Best Of Chicago This Weekend: 24 Events Not To Miss

David

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Post on Jul 26, 2025

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Best of Chicago This Weekend: 24 Events Not to Miss

Chicago, the Windy City, is buzzing with activity this weekend! From world-class music festivals to captivating art exhibitions and thrilling sporting events, there's something for everyone. Whether you're a lifelong Chicagoan or just visiting, this curated list of 24 unmissable events will ensure you make the most of your weekend. Get ready to experience the best of what Chicago has to offer!

Arts & Culture:

1. Grant Park Music Festival: (Check website for specific dates and times) This iconic free outdoor concert series offers a diverse program of classical music, attracting thousands each summer. Pack a picnic and enjoy a breathtaking performance under the stars. [Link to Grant Park Music Festival website]

2. Museum of Contemporary Art (MCA) Exhibition: (Check website for current exhibitions) The MCA consistently showcases cutting-edge contemporary art from around the globe. Explore innovative installations and thought-provoking displays. [Link to MCA website]

3. Chicago Shakespeare Theater Production: (Check website for show schedule) Immerse yourself in the world of Shakespeare with a captivating performance at this renowned theater. [Link to Chicago Shakespeare Theater website]

4. Street Art Walking Tour: Explore Chicago's vibrant street art scene with a guided walking tour. Discover hidden gems and learn about the artists behind the murals. [Link to a relevant Chicago street art tour company – example only, replace with a real one]

5. Second City Comedy Show: Experience legendary Chicago comedy at The Second City, the birthplace of many famous comedians. Prepare for a night of laughter and unforgettable sketches. [Link to The Second City website]

Food & Drink:

6. Taste of Chicago (If applicable): Check for dates. This massive food festival showcases Chicago's culinary scene with diverse food vendors and live music.

7. Chicago Pizza Tour: Indulge in the city's famous deep-dish pizza with a guided tour that takes you to some of the best pizzerias. [Link to a Chicago pizza tour company – example only, replace with a real one]

8. Wicker Park Brewery Crawl: Explore the craft beer scene in Wicker Park, known for its vibrant bars and breweries. (Note: Always drink responsibly).

9. River North Wine Tasting: Sample a variety of wines at a sophisticated wine tasting event in the heart of River North. [Link to a relevant wine tasting event – example only, replace with a real one]

10. Maxwell Street Market: Immerse yourself in the vibrant atmosphere of Maxwell Street Market, a historic open-air market with unique finds and delicious food.

Outdoors & Recreation:

11. Kayaking on the Chicago River: Explore the city from a unique perspective with a kayaking tour on the Chicago River.

12. Millennium Park Activities: Visit Millennium Park and enjoy activities like visiting Cloud Gate ("The Bean"), relaxing in Lurie Garden, or attending a free outdoor concert.

13. Bike Ride along the Lakefront Trail: Enjoy a scenic bike ride along the picturesque Lakefront Trail, offering stunning views of Lake Michigan. [Link to Chicago Park District website – biking information]

14. Navy Pier Rides & Entertainment: Experience the iconic Navy Pier with its Ferris wheel, carousel, and various entertainment options.

Sports & Entertainment:

15. Chicago Cubs Game (if applicable): Check the Cubs schedule for weekend games at Wrigley Field. [Link to Chicago Cubs website]

16. Chicago White Sox Game (if applicable): Check the White Sox schedule for weekend games at Guaranteed Rate Field. [Link to Chicago White Sox website]

17. Chicago Fire FC Soccer Match (if applicable): Check the Chicago Fire FC schedule for weekend matches. [Link to Chicago Fire FC website]

18. Concert at the House of Blues: Check their website for the weekend's lineup. This legendary venue hosts a diverse range of musical acts. [Link to House of Blues Chicago website]

Other Events:

19. Chicago Blues Festival (If applicable): Check for dates. This iconic festival celebrates the rich history of Chicago blues music.

20. Lincoln Park Zoo: Enjoy a free visit to the Lincoln Park Zoo, home to a diverse collection of animals. [Link to Lincoln Park Zoo website]

Festivals & Special Events: (Check local event listings for up-to-date information)

21-24. Check local event listings: Websites like TimeOut Chicago, Do312, and the Chicago Reader provide comprehensive listings of events happening throughout the city. Always check for specific dates, times, and ticket information.

Planning Your Weekend:

Remember to check the official websites for each event for updated information on dates, times, ticket prices, and any COVID-related guidelines. Plan your transportation in advance, especially if attending multiple events. Have a fantastic weekend in Chicago!