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Big Shoulders Historic Bar and Food Bus Tour

Eat and drink through the history of the oldest neighborhood beyond downtown Chicago.

This 2.5-hour-long bus tour explores Chicago’s food and drink history in Bridgeport, a historically working class neighborhood on Chicago’s South Side. Much of our time is inside venues, and we have a brief walking tour, too. On this South Side private group tour, guests explore the area’s history of industry and politics while enjoying beer or wine, good company, and classic South Side fare in a “secret bar.”


The title for this private tour comes from a Carl Sandburg poem. His phrase “big shoulders” has come to be a common reference to the city’s labor roots. Bridgeport is Chicago’s oldest neighborhood and borders an industrial district on the city’s South Side.

In its earlier years, the Bridgeport neighborhood communities were Lithuanian, German, Polish, Czech and Irish. Chinese and Mexican immigrants have moved in recent decades, joined by hipsters as well.

We go to three historic Chicago bars that are quintessential to Bridgeport history. One historic bar is actually a secret bar, and not open to the public. You’ll hear fascinating stories culled from the family lore of barkeepers. The foods served are elements in telling the story of the neighborhood. Foods we try include an authentic Chinese bao, Lithuanian beer, a Polish cookie, and the “mother-in-law” sandwich–a South Side Chicago specialty. It’s a culturally vibrant South Side food tour, which is our style on private Chicago tours!

For your private group pub crawl tour, guests eat, drink and learn in between being whisked from one experience to another on a luxury 18-passenger or 37-passenger coach. We also take a short walking tour for a more up-close experience with the neighborhood, including a look at homes and neighborhood corner buildings. Our driving portion of our tour includes the Chicago Stock Yards Gate, the former “Bucket of Blood,” the White Sox stadium, historic factories, art centers, street art murals and a quarry-turned-park.

Upgrade your meal options by adding Korean-Polish food and craft beer or cocktails at a cool, new-school Bridgeport spot.

Among our tour guides, this is one of our favorite tours for private groups. It is a fun and memorable way to really connect with South Side Chicago history, whether you are a local or visiting group. It’s an incredibly fascinating area of Chicago, making this private group tour option ideal for corporate team building, family reunions and birthday parties.


Who wants to listen to a volunteer tour docent rambling a bunch of memorized names and dates? Not us! Our expert Chicago tour guides are highly trained, fun, smart and passionate about Chicago architecture and history.

In business since 2010, we are proud to be a five-star-rated Chicago tour company on Yelp and TripAdvisor. Many of our Chicago architecture and neighborhood tours integrate historic bars, food and music history. We hope you’ll join us to explore stories and places locals don’t even know, both downtown and in Chicago neighborhoods!

As you decide on a private group tour of Chicago, this quick guide may help you understand if Chicago Detours is the right tour company for your special event.

All-inclusive rates are $80 per person including transportation, dinner, dessert, three drinks, gratuities, taxes, special gifts and more! This private food bus tour lasts three hours to three-and-a-half hours depending on the size (and speed) of your group. Minimum group size is 14.


2.5 Hours


Some Walking


  • White Sox stadium
  • Chicago Stock Yards Gate from 1875
  • Three historic, family-owned bars
  • Street art and murals
  • A quarry-turned-park
  • A historic bakery

Stories & Ideas

  • The culture of drinking around the turn of the 20th century
  • Stories behind each historic bar
  • Food history of the “delta tamale” in Chicago
  • The South Side’s unique fast food culture
  • History of the Chicago Stock Yards
  • Ties between drinking industry and Chicago politics

Tour Includes

  • Engaging tour guide commentary
  • Luxury coach transportation to/from any downtown office or hotel
  • Photo and video presentation via screens on bus
  • Driving tour of Bridgeport’s historic sites
  • Brief walking tour
  • Three servings of wine or beer per person
  • Choice of Chicago hot dog or mother-in-law sandwich
  • Authentic Chinese pork and meat baos
  • Polish cheese kolaczki cookies
  • All gratuities for servers, tour guide, and driver
  • Special gifts

Tour Location

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Call: 312.350.1131
E-Mail: [email protected]