Asking someone out takes guts. So give yourself props. The worst part’s over. Now the next question is, where do you go on your date? Even if you’re already in a relationship, it can be tough to come up with fun things to do in Chicago, but we got you covered. So iron your shirt and put on a nice pair of Oxfords. It’s time for Date Night: Chicago Edition.
Ballast Point Rooftop
Grabbing drinks at a brewery is always a nice choice for first dates or couples seeking new spots to explore. Opened in Summer 2018, Ballast Point hosts a beautiful rooftop in Chicago’s West Loop. Take a tour of the tap room or sit back and sample their expansive selection of craft beers while admiring a view of the city.
212 N Green St.
Chicago, IL 60607
Why go to dinner and a show when you can be part of the entertainment? This vintage lounge known for its intimate setting and drink specials hosts karaoke nights seven days a week. Get to know your partner based on their song selection and grow a little bit closer with a fun duet. For more speakeasies in Chicago, read our journal here.
343 S Dearborn St.
Chicago, IL 60604
Take your date on a romantic walk through this exotic park on Chicago’s southside. Also known as Garden of the Phoenix, this beautiful piece of Japanese scenery is hidden within Jackson Park, just east of the University of Chicago. Designed in 1934, the garden features cherry blossoms, stone lanterns, and a waterfall for a serene escape from the boisterous city life.
6401 S. Stony Island Ave.
Chicago, IL, 60637
War of the Worlds – Live!
In the mood for a show, but don’t feel like sitting in the same old movie theater? Relive the War of the Worlds broadcast that caused mass hysteria across the country 80 years ago. On Tuesday, October 23rd, Harold Washington Library will host a live performance of Orson Welles’ radio play in their auditorium as part of One Book, One Chicago. For even more free date night shows and screenings, check out the complete list of upcoming events on the Chicago Public Library’s website.
Harold Washington Library Center
Cindy Pritzker Auditorium
400 S State St.
Chicago, IL, 60605
Drink Date Laugh!
Come on, we already know you’re going to embarrass yourself. Why not do it in public? Every Friday, Laugh Factory presents Drink Date Laugh! where comedians share their awkward dating stories and pull audiences into the fun by asking them questions about their love life. It’s all in good spirit and everyone gets a laugh out of it. What better way to get humiliating dating stories out of the way than by announcing them to a cheering crowd?
Laugh Factory Chicago
3175 Broadway St.
Chicago, IL, 60657
2nd Fridays Gallery Night
Delve into Chicago’s rich art culture by visiting the Chicago Art District located in Pilsen. 2nd Fridays Gallery Night is free to attend and fun to explore with any partner harboring a creative side. Together, you can marvel at the displays and get to know the artists behind the fantastic creations.
1945 S Halsted St.
Chicago, IL, 60608
Perhaps the most classic plan for a date is dining along Chicago’s Riverwalk. Take in the scenery as you enjoy fine steak and drinks at Wollensky’s Grill in the heart of Chicago. Their glass-encased dining room above the river offers a beautiful view of the city skyline accompanied by a casual environment. End the night by taking a stroll along the Riverwalk and share a kiss under the glow of the city lights.
318 North State St.
Chicago, IL, 60654
Got any more great ideas for a date night in Chicago? Leave us a comment and also let us know if any of these worked out for you. Good luck!