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Five Things To Do in Chicago: Feb. 13 to Feb. 15, 2026
Don't let the cold hold you back — these weekend events are worth layering up for. See what's happening near you.
Sip and stroll at the Roscoe Village Wine Walk.
Stroll the shops along Roscoe Street and taste 20+ different wines at the Roscoe Village Wine Walk. In addition to discovering your new favorite bottles, participating shops also offer special discounts on apparel, home goods, and more.
Date: Feb. 13
Time: 5:30 p.m.–8:30 p.m.
Cost: $45
Location: Roscoe Street from Paulina to Western
More Info: eventbrite.com
Shop sustainably at the Handmade Market.
Need a last-minute Valentine's Day gift, or just want to support sustainable local crafters? Order a mimosa and hit the Handmade Market at the Empty Bottle, where a rotating cast of local crafters offer fresh selections every month. Expect an eclectic spread of handmade jewelry, glassware, fiber arts, handbags, clothing, paper goods, and other thoughtfully crafted finds.
Date: Feb. 14
Time: 12:00 p.m.–4:40 p.m.
Cost: Free
Location: The Empty Bottle
More Info: handmadechicago.com
Celebrate cultural pride at the Bud Billiken® All Star PAL Showcase.
For 96 years and counting, Chicago residents have welcomed back-to-school season with the Bud Billiken® Parade — a historic commemoration of African American pride and youth empowerment in the Windy City. This year is the first-ever Bud Billiken® All Star PAL, an exciting new event that features a full day of electrifying performances by youth dance teams from across the city.
Date: Feb. 15
Time: 1:00 a.m.–4:00 p.m.
Cost: $50
Location: Dr. Conrad Worrill Track & Field Center
More Info: ticketsignup.io
Get crafty at the Origami Open House.
A visit to the Garfield Park Conservatory is one of the best cold-weather activities in Chicago, and this weekend it gets even better with an Origami Open House open to all visitors. Kids and adults alike can stop into the Jensen Room and learn how to turn colorful sheets of paper into three-dimensional models of animals, plants, flowers, and more. If you miss this weekend, don't worry — the event takes place every second Saturday.
Date: Feb. 14
Time: 11:00 a.m.–2:00 p.m.
Cost: Included with reservation
Location: Garfield Park Conservatory
More Info: garfieldconservatory.org
Immerse yourself in nature at the Winter Tree Walk.
This easy winter hike is open to all ages and is a great way to get to know more about the North Park Village nature preserve. Participants will accompany the Nature Center's Land Manager, identify trees, and learn more about the ecological management of the area.
Date: Feb. 15
Time: 2:00 p.m.–3:00 p.m.
Cost: Free
Location: North Park Village Nature Center
More Info: anc.apm.activecommunities.com
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