Chicago’s Pope & The President
Famous Footsteps on Chicago's South Side
4 Days | Spring | Summer | Fall
Starting At $Flexible Pricing
This tour of Chicago’s South Side features 2 historical firsts – the first African American President of the United States, Barack Obama, and the first American Pope, Pope Leo XIV. Explore the Chicago locations that made these men who they are and be inspired by their journeys. This tour can be either a 3- or 4-day itinerary based on your group’s interests.
Highlights
Tour Highlights:
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Tour Inclusions:
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This tour is customizable based on your group’s interest. This could be done as a 4-day tour featuring President Obama and Pope Leo, a 3-day tour focusing just on President Obama or a 3-day tour focused just on Pope Leo. Just let us know what best works for your group.
StarrGroups Flexible Pricing:
- Customizable Comps
- Net Rates
- Luxury or First Class Hotels & Meals
- Starr Tours Motorcoach Transportation & Professional Tour Managers are available
Whatever you want, StarrGroups will be happy to structure tour prices to match your needs. Just let us know!
Itinerary
Day 1 – Chicago, IL
Arrive today in Chicago, IL where you enjoy a three-night stay on the south side of Chicago. Dinner is on your own this evening.
Day 2 – Obama’s Chicago Tour – Obama Presidential Center
After breakfast, meet your local guide for a personalized morning tour of Chicago, and the person we focus on is none other than Barack Obama, the 44th President of the United States. He is inextricably linked to the City of Chicago. For more than 20 years he lived and worked on the city’s south side. This is where he met his wife Michelle, who grew up in the South Shore neighborhood. On a guided tour of the Hyde Park neighborhood you focusing on Barack Obama’s life as a community organizer, professor, and resident. Key spots include his Kenwood home, the University of Chicago, Valois diner (one of Barrack’s favorites) and the all-new Obama Presidential Center site in Jackson Park.
Your afternoon will be spent at the new Obama Presidential Center. This museum and library aims to inspire, empower, and connect people to bring change home. The 19.3-acre Center is located on Chicago side side where President and Mrs. Obama began their journeys in public service. It is an education project commemorating the accomplishments of the 44th president of the United States.
The Obama Presidential Center Museum explores the promise and power of democracy through the legacy of President and Mrs. Obama. Journey through four levels of dynamic exhibits that tell the story of the First Family and the social movements that made their work possible. Exhibits include memorabilia from the Obamas’ time in the White House, stories of iconic moments from the President’s administration, and interactive activities for visitors of all ages and abilities.
The Center also features over 20 art installations that encourage you to open your imaginations and reflect on their ability to bring change home. Plus, see panoramic views from the Sky Room, the Museum’s culminating experience with unparalleled views of the places that made the Obamas. It is designed to be deeply contemplative and features iconic commissioned art installations by Idris Khan, Jenny Holzer and Carrie Mae Weems.
Dinner is included this evening at a local restaurant. (B,D)
Day 3 – Full Day Pope Leo Tour – Nuns 4 Entertainment Dinner & Show
After breakfast, meet another local guide for a full day tour celebrating Chicago’s own Pope Leo XIV. Embark on an inspiring guided journey through the vibrant Chicago Southland and celebrate the life of the first American Pope, Pope Leo XIV. Embrace the remarkable story of his life and explore the significant places that shaped him as a leader and a person.
Pope Leo XIV, born in Chicago’s Bronzeville neighborhood and raised in Dolton, has a deep connection to the area. His early faith experiences included serving as an altar boy and studying at the Catholic Theological Union. He taught at St. Rita of Cascia High School and Mendel Catholic High School, inspired by his family’s commitment to Catholic education.
Your guided tour will begin at his charming childhood home, a warm and inviting place filled with memories. From there, visit the parishes and schools that played vital roles in his early life and discover the notable landmarks in Chicago that left a lasting impact on his journey. Along the way, take a moment to stop at one of his favorite souvenir shops and enjoy a delicious bite at a legendary hot dog spot or ChiSox Bar & Grill, where you can savor a taste of Chicago’s rich culture. This guided tour takes you to the birthplace of a remarkable individual, allowing you to connect with his legacy.
End the day with Nuns 4 Fun Entertainment featuring a scrumptious, sinful dinner and a show at Gaelic Park. Nuns 4 Fun Entertainment is a religious comedy show. (B,D)
OR, Groups looking for different option can have dinner at Aurelio’s Pizza in Homewood. Aurelio’s is Pope Leo’s favorite pizza place having honored him with Poperoni™ Pizza, a traditional pepperoni pizza topped with a layer of cup and crisp pepperoni, giving the dish extra heat, crunch and flavor. After trying the Poperoni Pizza, don’t forget to capture unforgettable memories at the “Pope’s Table,” complete with papal-inspired décor and the “Priest’s Chair.”
Day 4 – Depart for Home
After breakfast, depart for home. (B)

