Walking Tour: Historic Chicago Pubs in River North and the Loop

Discover Chicago’s Hidden Drinking Gems on a Walk Through River North and the Loop

If you’re looking to combine your love of history, architecture, and authentic local vibe, the Walking Tour: Historic Chicago Pubs in River North and the Loop is a charming way to do it. For $65 per person, this 3.5-hour adventure takes you through some of Chicago’s most storied taverns, from the city’s oldest restaurant to a secret speakeasy. Led by knowledgeable guides, it’s a small-group experience that promises intimacy, insider stories, and a true taste of the city’s vibrant drinking culture.

What we love about this tour is its focus on local favorites, not tourist traps. You’ll visit four distinctive pubs, each with its own history and character — and get stories that bring these places to life. The second highlight is the seamless blend of architecture and storytelling; it’s not just about the drinks but about understanding Chicago’s neighborhoods and landmarks along the way.

A potential consideration is the moderate physical activity involved—be prepared to walk and climb stairs, as public transit stations aren’t all elevator-equipped. Also, remember drinks are at your own expense, so while the tour is quite affordable, you’ll want to budget for beverages if you choose to indulge at each stop.

This tour is perfect for adventurous history buffs, architecture lovers, or anyone wanting a more authentic Chicago experience beyond the typical tourist spots. It’s especially suited for those who enjoy engaging guides and a small-group setting, making it a flexible way to explore the city’s lively pub scene.

Key Points

• Authentic Local Pubs: Visit four beloved Chicago taverns, each with its own unique story.
• Architectural Highlights: Learn about Chicago’s historic buildings, including the Marquette Building.
• Expert Guides: Guides like Tom bring stories and photos that deepen your understanding of the city.
• Walking & Transit: The tour involves walking through neighborhoods and includes transit tickets for convenience.
• Aged 21+ Only: The experience is designed for adults ready to enjoy a drink and learn Chicago’s pub culture.
• Small Group: Limited to 10 travelers, ensuring a personal, engaging experience.

Walking Through Chicago’s Historic Drinking Scene

This tour offers an excellent way to get to know the city’s neighborhoods on foot while having a few drinks and listening to great stories. We found the itinerary well-balanced—combining historical landmarks with lively taverns, making the experience feel both educational and fun.

Meeting at the Marquette Building, you start in the lobby, where your guide sets the scene for Chicago’s architectural grandeur. The building itself, a symbol of early 20th-century design, gives you a taste of why architecture buffs might find this tour appealing. From there, you’ll stroll or take a quick transit ride to your next stop, the Berghoff Restaurant, which is claimed to be the oldest continuously operating restaurant in Chicago. Here, you can enjoy a drink inside a historic space that has served locals and visitors since 1898.

The Brehon Pub is renowned for its connection to Chicago’s media history, with stories about bribery and journalism that add a local flavor to your drink. This stop is also appreciated for its genuine atmosphere, not overly polished for travelers but full of character.

Next, the Green Door Tavern features a hidden speakeasy that pays homage to Chicago’s Prohibition-era past. The allure of a secret bar adds a bit of mystery and fun, and guides often share tales of Chicago’s underground drinking during the 1920s.

The tour concludes at Monk’s Pub, a long-standing bar full of German and Old English antiques that give it a cozy, old-world charm. Many reviewers, like Brandon G., highlighted how the tour’s guide’s knowledge and storytelling made the experience special, calling out Tom for bringing the city’s stories alive with photos and anecdotes.

What to Expect at Each Stop

Marquette Building: The tour begins here, with a focus on architecture and early 20th-century design. It’s a brief stop but sets the tone for the tour’s mix of history and cityscapes. The building’s lobby is free to enter, making it an easy starting point.

The Berghoff Restaurant: Inside the Adams Street Brewery, you’ll hear about the restaurant’s longevity since 1898. The setting is lively but historic, with a chance to enjoy a drink in a bustling atmosphere that’s been a part of Chicago’s social fabric for over a century.

Brehon Pub: Known for its media connections, this pub’s stories about bribery and Chicago journalism add an intriguing dimension. The ambiance is authentic, not touristy, and you get plenty of local flavor here.

The Green Door Tavern: Expect a slightly hidden gem with a speakeasy vibe. The guide will share tales of Chicago’s Prohibition days, and you might find yourself imagining what it was like to sneak a drink during those years.

Monk’s Pub: The tour wraps up in a bar filled with antique decorated walls and a friendly vibe. Here, you can linger over a final drink or snack, soaking in the historic atmosphere while reflecting on the day.

The Value of This Experience

At $65, this tour offers a lot more than just a pub crawl. It’s about getting to know Chicago through its architecture, stories, and local gathering spots. The inclusion of transit tickets makes moving between neighborhoods smooth and stress-free, and the small group size ensures personalized attention from guides like Tom, who clearly love sharing their city’s stories.

The fact that drinks are not included might seem like a downside, but it allows you the freedom to choose your budget and preferences. Plus, the tour’s focus on history and storytelling enhances the experience far beyond a traditional bar crawl.

The reviews reflect high satisfaction—guides are praised for their knowledge and engaging storytelling, which transforms simple visits into memorable stories you’ll remember long after you leave Chicago.

Who Would Love This Tour?

This experience is ideal for history enthusiasts, architecture fans, and those wanting an authentic taste of Chicago’s pub culture. It’s particularly suited for travelers who enjoy small-group adventures and appreciate stories behind the places they visit. If you’re interested in local legends and a behind-the-scenes look at Chicago’s neighborhoods, this tour hits the mark.

Final Thoughts

This walking tour blends Chicago’s architectural grandeur with its lively pub scene, creating an experience that’s both enriching and fun. You’ll learn about the city’s history, sample its local watering holes, and walk away with stories to tell. The knowledgeable guides, especially Tom, make all the difference, bringing the city’s past and present to life.

While it’s primarily for adults who are ready to enjoy some drinks and walk a bit, the tour’s intimate setting makes it a great choice for anyone wanting to explore Chicago beyond the typical tourist spots. With a good balance of history, local charm, and authentic taverns, this tour offers genuine value and a memorable way to experience Chicago’s neighborhoods.

FAQ

Is this tour suitable for all ages?
No, this tour is only for participants aged 21 and over, as it involves visiting bars and tasting alcoholic drinks.

How long is the tour?
The tour lasts approximately 3 hours and 30 minutes, making it a manageable yet fulfilling experience.

Do I need to pay for drinks during the tour?
Yes, drinks are at your own expense, giving you the flexibility to choose what and how much to indulge in at each pub.

What’s included in the price?
The tour includes transit tickets and a knowledgeable local guide, but not food or beverages.

Is the tour walkable, or does it involve transportation?
It involves walking between stops and includes transit tickets for convenience, especially when moving through neighborhoods.

What should I wear or bring?
Comfortable shoes for walking, and perhaps a small umbrella or jacket depending on the weather. Be prepared to climb stairs at some stops.

In the end, this Chicago pub tour offers a genuine slice of the city’s history and culture, served up with plenty of stories and local flavor. Perfect for curious travelers eager to see a different side of Chicago, it’s a small investment for a big, authentic experience.