Chicago Bucket List

Mark your calendars for Caturday, Oct 10th! 🐈🐾 Chicago’s beloved neighborhood cat-spotting walking tour is officially headed to Bowmanville (located within Lincoln Square) for a massive day dedicated entirely to local felines, cat costumes, and community fun!

These cat-spotting walks have been popping off in cities across the country—drawing hundreds of cat lovers out to hunt for pets—and now Chicago is getting its next edition. Kicking off at 3pm the guided stroll takes you through the quiet streets of Bowmanville to spot neighborhood cats hanging out on front porches, resting in “catios,” or peeking out of windows.

Expect full cat costumes (on both humans and kitties!), costume contests, and a festive neighborhood block party immediately following the walk. 🎃✨

📍 Got a cat in the neighborhood? The deadline to get your kitty on the official tour map is Sept 30th! Head over to The Lincoln Square Cat Tour to submit your pet, sign up to volunteer, or check out event details. Who’s going cat-spotting in October?!

There’s a secret sushi speakeasy inside a hotel in Lincoln Park 🔑🍣 Get the date night special for 2 at https://link.bucketlisters.com/GmQ7 👈 Watch a master chef prepare a 15-course omakase right in front of you at this exclusive 6-seat dining setup inside Hotel Lincoln. Upcoming dates: 9/27, 28, 29 & 30. Full schedule + tickets at our link in bio. Share this with your dinner date ✨

AS YOU WISH 🗡️✨ Nearly 40 years after the iconic 1987 film stole our hearts, The Princess Bride is officially coming to the stage and making its pre-Broadway world premiere right here in Chicago. 🎭

The massive new musical adaptation is set to run from July 19-Aug 22, 2027 at the James M. Nederlander Theatre, featuring original music and lyrics by the Oscar-winning duo behind Frozen (Robert Lopez and Kristen Anderson-Lopez) as well as choreography by the Tony winner Andy Blankenbuehler (Hamilton). Who’s excited to see this?! 📸: MGM

A Chicago legend took the field last night 🫔 ⚾️ The ‘Tamale Guy’ delivered the game ball for the White Sox as part of the team’s Hispanic Heritage Night celebration. You know it’s a good night when the Tamale Guy shows up.

You can find up to 30% OFF White Sox tickets at BucketListers.com via https://link.bucketlisters.com/WX1g 👈 - 📸 Chicago White Sox

Coming October 19th! 🧪🎃 Grab tickets at https://link.bucketlisters.com/Mww4 👈
Gather your coven for a spooky cocktail class in Chicago & Naperville, featuring:
🍸 Hands-on 90-minute witch mixology workshop
🔮 Craft 2 specialty Halloween cocktails
✨ Witchy decor & seasonal vibes
🍔 Full dinner menu available for order
Tag who you’re taking below! 👇

THIS WEEKEND 9/26 & 9/27 🎷✨ One of Chicago’s most beloved autumn traditions, the Hyde Park Jazz Festival, is officially back featuring nearly 40 free performances across 11 unique indoor and outdoor stages. Pro-tip: It’s open to the public and completely free to attend! Tag your crew to go with you 👇🏼

A HISTORIC MOMENT FOR CHICAGO SPORTS ⚾️ Chicago’s cross-town rivalry is officially making history: both the Cubs and the White Sox are headed to the 2026 MLB Postseason! 🏙️ In over a century of baseball, this rare double-playoff appearance has only happened four times in city history: 1906, 2008, 2020, and now 2026. Whether you’re repping North Side blue or South Side black and white, the city is about to be electric. Are you riding with the Cubs or the Sox this postseason?! Sound off in the comments! 👇