Obama in Chicago: His Hangouts and Life in Chicago

Let’s do a little history of Michelle and Barack Obama in Chicago. With the 2012 presidential elections coming up, I realized that I don’t know a whole lot about his life. Which is odd, since he’s President and calls Chicago home, specifically the Hyde Park and Kenwood areas. I’ve walked by his house many times, because my friend lived a block away. Our annual University of Chicago Campus and Neighborhood Tour during Family Weekend goes by his abode. So here’s an overview of the of Obama in Chicago focusing on Barack’s life here.

We’ll fast-forward through his early life: Barack Obama was born in in 1961 in Honolulu, where he was raised by his single mother through high school. He then went to Occidental College in LA before transferring to Columbia University in NYC. At Columbia, he majored in political science and specialized in international relations. How many people can say that their major is so relevant to their current job, right?

Community Organizing

Obama's First Job in Chicago Obama in ChicagoTwo years after graduation from Columbia in ’83, the Obama in Chicago era began. He moved here to work at the Developing Communities Project, a then-new, faith-based organization that came together to address issues of unemployment, poverty, and violence via job training and leadership development programs. The organization was inside this brick house in the Roseland community. Obama established the organization as a non-profit and was the first Executive Director, 1985-1988. The DCP is now in a new location, and today this house is a rectory for the church next door.

Law School Days

Barack Obama then headed to Cambridge for Law School at Harvard, and in his second year was the first black president of the Harvard Law Review. He graduated magna cum laude, aka “with great honor,” in 1991.

Chase Tower ChicagoBefore graduating though, Barack came back to Chicago as a summer associate intern, first for Sidley and Austin in Chase Tower (skyscraper on the bottom side of the picture) in ’89 and then at Hopkins and Sutter in the First National Plaza building (tower in the top end of the photo above) in’90. Michelle LaVaughn Robinson and Barack Obama met while working inside the iconic Chase Tower at 10 S. Dearborn. (We visit this building for our Loop Interior Architectural Tour actually.)

Married Life

Michelle was his assigned mentor and she initially found his requests to socialize inappropriate. He finally convinced her to go out. For their first date, they grabbed an ice cream at Baskin Robbins in Hyde Park. The ice cream shop is no longer there, but a plaque on a stone at its former location of Dorchester and 53rd marks the historical moment of Michelle and Barack’s first kiss.

Trinity Church Barack Michelle Obama in Chicago wedding locationThe two got married at Trinity United Church of Christ, which was located at 532 W. 95th St. The location is now used for educational programs and bears the name of the controversial preacher who sparked Obama to sever ties with the TUCC. The current church is a block to the east, pictured below.

Of course the wedding had a beautiful reception, held at the South Shore Cultural Center (exterior below).

South Shore Cultural Center Chicago Obama in ChicagoThis magnificent community building of Chicago was originally a private club with a gorgeous ballroom looking out to Lake Michigan.

Wedding in South Shore Cultural Center Obama in ChicagoOf course there are many more, like Valois, a Hyde Park diner with a special “Obama” menu, his barbershop at 5234 S. Blackstone, or his fancy gym, the East Bank Club in River North.

Regardless of who you vote for tomorrow, hopefully we can all come together with the pride of having a President who calls our city home, which has put Chicago in the international spotlight.


Share on facebook
Share on twitter
Share on pinterest
Share on linkedin

be a



Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

“Our guide Ellen was exceptional and gifted with a great personal touch.”


Tour Guide

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

“Jen was a perfect storyteller and kept us spellbound for hours.”


Tour Guide

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.


Tour Guide

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.


Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

“Marie was a bubbling fountain of information and contagious enthusiasm.”


Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
“Sonny was extremely knowledgeable about all things Chi-town.”
Wade K


Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
Katie K

Amanda Scotese

Executive Director and Tour Guide

I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
Shelby F

Book a chicago event

Let’s Connect!