The Ultimate Badass Chicago Bucket List

A badass recognizes a badass, and you, my friend, are a badass. And since we must maintain this status so that we stay the cooler, more superior friend, what better way to do so than through a series of activities and events that’ll have you doing new, awesome shit all year?

Luckily, we concocted the ultimate badass bucket list that everyone brave enough in Chicago must do. It’s a challenge for the fun and fearless, so let’s not get stuck in the same old bars, same old restaurants, doing the same things we always do year after year.


Add this to your New Year’s resolutions: every badass thing Chicago has to offer.



Freeze Your Ass off at the Polar Plunge

Chicago Polar Bear Club
Photo Credit: Chicago Polar Bear Club

Do a chilling challenge for a heartwarming cause. The Polar Plunge is an annual, winter event where participants take a dive into the cold waters. All proceeds benefit the Young Athletes of Special Olympics Illinois. The event takes place on January 26 this year!



Take a Water Taxi

Chicago Water Taxi
Photo Credit: Chicago Water Taxi Instagram

Take a new approach to commuting with a water taxi. C’mon, can you imagine people asking you which route you take to work, and you say, “the River”!? Classic.



Take a Ride With Chicago Helicopter Experience

Chicago Helicopter Experience

Photo Credit: Chicago Helicopter Experience

See things from a new perspective. Grab a friend and take an exciting helicopter ride around the city.



Get Spooked at Chicago Haunting Tours

Photo Credit: troytaylorgram Instagram

Explore the weird history of Chicago from gangster hideouts to crime scenes, to haunted houses and more.



Zoom Fast at a Chicagoland Racing Experience

Richard Petty Driving Experience
Photo Credit: Richard Petty Driving Experience

Take the ultimate racing experience. I promise you’re in for a thrill! Choose between driving or riding in a Nascar (but, since you’re a badass, you might as well drive).



Sing Your Heart Out at Lollapalooza

Photo Credit: Lollapalooza Instagram

Attend the annual Lollapalooza during the summer. It’s Chicago’s biggest music festival featuring a wide array of genres, artist, and bands, and if you haven’t been before, do you even live here?


Go on a Bar Crawl

Photo Credit: TBOX Instagram

There’s no better way to get lit than a bar crawl. You can check out annual festive crawls occurring in Chicago, or create one on your own.


Take a Stroll Through the Underground Pedway

Chicago Detours
Photo Credit: Chicago Detours Facebook

The Pedway is a system of underground tunnels and walkways, where you can navigate the city without the worries of the bitter cold or summer heat. They also have awesome Interior Architecture Tours.


Take a Leap of Faith at the Willis Tour Skydeck

Willis Tower Skydeck
Photo Credit: Willis Tower Skydeck Instagram

Visit Chicago’s tallest skyscraper and step out onto the ledge, suspended over 1,000 feet in the air. Get a selfie while you’re at it, just to let everyone know that mamma raised no punk.


Take Paddle Boarding Lessons

Chicago SUP
Photo Credit: Chicago SUP Instagram

Known as the hybrid of surfing and kayaking, Paddle Boarding is a fun activity for warmer weather. So grab a friend and take a class this year!


Let the Crown Fountain Spit on You

Millennium Park
Photo Credit: Millennium Park Instagram

On those toasting summer days, cool off at the Crown Fountain, where a 3D model spits out water.