Looking for date ideas in Chicago?

Chicago is one of the largest and most vibrant cities in the US. You’ll sometimes referred to as the windy city, Chicago is best known for its museums, distinct neighborhoods and passionate sports fans.

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Check out Chicago’s hot spots

Whether you want to shake up your dating routine or looking to find a cool new spot to meet someone new, you’ll want to check out these Chicago hot spots that are guaranteed to knock your next date out of the park.

Ball game at Wrigley

Catch a Chicago Cubs game at the famous Wrigley stadium. Grab a hotdog and let’s watch some baseball.

Actors perform on Chicago's Second City stage

Live comedy at the Second City

Share some laughs and enjoy the next generation of comedy superstars at The Second City.

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 at Bad Axe. Get your heart pumping and test your skills.

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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Storie a lieto fine di POF

Per il nostro anniversario, mi ha regalato un divertente biglietto che diceva: 'Sei la cosa migliore che abbia mai trovato su internet'.

Storie a lieto fine di POF

Per il nostro anniversario, mi ha regalato un divertente biglietto che diceva: 'Sei la cosa migliore che abbia mai trovato su internet'.

-Annie

Looking outside of 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.

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