Things to Do in Chicago This Weekend: Winter Jazz Fair, Travel & Adventure Show

From live music to cultural celebrations, there's something for everyone in the Windy City this weekend.

Published on Feb. 21, 2026

Whether you're looking for live music, sporting events, comedy shows, or cultural festivals, Chicago has plenty of activities and events happening February 20-22. The annual Winter Jazz Fair, 66th Folk Festival, Lunar New Year celebration at Navy Pier, and Travel & Adventure Show are just a few of the highlights taking place across the city.

Why it matters

Chicago is known for its vibrant arts, music, and cultural scene, and this weekend's lineup showcases the diversity of entertainment options the city has to offer. These events cater to a wide range of interests and age groups, providing something for everyone to enjoy as the city emerges from the winter months.

The details

The Winter Jazz Fair at the Chicago Cultural Center features live performances, panel discussions, and a vendor fair, while the 66th annual Folk Festival in Hyde Park celebrates blues, bluegrass, Cajun, and traditional folk music. Families can welcome the Lunar New Year with free performances and cultural traditions at Navy Pier, and the Black Makers Market highlights Black-owned businesses across Chicago neighborhoods. The Travel & Adventure Show at the Donald E. Stephens Convention Center offers travel inspiration, deals, and planning resources from industry experts.

  • The Winter Jazz Fair takes place on February 20 from 11:30 a.m. to 9:30 p.m.
  • The 66th annual Folk Festival runs from February 20 to February 21 at Mandel Hall in Hyde Park.
  • The Lunar New Year celebration at Navy Pier is on February 21.
  • The Black Makers Market is held every Saturday, including February 21.
  • The Travel & Adventure Show takes place on February 21 from 10 a.m. to 5 p.m.

The players

The Jazz Institute of Chicago

The organization that hosts the annual Winter Jazz Fair at the Chicago Cultural Center.

Mandel Hall

The venue in Hyde Park that hosts the annual Folk Festival.

Navy Pier

The iconic Chicago landmark that is hosting the Lunar New Year celebration.

Donald E. Stephens Convention Center

The venue that is hosting the Travel & Adventure Show.

Artifact Events

The event space that is hosting the charity gaming event on February 22.

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The takeaway

This weekend's lineup of events in Chicago showcases the city's vibrant arts, music, and cultural scene, catering to a wide range of interests and providing something for everyone to enjoy as the city emerges from the winter months.