By Jeff Rieter
You’re somewhere between Joliet and Rockford, halfway to your in-laws’ house, when your kid asks:
“Can I play Roblox on your laptop?”
And that laptop?
Yeah — it’s the same machine that holds your bank’s email, VPN credentials, sensitive client data, and access to your core processor.
You’re exhausted. Traffic’s backed up. Keeping them entertained sounds like a win.
But one wrong click, and suddenly your holiday cheer turns into a story nobody wants to tell:
“Chicagoland community bank faces exam findings after holiday travel data incident.”
Let’s make sure that’s not you this season.
We work with financial institutions from Frankfort and Orland Park to the Loop and the North Shore and beyond, and every December we see the same thing: smart people, good intentions… and risky holiday habits.
Why Holiday Travel = A Perfect Storm for Cyber Risk
If you lead IT, operations, or compliance at a Chicagoland financial institution, you already know the drill:
Regulations like GLBA and FFIEC guidance don’t take a vacation, even when your team does.
Holiday travel creates a perfect storm:
- Public WiFi that invites man-in-the-middle attacks
- Tired employees clicking without thinking
- Family members unknowingly accessing sensitive data
- Work and personal life blurred in hotel rooms, rental cars, and Airbnbs
Every January, when I sit down with Chicago-area bank and wealth leaders to debrief the year, there’s always at least one “you’re not going to believe what happened over Christmas” story.
It’s not about being paranoid. It’s about being intentional — especially in a regulated environment where a minor misstep can become major exam findings.
Before You Leave: 15-Minute Chicagoland Financial IT Travel Checklist
Every bank, credit union, and wealth firm in Chicagoland should treat this as standard protocol for any team member traveling over the holidays.
Security Essentials
- Apply all OS and software security updates
- Enable full disk encryption (BitLocker, FileVault) on all work devices
- Turn on remote tracking and remote wipe via your MDM
- Ensure devices auto-lock after 2 minutes idle
- Backup critical data securely to your cloud or core systems
- Test your mobile VPN connection before leaving
- Confirm policies for lost/stolen devices are clear and communicated
If you’re using managed endpoints with full disk encryption and MDM, a lost laptop at Midway or O’Hare becomes an incident — not a catastrophe. That’s the level we design for with our Chicagoland financial clients.
Family Access Rules
- Don’t allow personal use on company-issued devices
- If you must let a child or spouse use a device, create a separate user profile with no admin rights
- Pack a cheap, dedicated family tablet or laptop for entertainment —
a $200 Chromebook costs less than a breach or a bad exam
The Hotel WiFi Trap: Worse Than You Think
Chicagoland financial institutions are prime targets — and attackers know your CEO checks email from the hotel lobby just like everyone else.
Real talk: public WiFi is a hacker’s playground.
A fake “Marriott_Guest_WiFi” hotspot in the parking lot can intercept everything from client emails to VPN credentials.
If you wouldn’t read client account numbers out loud in a hotel lobby,
don’t send them over hotel WiFi either.
Your Safer Options
- Use your phone’s hotspot for all work involving client or account data
- Verify the exact WiFi name with the front desk
- Never access core systems or banking applications over hotel WiFi without a strong, enforced VPN
“Can I Use Your Work Laptop?” = Red Flag
Let’s say your kid downloads a game that’s actually a trojan.
Or installs a browser extension that logs keystrokes.
Or changes your Chrome settings without realizing it.
Suddenly, your exam is on thin ice, and you’re explaining why your endpoint protection and acceptable-use policies didn’t prevent it.
Instead
- Say no to work laptops for personal use — no exceptions
- If shared use happens, supervise it and scan/scrub the device afterward
- Better yet: don’t share at all
Smart TVs in Hotels = Dumb Security Risks
Logging into Netflix on that hotel smart TV? Fine — if it’s your personal account.
Logging into your work email or systems? Absolutely not.
Hotel TVs often retain data. The next guest could gain access if you forget to log out.
Worse, if your passwords are reused (it happens more than people admit), that login can follow you home.
Safer Options
- Cast from your own device instead of logging into the TV
- Use a media stick like Roku or Fire Stick that you control and wipe
- Set a calendar reminder to log out / reset devices before check-out
The Rental Car Privacy Problem
Most executives don’t realize this: when you sync your phone with a rental car’s Bluetooth, the system may store call logs, contacts, and even messages.
At best, it’s creepy.
At worst, it’s a compliance problem if sensitive client info is exposed.
30-Second Fix
- Delete your phone from the car’s memory before drop-off
- Clear navigation history if you used built-in GPS
- Skip Bluetooth entirely — use an aux cord or USB
The “Working Vacation” Boundary Dilemma
Chicago-area financial leaders often blur the lines:
A “quick” email check at dinner…
A call during a holiday movie…
A VPN login from the kids’ iPad hotspot in a cabin outside Rockford.
But multitasking increases risk. The more distracted you are, the more likely you are to:
- Click on phishing emails
- Skip VPN steps “just this once”
- Miss red flags in a spoofed website
Realistic Advice
- Set clear work windows (e.g., 9 AM and 4 PM) and stay off email the rest of the day
- Don’t work in public hotel spaces — screens and conversations are visible
- Use your hotspot for all work-related internet access, especially for banking systems
A Real Chicagoland Holiday Story (The Good Kind)
Last year, a south-suburban community bank had a laptop stolen from a rental car a few days before Christmas.
Because they had already:
- Enforced full disk encryption
- Locked down user accounts with least-privilege access
- Connected the device to MDM with remote wipe
…it never turned into a regulator conversation.
No client impact, no bad headlines — just an annoying travel story and a quick internal review.
That’s the difference between hoping nothing goes wrong and designing for when it does.
What If a Device Goes Missing?
If your laptop disappears at Midway or O’Hare, you’ve got about an hour to get in front of it before it becomes a serious incident.
Here’s your 60-minute plan:
- Use Find My Device or your MDM to locate it
- Lock or wipe the device remotely
- Change all work-related passwords immediately
- Alert your internal security team or MSP partner
- Notify your compliance / legal team if client data may be impacted
- Follow your incident response playbook so you’re ready if regulators ask questions later
The Bottom Line: Compliance Doesn’t Take Time Off
Whether you’re a CIO at a community bank in Frankfort, running ops at a Chicago credit union, or leading a boutique wealth firm in the Loop, you can’t afford a holiday breach.
It’s not about locking things down so tight you can’t enjoy your break —
it’s about being intentional with how your team uses technology while they’re on the road.
Because let’s be honest:
The best holiday memory should not be “Remember when we failed that security audit?”
Want Help Locking Down Holiday Travel for Your Team?
We help Chicagoland community banks, credit unions, and wealth firms build real-world, regulator-ready security protocols — without making staff jump through flaming hoops.
This is the same practical, non-fluffy guidance we share with leaders plugged into groups like the Illinois Bankers Association, Community Bankers Association of Illinois, and local business circles like the Frankfort Chamber.
If you’re reading this and thinking,
“This is exactly what my team does every December…”
…then let’s talk before someone’s kid accidentally becomes the star of your next exam finding.
Schedule a quick 15-minute consult
No pressure, just practical ideas to keep your data, clients, and holidays safe.
