418 Sheridan Road
Highland Park, IL 60035
Not only does Ravinia host between 15-20 outdoor performances by the world-acclaimed Chicago Symphony Orchestra, the Highland Park venue offers jazz masters, pop icons past and present, kids programming and special shows like a live edition of Prairie Home Companion. The annual festival (the oldest outdoor music festival in the country) peaks with the weather (June to September) and offers seating in the open-air theater as well as lawn seating that attracts the wine and candles crowd picnicking while anyone from Duran Duran to Tony Bennett and Lady Gaga take the pavilion stage. Traffic snarls during every show, so consider taking Metra so you can finish that bottle of wine.
337 E. Randolph St.
Chicago, Illinois 60601
Home base for Lollapalooza, Grant Park used to be the outdoor music venue in the city. Its history runs from the 1830s to the infamous 1970 Sly and the Family Show no-show concert that sparked riots to today’s annual concerts in association with Taste of Chicago. When Millennium Park opened in 2004, the Grant Park Music Festival and many of its weekly summer concerts moved there. In addition to the 25th version of Lolla taking over this lovely stretch of land, which boasts the Art Institute and breathtaking architectural views, Grant Park hosts the largest free blues festival on the planet and Taste of Chicago performances by artists such as Weezer, Erykah Badu, Janelle Monae, Jeff Tweedy, The Chieftains and Spoon.
The FirstMerit Bank Pavilion At Northerly Island
1300 S Linn White Drive
Chicago, IL 60605
Northerly Island’s website
In 20013, when Mayor Richard M. Daley ordered a nighttime stealth operation to bulldoze the tiny lakefront airport, Meigs Field, many were appalled. Now, it’s a fine an outdoor amphitheater on the 4,500-foot-long peninsula that is getting a little better with age. Farm Aid holed up here a few years ago and Bryan Adams, Heart, Modest Mouse, Gregg Allman, ZZ Top, Ray LaMontagne, Josh Groban and the country music Windy City LakeShake are on this year’s roster. Concert goers complain about typical negatives of an outdoor venue such as uncomfortable tight seating, iffy sound depending upon where you’re sitting and pricey concessions; however, on the plus side, there are skyline views and usually free parking at Soldier Field with a shuttle service.
1410 S. Museum Campus Drive
Chicago, IL 60605
It’s old, ginormous, and its stadium seating is unforgiving to the posterior. On the plus side, it’s near the lake, walkable from downtown and its enormity means performers like the Rolling Stones, Madonna and this year Beyonce and Coldplay have a stage, colossal television screens, room for fireworks and enough seats to make a stop in Chicago profitable. If it was good enough for the Grateful Dead to hand pick as the arena to wrap up a 50-year career, it must have some great vibes.
201 E Randolph St
Chicago, IL 60601
Experiencing a concert at the outdoor bandshell of Millennium Park is a sensory art explosion: watching and listening to musicians and dancers in the other-worldly shining steel design of architect Frank Gehry. Why should you care that the Grant Park Music Festival celebrates its 82nd season in 2016 at the Jay Pritzker Pavillon? It’s the only remaining free outdoor classical music event in the country. The 11,000-seat venue is now home to the Chicago Gospel Music Festival and the World Music Festival and it has welcomed artists as diverse as Wilco and The Decemberists.
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