I’ve written about a Napa trip that cost seven thousand dollars. So let me tell you about the other kind.
Four of us — me and my sisters — went to Chicago for four days. We stayed at the Fairmont, right by Millennium Park. And the hotel bill at the end of it was $546 total.
Split four ways, that’s about $137 each. For four days. At the Fairmont.
Here’s exactly how.
The points did the heavy lifting
We covered the stay with Amex points. That’s the whole trick, and it’s not a trick — it’s just the thing nobody plans far enough ahead to use.
The $546 was what was left over after the points: the part points don’t cover. We split it four ways and moved on with our lives.
I want to be precise about what that does and doesn’t mean, because travel content lies about this constantly. It does not mean the trip was free. It means the single biggest line item was already paid for months before we went — by a card someone was going to use anyway, on spending that was already happening.
That’s the difference between a cheap trip and a well-timed one.
The second trick: four people
A hotel room costs what it costs whether one person sleeps in it or four.
This is the least glamorous money advice in the world and it is undefeated. The Napa room I wrote about was big enough for four and it would have changed that trip’s math completely. In Chicago we actually did it, and it’s why a Fairmont stay came out to less than a tank of gas a day each.
If you take one thing from this post: book the room, then fill it.
What we actually did
Almost none of it was expensive, and that wasn’t a compromise.
A $30 jazz club. Winter’s Jazz Club, thirty dollars to get in. A real band, a real room, close enough to the piano to hear the pedals. That was the best night of the trip and I’d have paid a lot more for it after the fact, which is exactly the kind of value you can’t plan and should chase when you find it.
Bordel, in Wicker Park, which is a speakeasy and a cabaret — you go in for the cocktails and then there’s a burlesque show. Two nights out in one venue. Go with people you like.
Coffee shops near the Bean. Plural. We made a whole thing of it. Hero Coffee Roasters is down an alley with a lit-up COFFEE sign hanging off a fire escape, which is the most Chicago thing I can describe. Millennium Park is right there, the walking is free, and sitting in a good coffee shop with your sisters for two hours costs about six dollars and is somehow the part I remember.
Dinner, properly, like adults.
The part I want you to notice
Look at that list again.
The most expensive thing on it was dinner. The best thing on it was thirty dollars. And the hotel — the thing that usually decides whether a trip happens at all — was handled before we ever booked flights.
Cheap isn’t a destination. It’s three levers. Points for the big line. Bodies in the room for the rest. And then spending your actual money on the one or two things that turn out to be the memory.
Chicago and Paris taught me the same lesson from opposite ends of the price range: in Paris the best night was free street music during Fête de la Musique, and in Chicago it was a thirty-dollar jazz cover. Neither of those was the line I budgeted for.
If you’re planning this trip
- Start with the points, not the dates. Points reward planning; they punish spontaneity.
- Four people, one room. The math isn’t close.
- Fairmont if you can cover it — it’s right at Millennium Park, so the free stuff is out your front door.
- Bordel for a night out. Speakeasy and burlesque in one place, Wicker Park, worth the trip over.
- Winter’s Jazz Club. Thirty-dollar cover, and the best money I spent all trip.
- Hero Coffee Roasters for the alley alone.
- Budget for the coffee shops. You’ll spend more hours there than you expect and you won’t be mad about it.
The points that paid for this stay came from spending that was happening anyway. That’s the whole game, and it’s step one on the money checklist below. #bigsisenergy