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From corporate shuttles and special-event charters to family-focused subscription rides, Cannon Transportation delivers safe, reliable service tailored to your needs.

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Our Mission & Vision

Our Mission
To provide worry-free, on-demand transportation for families and professionals in the greater Chicagoland area—combining world-class hospitality with cutting-edge automation and unwavering safety standards.

Our Vision
To become Chicago’s most trusted mobility partner by building lifelong relationships through consistent performance, genuine care, and transparent pricing.

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Busy Parent, Peace of Mind

You juggle work, errands, and family life—let Cannon handle your children’s school runs with vetted drivers, real-time tracking, and guaranteed on-time arrivals so you never worry about morning logistics again.

Frequent Flyer, Stress-Free Travel

Whether it’s O’Hare or Midway, our airport transfer service ensures you catch every flight on time. Skip taxi lines and variable ride-share fees, and arrive relaxed and ready.

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Executive on the Move

Your schedule demands punctuality. With flat-rate subscriptions and priority booking, you’ll glide from home to office or that next high-stakes meeting without traffic stress or hidden surge pricing.

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Event & Group Coordinator

Planning a corporate retreat or wedding shuttle? Our turnkey charter solutions—from luxury sedans to sprinter vans—deliver polished, reliable service so you can focus on your guests, not the logistics.

Who We Serve

Busy Professionals seeking a dependable Executive Commute that eliminates parking headaches and unpredictable ride-share fees.
Families & School Communities valuing on-time school-run subscriptions with vetted drivers and real-time tracking.
Event Planners & Organizations needing turnkey charter and shuttle solutions for groups of any size.
Airport Travelers requiring punctual, door-to-door transfers between downtown and O’Hare/Midway.

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Why Choose Cannon Transportation

Safety-First Culture

Every driver completes comprehensive background checks and monthly safety audits; vehicles receive weekly inspections.

Transparent, Flat-Rate Pricing

Subscription plans start at $750/month with no hidden fees; charter rates begin at $65/hour with clear, upfront pricing.

Seamless Booking & Automation

Schedule rides online or via our app, sync with your Google/Outlook calendar, and receive instant confirmations and reminders.

Family-Focused Service

Drivers trained in child safety protocols and customer care ensure your most precious passengers travel with comfort and respect.

How It Works

Select Your Service
Choose a subscription plan (Executive Commute, School Run, Family Flex) or request a charter/shuttle quote.
Schedule in Seconds
Book your ride up to 30 days in advance through our website or app—available slots highlight in real time.
Ride & Relax
Track your driver, enjoy a professionally maintained vehicle, and let us handle billing, reminders, and support.

Executive Commute Subscription
1,200$
Every month
Perfect for high-rise residents & busy professionals in downtown Chicago
- • Up to 40 one-way rides/month
- • Service hours: 6 AM – 9 PM, Mon–Fri
- • Premium black SUV service
- • Priority booking & dedicated chauffeur
- • Complimentary wait time: 15 minutes
- • Service Distance: Within 10 miles of downtown core
Family Flex Subscription
750$
Every month
Ideal for families and professionals, occasional weekends
- • 12 one-way ride per month
- • Usable any day, including weekends
- • Cover school pickup and/or family errands
- • Airport runs and/or executive travel
- • Share with up to 2 household members
- • Ride rollover up to 1 month
Elite School Run Subscription
950$
Every month
Designed for parents at British International School & Latin School of Chicago
- • 2 round trips per school day (pickup + drop-off)
- • Includes one additional errand stop per week
- • Trained, background-checked drivers with experience in
- • Real-time ride tracking + SMS notifications for parent
- • Service Distance: Up to 8 miles from each school