The Ultimate Chicago Bucket List

It’s no surprise that Chicago is one of the biggest tourist destinations: we have miles of beaches, world-class museums, foodie neighborhoods and some of the thrill-seeking adventures. Take on this Chicago bucket list today, or save it for when you need an adventure.

1. Soar above the city and lake in a helicopter.

Get your thrill-seeking fix while taking in the breathtaking views of the city and Lake Michigan from your seat in a Chicago Helicopter Experience chopper. Choose from daytime, twilight or nighttime trips, each offering its own sense of adventure.

2. Grab a Chicago-style dog at Portillo’s.

And yes, you should always get the side of French fries.

3. Get out on the Ledge if you dare.

The Skydeck Ledge, the glass balcony extending four feet outside of the 103rd floor of Willis Tower, offering a terrifying experience and even better views from 1,353 feet off the ground.

4. Ride the river on a speedboat.

Experience full throttle slalom runs, sharp twists and turns, and feel the raw power and excitement of Seadog Extreme’s two 1400 HP engines. Also, enjoy music and a fun narration about Chicago throughout your cruise. YOU WILL GET WET!

5. Drinks at The Cindy’s Rooftop.

This rooftop bar offers some of the best views of the city, with an expansive look at Millennium Park and Lake Michigan.

6. Kayak along the Chicago Riverwalk.

Head down to the Chicago Riverwalk and rent a kayak to explore the waterway on your own, or take a guided tour. You’ll pass by architectural masterpieces and breathtaking city views, all while enjoying the great outdoors. If you even need to add a little extra excitement, kayak down the Chicago River at night, through the city and out to Navy Pier to watch the fireworks.

7. Eat Chicago’s famous deep dish pizza.

Lou Malnati’s, Giordano’s, Gino’s East, Pizzeria Uno…You can get it at any of these places!

7 Magnificent Mile Moments

8. Jet ski on Lake Michigan.

Looking for an adrenaline rush? Zoom across the surface of Lake Michigan with a jet ski rental.

9. Drinking in a secretive Tiki bar.

Three Dots and a Dash, a tiki-themed speakeasy, pouring out crazy tropical cocktails in vessels like glass skulls and treasure chests. How to get in: Locate the blue light behind Bub City in the alley between Hubbard and Illinois.