Employment Opportunities

We believe in Travel, Community, Health & Service

Bobby’s Bike Hike, America’s longest running city bike tour operator specializing in bike, walking and food tours since 2002, hires fun and energetic performers, actors, docents, and teachers every year to join our team of full and part-time Chicago Tour Guide Leaders. Imagine putting your performing and leadership skills to work while keeping in shape this season showing off the history and landmarks of our great city. We are in very high demand, so you can be the star of your own show in front of a packed tour.

To apply to open positions, please click the button link in the job descriptions below or email your resume to employment@bobbysbikehike.com.

Open Positions:

  • Tour Director
  • Summer Camp Counselors 
  • Tour Guides
  • Shop Coordinators
  • Mechanic
 
 
Tour Director
Summer Camp Counselors
Tour Guide
Shop Manager & Bicycle Mechanic
Shop Coordinator
View Job Post & Apply

 

$60,000 – $65,000 a year – Full-time

Are you the kind of person who thrives on motion, motivates teams with heart, and turns great ideas into unforgettable guest experiences? Bobby’s Bike Hike is calling your name. We’re America’s top-rated bike, walking, and food tour company, and we’re on the hunt for a passionate, detail-loving, people-powered leader to drive our front-of-house tour operations in both Chicago and Miami. No travel required, business location is in downtown Chicago.

Who We Are: Since 2002, Bobby’s Bike Hike has been transforming city exploration into award-winning adventures. With over 6,000 five-star reviews and multiple national accolades (hello, USA Today’s Top 10 Food Tours in America two years running), we blend travel, community, health, and next-level service into every tour we roll out.

Who You Are: You’re not just a manager—you’re a maestro of moving parts, a people developer, and a stickler for 5-star standards. You lead with empathy and confidence. You’re the first to step up, the last to leave a detail unchecked, and you love helping others shine.

Whether you’ve led teams in tourism, hospitality, education, coaching, or retail—if you’re excited by logistics, leadership, and leaving guests with lifelong memories, let’s talk.

What You’ll Do:

  • Own our Chicago and Miami front-of-house operations and ensure every experience starts and ends with excellence
  • Manage and mentor our team of guides and shop staff—building culture, refining skills, and inspiring growth. Share feedback and comments from guests and monitor track their scorecards, coaching them to 5-star standards
  • Train new team members and create a consistent rhythm of ongoing coaching
  • Anticipate and Solve on-the-fly tour route challenges and disruptions with style, grace, and a guest-first mindset, solving problems and communicating with team.
  • Set up new partnerships with restaurants, negotiate food/drink pricing for food tours, and ensure strong relationship moving forward
  • Create new and unique tour routes, developing scripts, partnering with restaurants, and training guides to 5-star standards
  • Improve operational processes to keep things running smoothly and smartly
  • Strengthen and grow partnerships with our food and cultural tour stops
  • Track performance metrics and support marketing efforts alongside our leadership team
  • Bonus Points (but not necessary for position): you have bike repair, mechanical skills.

Your Superpowers:

  • Bachelor’s degree in business, marketing, tourism—or street-smart equivalent
  • 2+ years of leadership experience (tourism, hospitality, or customer experience preferred)
  • Confident in tools like Google Drive, Slack, Trello, MS Office
  • Strong communicator with an eye for the details and a heart for the big picture
  • Weekend warrior (availability required!)

Why Bobby’s? Because we’re not just a tour company—we’re a movement. A movement rooted in:

  • Travel that opens minds and connects people
  • Community that uplifts local businesses and neighborhoods
  • Health of our guests, our team, and our planet
  • Service that goes beyond expectations, every single day

We’re growing fast and planning big. Join us now and you’ll help shape the future of Bobby’s—here in Chicago, Miami, and beyond.

Perks of the Job:

  • Full-time salaried position in a dynamic, high-growth environment
  • Collaborate with a passionate, professional, and playful team
  • Real opportunities for advancement as we expand to new cities
  • Be part of a values-driven company making real impact
View Job Post & Apply

 

$19 – $22 an hour – Part-time, Full-time

Bobby’s Bike Hike, America’s longest running city bike tour operator since 2002, specializes in bike, walking, kayak and food tours, as well as Outdoor Adventure Summer Camps.

We’re hiring fun and energetic Camp Counselors to join our downtown team for Bobby’s Bike Hike Outdoor Adventure Youth Camps running weekly, from June through August. Imagine putting your teaching and leadership skills to work while keeping in shape during the summer leading Chicago’s youth on engaging bike, hike, swim and kayak experiences of our great city.

If you are:

  • A teacher, camp counselor, storyteller and a leader
  • Passionate about history, culture, teaching, and outdoor recreation
  • Able and excited to swim, kayak, and ride a bicycle (at a leisurely pace)
  • High energy and full of enthusiasm
  • Convinced Chicago is the greatest city in the world
  • Are able to work Monday-Friday through the Summer Season (June-August).

Then Bobby’s Bike Hike Summer Camps could be a good fit for you! Previous camp counseling, or teaching experience, an active lifestyle, and speaking multiple languages are strong pluses. Current first aid and/or lifeguarding certifications are preferred. But personality, passion, and charisma are the primary requirements.

Why Bobby’s Bike Hike — Outdoor Adventure Summer Camps?

Founded in 2002, Bobby’s Bike Hike is Chicago’s largest outdoor recreation company focused on bike, walking, food and kayak tours, as well as Outdoor Adventure Camps. With over 6000 online reviews and a 5-star rating, we are proud to be consistently ranked as Chicago’s #1 rated Tour Company for the past 20+ years on Google, TripAdvisor and Yelp. Our company culture is what truly sets us apart, focused on travel, community, health and service. We’re excited to have you join our growing team of motivated camp counselors who are professional and fun, offering you an industry-leading training program to make sure you are ready to show off your leadership skills.

Bobby’s Bike Hike offers our Outdoor Adventure Youth camps for kids ages 8 – 16. Camps run weekly, 9 am – 4:30 pm Monday through Friday, from June to early September. Camps consist of biking, hiking, swimming, kayaking, games, and learning/exploring. We are looking for Camp Counselors and Camp Managers to help run these fun summer camps. Diversity matters and we seek a diverse workforce.
We are proud to be consistently ranked as the #1 Outdoor Adventure Company in Chicago for the past 20+ years on Google, TripAdvisor and Yelp. In the past year, we’ve received the following accolades:

  • USA Today rated us the top 10 tour companies in America (2023 Ranking)
  • TripAdvisor rated our company top 20 in the world. (2023 Ranking)
  • Entrepreneur Magazine rated us the 150 Top mom-and-pop companies in America to work for. We’re proud of our track record of success. (2023 Ranking)

Outdoor Adventure Camp Counselors

  • June 1 – September 4 (Weekly Camps)
  • Mon-Fri Shifts begin from 8:15am
  • Location: Ohio Street Beach, downtown Chicago

Part-time · $15 – $40 / hour

Schedules are flexible. Pay is an hourly base rate plus gratuities from our generous guests.

If You Are:

  • A storyteller, performer, actor, docent, tour guide, teacher or, more importantly, a leader
  • Passionate about history, culture, and food
  • Able and excited to walk or ride a bicycle a few hours a day (at a leisurely pace)
  • Have weekend availability
  • Convinced Chicago is the greatest city in the world

Then Bobby’s Bike Hike could be a good fit for you! Previous guiding experience, an active lifestyle, and speaking multiple languages are strong pluses. But personality, passion, and charisma are the primary requirements.’

Full-time · $20 – $22 / hour
Are you looking for a unique leadership role in the fast-paced and growing Chicago tourism industry? Are you passionate about the outdoors, adventure tourism, a healthy lifestyle, and take pride in excellent bicycle maintenance?

Chicago’s largest outdoor adventure tour company is looking for someone with a unique blend of shop and service management experience combined with bike maintenance (bike mechanic), to handle shop coordination and to run daily operations for our award-winning bike, walking, and food Tour Company located in downtown Chicago. With over 3,000 five-star online reviews and a #1 overall ranking for “Outdoor Activities in Chicago,” this is a rare opportunity to take an established, thriving business and help lead its growth success moving forward.

Bobby’s Bike Hike Chicago is not your traditional bike shop. We’re in the ever-expanding tourism industry so we have the same needs as a traditional bicycle shop plus offer a fleet of bikes for tours and rentals. We are growing rapidly and looking for leaders who have an excellent background in shop and service management and bicycle repair. This position not only offers great year-round salary and benefits but has profit-sharing potential so you can grow right alongside the company’s growth. And we’re growing quite fast!

Applicants must have at least two years of prior bike shop management experience, preferably running a service department or managing a service-based business.

Are you passionate about the following?

  • Developing and building a strong team around a shared set of principles.
  • Exceeding goals and running/growing a business.
  • Delivering exceptional experiences and service.
  • Managing in a fast-paced, professional work environment.
  • Taking pride in excellent bike maintenance.

Here’s what you’d do as our Shop and Service Manager in charge of in-shop coordination, shop management and service management.

In-Shop Coordination:

  • Build and develop an enthusiastic team of 8-12 ambassadors for Chicago, dedicated to providing lasting memories for our bike tour and rental guests through excellent service.
  • Create schedules to allow our staff to showcase their skills, develop new talent, and deliver excellent customer service.
  • Strive for balance and health – for our team, the company, and the environment.
  • Encourage feedback from our clients and staff, discussing ideas and bringing solutions to the rest of the leadership team.
  • Manage daily operations at Chicago’s largest outdoor adventure touring company, ensuring all shop procedures and initiatives are in order to reach your individual and company goals.
  • Extend your network by making connections within the Chicago tourism community.
  • Set an example for the team by exhibiting and consistently improving on our Culture and Shared
  • Values of Integrity, Inspiration, Balance, and Improvement, while taking pride in everything you do.
  • Manage any customer issues that might arise, finding a healthy outcome for both the guest and our company.
  • Manage our bike repair fleet and create a maintenance schedule maximizing fleet usage with minimal downtime, while reducing expenses and looking for ways to be more efficient and cost-effective.
  • Keep processes and procedures as simple as riding a bike.
  • This is a unique and rewarding role that requires a positive outlook and a specific skill set.

Shop Manager Role requirements:

  • Strong organizational skills to stay on top of multiple projects in a fast-paced environment.
  • Ability to set measurable goals and take responsibility for results.
  • Ability to work Saturdays and Sundays during our busy season, from March to October.
  • Feels comfortable leading staff and delegating tasks to others for maximum productivity.
  • Removes work process roadblocks to then hold the team accountable for results.
  • Passionately leads in- shop coordination and incorporates our tenets and shared values into the daily business model.
  • Driven by monthly and annual sales goals.
  • Creates an environment for positive staff growth and retention.
  • Proactively recruits new seasonal staff members by being a beacon of our values and culture.
  • Understands to always under promise and over deliver.
  • Loves brainstorming, problem-solving, being creative and resourceful.
  • Has a positive attitude and contagious enthusiasm for travel, community, health, and service

Service Manager Role requirements:

  • Applicants must have at least two years of prior bike shop management experience, preferably running a service department or managing a service-based business.
  • Servicing/maintaining both customer and company fleet bikes.
  • Pricing estimates for customer repairs.
  • Maintaining parts inventory and repair records.
  • Ordering shop materials, tools, parts and supplies.
  • Insuring cleanliness, efficiency, and safety of service area.
  • Conducting bike repair classes for employees and customers.
  • Updating service training documents.
  • Weekly meetings with General Manager.

Full-time · $13.50 – $15 / hour (part-time and full-time available)

Chicago’s #1 rated bike, walking and food tour company is looking for a qualified shop coordinator to assist our management team in front house day-to-day operations, communication, and sales. This full to part-time position will join our leadership team to help in day-to-day operations as well as being our driving force in creating great guest experiences for our growing company. The candidate should be prepared to work in a fast-paced and customer service-driven environment. This position has an hourly base, plus small bonus potential.

Responsibilities:

  • Learn and run the day-to-day front-of-house operations for our bike, walking, food tours and bike rentals.
  • Respond to customer phone calls and emails quickly and effectively.
  • Handle cash register, going over rental agreements with guests, and distributing bikes for bike rental guests.
  • Learn our various tour activities and be able to explain those to guests Daily duties as necessary.
  • Be an active brand ambassador for our company and Chicago.
  • Work directly with management to create a positive workplace environment through team-building activities.
  • Assist coworkers in daily operations, allowing guests to fully experience our beautiful city.
  • Collaborate with management and co-workers to better operations and day-to-day tasks, making all tasks as simple as riding a bike.

Daily Duties as Necessary:

  • Be an active brand ambassador for our company and Chicago.
  • Work directly with management to create a positive workplace environment through team building activities.
  • Assist coworkers in daily operations, allowing guests to fully experience our beautiful city.
  • Collaborate with management and co-workers to better operations and day-to-day tasks, making all tasks as simple as riding a bike.
  • Preferred Understanding of the Following:
  • Excellent communication skills, both written and verbal
  • Google Drive
  • Email
  • Fareharbor Reservation System
  • Slack

Why Bobby’s Bike Hike — Chicago Tours?

Bobby’s Bike Hike is Chicago’s premier tour company for bike, walking, food and cultural tours. We are proud to be consistently ranked as Chicago’s #1 Rated Tour Company for the past 11 years on Google, TripAdvisor and Yelp. Our company culture is what truly sets us apart. We’re excited to have you join our growing team of motivated tour leaders who are professional and fun, offering you an industry-leading training program to make sure you are ready to show off your talents and ability. Bobby’s Bike Hike offers on average 50-55 tours per week during the busy season, and offers both seasonal and year-round employment for all bike, walking, and food tour guides. We are looking for actors, actresses, teachers, performers, tour guides, docents and storytellers. Diversity matters and we seek a diverse workforce.

Schedules are flexible. Pay is an hourly base rate plus gratuities from our generous guests.

To Apply: please email applications to employment@bobbysbikehike.com

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