Chicago really does have it all—museums, restaurants, shopping, and the lake! The wide array of activities makes it the perfect place to find new and exciting places to go on a date. So whether you love the outdoors or want to settle in and see a theater production, Chicago has something for everyone.
Here are awesome first date ideas in Chicago:
If you haven’t been to The Chicago Theater yet, it’s time to plan a date there. It opened in 1921 and is grand in every sense of the word. From musicals to big name singers to comedians and more, check out upcoming events for something you and your date will enjoy.
You might be surprised the hiking opportunities in and around Chicago. Here is a map of different options from Backpaker magazine. Of course the Lakefront Trail is a fun and convenient place for a date walk, but why not venture out to new trails? The Cal-Sag Trail Run is also close but more rugged and winding.
Whether a romantic nature walk is in the stars for you and your date, or you both want to learn more about different plants, The Morton Arboretum is the perfect spot to start exploring. They even offer night time experiences with the trees all lit up. Don’t forget to bundle up!
What could be more fun than outdoor ice skating? At the McCormick Tribune Ice Rink, it’s free to enter and only $10 to rent skates. Even if your date is a shaky skater, no worries—make sure to hold hands.
Even if you’ve lived in Chicago a long time, you can’t get tired of Chicago-style pizza. How many are in the great Chicago area? Well, it’s time to find out and make a date of it! According to Chicago magazine, Coalfire is the best pizza in the city, but check out its best pizza in Chicago list for more options.
Chicago Cubs Fans
Show your Cubs pride and take your date to a game at Wrigley Field. Get dressed up in your fan gear, and don’t forget to bring a mitt—who knows? Maybe you’ll catch a fly ball.
Navy Pier is an easy and fun date. There are lots of things to do there, and in between you can walk the pier and gaze into the water. A visit to Navy Pier has to start with a ride on the Ferris wheel, and then you could move on and do a cruise, either sight-seeing or dinner.
You can’t get much better than Museum of Science and Industry. Why not check it out with a date? It has lots of exhibits to check out and even an Omnimax Theater with new and exciting shows.
Just the outside of the building is amazing, but step inside the Art Institute of Chicago and prepare to be wowed. Bring a date and explore the exhibitions and learn of artists near and far and all types of art, from paintings to photography to sculptures and more.
Plenty of TV shows are taped in Chicago, so head to a show with your date and be part of the studio audience! Steve Harvey, Jerry Springer, Judge Mathis… do a search and have some fun seeing how it all works and seeing a few stars in real life.