Looking for something exciting to do this week? Chicago and Will County are buzzing with activities from October 13 to October 19, 2025. Whether you’re a fan of live performances, seasonal festivals, or outdoor adventures, there’s something for everyone. From iconic music performances and improv comedy to family-friendly science workshops and thrilling fitness events, this week is packed with opportunities to explore, laugh, and connect. Here’s a curated list of must-attend events to help you plan your week.
Arts and Entertainment:
Chicago’s arts and entertainment scene is thriving this week with a variety of performances and shows:
- Yusuf/Cat Stevens at The Chicago Theatre: Experience an intimate evening of music and storytelling with the legendary singer-songwriter on Tuesday, October 14, at 8 p.m.
- The Best of The Second City: Laugh out loud at the iconic comedy troupe’s best sketches on Monday, October 13, at 8 p.m., at the Second City Main Stage.
- Dream Hou$e at The Den Theatre: Starting Friday, October 17, this surreal comedy play explores family, gentrification, and reality TV in a unique and thought-provoking way.
For those who love immersive experiences, Toil & Trouble at Goblin Market Manga & Curiosities on Thursday, October 16, offers a theatrical journey into fate and control.
Festivals and Markets:
Celebrate the season with vibrant festivals and markets in Chicago:
- Jacks Pumpkin Pop Up Chicago: Running daily from October 13 to October 19, this fall festival is perfect for pumpkin lovers and families looking for autumnal fun.
- 3rd Annual Halloween Vintage & Artisan Fest in Ravenswood: On Saturday, October 18, explore vintage finds, artisan goods, and classic car displays at the Ravenswood Event Center.
- Buntoberfest 2025: Support rescue rabbits while shopping for bunny-themed items at this unique makers market on Sunday, October 12, at Vaca’s Creamery.
In Will County, don’t miss the Haunted Hollows Fest on Friday, October 17, at the Will County Fairgrounds, featuring live entertainment, a haunted house, and interactive games.
Fitness and Outdoor Activities:
For those who enjoy staying active, there are plenty of outdoor events to choose from:
- Palos Park Spooky Shuffle: Join a 5K or 10K trail run/walk on Saturday, October 18, at Swallow Cliff Woods-South in Palos Park.
- Red Eye 5K in Joliet: Race through the Inwood Golf Course on Sunday, October 19, and enjoy a bloody mary at the finish line.
- October Wheel Weekend: Starting Friday, October 17, this festival for Cyr and Gym Wheel enthusiasts includes workshops, a circus show, and an Oktoberfest-style celebration at Willye B. White Park Playground.
For a more relaxed evening, head to Outdoor Movie Night in Plainfield on Tuesday, October 14, for a screening of The Nightmare Before Christmas.
Summary:
This week in Chicago and Will County offers a diverse lineup of events, from live music and comedy to seasonal festivals and fitness activities. Whether you’re looking to laugh, shop, or get active, there’s no shortage of options to make your week memorable. So grab your calendar, gather your friends and family, and dive into the vibrant culture and community events happening near you!
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