Looking for fun ways to spend the weekend in Chicago? From foodie festivals to ice sculpting and themed skate nights, the city is buzzing with events that everyone can enjoy. Here’s your ultimate weekend guide:
Chicago Restaurant Week (Jan 23 – Feb 8, 2026)
Food lovers, rejoice! Chicago Restaurant Week is back with a record-breaking 550+ restaurants participating across the city. Enjoy prix-fixe menus for brunch and lunch at $30, and dinner options for $45 or $60. It’s the perfect opportunity to try new spots or revisit your favorites.
Stranger Things Skate Night (Friday, Jan 30 | 6:00 PM – 8:00 PM)
Grab your skates and step into Hawkins for a night at Gallagher Way. Skate to your heart’s content and test your knowledge with Stranger Things trivia on the Gallagher Way video board. Remember: friends don’t lie. This event is one you won’t want to miss!
Cider Summit Chicago (Saturday, Jan 31 | 2:00 PM – 6:00 PM)
Head to Lakeview Terrace at Navy Pier for the 12th annual Cider Summit! Discover over 125 selections from more than 40 top cider, mead, and fruit spirit producers. This year also features a Pre-Opening tasting pairing cider with Molly’s Cupcakes, a treat for both your taste buds and your Instagram feed.
Live Ice Sculpting (Lakeview | Sat & Sun)
Bring your ideas and watch Master Ice Carvers turn a block of ice into incredible works of art!
- Saturday, Jan 31 | 2:00 PM – 4:00 PM – CTA Brown Line Station, 3411 N Paulina Ave
- Sunday, Feb 1 | 12:00 PM – 2:00 PM – St. Alphonsus Church, 1429 W Wellington Ave
This interactive event is perfect for families, friends, or anyone who loves a little winter magic.
Chicago is full of exciting events this weekend, whether you’re a foodie, sports fan, or just looking for a fun experience. Make plans now and enjoy all the city has to offer!