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

If you’re seeking an authentic way to experience Chicago beyond its skyline and museums, a guided pub tour in the downtown districts offers an entertaining, culturally rich option. This particular walking tour by L Stop Tours takes you through some of the city’s most storied taverns, blending history, architecture, and local flavor into a relaxed 3.5-hour adventure. It’s ideal for those who want to uncover Chicago’s hidden stories while sampling its vibrant pub scene—though drinks are on your own tab.

What we find especially appealing about this tour is how it combines local storytelling with visual highlights like the Marquette Building, along with visits to four beloved pubs. Plus, with small-group size and a knowledgeable guide, it promises a more intimate and engaging experience. However, it’s important to note that this is a 21+ activity, and not designed for those seeking a purely sightseeing-focused tour without the social aspect. If you’re a fan of history, architecture, and lively local spots, this tour could be just what you’re looking for.

Key Points

• A small-group experience with a maximum of 10 travelers ensures personalized attention.
• Visits include Chicago’s oldest restaurant, a media watering hole, a speakeasy-style pub, and a cozy English-German tavern.
• Tour highlights include landmarks like the Marquette Building and the Near North Side.
• Expert local guides share engaging stories, adding depth to each stop.
• It’s priced at $65 per person, offering good value considering the included guide and transit tickets.
• The tour ends at Monk’s Pub, a historic bar with a friendly atmosphere and tasty snacks.

How the Tour Fits into Your Chicago Experience

This tour isn’t just about knocking back a few drinks; it’s about being immersed in Chicago’s cultural fabric. Walking from one historic pub to another while learning about the city’s architecture and media history creates a layered experience that appeals to those who enjoy storytelling and authentic local spots.

The tours start at 4:00 pm, making them a perfect post-lunch activity that transitions into early evening—ideal for travelers who prefer afternoon outings or want to combine it with other downtown activities. The duration of roughly three and a half hours allows for a leisurely pace, giving time to enjoy each pub and absorb the stories without feeling rushed.

A Deep Dive into the Itinerary

Stop 1: The Marquette Building

Your journey begins in the lobby of the Marquette Building, a landmark notable for its architectural significance. Meeting here at 140 S Dearborn, you’ll gather with your guide and start soaking in the visual and historical context of the area. It’s a free, 30-minute introduction that sets the tone for the tour, offering a glimpse of Chicago’s architectural grandeur.

This stop helps anchor the tour, providing background that makes subsequent visits more meaningful. Expect stories about the building’s design and history, adding a layer of appreciation for the city’s architectural achievements.

Stop 2: The Berghoff Restaurant

Next, you’ll head to The Berghoff, Illinois’ oldest continuously operating restaurant, famous for its long history and classic German fare. Inside, you can enjoy a drink at the Adams St Brewery, while your guide shares fascinating tales about the restaurant’s origins dating back to 1898. The 45-minute stop here combines history and local flavor, giving you a taste of Chicago’s immigrant roots.

This pub offers a chance to sample the atmosphere of a storied hotel that has survived Prohibition, wars, and urban change. It’s a perfect blend of heritage and conviviality.

Stop 3: Brehon Pub

Moving on, your next stop is the Brehon Pub, a cozy Irish-style tavern. Here, the guide will tell a captivating story involving bribery and the Chicago media, making this stop more than just a drink break. Expect another 45-minute stay, allowing you to relax and take in the local pub ambiance.

Brehon Pub’s reputation as a lively, authentic Irish pub adds to its appeal, and the storytelling offers insight into some of Chicago’s more colorful history. It’s a great spot for those wanting a more intimate and lively experience.

Stop 4: The Green Door Tavern

The Green Door Tavern is a Chicago institution, featuring a hidden speakeasy style. This stop is sure to be a highlight, with your guide explaining the pub’s storied past and its secretive speakeasy vibe. The 45-minute visit gives you plenty of time to enjoy the environment and perhaps peek into the concealed speakeasy area.

This pub’s history of Prohibition-era clandestine drinks adds a layer of intrigue, and its classic Chicago bar feel makes it a must-see for lovers of vintage taverns.

Stop 5: Monk’s Pub

Your tour wraps up at Monk’s Pub, a beloved fixture filled with German and Old English antiques. Over the final 45 minutes, you can enjoy a last round of drinks or some snacks, while soaking in the cozy, historic atmosphere. This spot offers a warm ending to your exploration and a chance to reflect on the stories shared.

What to Expect as a Participant

The tour includes transit tickets, which means your guide will help navigate from one pub to the next efficiently. The group size is small, capped at 10, ensuring your guide can provide tailored stories and answer questions. The moderate physical activity involved — walking and climbing stairs — is manageable for most, but not suitable for those with mobility issues.

Drinks are not included in the price, so you’ll be responsible for your own beverages. The $65 ticket covers the guide, tickets to certain landmarks, and the overall experience. It’s a fair price considering the rich storytelling and the chance to visit four historic pubs, each with its unique character.

Authenticity and Highlights According to Visitors

Reviews consistently point out the knowledgeable guides, who bring stories to life with photos and local insights. One reviewer raved, “Tom is great,” emphasizing how a friendly, well-informed guide makes all the difference. Another noted that the tour offered “a little of everything—architecture, stories, pubs, and nice views”—highlighting the tour’s well-rounded appeal.

Participants also appreciated how the tour managed to blend history, architecture, and local culture into an engaging package, rather than simply focusing on drinking.

Is This Tour Right for You?

If you enjoy learning about a city’s past, especially through stories linked to its landmarks and local businesses, this tour will resonate. It’s ideal for adults aged 21 and over who want to combine a relaxed social experience with cultural insights.

However, if you’re not comfortable walking or climbing stairs, or if you prefer a more traditional sightseeing tour with no social element, you might want to look elsewhere. This experience is best suited to those who appreciate storytelling, authenticity, and a lively pub atmosphere.

The Sum Up

This guided walking tour of Chicago’s historic pubs offers a compelling way to spend an afternoon or early evening exploring the city’s architecture, history, and lively tavern culture. With a small group and expert guides, you get personalized storytelling that enhances each stop, from the venerable Berghoff to the secretive Green Door.

The price point of $65 per person delivers good value for the combination of local insights, landmark visits, and a memorable social experience. It’s especially suited for travelers who want a relaxed, authentic taste of Chicago’s nightlife and history, avoiding tourist traps and discovering hidden gems.

Whether you’re a history buff, a pub enthusiast, or simply looking for a different way to experience downtown Chicago, this tour offers a fun, enriching alternative to typical sightseeing.

FAQ

Is this tour suitable for people with mobility issues?
The tour involves walking and climbing stairs, so it’s best suited for those with moderate physical fitness. Not all train stations are fully accessible, which is something to consider.

Are drinks included in the tour price?
No, drinks are not included. Participants are responsible for their own beverages at each pub.

What is the starting point for the tour?
The tour begins at the Marquette Building, located at 140 S Dearborn St, in the lobby.

What is the tour duration?
It lasts approximately 3 hours and 30 minutes, with about 45 minutes at each pub plus stops for sightseeing.

Is this tour suitable for non-US citizens?
Yes, but please remember it’s for those aged 21 and over. You’ll need valid ID to enjoy the pubs.

Can I cancel the tour?
Yes, free cancellation is available up to 24 hours before the start time, with a full refund.

Does the tour cover other attractions besides pubs?
Yes, it includes visits to landmarks like the Marquette Building and explores the Near North Side neighborhood.

How many people are on each tour?
The maximum group size is 10, ensuring a more personalized experience.

Embark on this engaging exploration of Chicago’s past and present through its pubs, architecture, and stories. It’s a memorable way to see the city from a different perspective, blending history with lively local culture—perfect for those seeking an authentic downtown experience.