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We Hire the Best Chicago Tour Guides

Tour guide jobs in Chicago Chicago Detours invites top talent to join our team and become a top-notch Chicago tour guide. The number one requirement is passion – you must have an exceptional enthusiasm for architecture, history, the arts, and storytelling. Additionally, you need a strong desire to share this enthusiasm with others – whether through work as a tour guide or via marketing our tour guide services. Our tour guides are hired because of their charisma as well as their background as educators.

Current Open Positions as of December 2019:

  • Full-Time General Operations and Team Manager

Application Requirements for All Positions:
In order to best articulate your qualifications and know if our style of tour fits for you, come on one! We recommend our Loop Interior Architecture Walking Tour. 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].

Current employees share their thoughts on working with Chicago Detours:

  • Learning all the time about history, Chicago, marketing, tourism, and more.
  • Pleasure of connecting with people and sharing stories on tours.
  • With new challenges and projects constantly, the job never gets boring.
  • Being able to work with passionate like-minded individuals.
  • I like seeing people on our tours enjoy themselves and learn something new.
  • 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 General Operations and Team Manager

We are a growing small business seeking a creative-minded business person to guide our operations, human resources and financial planning to the next level. If you have a passion for Chicago history, architecture and the Chicago River, then you are especially encouraged to apply. We are looking for someone with diverse administrative experience who wants to elevate their career. We will provide extensive training and support the educational and professional development with the chosen candidate for this full-time position with benefits.

Key Responsibilities include and are not limited to:

  • Financial Planning & Analysis: Financial planning and projection. Track and report Bookings, Revenue, and Profit against annual, quarterly and monthly goals.
  • Human Resources Management: Collaborate with Private Tour Coordinator, Marketing Coordinator, and Public Tour Coordinator to share reports that will promote growth and assist in opportunity pipeline management. Oversee payroll and benefits administration.
  • Office Operations: Analyze and organize office procedures to increase efficiency and productivity.
  • Tour Finance & Accounting: Analyze tour profit margins. Organize system for accounts payable and expenses. Reconcile labor accounting data. Provide a revenue forecast based on project assignments and schedules.
  • Billing/Invoicing/Collections: Manage freelancer who checks accuracy of billing, accounting and receivables.
  • Website Management: Oversee the work of our Webmaster.


  • 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, understanding of and experience with the Tableau, 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.
  • Background in managing vendors on business systems implementation projects.


  • Paid vacation
  • Paid sick days
  • Health insurance
  • Dental insurance
  • CTA stipend
  • Fun, creative working environment
  • Free walking and bus tours of interior architecture, historic bars, jazz and blues, and Chicago neighborhoods
  • Flexible work schedule
  • Educational team outings
  • Office is in the beautiful and historic Monadnock Building.


Professional Chicago Tour Guides

We have closed applications for tour guides for this season. However, if you would like to express your interest, we highly recommend sending an application all the same! Our tours operate year-round so you must have flexible availability all year, including Saturdays and some weekdays. This job is perfect for freelancers and adjunct teachers. The best way to be able to articulate your qualifications is to come on a tour for yourself.. We recommend attending the Loop Interior Architecture Tour before applying. Then if you are invited to an interview, we will refund the value of your ticket in gratitude for your time. 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 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 stories.

Preferred qualifications:

  • An impressive knowledge of Chicago’s past and present.
  • Background in art history, architecture or other kind of visual art.
  • Fluency in French, Spanish, Italian, German, Russian or Chinese a plus.
  • Master’s degree in relevant studies

We say that our tours “bring people to explore stories and places locals don’t even know.” Thus we attract a hipper, younger and more active crowd of guests than you may expect for a tour company. Many of our guests are Chicagoans. Opportunities to grow include leading private group tours, training for our fun Historic Bar Tour, and guiding bus tours of jazz and blues history.

Every Chicago Detours tour guide undergoes several weeks of training. We pay a competitive per-tour 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.


Call: 312.350.1131
E-Mail: [email protected]