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Savor the Magic of Chicago: A Weekend of Apples, Wine, Food, and Art

Juliana Yeager

🍂Chicago is buzzing with fall energy this weekend. The city has something for everyone. You can enjoy apple-cider doughnuts and small-town charm at the 38th Annual Lincoln Square Ravenswood Apple Fest. You can sip vintages at Lincoln Park Wine Fest or enjoy the festive atmosphere at St. Benedict’s Oktoberfest. Meanwhile, strolling through creative storefront galleries at the West Town Art Walk offers a unique artistic experience. The weekend promises a perfect mix of flavor, games, and art. Here’s your guide to what’s happening around town.

🍎 38th Annual Lincoln Square Ravenswood Apple Fest 2025

📍 Location: Lincoln Avenue between Lawrence and Sunnyside Avenues, Chicago, IL
📅 Dates: Friday, October 3 – Sunday, October 5, 2025
⏰ Event Hours:

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The Lincoln Square Ravenswood Apple Fest is a cherished fall tradition in Chicago. It celebrates the season with a variety of activities for all ages. The event features over 80 local vendors offering apple-themed treats, crafts, and seasonal goods. Live music performances take place throughout the weekend. Meanwhile, the dedicated Kids Zone at 4513 N Lincoln Avenue offers a range of family-friendly activities from 10:00 AM to 4:00 PM each day. Proceeds from the event support local beautification projects and community nonprofits.

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🍷 Lincoln Park Wine Fest 2025

📍 Location: Jonquil Park, 1001 W Wrightwood Ave, Chicago, IL
📅 Dates: Friday, October 3 – Sunday, October 5, 2025
⏰ Event Hours:

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The Lincoln Park Wine Fest returns for its ninth year. It transforms Jonquil Park into a vibrant open-air market featuring wine and food pavilions. The event offers a variety of wines from around the world. Sommeliers and brand ambassadors are available to guide tastings. General Admission includes 12 standard tastings and a commemorative wine glass. VIP Admission offers additional specialty tastings, access to a private tasting area with seating and restrooms, and a separate VIP entrance. Live music and artisan vendors add to the festive atmosphere. Proceeds from the event support improvements to Jonquil Park.

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🎠 St. Benedict’s Oktoberfest 2025

📍 Location: St. Benedict Parish, 3941 N. Bell Ave., Chicago, IL
📅 Dates: Friday – Sunday, October 3 – 5, 2025
⏰ Event Hours: Friday 4:00 PM – 10:00 PM; Saturday 1:00 PM – 10:00 PM; Sunday 1:00 PM – 7:00 PM
💰 Admission: Free; daily wristbands for unlimited games and activities $10/day or $20/weekend; supervised kids’ area Saturday night $15/child

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St. Benedict’s Oktoberfest is a long-running, family-friendly festival celebrating German heritage, food, and community spirit. The event features carnival rides and games suitable for all ages, a supervised kids’ area on Saturday night for ages 4–10, and daily wristbands that grant unlimited access to attractions like inflatables, slides, and obstacle courses. Attendees can enjoy traditional German cuisine, beer, wine, and soft drinks, while live music performances enhance the festive atmosphere. With a welcoming environment for families, this Oktoberfest offers something for everyone, from children enjoying rides and activities to adults savoring food, drinks, and entertainment.

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🖼️ West Town Art Walk 2025

📍 Location: West Town, Chicago, IL – Start at any participating business
📅 Dates: Friday, October 3 – Sunday, October 5, 2025
⏰ Event Hours:

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The West Town Art Walk is a self-guided exploration of Chicago’s vibrant West Town neighborhood. It showcases a variety of local galleries, boutiques, museums, and restaurants. This year, the 15th edition features over 50 participating venues, including Lost Girls Vintage, Ukrainian Institute of Modern Art, Goose Island Fulton St Taproom, HIRO Bar + Izakaya, and Volume Gallery. Visitors can enjoy visual art, fashion, music, and culinary experiences throughout the weekend. In addition, guided public art tours are available on Saturday and Sunday. These tours provide deeper insights into the neighborhood’s artistic landscape. Many venues and activities are family-friendly, so visitors of all ages can explore and enjoy the neighborhood’s creativity together.

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🍁 Wrap-Up
With apples, wine, games, and art filling the city streets, Chicago proves that fall weekends are made for exploring. Whether you spent your time savoring flavors, experiencing German culture, or wandering through creative spaces, there are many ways to enjoy the season. This is just the beginning of autumn’s lineup in the city. Be sure to mark your calendars for more seasonal fun.

Take a look at last weekend’s highlights and see the fun Chicago had before planning your weekend adventures.

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