Chicago Travel Tips: 8 Must-See (Unique) Locations for Your First Chicago Visit

Header Image
May 14, 2018

There are plenty of must-see locations for your first visit to Chicago. With our beautiful waterfront, expansive skyline, and plenty to do, it’s easy to fill your to-do list for your first time in the Windy City.

While the popular locations are non-negotiable, we love all the unique locations, holes in the wall, and fun experiences Chicago has to offer. Here are our 8 favorite unique spots.

1. Oz Park

Oz Park is just what you’d picture – a dedication to L. Frank Baum and the magical world of The Wonderful Wizard of Oz. Littered with statues paying homage to the stories, this park is perfect for the young and the young-at-heart alike.

2. Tiffany Dome

Visit the Chicago Cultural Center and discover the beauty of the Tiffany Dome, the largest of its kind in the world. Restored in 2008, this unique work of art spans over 1,000 square feet and contains over 30,000 pieces of glass.

3. The Violet Hour

This speakeasy style cocktail bar features unique and high-end drinks that are sure to please our locals and out-of-towners alike. Check out The Violet Hour to get a different take on the Chicagoan bar scene.

4. Graceland Cemetery

In this park-like cemetery, you’ll find the final resting places for a number of infamous Chicagoans. The Graceland Cemetery is a great place for a walk, enjoying the pristine grounds, and reveling in the beautiful architecture.

5. Myopic Books

Filled with classics and new treasures of all kinds, Myopic Books is a must-see for every book lover. Live poetry readings and live music keep the the store alive and filled with the pulse of our city.

6. National Italian American Sports Hall of Fame

Famous Italian American sports heroes and memorabilia grace the halls of the National Italian American Sports Hall of Fame. Bring the whole family to learn about the incredible impacts made by these legends.

7. Tribune Tower Walls

During your visit to the famous Magnificent Mile, don’t miss the extraordinary artifacts within the base of the Tribune Tower. Historical artifacts retrieved by correspondents of the Tribune during the late 19th/early 20th centuries were placed in the building’s structure and labeled with the origin.

8. Green Mill Jazz Club

We couldn’t leave you with a list of Windy City hotspots that didn’t include a local jazz club, and the Green Mill Cocktail Lounge won’t disappoint. With over a century’s history of hosting the best that jazz has to offer, today’s artists are no different.

Enjoy these eight unique Chicagoan locations for your first trip to the Windy City and you’ll be glad you came. While you’re here, don’t forget to come see us at Chicago Trolley for the best hop on hop off tour of Chicago.