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Sweetest Day Comedy Jam

        <h2>Guide to Live Events in Chicago: Concerts, Sports and Shows Near You</h2>
<p>Chicago, IL, boasts an unparalleled lineup of live entertainment—from rock concerts and theater productions to playoff games and music festivals.</p><p>With Vivid Seats, you can easily secure tickets to see your favorite teams and chart-topping artists live.</p>
        
        <h2>Things to Do in Chicago This Week</h2> 
        
<p>Chicago is buzzing with top-tier concerts thrilling baseball and world class fights this week. Pop powerhouse <a href="https://www.vividseats.com/tate-mcrae-tickets/performer/120648">Tate McRae</a> lights up <a href="https://www.vividseats.com/tate-mcrae-tickets-chicago-united-center-8-15-2025--concerts-pop/production/5359421">United Center</a> and rock fans can catch the <a href="https://www.vividseats.com/goo-goo-dolls-tickets/performer/330">Goo Goo Dolls</a> at <a href="https://www.vividseats.com/goo-goo-dolls-tickets-chicago-huntington-bank-pavilion-at-northerly-island-8-13-2025--concerts-rock/production/5361324">Huntington Bank Pavilion at Northerly Island</a>. Out on the diamond the eccentric <a href="https://www.vividseats.com/savannah-bananas-tickets--sports-minor-league-baseball/performer/86474">Savannah Bananas</a> bring their antics to <a href="https://www.vividseats.com/savannah-bananas-tickets-guaranteed-rate-field-8-16-2025--sports-baseball/production/5272654">Rate Field</a> while the storied <a href="https://www.vividseats.com/chicago-cubs-tickets--sports-mlb-baseball/performer/162">Chicago Cubs</a> defend Wrigley at <a href="https://www.vividseats.com/chicago-cubs-tickets-wrigley-field-8-17-2025--sports-mlb-baseball/production/5099873">Wrigley Field</a>. Cap the week off with the <a href="https://www.vividseats.com/ufc-ultimate-fighting-championship-tickets--sports-boxing-and-fighting/performer/1905">UFC - Ultimate Fighting Championship</a> back at <a href="https://www.vividseats.com/ufc---ultimate-fighting-championship-tickets-united-center-8-16-2025--sports-boxing-and-fighting/production/5755466">United Center</a> for a night of high stakes action.</p>        
        <h2>Things to Do in Chicago Next Week</h2> 
        
<p>Next week in Chicago you can rock out with <a href="https://www.vividseats.com/nine-inch-nails-tickets/performer/610">Nine Inch Nails</a> at <a href="https://www.vividseats.com/nine-inch-nails-tickets-chicago-united-center-8-20-2025--concerts-rock/production/5533334">United Center</a> or sway to <a href="https://www.vividseats.com/rob-thomas-tickets/performer/6949">Rob Thomas</a> at <a href="https://www.vividseats.com/rob-thomas-tickets-chicago-huntington-bank-pavilion-at-northerly-island-8-20-2025--concerts-rock/production/5739806">Huntington Bank Pavilion at Northerly Island</a> on the 20th. Dance under the stars with <a href="https://www.vividseats.com/above-and-beyond-tickets/performer/23094">Above and Beyond</a> on the 22nd and catch alternative anthems from <a href="https://www.vividseats.com/simple-plan-tickets/performer/4090">Simple Plan</a> on the 24th at the same lakeside venue.</p><p>If stadium energy is your style, root for the <a href="https://www.vividseats.com/chicago-cubs-tickets--sports-mlb-baseball/performer/162">Chicago Cubs</a> at <a href="https://www.vividseats.com/chicago-cubs-tickets-wrigley-field-8-21-2025--sports-mlb-baseball/production/5099887">Wrigley Field</a> at a matinee on the 21st then close out the week with pop’s latest sensation <a href="https://www.vividseats.com/benson-boone-tickets/performer/142849">Benson Boone</a> back at <a href="https://www.vividseats.com/benson-boone-tickets-chicago-united-center-8-23-2025--concerts-pop/production/5737371">United Center</a>.</p>

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Concert, Comedy, Sports & Theater Tickets in Chicago, IL

Live Events near Chicago, IL

Wintrust Arena

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Sweetest Day Comedy Jam at Wintrust Arena

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Sweetest Day Comedy Jam Wintrust Arena in Chicago, IL Sat, Oct 18 at 8:00pm