Locations: KY | CHI
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What Are Some Things to Do in Chicago When It’s Raining?

You’ve been eagerly planning your Chicago adventure, but the weather has other ideas; it’s raining, the sidewalks are slick, and your outdoor plans seem impossible. Don’t let the rain put a damper on your trip. With The Barrel Run‘s brewery tours, you can turn a gloomy day into an exciting, one-of-a-kind experience. From architectural wonders to rich history and craft beer culture, our tour lets you see the best of the city while staying dry, comfortable, and entertained.  

Take in the City’s Iconic Architecture on the Barrel Bus

Rain or shine, Chicago’s architecture stands out as some of the most stunning in the world. But on a rainy day, walking around to admire it can feel like a chore. That’s where The Barrel Run’s unique Barrel Bus comes in. Shaped like an oversized wooden barrel and fully climate-controlled, this cozy vehicle lets you take in the beauty of Chicago’s landmarks without worrying about the rain.  

Relax in comfort as we roll through the city’s vibrant neighborhoods and architectural highlights. We’ll drive you past iconic sights like the Chicago River, Holy Name Cathedral, and some of the skyscrapers that define the city’s skyline. Along the way, you’ll hear fascinating stories about the visionaries who shaped Chicago into the architectural hub it is today. Sit back, stay warm, and enjoy the city’s timeless beauty, all from the dry, inviting interior of the Barrel Bus.  

Learn About the City’s Prohibition-Era History

Chicago is a city with a story, and rainy days are perfect for diving into its rich and dramatic history. Our expert guides are masters at bringing the past to life, sharing tales that will transport you to the roaring 1920s, a time when prohibition ruled the city, and speakeasies flourished.  

On our prohibition-themed tour, you’ll uncover Chicago’s darker side, learning about the mobsters like Al Capone who turned the city into their stomping ground. Visit historic locations tied to the era’s underground culture as stories of speakeasies, bootlegging, and secret tunnels unfold. The rain adds an atmospheric touch, making the tales of smoky bars and shadowy deals feel even more vivid and authentic. It’s an experience that takes you beyond the surface and into the soul of Chicago’s history.  

Explore the Craft Beer Scene Like a Local

Chicago is home to one of the most exciting craft beer scenes in the country, and The Barrel Run brings it right to you, no matter the weather. Rain won’t stop you from discovering the passion, creativity, and flavors behind the city’s best brews.  

Our tour includes stops at three exceptional breweries, each offering a unique experience. You’ll visit destinations like Revolution Brewing, Goose Island, and Haymarket Pub & Brewery, places that have played a key role in Chicago’s beer renaissance. At one stop, you’ll even get a behind-the-scenes tour of the brewing process, learning how the journey from grain to glass unfolds.  

Stay Dry While Enjoying Award-Winning Drinks

Bar hopping in the rain? No thanks. The Barrel Run makes sure you never have to traverse wet streets or crowded sidewalks to enjoy Chicago’s incredible drink scene. Our guided tastings are curated to give you the best of the city’s craft beer culture, without any of the hassle. Each stop offers something unique, from hoppy IPAs to malty ales, so you’ll walk away with a true taste of Chicago’s diverse brewing landscape.  

Make Rainy Days in Chicago Unforgettable

Don’t let a little weather keep you from experiencing one of America’s greatest cities. With The Barrel Run, you get the complete Chicago experience—architecture, history, culture, and incredible drinks—all while staying comfortable and dry. Our unique Barrel Bus, expert guides, and carefully curated stops will leave you with a deeper appreciation for what makes Chicago truly special. Contact us today to book your tour and get ready for the ultimate rainy day adventure.