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:
$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:
Your Superpowers:
Why Bobby’s? Because we’re not just a tour company—we’re a movement. A movement rooted in:
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:
$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:
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:
Outdoor Adventure Camp Counselors
Part-time · $15 – $40 / hour
Schedules are flexible. Pay is an hourly base rate plus gratuities from our generous guests.
If You Are:
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?
In-Shop Coordination:
Shop Manager Role requirements:
Service Manager Role requirements:
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:
Daily Duties as Necessary:
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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Gift an adventure that is truly one-of-a-kind!
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