The Best Chicago Street-Festival Dates

After sifting through schedule upon schedule, we’ve determined which festivals have the best summer-date vibes, and which ones are sure to set the scene for mixing and mingling.

The Best Rooftop and Patio Dates in Chicago

On a beautiful day, there’s nothing worse than being confined to the great indoors. Thankfully, al fresco dining and drinking abounds in Chicago this time of year.

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Panini Sticks, Flaming Shots & 4 More Great Chicago Foodie Dates

In search of inspiration for a great date? Look no further.

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Rooftop Ice Skating, Open Mic Night & 4 More Great Chicago Date Ideas

In search of inspiration for a great date? Look no further.

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12 Beers of Christmas, Red Velvet French Toast & 7 More Great Chicago Foodie Dates

In search of inspiration for a great date? Look no further.

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Sweet Potato Pecan Pie, Snickerdoodle Muffins & 7 More Chicago Foodie Date Ideas

In search of inspiration for a great date? Look no further.

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5 Proven Ideas for a Great Chicago Date

Chicago singles are laid back without being boring, quirky without being precious. Check out 5 components to mix and match for the perfect Windy City date.

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Where to Date in Chicago: The Top 10 Date Spots

Curious where Chicago singles like to take their dates? Find out now.

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Hey, Chicago Daters: Enter the “Woo the Wingman” Contest and Win a Hot Date!

Want to go on a date with a hot Chicago bachelor — and win a great prize pack, too? Now’s your chance.

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Chicago Date Idea: SummerDance In The Park

You and your date will begin to understand why all those romantic songs from the first part of the last century were about “Twisting the night away” and “dancing cheek to cheek.”