Spring break doesn’t have to cost $14,000.
It isn’t when you travel, it’s where you go when. I’m Dave, a Chicago dad who has turned 5 million points into 35+ family trips from O’Hare. Now I plan those trips for other Chicago families.
Real prices, researched by hand. No airline, hotel, or card company pays me anything.
One real family trip, broken down
Twice a month: a Chicago family, their constraint, and exactly how much we found. Free.
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It isn’t when you travel. It’s where you go when.
Every Chicago family knows spring break is expensive. What almost nobody knows is that it’s only expensive at some destinations, and they’re the ones families pick first. The Caribbean and Mexico have their own busy season from December through April, and spring break lands right in the middle of it.
Your dates are probably fixed. The destination usually isn’t.
Cancún at spring break: flights cost 272% more than in May
Grand Cayman: 228% more
San Juan: 162% more
Tokyo: 28% more
Orlando: 10% more
London: no premium at all
HOW IT WORKS
From your dates to a plan you can book.
Three steps. You book everything yourself, in your own name.
1
Tell me about your trip
A short intake form: your dates, your crew, your budget, and the trip that went wrong last time.
2
Get your Reality Check
Within 2 business days: what your trip really costs, which constraint drives the price, and what flexing each one is worth. If it can’t work, take a full refund.
3
Get your plan and book it
Your full plan, then you book in your own name so every reservation and point stays yours. I re-check prices before you book.
TWO WAYS I CAN HELP
Pick the plan that fits your timeline
Traveling in the next few months? Start with the Review. Dreaming about a trip a year or more out? That’s the Roadmap.
Trip Confidence Review
$199
Your near-term trip, researched, priced, and planned, so you book knowing you got it right.
Reality Check within 2 business days
Up to 3 destination or package options
What shifting your dates 1–3 days is worth
Hotels matched to how your family travels
Full plan within 5 business days
The Dream Trip Roadmap
$399
The trip you keep talking about, funded with points you haven’t earned yet. For trips 12+ months out.
Reality Check within 2 business days
A household card-and-points earning plan
Sequenced around approval rules and your real life
Your true all-in cash cost, every fee shown
Milestones tracked for you
Booking walkthrough when award seats open
One payment, never a second charge
100% money-back guarantee on both. I guarantee the quality of the work; the market sets the prices.
MEET DAVE
Hi, I'm Dave.
I'm a Chicago-area dad of two. Since my kids were born sixteen years ago, I've earned more than five million points and miles through credit card sign-up bonuses and turned them into more than thirty-five family trips: London, Dublin, Grand Cayman, Banff, the St. Regis in Puerto Rico, and more Orlando runs than I can count. Same four seats, same O'Hare departures, same real-world budget as every Chicago family. Four Seats from ORD is me building those plans for yours.
Planned with points: London, Dublin, Grand Cayman, Banff, Puerto Rico, Palm Springs, Bar Harbor, Savannah, Las Vegas, Colorado Springs, Orlando ten times, and counting.
READY WHEN YOU ARE
Let's plan your family's next
trip from O'Hare.
100% money-back guarantee. If your plan isn't thorough, specific, and actionable, I'll refund every dollar, no questions asked. I guarantee the quality of the work; the market sets the prices.
Reality Check within 2 business days.
No airline, hotel, or card company pays me.
Made for Chicago families.
Start free
Twice a month: a Chicago family, their constraint, and exactly how much we found. Free.
Traveling soon?
The Trip Confidence Review: your near-term trip researched, priced, and planned.
Dreaming a year out?
The Dream Trip Roadmap: the points plan that pays for most of it.
Your dates are probably fixed. The destination usually isn't.
Not sure where to start?
Get three free destination ideas matched to your dates and nonstop flights from O'Hare.