago. We’re big fans of pizza at Chicago institution Gino’s East, where hundreds of couples have found love for pizza before, scrawling their names on its walls as a sign of their enduring devotion: to pizza and to each other!

Spend the day at the 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. Possibly the most popular zoo in the Midwest. And free to the public, Lincoln Park Zoo prides itself on the high quality of care provided to all of its inhabitants. You’re sure to find your favorite animal here. And whether you share a love of lemurs or a passion for the pygmy hippo (who doesn’t?). A date at the zoo is sure to be a memory to last a lifetime.


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