🎊  Celebrating 50 Years Serving Chicago  ·  1976 – 2026  🎊
🎉 50th Anniversary

Chicago's Courier.
Since 1976.

Same-day delivery across Chicago and the suburbs — rush, priority, or standard. Bike messengers, medical courier, airport pickup. Now available 24/7 with Haley, our AI team member.

50+
Years
24/7
Available
TSA
Certified
📞 Call Now — (312) 786-2288 Client Portal →
Or ask Haley · Available at (312) 786-2288 · 24 hours a day
Haley, Comet Messenger AI
Haley is Live Now
Answers every call · Orders instantly
📞

Answers Every Call

No hold music, no voicemail. Haley answers day or night, every day of the year.

📦

Instant Order Entry

Place a pickup in under 60 seconds. Quotes and orders handled immediately.

🗺️

Real-Time Tracking

Route, track, and delivery updates in real time — always know where your package is.

🔒

TSA Certified

Trusted with secure airport, medical, and sensitive deliveries across Chicago.

Meet the Team

Always On.
Always Ready.

Live Now · (312) 786-2288

On our 50th anniversary, we introduced Haley — Comet's AI-powered team member. She answers every call, places orders instantly, and keeps growing in capability every single day. Whether it's a midnight rush or a Sunday delivery, Haley is always available — no hold time, no voicemail.

  • ✅ Answers calls 24 hours a day, 365 days a year
  • ✅ Instant quotes — no waiting
  • ✅ Order entry — placed immediately
  • ✅ Account & billing management
  • 🔜 Shipment tracking updates — coming soon
🧠

Learns Every Day

New skills added constantly — Haley gets smarter with every update.

🤝

Knows Your Account

Full account context on every call — no repeating yourself.

Haley, Comet Messenger AI
Haley
AI Customer Service · Comet Messenger
📞 (312) 786-2288
Est. 1976

Five Decades of
Serving Chicago

Founded on a simple promise — fast, reliable delivery for a city that never stops. Fifty years later, that promise still drives everything we do.

1976
Founded by Jim Sailer & Darlene Little
Comet Messenger Service opens its doors in Chicago, built on a simple promise: fast, reliable delivery for the city that never stops.
1980s
The Bike Messenger Era
Our fleet of cyclists becomes a fixture in the Loop — weaving through traffic to keep Chicago's businesses running.
2000s
Online Order Portal
Comet embraces the digital age with an online dispatch portal — easier ordering, tracking, and account management.
2010s
TSA Certified
Comet earns TSA certification, expanding into secure airport and medical courier services across Chicago.
2026
Haley Joins the Team
On our 50th anniversary, we introduce Haley — our AI team member, available 24/7, ushering Comet into a bold new era.
What We Deliver

Chicago Courier Services

Same-day courier

Same-Day Courier

Rush delivery across Chicago and surrounding suburbs. Documents, packages, and freight — delivered with urgency.

Bike messenger

Bike Messenger

Our legendary cyclists navigate the Loop and neighborhoods faster than any vehicle. A Chicago icon since 1976.

Medical courier

Medical Courier

HIPAA-compliant, temperature-sensitive, time-critical medical deliveries handled with the utmost care.

Micro move

Micro Move

Small moves, big results. Furniture, office equipment, and personal items moved quickly across the city.

Airport delivery

Airport Delivery

TSA-certified pickup and delivery to O'Hare and Midway. On-time, every time — even when your flight isn't.

🚀

Ready to Ship?

Call Haley at (312) 786-2288 anytime — or log in to your client portal to place an order instantly.

Ready to Get Started?

Join hundreds of Chicago businesses that trust Comet Messenger for their same-day delivery needs.

📞 (312) 786-2288 Client Portal Login → Email Us
Comet Messenger
Client Portal
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Need access? Call (312) 786-2288