The 350 capacity venue is a neighborhood gathering spot where locals linger for coffee, wi-fi, snacks and beer by day and everyone comes for live music and beer by night (the bar has 56-draft lines of local, regional and international ales, stouts, barleys, and ciders). Expect an array of ticketed and free events showcasing national and global performers of pop, art-rock, psych, folk, electronic, jazz and everything in between and beyond. The performance venue has great acoustics, the lighting is spot-on and the space feels intimate but never cramped. The patio is open year-round and it’s dog-friendly during the day.

Who better to design a space to play than musicians themselves? That was the goal when creating SPACE (which stands for Society for the Preservation of Art & Culture) located just north of Chicago in Evanston. Every part of the venue, from the aesthetics to the audio and lighting technology, was designed to allow for great creative expression. The result is sound that keeps musicians and fans coming back, sightlines that allow everyone to enjoy the show and no seats that are more than 40 feet from the stage which allow a level of intimacy rarely found these days. SPACE hosts local and national touring acts and there’s an outdoor concert series, Out of Space, presenting fabulous artists at Temperance Beer Co.

Don’t let the name of the place fool you – while it has folky performers, this excellent, intimate concert hall offers shows ranging from African music to a full Cuban salsa band (with dancing!). The venue recently hosted Steve Earle, Lucinda Williams, Patti Smith and other cutting edge artists, too. There’s not a bad seat in the theater, so don’t hesitate to buy seats in the upper level. The venue, which is also a music school, was built by musicians for musicians. Ticket prices are extremely reasonable and even more so if you’re a member. Parking is available across the street in a lot or along the street (both are metered). There are more than a few excellent restaurants on the block, so consider grabbing dinner before or after a show for a completely wonderful evening in Chicago.

Trendy folks and jazz aficionados regularly flock to this cool joint. Once a hangout of Al Capone, Charlie Chaplin and Gloria Swanson, the place oozes character. It was also a speakeasy during Prohibition, meaning that Green Mill retains a historic air of the Roaring ’20s. Swing music is offered Tuesday and Thursday, Wednesday night features a gypsy jazz band (with guitar, violin, oud, reeds, cimbalom and drums) and Sunday features poetry slams and more jazz late night. Cocktails are reasonably priced but if you want to sip from a table, get there early and definitely before the bands go on because Green Mill can get packed.

Music fans love the intimacy, yet never feel too crowded at Lincoln Hall. Patrons can actually see and hear the band because of excellent acoustics and sightlines from the main level as well as upstairs. In addition to notable performers and a variety of talent booked at Lincoln Hall, drinks (which include a good draft list) are reasonably priced and you should be able to score parking nearby. The venue is also near the Fullerton Red/Purple/Brown elevated train station making public transportation a snap. Nearby restaurants (some of which are BYOB) make it easy to get good grub before you head to the show, although there is an on-site restaurant offering sandwiches and bar snacks. Tickets can sell out quickly so be sure to order online before arriving so you’re not disappointed.

The Chicago Symphony Orchestra’s Symphony Center is a grand space with great acoustics and beautiful architecture. Add to that one of the country’s best orchestras (they’ve won more Grammy Awards than any other ensemble in the world) and seeing a show here will likely be a night to remember. While classical music is the focus, Symphony Center hosts guest performers like The Chieftains, SF Jazz Collective, various chamber and civic orchestras, and special presentations like Star Wars: Return of the Jedi concert. There are also Q&A sessions with conductors and creative directors, as well as multimedia presentations. Even those who don’t like classical music will marvel at the architecture and sound. Student prices and special shows for families are available, too.

The venue that the New York Times calls “a musical gem” is standing room only but even when it’s packed it’s a fabulous room for live music. Some of the biggest names as well as emerging artists in folk, swing, Zydeco, big band, country, blues and rock play this Berwyn venue. Don’t overlook it because it’s not in the city proper. Public transportation is nearby (it’s six blocks from the Forest Park blue line stop at Oak Park Avenue) but there are also parking spots nearby. FitzGerald’s doesn’t serve food so hit up a nearby restaurant first if you’re hungry, Oak Park has plenty. There’s an Italian place right next door to the venue that will deliver your food to the club, too. Bartenders are attentive and drinks are very reasonable. An outside patio with chairs and tables makes it easy to take a break.

If you want to visit a venue that’s a favorite of musicians, Tonic Room is your spot. For nearly 20 years, the intimate club has served live music six nights a week and patrons love being close to the performers. Tonic Room is often the club many artists book when their tour takes them to Chicago for the first time. Take a look next to you (is that Chance the Rapper?) because the club boasts a tight family of Chicago musicians that frequent the Lincoln Park venue to support fellow artists. Monday nights feature an open jam but other nights you could witness a Grateful Dead or Pink Floyd experience; a funk band from Boston; a Nashville singer-songwriter; or any number of reggae, hip-hop, blues, rock and jam bands.

Jay Pritzker Pavilion is not only an architecturally stunning venue in downtown Chicago, but it has an outstanding sound system and provides a wide variety of high-caliber concerts for free if you sit on the lawn. The Grammy-nominated Grant Park Symphony Orchestra and Chorus perform here, but so have names like Idina Menzel, Wilco, Tori Amos and the Lyric Opera of Chicago. In 2019, the Grant Park Music Festival celebrated its 85th season while Millennium Park celebrated its 15th birthday. Among the spectacular Grant Park Music Festival concerts at the Jay Pritzker Pavilion in 2020 are a mix of Beethoven masterpieces and rarely performed gems; the annual Independence Day Salute featuring rousing marches and patriotic anthems; and a Broadway extravaganza. It’s a perfect place to bring a blanket, camping chairs, food and drinks and enjoy a summer night. Take in live music, stunning architecture and the gorgeous city skyline.

Music fans and musicians love this sweet 100-year old spot that has a bar in the front and a performance space in the back. You could catch Jeff Tweedy or The Dream Syndicate one night, a young torch singer the next, Jon Langford and Sally Timms performing an impromptu Sunday afternoon show, a blues jug band, experimental dance artists and various surprises like Andrew Bird adding a whistle from the crowd. Truly a community gathering place, The Hideout also hosts stand-up comics, political debates and monthly talk shows. But always, live music, especially alt-country for which the bar is known. The Picnics on the Porch series in summer is an outdoor event hosting national acts like Robbie Fulks, Joan Shelley, Jake Xerses Fussel, and some of the best local talent. Read about The Hideout’s history on its website and you’ll love it even more.