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Daily Email - Wednesday - 4/30/2025

Hey, heyyyy Chicago!

Enter for a chance to win a pair of 2-day passes to Evanston Folk Festival. Featuring performances from Iron & Wine, Margo Price, Tune-Yards, Bonny Light Horseman and 30 other artists and so much more. Don’t miss your shot.*

JUST ANNOUNCED

WIN STUFF WEDNESDAY

You can’t be a winner if you don’t even try! Enter one of the HUNDREDS of amazing giveaways on our giveaway page and get one step closer to the show of your dreams (for free!).

DOSTUFF, PROVINCETOWN BUSINESS GUILD, PRIDEAWAY STAYS PRESENT:

🌈 YOUR DREAM PTOWN PRIDE GETAWAY AWAITS! 🌈

Enter to win a Flyaway to the most vibrant Pride celebration on the East Coast! We're giving our lucky winner (and +1) a monumental Provincetown Pride weekend filled with dancing, laughter, and pure joy.

YOUR FABULOUS PRIZE INCLUDES:

Tickets to the Pride Kickoff Dance Party AND Queer Comedy Showcase

Two nights of luxurious accommodations (June 6-8)

$600 flight credit to whisk you away to Cape Cod

Ptown isn't just any Pride - it's a historic LGBTQ+ haven that comes alive with dazzling dance parties, hilarious comedy, a bustling Pride Market, the "Feet Over Front Street" 5K, and endless opportunities to celebrate authentically YOU!

Enter now to experience the magic where the LGBTQ+ community has celebrated for generations! Your perfect Pride weekend awaits! 🏳️‍🌈

ON THE WAY

💃 Cinco de Mayo

Events All Weekend!

Whether you’re celebrating the success of the batalla de Puebla or you just want an excuse to have fun - Cinco de Mayo in Chicago is always one to remember!

🎸 Boston Manor

Tomorrow at Subterranean (7PM)

Pop-punk isn't dead—it's just evolved. Boston Manor is bringing their angsty anthems to Chicago this May, proving that you can still scream your feelings and look good doing it. It's like your high school diary set to music, but with better production values.

🎤 Reggie Watts Live

Tomorrow at Thalia Hall (8:30PM)

If you haven't experienced Reggie Watts live, do you even know what surreal comedy is? This May, he's bringing his mind-bending improv and musical genius to Chicago. It's like if your brain went on a psychedelic trip and came back with a stand-up special.

🐎 Kentucky Derby

Saturday at Various Locations

Put on your fanciest hat and your most judgmental side-eye—it's Derby Day in Chicago. Whether you're sipping mint juleps or pretending to understand horse racing, got out and embrace your chance to be part of the spectacle.

🥒 Pickle Fest

Saturday in Wrigleyville (12PM)

Relish in the moment of all things pickle! On Saturday, Chicago’s annual Pickle Fest returns with more drinks, live music, photo ops, and fun than ever before. Grab your tickets today - it’s gonna be a great brine, uh, we mean, “time”!*

The Hop

Step back in time at The Hop, Jewel-Osco’s free, family-friendly celebration filled with 1950s-inspired fun, dancing, and springtime treats! Enjoy diner fare, an old-fashioned candy bar, live DJ entertainment, games, costume contests, and more. Adults 18+ can join the dance marathon to win prizes and earn up to $7,500 for local charities supported by the Jewel-Osco Foundation.

Nourishing neighborhoods for over 125 years, Jewel-Osco invites you to dance, play, and give back— register now and enter to win a $250 Jewel-Osco gift card!

LOCALS ONLY

  • Ever had a Brazilian-style brunch? Brasero is serving up just that every Sunday! Get eating!

  • Friday is National Matcha Day! Grab a green drink at Swadesi Cafe where they’ve even got a Key Lime Matcha!

  • May is AAPI (Asian American and Pacific Islander Heritage Month)! See our list of events to celebrate!

🎟️ LIKE FREE TICKETS?

Do312 MORE Members get at least one pair a month. Get started with a Free Preview today to see what we have for you. Like a:

  • Trio of Tech-House Legends @ PRYSM

  • Honky-Tonk Revival with a Retro Twist @ Joe's Bar

  • Desert Blues Meets Ambient Jazz @ Lincoln Hall

After your free preview, Membership is $7/mo. Cancel anytime.
Browse ticket matches before starting a trial / joining.

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Go Outside!