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Looking for date ideas in Chicago?

Chicago is one of the largest cities in the US. Sometimes referred to as the windy city, Chicago is known for its museums - The Art Institute of Chicago being one of the largest. Chicago has an average of 86 million visitors per year, many of which are attracted to the 3, 000 hectares of city parks. There are 77 distinct neighborhoods within Chicago, all of which reflect the hardworking values of American community. Chicago is also known for it’s passionate sports fans for teams such as the Blackhawks, Cubs, Bears, Blackhawks, Bulls, and White Sox to name a few.

Ball Game at Wrigley

A great way to enjoy some food and get to know your date, Wrigley Stadium hosts the Chicago Cubs. The stadium opened in 1914 and is a historical part of baseball. The atmosphere is comfortable and accepting.

Actors perform on Chicago's Second City stage

Comedy at Second City

A great way to relax and get to know someone, enjoy the comedy at The Second City. 7 days a week you can see the next generation of comedy superstars.

Multiple axes and wood stand on the ground in Chicago's Bad Axe

Chuck Axes at Bad Axe

Feeling fierce? Why not throw some axes! Find out how good you are at throwing an axe at Bad Axe. You and your date will enjoy the excitement and intrigue of the art of axe throwing.

Free POF Dating App for Chicago

Go on memorable dates in Chicago

As the world’s largest dating site, Plenty of Fish knows all the work that goes into two singles connecting for their first date. We’re focused on making it fun, easy, and free to find the other half that understands the real you in Chicago.

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Livestreaming on the POF dating app

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Every day, our members are meeting their forever blanket thief, Ikea sherpa, personal spider hunter... you get the point. We couldn't be prouder of all the brave souls out there finding their other half, just like these two lovebirds:

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David & Andrea

The long messages back and forth, hours spent talking on the phone and looking forward to seeing each other after each date, it was wonderful...

Chicago to date?

Whether you live on the outskirts of Chicago, or are looking for singles in nearby towns, Plenty of Fish has your back. We have tons of members looking to date just outside of Chicago. We’re pumped to help you start dating a match who will know exactly how amazing you are.