The Best Spots To Listen To Live Music Outside This Summer

The best places to eat, drink, and enjoy outdoor live music in Chicago.
The Best Spots To Listen To Live Music Outside This Summer image

photo credit: The Northman

Though that “Gr8 Pump-Up Jamz” playlist you made six years ago may be great, nothing beats listening to live music outside after 18 months of winter. And when paired with some snacks and a cold beverage, there’s no better way to experience summer in the city. From small jam sessions at a local watering hole to full-on orchestral performances at Millennium Park, these are the best places to eat and drink while listening to outdoor live music.


photo credit: The Northman


River North

$$$$Perfect For:Drinking Good BeerDrinks & A Light BiteLive MusicBig Groups
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Unrelated to 2022’s intense Viking epic, this Northman in River North is a spacious beer garden by the river (also a relaxing place to decompress after watching The Northman). It has plenty of picnic tables, room to play bags, and a large covered stage area where you can order drinks and snacks while listening to music. They have performances from Memorial Day weekend through Labor Day weekend, so check out their event calendar for updates.

Sleeping Village is a great bar and concert venue that has performances ranging from DJs and indie bands to comedians. And we especially like seeing shows out on this Avondale spot’s patio. The large picnic tables are great for hanging with friends, and you can occasionally catch an outdoor music set. Check their calendar for important event info (plus, equally important info about $1 beer nights).

Phyllis’ Musical Inn is a Wicker Park legend that has been around since 1954. Originally a spot for polka enthusiasts, this bar and venue has evolved to feature everything from country to punk rock. Though 80% of the year's performances take place on their little indoor stage, when it’s finally nice outside, you can enjoy the music in their beer garden.

Pilsen’s Thalia Hall is a great indoor concert venue, but their adjoining bar, Tack Room, is also great if you don't want to worry about paying for tickets. Tack Room’s outdoor summer line-up has a wide range of piano-focused sets featuring artists performing original songs and even audience requests, all of which you can enjoy from their outdoor patio. Their regular menu has food like cheeseburgers, mussels, and wings, and they also have a ceviche and salsa music series with an in-house band, the Tack Room Rumberos. Click here for their performance calendar.

You just spent an afternoon at Loyola Beach in Rogers Park and want to check out some live music. Luckily Semilla’s is just a few steps away. Every Friday and Saturday this wine bar has solo guitar performances on their outdoor patio accompanying their Mexican-Peruvian menu full of dishes like piri piri chicken, quesadillas, and ceviche. And because their patio is covered, you won’t have to worry about getting drenched during a random Chicago rainstorm, or applying your ninth layer of SPF 120 for the day.

Archie’s Cafe is a casual Rogers Park spot that feels more like hanging out at a friend’s house than a restaurant. It has coffee, booze, and a rotating food menu that includes a little bit of everything. Certain nights are devoted to pizza or pasta, while on weekends it functions as a breakfast, lunch, and dinner spot serving everything from breakfast sandwiches to tacos. And during the summer, they frequently have musicians performing on the sidewalk, from lunchtime acoustic guitar sets to full-fledged jam sessions that end at their “midnightish” closing time.

Just off of the Morse Red Line is Le Piano, a Rogers Park jazz bar. And in the summer, the grand piano gets to see the light of day during their outdoor performances that are part of Chicago’s Alfresco program. Le Piano hosts musicians covering a wide range of genres including classical, jazz, and blues. In addition to cocktails and wine, you can find dishes like lamb chops or chicken with a tarragon wine sauce.

photo credit: Sam Rice



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For Booze and Blues, head to Ina Mae Tavern in Wicker Park on Thursdays. From 7pm-10pm, they have $10 Old Fashioneds and a live blues set. You can also order from their delicious southern menu, which has staples like fried chicken and po boys. And though you might feel full afterward, the sight of their sugar-covered beignets will make you remember that you have a second stomach just for desserts.

Babygold Barbecue is attached to Fitzgerald’s, a Berwyn bar and performance venue that’s been around since the 1980s. It’s a great place to hear live music throughout the year with two indoor stages hosting anything from local funk bands to touring jazz ensembles. But it’s their third performance venue, an outdoor patio, that makes this place worth leaving the city limits. You can enjoy the tunes, sip on a frozen paloma, and stuff your face with ribs. Check here for their performance calendar.

If you’re looking for a place that has live music every night, The Dock at Montrose Beach in Uptown is a must-visit. Their music series begins Memorial Day weekend and features artists and bands covering a wide array of genres from Latin jazz, to funk, to rock, all accompanied by a crisp lakeside breeze. Sit on the beach, or grab one of the tables with beach umbrellas. You can also order food like tacos and burgers without getting a farmer's tan.

Upbeat funk and R&B jams, delicious food, and a long wine list—three very valid reasons to hang out for as long as possible at Bronzeville Winery. A fourth is live music Sundays on their plant-filled sidewalk patio. You can expect everything from DJ sets to solo jazz trumpet—and all of the above make dishes like seared watermelon steak even better.

Located on 63rd St. Beach in Woodlawn, Reggies on The Beach is the newest addition to the Reggies family, who also have music venues Rock Club and Music Joint. This Jackson Park beach version follows the same tradition with local acts performing everyday—from high energy rock shows to toned down acoustic sets. They also have a short menu with burgers and quesadillas. The food, music, and beautiful lakeside view will make you forget it was 30 degrees in April.

Though Navy Pier is a tourist sinkhole that most locals make every effort to avoid, it’s also one of the best places to catch free live outdoor music. From their beer garden to their Wave Wall Staircase, there’s performances here every Sunday, Thursday, and Friday. You can hear local rock bands, jazz groups, and a weekend festival in August highlighting the music of the Latin American diaspora. If you get hungry, you can grab a burger or hotdog from the beer garden, or check out one of the not-terrible Navy Pier restaurants like Billy Goat Tavern or Giordanos. Check back here for their event calendar.

Museum of Contemporary Art Chicago image

Museum of Contemporary Art Chicago


Every Tuesday in June, the MCA has free live jazz on their back terrace from 5:30-8:00pm. You can reserve seats online, or, if you want to make a picnic out of it, you can experience the music (and hopefully not too humid weather) on MCA’s lawn. Though outside food or alcoholic beverages aren’t allowed, there’s a small menu of things like sliders and tacos along with beer and cocktails. Tuesdays are also free museum days for Illinois residents, so you can have lunch at the reopened Marisol, an afternoon of surrealist photography, followed by an evening filled with Charles Mingus. Click here to see the line-up.

Pier 31 Restaurant in Douglas is a great place for live music and a quick bite after falling asleep on the beach and giving a compelling performance of Person Imitating Bread Turning Into Toast (coming soon to the MCA). They have local musical acts like soul bands and live DJ sets and a small menu with food like nachos and burgers—all of which can help take your mind off your newly acquired sunburn.

From June to September, The Jay Pritzker Pavilion in the Loop is one of the best places to listen to live music outside. Here, you can listen to a set from Wilco frontman Jeff Tweedy, return for some Tchaikovsky with The Grant Park Orchestra, and then come back on a weekend for Jazz Fest. Outside food and drink is allowed, which makes these concerts perfect for picnics. But if the mere thought of formulating a plan dries out your tongue and triggers the appearance of hives, you can just grab a beer and bratwurst from one of the surrounding concession stands. Click here for the Millennium Park event calendar.

Waterfront Cafe is an Edgewater restaurant that's attached to a coach house in Berger Park. They have a large patio which regularly features a variety of music sets from small jazz trios to solo songwriter performances. They have a takeout window where you can order drinks and food like nachos, salads, and a lobster roll. If you're looking for an outdoor spot to hear some music by the lake that's as far away as possible from rambunctious boat parties of The Play Pen, this is a great option.

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