For the first three decades after Chicago was incorporated as a town in 1833, slavery was legal in the United States. And for as long as slavery existed, there were people who tried to escape bondage — often walking hundreds of miles, hoping to settle in a safer place.

These “freedom seekers” sometimes got help on that journey. You’ve probably heard of the Underground Railroad, an informal network of people who offered shelter, protection, food, clothing and advice to freedom seekers.

The Underground Railroad existed throughout Illinois, including in Chicago.

Multiple listeners have asked Curious City why Chicago isn’t better known for its participation in the Underground Railroad. And if Chicago had stops, where were they?

One thing that’s important to keep in mind is that Chicago was in the midst of transforming from a frontier town to a bustling (but still quite small) city throughout the mid-1800s. Between 1833 and 1850, Chicago’s population increased from roughly 300 to just under 30,000 residents. Nevertheless, enslaved people from the South did travel north to Chicago and its suburbs during this period seeking freedom. Free Black people in particular played a major role in supporting freedom seekers as they arrived in or passed through the city.

When Congress passed the Fugitive Slave Act in 1850, the new law fundamentally altered Chicago’s place for formerly enslaved people seeking freedom. Prior to 1850, Chicago was a destination, a “city of refuge.” Between 1850 and 1865, when slavery was finally abolished, Chicago’s role became more complicated. It was still a place where Black people seeking freedom settled and put down roots — getting involved in the growing economy, building social institutions and leading abolitionist organizing. But because of new dangers posed by the Fugitive Slave Law, the city was often treated as a stop along the way to surer safety in Canada.

Chicago before the Fugitive Slave Law (1833-1850)

Many freedom seekers reached Chicago by traveling north along the Mississippi River. Following the river provided a helpful guide north and also made it more difficult for trackers to find freedom seekers; the water could wash away footprints and cover scents.

The people who lived along the Mississippi River in the 1830s were more diverse than those in many parts of the United States. There were, of course, white people — but there were also free and enslaved Black people, and Indigenous people. That diversity made it less clear who was enslaved and who was not, and thus easier for a freedom seeker to pass unnoticed.

According to Larry McClellan, professor emeritus of sociology and community studies at Governors State University, “One of the reasons Chicago became such an important goal for people was because of this Mississippi River Valley culture. Word was passed very easily, and so very early on, word reached all the way to New Orleans that one of the ways to freedom was to get yourself to Chicago,” he explained. “And the word gets to Black people living on plantations. And they know if they can get to the Mississippi River Valley, and head north, they can find their way to freedom.”

Before 1850, historians say Chicago was a relatively safe destination for freedom seekers. “It was really quite a safe place for Underground Railroad freedom seekers to put down roots and be able to benefit from their labor,” historian and author Glennette Tilley Turner said.

Some freedom seekers continued on from Chicago to Canada, where slavery had been outlawed since 1834. But in general Chicago was considered a “city of refuge” for Black people during this time, as described by historian Lawrence D. Reddick.

The Fugitive Slave Law of 1850

In September of 1850, Congress passed the Fugitive Slave Act, part of a package of bills designed to avoid a civil war between pro-slavery and anti-slavery states. The American Civil War began just over a decade later.

The Fugitive Slave Law gave enslavers the right to re-enslave freedom seekers who had escaped and journeyed north to free states. It also made helping freedom seekers illegal and punishable by fines or imprisonment. Enslavers often worked in cooperation with law enforcement, posting newspaper ads offering a reward for freedom seekers’ capture and relying on local sheriffs to arrest and return formerly enslaved people based on their descriptions.

Chicago after the Fugitive Slave Law (1850-1865)

The Fugitive Slave Law made Chicago a more dangerous place for freedom seekers.

Previously, the Underground Railroad helped people get to Chicago. After 1850, the Underground Railroad helped many people pass through Chicago to Canada. Additionally, a fair number of Black people who had found freedom in Chicago and even bought property fled, leaving behind their homes and belongings, according to historian Christopher Robert Reed

In his book Black Chicago’s First Century, Reed quotes an unnamed “Oldtimer” whose account of life in Chicago as an early Black settler was published by the Illinois Record in the late 1890s. After the Fugitive Slave Act was passed, the Oldtimer recounts, “The kidnapping of the fugitive slaves by slave owners, assisted by some of the low whites and the officers of the city, was the chief conversation among our people.”

The Western Citizen, a Chicago-based abolitionist newspaper, sometimes printed accounts of attempts to re-enslave Black Chicagoans — as well as ways that anti-slavery citizens could resist the new law.

Historians have identified a handful of places freedom seekers passing through Chicago sought refuge. These included the Tremont House hotel, the home of abolitionist John Jones and Quinn Chapel A.M.E. Church — all located within a few blocks of one another near today’s downtown.

Quinn Chapel is perhaps the best-known Underground Railroad stop in Chicago. In Black Chicago’s First Century, Reed writes specifically of four women congregants of the church — Emma Jane Atkinson, Joanna Hall, “Aunt Charlotte,” and a fourth woman whose name was likely Mary Richardson Jones — who served as conductors on the Underground Railroad and harbored freedom seekers in their homes.

According to genealogist and author Tony Burroughs, who has researched the Underground Railroad extensively, there are undoubtedly many places in the city where freedom seekers found shelter or food that were not regular Underground Railroad stops and about which we can know very little. “When freedom seekers traveled through free states it was not uncommon for them to sleep in barns or wherever they could on the way north,” he explained. “They sometimes even went inside houses and asked for food if they thought it was safe.”

A patchwork history

Larry McClellan says many twentieth-century accounts of the Underground Railroad in Chicago proved to be little more than rumors. “The big problem we have with this is that all the time, people are identifying Underground Railroad sites that simply are not. In the 1870s and ’80s, after the Civil War, it was a very prestigious thing to have been involved in the movement for abolition,” he explained.

More recently, historians and researchers like Christopher Robert Reed, Tony Burroughs, Glennette Tilley Turner, Karen Lewis, Larry McClellan and others have done the painstaking work of searching for these records and piecing together fragments of this history.

Part of why it’s so difficult to find records of Underground Railroad activity in Chicago is that the work was inherently dangerous. For freedom seekers, the stakes were incredibly high. People who were caught seeking freedom could be re-enslaved. Those who helped them faced fines and incarceration. So there was an incentive to not keep records in the traditional sense. Because of this, the historical record skews towards those who had power: enslavers’ ads in newspapers offering rewards for returned freedom seekers, bills for “services rendered” by law enforcement for the arrest of a formerly enslaved person. So while we have glimpses of the people who risked their lives to seek freedom — and those who helped them — many of their stories remain untold.

Olivia is a journalist and podcast producer. Follow her @viaOliviaR

Maggie Sivit is Curious City’s digital and engagement producer. Follow her @magisiv

Thanks to WBEZ archivist Justine Tobiasz for assistance with this story.