The dating scene in Chicago can be eclectic and exciting. As a single socialite in Chicago, there are plenty of opportunities to meet new people and go on fun dates. In fact, 33% of the population in Chicago is single! Whether you are single or just dating around, here are three popular dating (and meeting) spots in the city:


For a low-key night out, there are a host of different festivals in Chicago all throughout the summer months. Whether you are looking for good food, music, culture or art, here are a few of the must check out:

Taste of Chicago – the city’s beautiful Grant Park is the place to be for the world’s largest food festival with live music. This event has been held in July every year since 1980.

The Boulevard– a summer party with a Brazilian flavor. Enjoy food, music, dance and art at Logan Square, in August.

Chinatown Summer Fair– what fun to watch the dragon and lion dance procession, while enjoying Chinese food, music, arts and crafts.

Act Like a Tourist

There’s nothing wrong with exploring the city and acting like a tourist for a day. Take a stroll around Millennium Park (or picnic and watch one of their outdoor concerts), hop on or off the trolley, ride the Sears Tower and take selfies from 110 stories up, take  a river cruise, visit the art museums and aquarium and just goof off like a big kid. You only live once!

Da Bears, Da Bulls

Depending on the time of year, Chicago is a sports lover's dream city. You can always find a game to watch in the Windy City. Have fun watching the Bears, the Bulls, the Cubs, the White Sox, or the Blackhawks. Put on your fan gear, grab some cold beers for tailgating, and head on down to the stadium.

Chicago Mingles Beer Cheers at Brewery
Chicago Mingles Beer Cheers at Brewery

For more great date night ideas, follow Cupid’s Cronies Chicago Matchmaker on Facebook and Twitter.