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Chicago is a perfect destination for music lovers, so Culture Trip has broken down your ideal seven-day itinerary that hits all the city’s best music highlights. Whether you’re coming in from out of town or just planning a staycation, this guide has every venue, bar, and retail recommendation you need to fulfill your music obsession.
Set the right tone for your music-filled Chicago stay by booking a room at the Hard Rock Hotel. You won’t find another place for miles that’s as dedicated to music lovers as this one. Obviously, it has a rock n’ roll theme throughout the space, including stunning décor, unparalleled history, executive suites, and even the opportunity to rent out guitars during your stay. Check in on a Monday right downtown and start exploring the Loop.
Reckless Records is a legendary Chicago music store made famous by John Cusack’s 2000 movie, High Fidelity. It has three locations in the city, and one outpost is close to the hotel. Stop in for a leisurely afternoon of browsing vinyl records. Once you’ve worked up an appetite, get your touristy guilty pleasure out of the way with a visit to the Hard Rock Café. You can add a new T-shirt to your likely growing collection and just soak in the music-nerd atmosphere. Although it’s not an official Hard Rock Live location, the café does have occasional shows. Maximize your music intake by checking out their calendar and planning accordingly.
Put the West Loop on tap today with stops at two different but well-known venues. City Winery and Bottom Lounge are just around the corner from each other and close to the Green Line, making them your perfect Tuesday double header. Both are small, live music venues with attached restaurants. At City Winery, you’ll get a more upscale and classy lineup. They feature local artists, big names, themed wine dinners, and more. The music all depends on the day, but you’ll always have a great dining experience.
Bottom Lounge offers a more hardcore, underground scene experience. Though not technically below ground, the venue’s pit-only concert space feels like you’re partying in someone’s dark basement or garage. It’s intimate and raw, making for an unforgettable night. Their attached restaurant is for adults over the age of 21 and offers tasty American eats with Chicago sports always playing on the flatscreen TVs.
Start out slow today with a trip to the North Side shopping stops Audio Archaeology in Rogers Park and Chicago Music Exchange in Roscoe Village. Both are incredible music retailers in which you could easily get lost. Browse massive vinyl collections, vintage music paraphernalia, instruments, sheet music, turntables, record players, and more. If you have something in mind, one of these places will have it. Audio Archaeology even offers appraisals of your vintage music items for a small fee.
The two stores do close at 7 pm, which leaves your evening open. Compare a few calendars and catch a live show at one of the North Side’s staple venues. Riviera Theatre, the Metro, and Aragon Ballroom are all reliable options.
Take a different approach on Thursday by soaking in some culture. The Chicago Cultural Center in the Loop is a fantastic place to get to know the city’s most talented for free. Check out art exhibits, theater showcases, dance performances, and live music.
Just down the street, you’ll find the Chicago Symphony Center, which is home to the Chicago Symphony Orchestra. Their shows may not be free, but it’s more than worth it to see and hear the 112-year-old venue filled with beautiful music. Cap off your classy evening around the corner with drinks at Miller’s Pub, a famous Chicago watering hole since 1935. It’s been frequented over the years by the likes of Frank Sinatra, Jimmy Durante, Marilyn Monroe, Jay Leno, and many others.
This weekend is all about a throwback to Chicago’s musical heyday. The history of jazz and blues music in Chicago spans an entire century, churning out some of the greatest musicians the world has ever seen. See a show on Friday night at Buddy Guy’s Legends in the South Loop. Guy himself plays annual shows there every January, but throughout the rest of the year, they have shows every night of the week.
And don’t forget to stop into Jazz Showcase just two blocks away. It’s been a Chicago institution since 1947, owned, operated, and curated by father and son Joe and Wayne Segal. In between shows, grab a bite at a different kind of Chicago institution. Harold’s Chicken Shack serves up the best fried chicken in the city, and it’s just across the street from Buddy Guy’s.
Saturday is a marathon, not a sprint, so get on the Red Line and head north. Stop off in Lincoln Park for Dave’s Records, a store taking you back in time to a place well before internet streaming and even before CDs. Then break for a drink at Delilah’s Chicago, a punk rock bar spinning tunes and slinging more than 300 different types of whiskey. Continue to Lakeview and hit Gramaphone Records, another amazing record store waiting for you to find all of their hidden treasures. It specializes in house music and gives off a nightclub feel.
Keep the club vibes going with a visit to Berlin Nightclub off the Belmont stop. It’s one of Chicago’s most popular LGBTQ bars and is famous for attracting an eclectic mix of partiers and never-ending dance tunes. And before you burn out, make one last stop at the pinnacle of your music-lovers week. At 112 years old, Green Mill in Uptown is the most historic jazz club in Chicago, and possibly even the world. It’s seen every great musician imaginable, was a favorite hangout of Al Capone and stays open past 5 am on Saturday nights. Kick up your heels and get dancing because tonight is one for the record books.
It’s been a long week, so keep things light on the last day. The House of Blues is a national chain that sees a lot of amazing acts, and while they’re worth a visit on any night of the week, their weekly Gospel Brunch on Sundays is a special treat all its own. Tickets include an all-you-can-eat buffet that features breakfast food and Southern dishes. You’ll also be treated to local musicians performing both contemporary and traditional gospel music while you eat. It’s perfect for a hangover or just a Sunday morning with the family. Enjoy!