Grammy-winning vocalist Dee Dee Bridgewater, acclaimed pianist Cyrus Chestnut and Hawaiian slack-key guitar masters George Kahumoku Jr. and Led Kaapana are among the well-known artists set to appear at San Jose Jazz Winter Fest Feb. 15-28, organizers have announced.

The lineup also includes the San Jose State University Jazz Orchestra, Knower, Lulo Reinhardt, Calum Graham, Marek Pasieczny, Michael Chapdelaine, Jeff Peterson, Mike Clark’s Four and More; Mark Guiliana Jazz Quartet; A Circle Has No Beginning by Sameer Gupta featuring David Boyce, Veronica Swift, the Benny Green Trio, Jacob Jolliff Band, Loston Harris Trio, Organ Extravaganza with Ronnie Foster and La Misa Negra, among others.

Presented at venues in downtown San Jose and in Palo Alto, the festival has more than 25 shows presented by San Jose Jazz, which also hosts the popular annual Summer Fest in August as well as other concerts.

“We couldn’t be more thrilled to have jazz icons Dee Dee Bridgewater and Cyrus Chestnut as headliners of Winter Fest, while we feature many of the world’s greatest instrumentalists with International Guitar Night and Masters of Hawaiian Music,” said San Jose Jazz Executive Director Brendan Rawson.

Venues this year will include the re-opened Hammer Theatre in downtown San Jose as well as Oshman Family JCC in Palo Alto.

Tickets are $5-$40 per show and are on sale now. A Fest Pass, which grants admission to select shows, is $260. For more information, visit: sanjosejazz.org/winterfest.

Here are some of the lineup highlights:

Dee Dee Brigewater: She’s a vastly acclaimed vocalist, who has won three Grammy Awards for such efforts as the Ella Fitzgerald tribute “Dear Ella.” She’s also won a Tony Award for her role as Glinda in “The Wiz” in 1975. Bridgewater, whose latest studio album is 2017’s “Memphis … Yes, I’m Ready,” performs at Winter Fest with the San Jose State University Jazz Orchestra under the direction of Dr. Aaron Lington. (Note: San Jose Jazz’s High School All Stars perform at the concert at 6 p.m.) Details: 7 p.m. Feb. 18; Hammer Theatre Center, San Jose.

Cyrus Chestnut Trio: A versatile virtuoso on piano, Chestnut has performed with such major players as Wynton Marsalis, Freddie Hubbard, Branford Marsalis, Chick Corea, Dizzy Gillespie, Jon Hendricks and Betty Carter over the years. His deep catalogue includes his excellent tribute to the King of Rock ‘n’ Roll — 2007’s “Cyrus Plays Elvis,” as well as his 19th album as a bandleader, 2017’s “There’s a Sweet, Sweet Spirit.” Chestnut is accompanied by bassist Eric Wheeler and drummer Chris Beck in the trio. Details: 8 p.m. Feb. 15; Café Stritch, San Jose.

Masters of Hawaiian Music: The slack-key guitar show features two of the genre’s legendary performers — George Kahumoku Jr. and Led Kaapana — as well as rising star Jeff Peterson. Kahumoku is a four-time Grammy winner who is known as “Hawaii’s Renaissance Man.” Kaapana has worked with such artists a Alison Krauss, Jerry Douglas, Dolly Parton and Chet Atkins. Peterson has won a number of Na Hoku Awards (Hawaiian equivalent of a Grammy) and had five songs featured in the award-winning George Clooney film “The Descendants.” Details: 7 p.m. Feb. 23; Café Stritch, San Jose.