Work with us


your new you awaits you!

We are quickly growing and looking for creative, driven people to join our team!

Chicago Detours has pivoted to be a virtual tour company and is experiencing unprecedented demand.

Application 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 tours! If we invite you in for an interview, your ticket fee will be refunded to you as a thanks. This is not a requirement for applying but is strongly recommended. To apply, please email resume, cover letter, and favorite thing to do in Chicago (one paragraph max) to [email protected].

What current employees think about working with Chicago Detours:

What I love about my job:

  • Learning all the time!
  • Pleasure of connecting with people and sharing stories on virtual tours.
  • 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 are one of few tour companies to have kept going and we are currently poised for growth!

Must-have qualities for new hires:

  • 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 in-the-moment, creative problem solving.
  • Fun personality.
  • Patient and resourceful.
  • Super excited about niche aspects of Chicago/history/arch and our tours!

Full-Time Business Development Manager

We are a growing small business seeking a creative-minded business person to guide our business development to the next level through efficient operations and strategic financial planning. If you have a passion for travel, history, architecture, then you are especially encouraged to apply. We are looking for someone with 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.

Key Responsibilities include and are not limited to:

  • Sales: Generates new revenue through lead generation and opportunity pipeline management. Manages our Sales Coordinator.
  • Financial Planning & Analysis: Financial planning and projection. Analyze virtual tour 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, category growth objectives, strategies and key business topics to the 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 across internal and external organizations 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.


  • 3-7 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, growing 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 working environment
  • Flexible work schedule
  • Educational team outings
  • Option to work in our office in the beautiful and historic Monadnock Building.

Professional Virtual Tour Guides

Background in tourism not required — teaching experience is more important. While most tour companies use volunteer or docent guides, we pay our professional tour guides for their expertise and hard work. We do not hire entertainers and actors – rather we look for fun and enthusiasm in addition to knowledge in the tour guides for our virtual architectural and historical tours.

Required qualifications:

  • Clear presentation and public-speaking skills.
  • An enthusiastic presence and a desire to connect with people.
  • Experience as a teacher.
  • A love for storytelling.
  • Comfort using Zoom.
  • Flexible schedule.

Preferred qualifications:

  • An impressive knowledge of Chicago’s past and present.
  • Background in art history, architecture or other kind of visual art.
  • Master’s degree in relevant studies

Virtual tour guides will undergo several weeks of training in virtual experience management. We pay a competitive hourly rate for this part-time, contract position. Creative-thinking over-achievers are especially encouraged to apply.

Chicago Detours is an Equal Opportunity Employer – Minority / Female / Disability / Veteran / Gender Identity / Sexual Orientation.

ready to book a virtual event?