Chicago O'Hare

Chicago is generally known for three things; architecture, food and lots of snow. But one of the things we’re becoming a front-runner in is our summertime festivals. Each year the city of Chicago and surrounding suburbs come together to produce and host hundreds of festivals for all walks of life. From food festivals to free summer music series and jazz festivals, there is something to do for anyone at any time.

Some more good news: our festivals go right through September, so the summer fun doesn’t need to end in August.

For the Music Fan

Many know Chicago’s Lollapalooza as one of the biggest 4-day music festivals in the nation – hundreds of thousands flock to Grant Park to experience this event every year. But what you may not know is that the city also hosts one of the best jazz fests around, the annual Live Jazz Fest. For decades, this genre of music single-handedly molded the sounds of Chicago. That history continues to inspire people to visit our city, the birthplace of some of the most famous and talented jazz musicians in the world.

When: August 24– September 2, 2018

Where: Millennium Park and Chicago Cultural Center

Cost: Free

Headliners include: Composer, pianist and radio personality Ramsey Lewis; noted jazz vocalists Kurt Elling and Dianne Reeves; and funk legend Maceo Parker.

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For the Foodie 

Photo Credit: LaCour Images

Yes, Chicago has a stellar restaurant scene but how can anyone manage to dine at them the best spots in one trip? Luckily, our local festival event planners have figured that one out for you with several food-driven festivals taking place throughout the summer.

One of the biggest and best festivals, the go-to food fest above all others, is Chicago Gourmet. This annual three-day foodie heaven starts with a bang with a Friday Hamburger Hop throwdown. This is where chefs, foodies, influencers and restaurant owners all gather for what I affectionately call a “Foodie Prom” to kick off the weekend. If you haven’t had your fill at the hop, head on over to Millennium Park and nosh on food from some of the most popular restaurants in town. Or, catch one of the many cooking demos happening while you sample some vino at the pavilion. This event isn’t free but absolutely worth every single penny.

When: September 28–30, 2018 | 6 AM–11 PM

Where: Millennium Park

Cost: $180 daily | $295 weekend pass

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For the Vino Lover

If you’re looking to sip on some world-class wines, be sure to check out the Windy City Wine Fest. With over 300 + wines to sample from around the world, this annual sommelier extravaganza at Buckingham Fountain in Grant Park offers up great vino, fantastic views of the city and of course a great education on how and what to drink.

Photo Credit: LaCour Images

When: Daily 8 AM–11 PM, April–October

Where: Buckingham Fountain in Grant Park

Cost: $45, advance $35 |designated driver $15

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For one of the best local and flavorful experiences, be sure to swing by one of these fun festivals.

Kelly