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Chicago Outdoor Festival Guide

An insider’s guide to finding the best sounds, views and flavors at Chicago’s outdoor festivals.

A typical Chicago summer features a few constants: Someone in your life won’t quit bellyaching about baseball. You’ll visit a legit sand beach, without ever leaving the city limits. And at some point, you’ll find yourself shoulder to sweaty shoulder with what seems like all of humanity, crowding a park or street to sample the city’s finest offerings in music, food and culture. 

Across the metro, mega-festivals and cute neighborhood parties pack the calendar every weekend. The best-known fests draw enormous crowds, for good reason: The food is incredible. The musicians are world-class. And it’s pretty fun to celebrate the best of summertime with thousands of new friends. 

Our tips for enjoying the biggest and busiest fests will help you strategize your outings, with advice for beating lines, choosing eats that you’ll still be sighing about on Monday, and scoring the best experiences and vantages. (Some aren’t even at the festival grounds themselves!)

 August 18-19 North Avenue Beach

Chicago Air and Water

Chicago Air and Water Show; photo courtesy of Choose Chicago

Now in its 60th year, the free Air and Water Show attracts top civilian and military pilots and aircraft for a two-day thrill drill. North Avenue Beach is front row to the action, but you can see the show without going to the show. These are some great viewing spots:

  • The 360 Chicago attraction on the 94th floor of the John Hancock Center, or a floor above at The Signature Room at the 95th, which has an annual viewing party.
  • The towering Centennial Wheel at Navy Pier.
  • The Lakefront Trail in Lincoln Park, near Diversey Harbor and the A Signal of Peace sculpture.
  • Anywhere downtown, really—you’ll likely glimpse planes and hear them roar.

 June 8-10 Millennium Park

The Great Migration brought a wave of blues to Chicago in the 1950s, and the city’s largest free music festival celebrates the genre. Before taking in headliners at Jay Pritzker Pavilion, explore  landmarks that celebrate the birth of urban blues:  

  • Chicago icon and blues guitarist Buddy Guy lends his name and soulful spirit to Buddy Guy’s Legends, a hot venue for touring acts—and a great spot for gumbo. 
  • A striking new 10-story mural of Muddy Waters, who is dubbed The Father of Modern Chicago Blues, livens up a high-rise at 17 N. State St. 
  • Book a Chicago Jazz, Blues and Beyond Bus Tour with Chicago Detours. Stops include clubs, churches and studios where the urban blues came to life.

June 8-10 Lincoln Avenue, NorthCenter

Ribfest Chicago

Ribfest Chicago; photo by Beking Joassaint

Anyone who braves the crowds at this popular festival can vote for their favorite ribs. But based on last year’s offerings, you’ll also want to save room for non-’cue fare: 

  • Loaded Tater Tots, Celtic Crown Public House Crispy tots bathe in a creamy cheese sauce, with a generous bacon garnish.  
  • Guinness Ice Cream, Mrs. Murphy and Sons Irish Bistro Last year’s People’s Choice winner for ribs gets kudos for this malty treat. 
  • Piña Colada Acapulco Style, El Campeón Wash down your ribs—and your worries—with this cocktail served in a fresh pineapple.
  • King Mac, BBQ King Smokehouse Share a savory sundae of mac ’n’ cheese, fried onions, BBQ sauce and pulled pork.

 June 9-10 Printers Row, South Loop

A century ago, this neighborhood was the country’s publishing hub. Today, it hosts a festival for word nerds. Don’t leave home without these five must-haves:  

  • Schedule More than 200 authors will participate in panels, readings, Q&As and demonstrations. Because free talks are first come, first seated, arrive early to events. 
  • Event tickets Admission to the festival is free, but a few big-name author appearances have a fee. Grab tickets ASAP—they sell out. This year’s schedule will be posted sometime in May.
  • Camera Capture the area’s bookish architecture. Park benches look like printing blocks, with reverse type; at 720 S. Dearborn, terra-cotta murals show moments in bookmaking history.  
  • Cash More than 100 independent booksellers from across the country display new, used, rare and antiquarian titles. A few sellers will take your card, but cash is king.
  • Book Bag (or two) After browsing literary treasures (and extras that might include vintage maps and movie posters), you’ll need a tote to transport your finds.

 All Summer Highland Park

For more than 100 years, America’s oldest outdoor music festival has lured fans with its lush grounds and lawn-chair spirit. Though you can preorder a picnic dinner or dine at on-site restaurants, we prefer packing a cooler with good eats (and a chilled bottle). For fun, include a music-inspired dish:

  • June 23 & 25 Roger Daltrey with members of The Who Band and Ravinia Festival Orchestra Savor a to-go In-A-Gadda-Da-Vida Salad from Fat Tommy’s as you rock to The Who’s Tommy album.
  • August 23 Sugarland Lead singer Jennifer Nettles loves to bake her great- grandmother’s coconut pie. Raise a fork to that tradition by ordering a Coconut Custard pie from Hoosier Mama Pie Company.
  • August 25 Jason Mraz and Brett Dennen Jason, of “I’m Yours” fame, finds happiness in being a vegetarian and owning an avocado farm. Chill to his vibe by packing veggie wraps with chips and guac.

 July 11-15 Grant Park

Taste of Chicago

Taste of Chicago; photo courtesy of Choose Chicago

With dozens of vendors and 1.6 million attendees, it’s easy to get overwhelmed at this foodie fest. You’ve got only so much stomach space, so here’s a sampling strategy:

  • Plan ahead You’ll need tickets to buy food, so review the online guide to estimate how many tickets you’ll need for what you want to eat. 
  • Snap the menus Take photos as you pass interesting vendors to note your can’t-miss bites. And don’t forget to swing by the pop-up restaurants, which often offer unusual fare.  
  • Dodge the rush Aim to visit midweek between 3 and 6 p.m. to avoid the largest crowds and longest waits. (That makes it easier to backtrack for missed tastes, too.)

August 2-5 Grant Park

Lollapalooza

Photo courtesy of Maclay Heriot/Lollapalooza 

More than 170 acts play for a 400,000-plus crowd during four days of music nirvana. Despite Grant Park’s high capacity, general admission tickets have already sold out, but they’re still available on the secondary market. Here are two ways to rock the show:

For The Frugal Fan

  • Check in Sleep in a transit-friendly suburb or at an Airbnb (downtown hotels may jack up rates).
  • Get in Find a cheap general admission ticket on StubHub or Craigslist.
  • Drink Bring an empty bottle to refill at free water stations around the park.
  • Relax The grounds get messy, even without rain, so bring a towel to sit on.

For The Posh Partier

  • Check in Get a place downtown, but book now, because hotels fill quickly.
  • Get in Purchase The VIP or Platinum Experience (from $650 per day).
  • Drink Enjoy the complimentary VIP food, massages and cocktails—oh, and wood-paneled bathrooms with AC. 
  • Relax Hang out at the four stages that offer shaded VIP-only lounges.
 

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