Bowling With Santa
Monday, Dec. 23, 1:30 – 6 p.m., Robert’s Westside
Join us for a festive afternoon of bowling with Santa. Wear your best Santa suit or holiday outfit and enjoy two games, shoe rental, pizza, and access to pool tables at Circle Lanes. 7321 Madison St., Forest Park
How it works: Check in at Bobby’s: 1:30- 2:30 p.m. Depart as a group to Circle Lanes at 2:45 p.m. Bowling With Santa: 3 – 6 p.m. Head back to Bobby’s at 6 p.m.
Wine Tasting with Anfora Wine Merchants
Wednesday, Dec. 18, 7 p.m., R Titus Designs
Enjoy a curated selection of wines from Anfora while shopping for last-minute gifts at R Titus Designs Studio. Enter to win raffle prizes with purchase (*see details in-store). RSVP at pp.events/rtitusdesignswinetasting. 143 S Oak Park Ave., Oak Park
Crosstown Exotics Reptile Show
Sunday, Dec. 22, 3 p.m., Forest Park Public Library
Celebrate Shelly’s “birthday” with a reptile show by Crosstown Exotics. Discover fascinating creatures and learn all about them in this fun, family-friendly event. Perfect for kids of all ages. 7555 Jackson Blvd., Forest Park
Jazz Prayer: Finding the Light
Friday, Dec. 20, 7 p.m., Good Shepherd Lutheran Church
Celebrate the season with an evening of live jazz, thoughtful readings, and a carol sing-along. Enjoy refreshments at 7:10 p.m., followed by the service at 7:30 p.m. All are welcome. 611 Randolph St., Oak Park
Meet Me for Lunch at Rustico
Friday, Dec. 20, 11:30 a.m. – 1 p.m., Rustico
Join the Chamber for a casual sit-down luncheon with small group networking. Enjoy Spanish-Italian fusion dishes like tapas, wood-fired pizzas, and homemade pastas while connecting with fellow members. 155 S Oak Park Ave., Oak Park
Carnival’s Christmas Corner
Saturday, Dec. 21, 10 a.m., Oak Park
Bring the whole family to this free holiday event. Enjoy photos with Santa, wish list letter writing, and festive treats like hot cocoa and cider. Fun for all ages. 824 S. Oak Park Ave., Oak Park
Celebrate Kwanzaa
Monday, Dec. 30, 6 – 8 p.m. Oak Park Public Library
Honor the Black American Harvest celebration with dance, drumming, poetry, and storytelling. Enjoy performances by Hassani Cannon on drums and Kuumba Kids dance, local cuisine, and a Libation Ceremony led by Ade Adeyeme. Open to all. Register at oppl.org/calendar. 834 Lake St., Oak Park
Chicago Funk Mafia
Friday, Dec. 20, 6:30 – 10:30 p.m., Robert’s Westside
Kick off the holidays with Chicago Funk Mafia’s mix of originals and covers. Featuring special guests Henry Alden Carpender on trombone and Rufus Parenti on saxophone. Boost your holiday cheer—don’t miss this festive night of funk. 7321 Madison St., Forest Park
Free Sing-Along Messiah Concert
Sunday, Dec. 22, 3 p.m., First United Methodist Church of Oak Park
Join the Apollo Chorus of Chicago for Handel’s Messiah. Sing along or simply enjoy as an audience member. Admission is free, with a free-will offering benefiting Housing Forward. Musical scores available for $10 at the door. Accessible entrance on Oak Park Ave. Details at firstumcoakpark.org. 324 N. Oak Park Ave., Oak Park
Multiple Goods Fair
Tuesday, Dec. 24, 10 a.m. – 4 p.m., Compound Yellow
Discover a vibrant selection of unique items, including hot sauce, ceramics, and apparel, at the Multiple Goods Fair. Celebrate the season with Compound Yellow and explore the creativity of local makers. 244 Lake St., Oak Park
The Heartwreckers: A Tribute to Tom Petty & The Heartbreakers
Saturday, Dec. 21, 6:30 – 10:30 p.m., Robert’s Westside
Enjoy a night of Tom Petty hits performed by The Heartwreckers. General admission tickets are $20, with reserved seating available for $30 per seat (sold in groups of 4-6). Seating is first come, first served for General Admission. Don’t miss this tribute concert. 7321 Madison St., Forest Park
Duff Driscoll Nonet Performs: Miles Davis’ ‘Birth of the Cool’
Sunday, Dec. 29, 7:30 p.m., Robert’s Westside
Experience a live performance of Miles Davis’ Birth of the Cool, a groundbreaking jazz album released in 1957. This performance will feature the innovative arrangements of Davis’ nonet, blending Afro-American and classical music techniques. Tickets: $20. 7321 Madison St., Forest Park