By Craig Davis, craigslegztravels.com
Buying tickets for an out-of-town concert is always risky. Musicians become ill, shows get postponed or canceled.
Perhaps we should have known better than to invest in premium-priced resale tickets and plan a 1,200-mile journey to see a group called Pretenders.
But we’ve been fans of Chrissie Hynde’s music since the ‘80s. So it was a jolt to receive an email three hours before the show we’d traveled from South Florida to see at the Chicago Theater informing us of a postponement due to an illness in the band – turned out the drummer was unable to perform.
We weren’t the only ones similarly burned who found musical solace that night at Buddy Guy’s Legends, the iconic Chicago blues venue.
That was evident when we overheard a woman at the next table declare loudly, “Chrissie Hynde is dead to me!”
Fortunately, the Chicago music scene is very much alive. No better place to confront the blues, and know you’ll leave happy, than Buddy Guy’s.
We were treated to a band with two legendary Chicago blues players. Gary Martin, known locally as “The Prince of the Blues,” and John “Mad Dog” Watkins are both members of the Chicago Blues Hall of Fame and going strong in their 70s.
They are young pups compared to the club’s namesake. Buddy Guy, an eight-time Grammy winner, took a break from his farewell tour to celebrate his 88th birthday on July 30, 2024; we missed it by a few days, but here is a video from his appearance.
Buddy Guy’s Legends is justifiably regarded as Chicago’s premier blues club – voted Best Blues Club by CitySearch every year since 2005 – with leading local and national acts seven nights a week. The Cajun fare on the menu measures up too.
Chicago’s vibrant music scene
There are plenty of other options for live music in Chicago, which ranks high on that regard among American cities, particularly for blues, jazz and R&B.
As you’d expect from the home of the Blue Brothers.
In three nights on the prowl we hit a winning trifecta including Buddy Guy’s that helped make up for missing out on the Pretenders.
The Jim Cooper Quintet performs at Andy’s Jazz Club in Chicago, with the group leader on the vibraphone. (Craig Davis, craigslegztravels.com)Andy’s Jazz Club
This venerable River North venue in the shadow of the Michigan Avenue overpass feels like a trip back in time.
Andy’s Jazz Club does have a long history back to the early 1950s when it was a hangout for newspaper workers. Jazz became a staple in the ’70s. Today it is an old-fashioned supper club with 75-minute shows nightly at 6 p.m., 8:15 and 10:30.
The Saturday night headliner was the Jim Cooper Quintet, with the band leader playing the vibraphone, which is an instrument you don’t hear everyday. Their set was a tribute to Chicago jazz composers, including originals by Cooper, plus arrangements of classic jazz standards.
The music was as pleasing as the 12-ounce New York strip, which came out fast, hot and grilled just right. The show was over too soon, but Andy’s is a place we intend to return to.
The Chris Green Quartet performs at Winter’s Jazz Club in Chcago’s Streeterville neighborhood with the group leader on the saxophone. (Craig Davis, craigslegztravels.com)Winter’s Jazz Club
This hideaway a few blocks from the Navy Pier in the Streeterville neighborhood turned out to be a real find. It did take a real effort to find Winter’s Jazz Club, down a stairway next to Robert’s Pizza and through a couple of long hallways.
We were glad to find our way to the cozy room just in time for the Chris Greene Quartet to begin its set. To me, jazz is best when it is driven by saxophone, and Chris Greene’s playing was satisfying in that regard.
Giving the intimate setting of the room and Greene’s dry wit and banter between songs, it felt like we were listening to music in a friend’s living room. The setting was friendly and the cocktails mixed just right.
Turns out the best way to get to Winter’s Jazz Club is on the backside of the Lofts at River East building — behind Target Express and below Pinstripes. Address is 465 N. McClurg Court.
Blue Chicago is a classic old-school blues club in the River North district known for promoting local talent, with an emphasis on female performers. (Craig Davis, craigslegztravels.com)Bonus club: Blue Chicago
We didn’t make it to my other favorite blues club, which I’ve visited on previous trips to the city. Blue Chicago is a classic old-school blues club in the River North district (536 N. Clark St.), homey and as authentic as you’ll find.
The space is compact and the vibe is high-energy. The emphasis is on Chicago talent, and is known for showcasing local female singers.
Note that only drinks are served, no food. Also, payment is cash only; there is an ATM on premises.
More Chicago live-music venues
Our experience just scratched the surface of Chicago’s live-music venues.
Here are some guides to more options:
The best jazz clubs in Chicago
Where To Go For Live Music In Chicago
The best blues music clubs in Chicago
What to do by day in Chicago
Chicago River boat tours
Evidence of the pride Chicagoans take in the appearance of their city can be seen in the many boats running architecture tours on the Chicago River.
We chose First Lady Cruises because the onboard narration is provided by trained docents from the Chicago Architecture Center, and we weren’t disappointed. Docent Mitzi exhibited remarkable knowledge of how Chicago developed from the ashes of the great fire of Oct. 8, 1871 to become what has been dubbed the “Architectural Capital of the United States.”
She recounted the interesting and often colorful backstories of many significant buildings, including the genesis of their design, financing and construction – successes and failures.
Highlights included the story of how the Chicago River was engineered to reverse its flow away from Lake Michigan and toward the Mississippi River watershed to keep sewage from fouling the city’s supply of drinking water.
Mitzi also confided that Chicago’s moniker as the Windy City is not necessarily due to the stiff breezes off the lake but rather to the talkative and often boastful nature of its inhabitants – the “Encyclopedia of Chicago” ascribes the trait specifically to its notoriously “windy” politicians.
When it comes to architecture, Chicago has reason to boast. In 2023 the city was chosen as the “Best North American Destination for Architecture Lovers” by Buildworld. The British construction materials supplier ranked Chicago’s architecture No. 6 in the world.
Clearly, Chicago is a city that celebrates its grand array of skyscrapers, including the iconic Wrigley Building, the Gothic giant Tribune Tower and the 110-story Willis Tower, formerly known as the Sears Tower and for a while the tallest building in the world. (Skydeck at Willis Tower is another distinctly Chicago attraction we’ll check out on the next visit.)
But on a sunny day in July there were plenty of tourists content to celebrate a scenic boat ride with a cold beverage and hot pretzel by the river side at Northman Beer Garden. For those who want to know more about the buildings, anyone who takes a First Lady cruise is entitled to $5 off admission to the Chicago Architecture Center, situated near the river.
Allure of the Bean
Crowds gravitate to the brightly gleaming object as if it were an alien spacecraft calling them home or a religious icon drawing them to enlightenment.
But main reason visitors to Millennium Park in Chicago’s downtown Loop are drawn to “the Bean” because it is the ultimate selfie magnet, even if most who see it don’t know its official name is Cloud Gate.
Initially, Indian-born British sculptor Anish Kapoor took offense to the Bean nickname, which he termed “completely stupid.”
But in a 2017 visit to Chicago, 11 years after his masterwork was completed, Kapoor acknowledged that “I call it ‘The Bean,’ too,” adding, “It’s great for it to have a colloquial name, its own lingo.”
Just don’t refer to the sculptor as Mr. Bean.
People flock to the popular ‘Bean’ in Chicago’s Millennium Park to photograph themselves in the reflection of the giant sculpture. (Craig Davis, craigslegztravels.com)His creation does resemble a giant, chrome kidney bean. It is truly massive, weighing in at 110 tons.
Kapoor’s creation is a marvel of artistic engineering, shaped by 168 steel plates computer cut and welded into a seamless finish. It is 33 feet high, 42 feet wide, and 66 feet long, and you can walk under the middle of it.
The Bean is Chicago’s Eiffel Tower, though its profile is horizontal in contrast to the city’s renowned skyscrapers.
But its allure is chiefly in the opportunity to photograph oneself in its reflection. While some people take the classic selfie with the Bean behind them, the irresistible alternative is to face it and capture one’s image among the crowd gathered around it. In that way you become joined with a sea of strangers as if in a historic moment.
The Bean has been receiving more attention than usual since reopened to the public in June 2024 after being closed for nearly a year for renovations to the surrounding plaza.
Millennium Park animated fountains
Don’t get bogged down by the Bean, there is more to see in Millennium Park. Just to the south along Michigan Avenue is another unusual public art attraction, the Crown Fountain, also widely known by a colorful nickname: the spitting fountains.
The Crown Fountain in Chicago’s Millennium Park is often referred to as the ‘spitting fountains.’ There are two 50-foot tall towers at either end of a 232-foot black granite reflecting pool. (Craig Davis, craigslegztravels.com)It consists of two 50 foot tall towers at either end of a 232-foot black granite reflecting pool. Water pours down the walls to replenish the pool creating a popular place for kids to cool off in the summer heat.
The real cool aspect of the Crown Fountain is that faces of actual Chicago residents are projected on LED screens on the facing interior walls. Not only do the faces change every five minutes, at regular intervals water spews through an outlet in the screen to give the illusion of water spouting from their mouths.
Hence: the spitting fountains.
For more about Chicago’s Millennium Park visit ChooseChicago.com
Ride the big wheel at Navy Pier
For a different perspective on the Chicago skyline, take a ride on the nearly 200-foot-high Ferris wheel at the Navy Pier near the Lake Michigan shore and mouth of the Chicago River. The gondolas are enclosed and air-conditioned, and we had a wait of only about 15 minutes.
For families with kids visiting Chicago, the Navy Pier is a must place to go. The city’s answer to Coney Island has several rides as well as mini-golf, a funhouse maze and the Time Freak Game. It is also site of the Chicago Children’s Museum and the Tony Award-winning Chicago Shakespeare Theater.
On your way out, stop for a cold one at Harry Caray’s Tavern. The late, great Cubs announcer’s watering hole also has a full menu and live music throughout the summer.
Notable discoveries and surprises in Chicago
City founder: On our first night in the city we stopped to read the inscription on a statue next to Michigan Avenue above the north bank of the river and learned that the founder of the city was an African-Caribbean man born in Haiti. Jean Baptiste Pointe DuSable was the first non-indigenous person to recognize the economic potential of Chicago.
In the 1770s DuSable opened a trading post next to the river where the Apple Store is now located and established the settlement that became Chicago. In 2021, Lake Shore Drive was renamed Jean Baptiste Pointe DuSable Lake Shore Drive.
Armenian restaurant: Many visitors in quest of Chicago-style food come to sample deep-dish pizza, hot dogs and Italian beef sandwiches. Sayat Nova in the Streeterville area was a detour in a different direction. The chilled mezza hummus, lamb shish kebob, paklava (Armenian version of baklava) and strong Armenian coffee, as well as the décor and ambiance, reminded us of similar cuisine we experienced during a recent cruise stop in Türkiye.
Sidewalk gardens: The biggest surprise about the famed Magnificent Mile along Michigan Avenue was finding it in full bloom. This is by design in keeping with the city’s motto: “Urbs in Horto” (City in a Garden). It is a source of city pride that each growing season property owners, property managers and landscape contractors collaborate on elaborate displays of colorful gardens.
The focus is on Michigan Avenue with flowering plants filling the medians and brilliant sidewalk flower beds. But also on side streets outside of restaurants, hotels and assorted other businesses. They even give out prestigious Magnificent Mile Beautification Awards with judging in five categories each year. The impact is that a stroll down the street feels like a walk in the park.
Bonus tip: Looking for the ideal breakfast to get you started on a day of exploring Chicago, Egg Harbor Cafe is the place. It was like a home-cooked meal in a friendly atmosphere with quality ingredients that came out hot and fast. That’s why we returned each day we were in the city to the Egg Harbor in the Streeterville area.
There are two Egg Harbor Cafes in Chicago and more in Illinois, Wisconsin and Georgia. Great feature is you don’t have to get there early; they serve breakfast until 2 p.m., as well as lunch.
A trip to Chicago isn’t complete without hearing live blues and a visit to the ‘Bean.’ (craigslegztravels.com)More from Craigslegztravels
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Fiction by Craig Davis
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