Secrets of Chicago: 5 Hidden Spots You Need to Check Out

By Natasha Gabrielle

Planning a trip to The Windy City? While in Chicago, you can see a lot more than just the big city highlights like The Bean, Millennium Park, and Wrigley Field. If you head off the beaten path, there are some fantastic gems.

Pre-Prohibition Drinks

Looking for a place to grab a cocktail? Check out The Violet Hour in Wicker Park. This speakeasy-style bar is known mostly by locals, and it offers a hip, chic vibe and creative house-made drinks. Be warned—the drinks are strong!

Billiard Balls & Poker Chips

Feeling competitive? Play your favorite games at Chicago’s Game Room. This lounge is the place to play all your favorite childhood games like checkers, foosball, cards, and more. Of course, there are plenty of drinks and finger foods to enjoy, too. You can find this wonder on the second floor of the Chicago Athletic Association.

Treat Yourself

Taste all the chocolate your heart could desire at the Chocolate of the Pen buffet. You can experience this at the Peninsula Chicago’s Chocolate Bar on Friday and Saturday evenings. Guests can eat as many chocolatey snacks and desserts as they’d like—coffee, cappuccino, and espresso are included in the entry fee.

Local Culture

If you love learning about the places you visit, you’ll want to spend time at the Chicago Cultural Center. Many people don’t know about this great attraction. Guess what—entry is always free! Not only is the architecture here gorgeous, but you’ll learn a lot, too. This gem is a great spot to spend a whole afternoon.

Get Your Nose in a Book

Calling all book nerds! Be sure to head to Myopic Books. This hidden gem of a bookstore features thousands of secondhand books just waiting to be paged through and the shop has a lot of character.

Be sure to check out the lesser-known sites when you plan your own Chicago adventure. No matter what you plan to do during your trip, you’re sure to create lasting memories of the Windy City.

MORE STORIES LIKE THIS

Top 5 Places to Travel: Stories from a World Traveler

Work and wanderlust have kept me on the road 200 days or more every year for the past three decades, until this...

Step Back In Time and Into the Wild with a Trip to Orcas Island

The benefits of travel go far beyond a simple change of scenery or the ability to engage in non-routine activities. One of...

Finding Prince: Dog-Friendly Road Trip in West Virginia

West Virginia is a pet-friendly paradise with outdoor adventures and scenic road-trip routes. It’s also where one sweet pooch found his way...

Utah’s Dark Skies: Canyonlands National Park

Take in the skies while floating and hiking in Labyrinth Canyon. Sights include towering canyon walls, remnants from early river runners...