Work with us


Join our team!

We are quickly growing and looking for creative, driven people!

Chicago Detours has pivoted to being a virtual events company and is experiencing unprecedented demand. 

Available jobs as of 1/8/21:

How to Apply

All positions are remote. You don’t have to live in Chicago, but some familiarity with our city and its history is preferred.

To apply, please email resume, cover letter, and favorite thing to do in Chicago (one paragraph max) to [email protected].

Suggestion for All Positions:

In order to best articulate your qualifications and know if our company culture is a fit for you, come on one of our public virtual events! You can also track down past examples on our YouTube page if the timing doesn’t work out for you. This is not a requirement for applying, but it is strongly recommended.

What current employees say

"What I love about my job"

  • Learning all the time!
  • Pleasure of connecting with people and sharing stories on virtual events.
  • With new challenges and projects constantly, the job never gets boring.
  • Working with passionate and like-minded individuals.
  • Because of the creativity of the team, we have successfully pivoted during the pandemic from being a tour company to a virtual events company. 

"What we look for in our team"

  • Flexible and adaptable.
  • Detail-oriented and thorough; likely to see a task through.
  • Generous and open-minded.
  • Ability to go with the flow and do creative on-the-fly problem solving.
  • Fun personalities welcome!
  • Patient and resourceful.
  • Super excited about niche aspects of Chicago’s history and architecture and our virtual events!


We are looking for enthusiastic presenters with experience in presenting in front of groups. We are actively recruiting for a host to learn our “Badass Women of History” event, which celebrates diverse women whose stories still resonate with us today. We believe in sharing history that includes a variety of perspectives. We encourage applications from people of color or members of historically marginalized communities.

This job is an opportunity for professional enrichment, and is just a small side gig. After training, time commitment may start around 1-4 hours per week. 


  • Clear presentation and public-speaking skills.

  • An enthusiastic presence and a desire to connect with people.

  • Experience as a teacher or tour guide.

  • A love for storytelling.

  • Comfort using virtual event platforms like Zoom.

  • Flexible schedule.


  • An impressive knowledge of Chicago’s past and present.

  • Background in art history, architecture or other kind of visual art.

  • Bachelor’s or Master’s degree in relevant field of study

Virtual event hosts will undergo several weeks of paid training in virtual experience management for remote events. We pay an hourly rate for this flexible, part-time, contract position. Creative thinkers and over-achievers are especially encouraged to apply.

Full-Time Business Development Manager

We are a growing small business seeking an experienced business development manager. This person will guide our business development to the next level through efficient operations and strategic financial planning. If you have a passion for travel, history, architecture, and stories, then you are especially encouraged to apply. We are looking for someone with a diverse professional background who wants to elevate their career in a virtual, start-up environment.

This is a full-time position with benefits and profit sharing.


  • Sales: Generates new revenue through lead generation and opportunity pipeline management. Manages our Virtual Events Sales Coordinator.
  • Financial Planning & Analysis: Financial planning and projection. Analyze virtual event profit margins. Track and report Bookings, Revenue, and Profit against quarterly and monthly goals.
  • Human Resources Management: Manage our Administrative Assistant for payroll and benefits administration.
  • Office Operations: Analyze and organize office procedures to increase efficiency and productivity.
  • Overall business guidance: Communicates insights, growth objectives, strategies and key business topics to the virtual events team.


  • A flexible, creative, entrepreneurial spirit and a demonstrated passion for the mission and values of Chicago Detours.
  • Able to take ownership and drive activities to completion.
  • Strong verbal and written communications skills are a must, as well as the ability to work effectively with limited direction.
  • Self-motivated, action-oriented, multi-tasking individual with a sense of urgency and strong follow-through.
  • Experience in finance, business management, human resources, and sales operations in small to mid-scale companies.
  • Background in Excel and QuickBooks.
  • Strong business acumen including but not limited to:
    • Understanding of financial statements
    • Ability to lead Program Finance
    • Advanced Excel skills
  • BS/BA degree in business, accounting or administrative-related field.


  • 5 to 15 years of experience in business management and operations with start-ups and/or established companies.
  • Proven experience optimizing project accounting and billing systems.
  • Able to operate autonomously in a fast-paced, small business.
  • Exhibits sound business judgment, strong analytical skills, and a proven track record of taking ownership and leading data-driven analyses to support and grow a business.
  • Experience using BI tools and CRM software.


  • Paid vacation
  • Paid sick days
  • Health insurance
  • Dental insurance
  • Fun, creative company culture
  • Flexible work schedule
  • Educational team outings
  • Remote work
Chicago Detours is an Equal Opportunity Employer – Minority / Female / Disability / Veteran / Gender Identity / Sexual Orientation.

ready to book a virtual event?