Celebrate Barack Obama Day At These Presidential Locations

August 4th, 2018 is the first inaugural Barack Obama Day here in Illinois. This new state holiday celebrates President Obama and his time in office. POTUS 44 rose to prominence and began his political career here in Chicago, of course. As only the fourth Illinoisan to become President, he will always have a special place in locals’ hearts. Here I highlight some Chicago locations worth visiting to celebrate Barack Obama Day. You can visit many of the South Side spots on our Neighborhoods and Cultural Diversity Bus Tour, Transformations on the South Side Bus Tour, or University of Chicago Campus Architecture Tour.

Barack Obama Day Chicago Skyline Promontory Point
The Obamas looking at the Chicago skyline. Photo by Pete Souza via Wikimedia.

President Obama’s Home

Barack Obama Day Kenwood Hyde Park Obama House
There will be much less snow and fewer security fences if you visit on Barack Obama Day. Photo via Wikimedia.

When I moved to Hyde Park in 2009 it felt like I could sense them everywhere. Barack and Michelle Obama had been familiar neighborhood figures for 15 years. Their first kiss was down the block from me, at a Baskin-Robbins at Dorchester and 53rd. They both worked at the University of Chicago, where I studied. Their first home was in a condo near Harold Washington Park, where’d I’d walk after class. They were everywhere!

Most tangibly, the Obamas’ house is at the intersection of Hyde Park Blvd. and Greenwood, right on the border of the Kenwood neighborhood. They made big move to 1600 Pennsylvania Ave in 2009 and still live in DC as of 2018. I once updated his mailing address in the donor database during my grad school internship. Closest I’ll ever come to global importance!

The Obama Home is a gorgeous Georgian mansion which sits right across the street from the historic KAM Isaiah Israel congregation. Concrete barricades and a cadre of Secret Service agents protected the red brick building until last year, but today you can easily saunter down Greenwood to admire the Obama Home and Kenwood’s many other stately residences. Of course, their current residence is still in Washington.

Valois Restaurant

The Valois Restaurant, on 53rd Street, is reportedly President Obama’s favorite Hyde Park restaurant. He was a regular visitor in his pre-POTUS days and visited again just before making his presidential farewell speech in Chicago. Valois, a cafeteria-style neighborhood staple, loves the former President right back. They even have his favorite menu items displayed for visitors.

Valois is a good place to marvel at just how rapid President Obama’s political ascension was. Step back in time 15 years and it would have been no big deal to see Barack, Michelle, and their two young daughters stepping up to the counter here for a classic bacon-and-eggs breakfast. If you stop by on Barack Obama Day you’ll likely see this humble diner mobbed with fans and sightseers thrilled to experience just a brush with the Obamas. For me, the Obamas’ dramatic rise to national prominence underlines just how much they exemplified the best of the American Dream.

University of Chicago Law School

University of Chicago tour law school Eero Saarinen night

Barack Obama’s main job before his election to the U.S. Senate was as a Lecturer at the University of Chicago Law School. He taught Constitutional Law there from 1992 until his election to the Senate in 2004. The Law School is one of the most prestigious in the world – in the same class as Harvard, Yale, and Stanford.

The Law School’s architecture is probably the most unique on this Barack Obama Day Tour. Famed Finnish-American architect Eero Saarinen designed the central building and courtyard, which opened in 1959. He was a master of mid-century Modern architecture, and the Law School is one of his rare Chicago designs. I love how open and airy its spaces are – the lush Midway Plaisance and serene reflecting pool seem to come right inside the building.

Chase Tower

Chase Tower one is well out of Hyde Park, but still a key stop for a Barack Obama Day tour. The former First Chicago Plaza, which our Loop Interior Architecture Walking Tour visits, was once host to the Sidley Austin law firm. Sidley Austin is one of the oldest and most prestigious law firms in the country. As you can see below, the firm’s offices were at the tower for decades.

Chase Tower is where Barack and Michelle first met. Michelle was an associate at Sidley Austin for three years after graduating from Harvard Law. In the summer of 1989 she was assigned to mentor a hotshot young law student from Harvard: Barack Obama. As this Washington Post feature explains, the young lawyers were instantly smitten with each other.

I’ve stood inside that building for countless hours, signing people in, guiding the tour, even shaking Senator Tammy Duckworth’s hand once. Nevertheless, it’s always surreal to imagine the young Obamas stepping out of an elevator together into that spacious lobby.

Other Spots for Barack Obama Day

These three locations just scratch the surface of Obama-related locations in Chicago. The dude lived here for the better part of 20 years after all! In fact, we ran down some of these locations in a blog post a few years ago. I definitely recommend taking the time to visit the South Shore Cultural Center. A beautiful piece of architecture and its history tell us so much about the South Side in the 20th Century.

As we commemorate the inaugural Barack Obama Day here in Chicago, we’ll patiently await their return to us!

– Alex Bean, Content Manager and Tour Guide


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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.

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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.

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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.


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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.


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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.

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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.
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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.

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Amanda Scotese

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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.
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