Illinois, 4 places we take you
Chicago blues and jazz tours start with one fact: when the Delta came north, it plugged in. Chicago gave the blues electric guitars and a backbeat, recorded them at Chess on South Michigan Avenue, and still plays them every night of the week.
From $1,9902 tours that go there
Between 1910 and 1970 about six million Black Southerners moved north, and Chicago, at the end of the Illinois Central line from Mississippi, took many of them. Muddy Waters arrived in 1943, plugged his guitar into an amplifier to be heard in the noisy South Side bars, and with Howlin' Wolf, Little Walter and Willie Dixon made the records at Chess that the Rolling Stones and Eric Clapton grew up on.
The South Side clubs of that time are mostly gone, but the blues moved to the North Side and downtown, and Chicago still has more of it than any other city. Our tour adds the city's jazz, at the Green Mill in Uptown, where Al Capone had a favorite booth.
2 tours
New Orleans, Mississippi Delta, Memphis and Chicago
New Orleans, Clarksdale, Memphis, Chicago
The Great Migration route in nine days: from New Orleans jazz up through the Delta and Memphis, then overnight on the City of New Orleans train to the Chicago blues.
From $4,590 per person, double room
See the tourChicago
Chicago
Four nights of Chicago music: the Chess studio by day, Buddy Guy's club, the North Side blues bars and the Green Mill, where Capone's booth still faces the door.
From $1,990 per person, double room
See the tourPrices per person sharing a double room; day tours per person. Flights to the start city are optional and priced on each tour.
The places
From 1957 to 1967 Chess Records worked from a narrow building at 2120 South Michigan Avenue, then a row of record companies. Muddy Waters, Howlin' Wolf, Chuck Berry, Bo Diddley and Etta James all recorded upstairs, and in 1964 the Rolling Stones came to cut a song named for the address.
The building now belongs to Willie Dixon's Blues Heaven Foundation, set up by the bassist and songwriter's widow. Tours show the restored studio and the stairs where the musicians waited, and the garden next door has summer concerts.
Tours that visit Chess Records
Buddy Guy came to Chicago from Louisiana in 1957, played guitar on hundreds of Chess sessions and opened his own club in 1989. Legends moved in 2010 to a bigger room on Wabash Avenue in the South Loop, with Louisiana cooking and walls full of guitars from his friends.
The club has blues every night, with free acoustic sets at lunch. Every January Buddy Guy himself plays a month of shows there, and they sell out as soon as they are announced. We book a table for dinner and the first two sets.
Tours that visit Buddy Guy's Legends
The Green Mill on North Broadway in Uptown opened in 1907, and in the 1920s one of Al Capone's men held a share. His favorite booth, with a view of both doors, is still there. The room is dark, red and green, with a long bar and a small bandstand, and it has hosted jazz most nights for decades.
Sunday nights belong to the Uptown Poetry Slam, which started here in 1986. Our groups come on a weeknight for a set of straight-ahead jazz, sitting close enough to see the drummer's hands.
Tours that visit The Green Mill
Kingston Mines, on Halsted Street in Lincoln Park, has been a North Side blues club since the 1970s and is open late every night. It has two stages in two rooms and the bands alternate, so the music never stops from early evening until four in the morning.
It draws a young crowd and a lot of visitors, but the players are the real Chicago circuit, and many of them also play the South Side clubs on other nights. Our tour leader takes the group on the last night and leaves the late hours to the brave.
Tours that visit Kingston Mines
Getting around
The Red Line runs from the South Loop to Uptown in 30 minutes; we buy the passes.
For Chess Records on South Michigan and the late return from the North Side.
The South Loop, Grant Park and Millennium Park are all walkable from our hotel.
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Tour vanAmtrak trainRiverboatShort flight Map tiles: © Esri, HERE, Garmin © OpenStreetMap contributors. Lines join the stops in tour order in simplified form.
What is included
Best time to visit
June has the free Chicago Blues Festival in Millennium Park, and summer brings outdoor concerts everywhere. Winters are cold, but the clubs are warm and January has Buddy Guy's residency.
At a glance
Questions
A few neighborhood bars still have blues on weekend nights, and our guide takes the group to one when they are open. Most clubs moved north and downtown.
Yes, it is part of the tour. Blues Heaven runs the visits, and the times change, so we confirm them a few weeks ahead.
In early June in Millennium Park, free. Our June date is timed to it.
On the Blues Highway tour, yes: the City of New Orleans overnight in sleeper rooms, arriving in Chicago in the morning.
From December to March, very. We visit in all seasons, and the clubs are always warm.
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