Can we talk about the worst travel day I had in Chicago last fall

I landed at O'Hare at 6 PM on a Tuesday. My budget flight from Newark was $47 so no complaints there. But then the train to downtown stopped for 40 minutes. Then my $30/night hostel lost my reservation. Ended up sleeping at the airport on a bench until 4 AM. What's your worst single day on a cheap trip?

2 comments

2 Comments

grant7281mo ago

Dude, WAIT - his AirBnB actually canceled on him just because he was late? That is INSANE to me. I get being annoyed about a late check-in, but completely canceling someone's booking over that? That's brutal. And he walked a MILE with a backpack in Chicago fall weather? Those winds off the lake are no joke, that must have been absolutely miserable.

thompson.robin2mo ago

Honestly, my buddy had a similar mess in Chicago last fall. He flew in on some super cheap red-eye and the blue line broke down right after Rosemont. He ended up walking a mile in the cold with his backpack to catch a bus that took him to a random part of town. The whole thing took like 3 hours longer than it should have, and by the time he got to his AirBnB they canceled his booking because he was so late. Ngl, he just sat at a 24-hour diner and ate pancakes until the sun came up. Tbh, that city will humble you fast if you're on a budget.