A Weekend of Secret Speakeasies in Chicago

Chicago, a city known for its vibrant nightlife, rich history, and cultural diversity, holds within its heart a clandestine culture rooted in the Prohibition era. Secret speakeasies, those hidden bars that hark back to the days of bootlegging and jazz, offer unique experiences that are cherished by locals and visitors alike. This weekend, embark on a thrilling adventure through the streets of Chicago as you uncover its best-kept bars, each with its own story, ambiance, and, of course, a tantalizing selection of cocktails.

The Essence of Speakeasies

Originating in the 1920s during the Prohibition when the sale of alcoholic beverages was banned, speakeasies were hidden venues where patrons could enjoy drinks in secret. They were often disguised as legitimate businesses, down alleyways, behind unmarked doors, and through hidden passages. Today, Chicago boasts a plethora of these hidden gems, allowing modern-day revelers to step back in time and indulge in the luxuries of the past.

Planning Your Speakeasy Adventure

Before embarking on your journey, it’s best to plan a route. While some speakeasies are easier to find, others require reservations, passwords, or simply a knack for exploration. Here’s a guide to make the most of your weekend:

Friday Night Warm-Up

Kick off your weekend at The Violet Hour in Wicker Park, a chic watering hole recognized for its ambiance and craft cocktails. With its moody lighting, plush seating, and exceptional cocktail menu, it is the ideal starting point. Reservations are highly recommended, as this spot can fill up quickly. Try the ‘Violet Hour Gimlet’ and enjoy the exquisitely curated flavors.

After soaking in the atmosphere, make your way to Three Dots and a Dash in River North. This Tiki bar, hidden behind a discreet door, offers a tropical twist on the speakeasy experience. Sip on their ‘Scorpion’, a combination of rums and fresh fruit juices that will transport you to an island paradise. Don't forget to enjoy the vibrant decor that adds to the overall vibe.

Saturday Speakeasy Safari

Your Saturday starts at The Green Mill Cocktail Lounge, one of Chicago's oldest bars that has preserved its original decor since the 1920s. Rumored to have been frequented by notorious gangster Al Capone, its storied history enhances your drinking experience. Get ready to be entertained with live jazz music while you enjoy an old-fashioned cocktail.

Next, stroll over to Rooftop at the Wit for a more modern twist on the speakeasy theme. Although it is a rooftop bar, its hidden entrance gives off the secretive vibe. Take in stunning city views as you sip on a ‘Wit Spritz’, a refreshing mix of prosecco, St. Germain, and soda.

As dusk settles, head toward Bar DeVille. This cozy, dimly lit bar is tucked away in Lincoln Park and offers a relaxed atmosphere featuring an excellent selection of cocktails. The ‘Mezcal Margarita’ here is a must-try, showcasing unique flavors and a smoky twist.

Late Night Discoveries

For those who wish to push into the wee hours, consider an expedition to Untitled Supper Club. This venue features a hidden entrance and offers live music, dining, and craft cocktails. The nostalgic decor takes you on a journey through time. Order the ‘Bourbon Smash’ and feel the magic of a night filled with entertainment.

Sunday Funday

On Sunday, ease into your day at Lost Lake, an exotic tiki bar with an enchanting atmosphere. With a password required for entry and a selection of cocktails inspired by tropical flavors, it’s the perfect post-party recovery spot. Be sure to try the ‘Zombie’ cocktail, known for its powerful punch.

For brunch with a twist, head to Prohibition on the West Side, where the brunch menu merges classic dishes with innovative twists. The speakeasy feel is accentuated by the decor, which takes you back to the Prohibition era. The ‘French Toast Casserole’ paired with a ‘Mimosa’ will kickstart your day.