Chicago: The Second City, The Second Chance

Faith in Action

Chicago, Illinois
Business Exploration & Workforce Ministry

1 Week of Service  •  Cultural Immersion  •  Servant Leadership

Did You Know?

Chicago is famously nicknamed “The Second City” — a phrase originally meant as a slight comparing it to New York, later embraced as a badge of resilience and reinvention (and now also the name of its legendary comedy theater). Despite being headquarters to some of the world's biggest businesses, Chicago also faces one of the highest rates of urban homelessness in the country, with thousands of residents seeking exactly what the city's nickname promises: a second chance.

The Second City, The Second Chance

Paul wrote that “if anyone is in Christ, the new creation has come: the old has gone, the new is here” (2 Corinthians 5:17). Chicago's own nickname carries an echo of that same idea — a city built on resilience and reinvention after adversity. Your team will partner with a local shelter's job-readiness program, sitting down with unhoused neighbors to hear their work histories and skills, and supporting staff as they match people with jobs suited to what they already know how to do. It's slow, relational work — no quick fixes, just showing up and listening well. Students who serve in Chicago come home changed — not because they solved homelessness, but because they discovered what it looks like to help someone write their own second chapter.

The Worldwide Faith in Action Difference

Cross-Cultural Ministry • Daily Devotions • Local Shelter Partnership • Workforce & Job-Readiness Ministry • Global Business & Industry • 1 Week of Hands-On Service

The Worldwide Navigators Difference

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Sojourn – Gain a better understanding of the community you’re visiting. Learn about different religions or spiritual practices. How do these impact the communities? How does religion or spirituality influence local traditions?

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Savor – Will you choose sweet or savory? Take the time to visit local markets and discover unique local ingredients. Learn how to prepare traditional meals & local favorites.

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Tip of the Tongue – Each morning, take the time to learn a few basic greetings and phrases in the local language. Learn how to write greetings & your name in the local script.

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A Wrinkle in Time – History influences our present. Discover the history of the country you visit. Hear the stories of your guides & their family history. Where do they come from?

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Journal Journeys – Take some time to reflect on the day’s events and document your journey. Spend a moment journaling about the day had & day ahead. These are memories for a lifetime!

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Culture – From local dances, festivals, or simple gestures to communicate – all of these make up a country’s culture. Learn and practice cultural norms & how to show respect in the culture you visit.

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Itinerary

Welcome to Chicago! After arriving, we’ll settle into our accommodations and gather for a welcome dinner. Opening devotional and orientation: what does it mean to serve as the hands and feet of Christ in your own country, in a city many of us think we already know?

Tour McDonald’s training campus at Hamburger University, then see the city from the top at the Willis Tower Skydeck. In the evening, take a river boat cruise discussing the business and architectural history behind Chicago’s skyline. Evening devotional on cultivating a servant’s heart.

Venture to the Amazon Fulfillment Center to see modern logistics at work, then visit Pullman, a planned community built during the Industrial Revolution around one company’s vision — and the site of a pivotal moment in American labor history. Climb to the top of the John Hancock Center for another sweeping skyline view. Evening devotional on the dignity of work.

Meet our local shelter partner and their job-readiness program staff. Training on respectful interviewing practices, active listening, and how to help someone identify transferable skills. Devotional: praying for the week ahead.

Our week of service begins! Alongside program staff, sit down with shelter guests to hear their work histories and skills, help draft simple resumes, and support staff as they identify job opportunities matching each person’s background. Afternoons include team debrief and reflection.

Continue interviews and resume support alongside program staff. Team members also assist with practical shelter needs — meal service, facility support, and simply spending time with guests.

Service continues, with today’s devotional focused on second chances and new creation. Afternoon: continued interviews and job-matching support.

Service continues. Today’s devotional theme centers on every person having a story and a skill worth naming. Evening: shared meal with shelter staff and guests.

Our final day of service wraps with a closing celebration alongside shelter staff and the guests we’ve come to know this week.

A joyful close to the week’s work: catch a Cubs game at historic Wrigley Field, one of the oldest ballparks in America.

Snap a picture next to “The Bean” while strolling through Millennium Park, then spend your final evening along the Navy Pier.

Final group devotional and debrief: what did God teach us this week? Depart for home.

Choose Your Impact

Every Faith in Action mission trip pairs a full week of hands-on service with a tour component that immerses students in local history, culture, and faith. This Chicago itinerary can be shortened, extended, or modified to fit your school’s calendar and budget.

  • Value — 9–10 Day Group Trips

Ground Transportation • 2.5–3 Star Accommodations • Daily Devotions & Debriefs • 2 Meals Per Day • Job-Readiness Program Materials • Daytime Tour Director • 5 Days of Service (Workforce Ministry)

  • Classic — 11–12 Day Group Trips

Ground Transportation • 2.5–3 Star Accommodations • Daily Devotions & Debriefs • 2 Meals Per Day • Job-Readiness Program Materials • Daytime Guided Tour Director • 5 Days of Service (Workforce Ministry) + Business Exploration & City Excursions

  • Epic — 12+ Day Group Trips

Ground Transportation • 3.5–4 Star Accommodations • Daily Devotions & Debriefs • 2 Meals Per Day • Job-Readiness Program Materials • 24/7 Guided Tour Director • 5 Days of Service (Workforce Ministry) + Extended Business & Cultural Immersion • Final Night Celebration Dinner & Commissioning Service

Interested in adding or modifying activities? All Faith in Action itineraries can be customized — extend the service week, add a second shelter partner, or swap in additional business or cultural excursions.

Value

3-6 Day
Group Trips

Classic

7-12 Day
Group Trips

Epic

7-14 Day
Group Trips

Interested in adding or modifying activities? No problem! All Worldwide Navigator itineraries can be customized to your liking!

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years' experience
8
countries
45
Customizable trips
170
Travelers
9050
Individuals impacted
260850

In collaboration with our partners

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