$63 To Chicago

ORD United Club
CTA & Fairmont Chicago
Tornado Warnings & The Flight Home


This trip was inspired by the slogan that I read somewhere (probably FlyerTalk or Milepoint) “Follow the fare!” A few months ago, someone posted a mistake fare on FlyerTalk. It was a routing from NYC to ORD (Chicago)… for $63 round trip! For that price, I didn’t even bother checking with Joann first; I was following the fare!

$252.80 for 4 Passengers

With no immediate desire to visit Chicago, I just picked a weekend and booked the flights. I even convinced a few friends to come along for the ride. Hard to resist a great deal! It’s funny how a few years on FlyerTalk will make you chase the deal first and the destination second.

A few weeks ago, with our trip approaching, we started to figure out what we wanted to do. Neither Joann nor I had been to Chicago since we were kids so we wanted to hit all the must-do stuff – Sears (Willis) Tower, Magnificent Mile, deep dish pizza, Chicago hot dogs, a boat tour, etc.

chicago deep dish pizza

Yup, I’d pay $63 just to eat that for 2 days.

With a little over 48 hours in the Second City, our list seemed pretty doable. And fortunately enough, a TravelZoo special came up two days before our flight for a cheap rate at the Fairmont Chicago, right in downtown Chicago. It was a perfect storm (more on storms later).

But before all that, we’d still have to conquer a JFK-IAD-ORD routing starting at 6am on a Saturday