The summer season in Chicago is as good as you’ll find in any city, anywhere. Something about suffering through a brutal winter just makes everyone appreciate great weather that much more, and the energy that it creates is contagious. The city also has a great music scene, so obviously, people have created some awesome music venues to listen to it outdoors. Sure, there are the annual mega festivals like Lollapalooza, Riot Fest, Pitchfork, North Coast Music Festival, and Spring Awakening, but they are expensive, and there’s so much more than just those. If you’re looking for a great spot to enjoy some tunes out in the summer weather, check out our picks for the best venues to listen to music outdoors in Chicago.
Ravinia Festival runs all summer long and is the oldest outdoor music festival in the country. Although Ravinia is located way up in the North Shore suburbs, direct train service from downtown makes it an easy journey to this great venue. The music used to be mainly classical and opera with occasional blues, jazz, acoustic, and world music, but these days you’ll also find rock, hip hop, country, and lots more. Food and drink can be purchased from food trucks, but if you’re on the lawn you can bring in your own picnic.
Where: 418 Sheridan Rd, Highland Park, IL 60035
2. The Dock at Montrose Beach
When you’re not looking for the full concert experience but you still want to groove out to some great tunes outdoors, head to The Dock at Montrose Beach. This great little bar and restaurant is located right at the beach and has live music every night all summer long. The food and drinks are always solid, and the music is really good. The setting is what really brings it all together, and after a couple of cocktails, you might just feel like you’re in the Caribbean.
Where: 200 W Montrose Harbor Dr, Chicago, IL 60601
3. Wrigley Field
Wrigley Field is hallowed ground for baseball fans and it’s an amazing place to catch a game, but the Friendly Confines also host occasional concerts. An outdoor concert on a Chicago summer night is great anywhere, but it’s next level at one of the city’s best-known landmarks. There are typically only one or two concerts per year, but these events draw classic acts like Jimmy Buffett, Pearl Jam, Billy Joel, and Journey. Check the normal Cubs ticketing website to find out who’s playing this summer in the old ballpark.
Where: 1060 W Addison St, Chicago, IL 60613
4. Northerly Island
Northerly Island is a former airport and now a nature reserve, so it seems like an unlikely place to catch a concert, but the Huntington Bank Pavilion at Northerly Island is actually one of the city’s best outdoor venues. From the location jutting out into the lake, you get incredible views looking back over the water toward the downtown skyline, and a nice breeze to cool you off during the summer heat. Many of the best touring acts passing through the city in the summer play Northerly Island so there’s always a good show to catch.
Where: 1300 S Linn White Dr, Chicago, IL 60605
5. Grant Park and Millenium Park
The Jay Pritzker Pavilion in Millennium Park and the fields of nearby Grant Park host some of the best outdoor music series you’ll find anywhere, and most of it is completely free. The one paid event is Chicago’s biggest and most famous music festival, Lollapalooza, which takes over Grant Park for a weekend. The city’s biggest free concert also takes place here with the annual Chicago Blues Fest.
The Pritzker Pavilion hosts evening concerts all through the summer, where you can bring a picnic blanket, food, and even beer and wine, and grab a spot in the grass at one of the most scenic spots in Chicago. For classical, check out the Grant Park Music Festival program, and for a mix other genres, there’s the Millennium Park Summer Music Series. There are also a few other nice concerts sprinkled in throughout the summer. It’s a bit confusing that there are so many different concerts held in the two parks under different music series, but you can find a schedule of all of them on the city’s website for the park.
Where: Downtown in Grant Park and Millennium Park
6. Pier 31
A lot of the places on this list have great views of the city, but none are better than Pier 31 at 31st Street Beach. This casual beachside bar and restaurant has cold drinks, a walk-up window serving decent food, and live music every day of the summer. From DJs to bands, and nights of salsa and bachata dancing, there’s something here for everyone. Sitting at the beach on a clear summer day with unobstructed views to the skyline just a few miles away might be the best place to be on a summer day or night. Add in some good tunes and a cocktail and you’ve hit peak Chicago summer enjoyment.
Where: 3101 S Lake Shore Dr, Chicago, IL 60616
7. Neighborhood street festivals
Every summer, around 400 different neighborhood street festivals are held on weekends throughout Chicago. These range from celebrations of different ethnic heritages, specific music genres, festivals around one food type, craft fairs, and tributes to certain streets or neighborhoods. Nearly all of these have live music and some festivals get some very good acts. Almost all of these festivals have a suggested donation of just $5 to $10 and it supports neighborhood associations, so they’re a great value. The best music is usually at Do Division Fest, Logan Square Arts Fest, Taste of Randolph, and Wicker Park Fest.
Where: Various locations around the city