We talked about their perceptions of Trump, and whether Clinton and the Clinton empire is corrupt. And we talked about the Afghan war. And George bush. And nuclear weapons. You name it. I got through quite a few cocktails that night, there was quite a lot to talk about.
One of the locals said to me that I had to remember that Chicago was something of a working class city. Not as wealthy or as important as New York, or as barking mad as Los Angeles. The closest you'll probably get to salt of the earth Americans.
And what I took from those conversations is that, in Chicago at least, they're as perplexed as the rest of us. One woman told me that in a country of 350-odd million people, she can't believe that these are the two best candidates they've come up with to be president.
All were frustrated by the lack of policy. All were frustrated that Trump's treatment of women and Clinton's email scandal have become central to the election. What is best for America and Americans had fallen by the wayside, really. And they were also really concerned about how the rest of the world was viewing them right now.
Anyway, after the debate we all decided to carry on partying and so we went to this place called 'Howl at the Moon' and it was duelling piano bar. Two women on stage with back to back grand pianos with the support of a brilliant band, banging out some pretty amazing music.
And so as the night went on we kind of forgot about Trump and Clinton but when I left, in the wee hours, I did ask this group - there were about six of them - how they were going to vote. And half said they didn't know and the other half said they weren't going to. They were going to withhold their vote because they didn't want either candidate.
I wonder how many Americans share their view? It did make me realise that this election is going to be a bit like Brexit. It's impossible to pick which way it will go - we'll just have to wait to see how America votes on the day.
My only regret is that I'm not in that bar in Chicago - cocktail in hand - on election night because I think we're about to witness a remarkable political event, and it will ultimately have huge ramifications for trade, for the global economy, for immigration, for diplomacy, and for global security.
No pressure, America.