Fall in Love With 7 of the Best Date Ideas in Chicago

Happy couple standing outdoors and enjoying one of the best date ideas in Chicago.

Choosing between the best date ideas in Chicago isn’t always easy. The city has so much to offer, from romantic restaurants to outdoor experiences to fun couple activities. But, this vast choice can make things feel overwhelming for Chicago singles who’re looking to organize the perfect date.

That’s why EliteSingles is here to help! If you’re on the hunt for some of the best date spots in Chicago, you’ve come to the right place! Whether it’s for a first date with an exciting new match or a monthly date night with a long-term partner, we’ve put together seven of our favorite date ideas in Chicago below!


What Are the Most Popular Date Spots in Chicago? 7 Top Picks

Whether it’s your first date or fifth, making a lasting impression is key to building a healthy relationship. When all you crave is something fun to break the ice — or you just want to bond over a new shared experience — it’s worth having a few fun date ideas in Chicago up your sleeve. Below, picked some of our all-time favorites! With a little something to suit every taste, time, and weather, here is our choice of seven date ideas, Chicago style…


1. Go Boating on Lake Michigan

Nothing beats a classic walk along the Lakeshore – or does it? For a fun Chicago date idea 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 a ship for the day. Although, 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 with 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 date spot in Chicago!


3. Follow in Capone’s Footsteps at the Green Mill

As far as first date ideas in Chicago go, this one is hard to beat. The Green Mill Cocktail Lounge was reputedly Al Capone’s favorite and thought to be one of the oldest-running jazz clubs in the States.

It’s a truly 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, and, 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 date ideas in Chicago, 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 professionals to absolute beginners. The charming indoor venues at Irving Park, Wilmette, and Glenview are also some of Chicago’s most popular rinks since they give you a chance to skate and date year-round too. Either way, wear clothes you don’t mind getting wet and treat yourselves with a warming, well-earned coffee afterward.



5. Laugh It up at The Second City

There’s no denying that of all our 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 who stay together the longest. Our 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’.


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 enjoys. And, since the waiting time for a quality pie is around 45 minutes, you’ll have plenty of time to get to know each other better. Don’t underestimate the power of the pizzeria when researching date night ideas in Chicago.

We’re big fans of 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 favorite Chicago date ideas. 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 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 offer the perfect start to a long-lasting connection.


Pick Your Favorite Chicago Date Ideas!

With so many potential date ideas in Chicago, it can be difficult to choose just one. Why not pick a couple of your favorites from the list above and try them out on your next date? Need to find the right person to take on one of our top Chicago date spots? Join EliteSingles today to start making meaningful connections with like-minded singles!

About the author: Michael Middleton

Michael Middleton is an editor for EliteSingles.

See more articles written by Michael Middleton