Taking It to the Streets

The hottest cities for cool summer street fairs.

By Maureen Sullivan for MSN City Guides

Kids in the summer have ice cream, long hours of daylight in the evening and even longer days at the pool to look forward to. For many adults, summer is all about the street fair. Some are neighborhood festivals, while others honor a particular ethnic heritage. A street fair can center around a parade or emphasize food or live music. Whatever the impetus, all are about celebrating the season and, most of all, having a good time.

Some cities seem to be meccas for street fairs. Below are some metro areas that have a bevy of choices for these summer festivals, plus highlights of some of the most major of those parties. It’s impossible to list them all—we’ve tried to limit these to ones that span weekends instead of months—so surely there are many more out there. These are just a few that it wouldn’t be summer without.

Note: While the bulk of these occur between now and Labor Day (and are focused as much as possible on actual street fairs rather than larger music or art festivals), we’ve included a few that stretch beyond that traditional end to summer, simply because they extend the season and you won’t want to miss them.
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Related: 

• Great Urban Beaches 
• Top 10 Outdoor Dining in the U.S.
• 10 Urban Escape Plans
• Find Fairs, Festivals Near You

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Chicago
Summer in Chicago is legendary—the Cubs, the beer, the brats, the beer … you get the idea. It’s all about enjoying it being one of the two seasons Chicagoans joke that they have: winter and construction. With the inconveniences of construction season come the joys of summer street festivals, and plenty of them: Chinatown Summer Fair (July 19), the Dearborn Garden Walk and Heritage Festival (July 19) and Wicker Park Fest (July 25-26)—and that’s just a smattering of the ones occurring weekly all summer long.

There’s a few we’d be remiss not to single out. Retro on Roscoe (Aug. 1-2) is touted as Chicago’s most popular neighborhood fest. More than 50,000 people descend on Roscoe Street for antique cars; cover bands playing throwback music of the ’70s, ’80s and ’90s; and the Windy City Chili Cook-Off.