Last spring I rolled into Chicago Union Station with a duffel bag, $180 in my daily budget, and absolutely zero desire to spend most of it on a hotel room. I’d been to Chicago twice before — once for a work conference back in my corporate days (when someone else was footing the bill) and…

So there I was, staring at my laptop screen at 11 PM on a Tuesday, trying to find a decent place to stay in Chicago for under $150. I’d been invited to speak at a small travel conference, and while they were covering my flight, I was on my own for accommodations. The Hyatt Regency…

I’ll be real with you – when I first heard about Virgin Hotels Chicago, I basically laughed out loud. Me? Staying at a trendy Virgin property in one of America’s priciest cities? Yeah, right. That sounded about as likely as me suddenly developing a taste for $200 tasting menus. But here’s the thing about budget…

I’ll be honest with you – the Chicago to Boston route used to make me irrationally angry. Like, yelling at my laptop screen kind of angry. Here’s this super popular business route with tons of daily flights, and somehow I kept seeing prices that made me want to just stay home and FaceTime my friends…

So here’s the thing about the Chicago to Houston route – I’ve probably flown it more times than I’ve successfully meal-prepped for an entire week, which is to say, a lot. My sister moved to Houston back in 2019, and as someone who refuses to pay full price for basically anything, I’ve turned finding cheap…

I’ve lost count of how many times I’ve made the Chicago to Houston run. Seriously, it’s got to be at least twenty flights over the past few years, mostly because I’ve got friends in Houston and honestly, Texas in winter beats the hell out of Chicago’s frozen tundra situation. But here’s what I’ve learned: this…

So there I was, halfway through a lukewarm airplane croissant somewhere over the Atlantic, when the pilot’s voice crackled through the intercom. “Ladies and gentlemen, due to severe weather conditions in Chicago, we’ve been denied landing clearance and will be diverting to Milwaukee.” The collective groan from 300 passengers was pretty much instantaneous. That was…

So here’s a confession: I’ve flown between Philadelphia and Chicago approximately 23 times in the past three years. I know, I know – that sounds excessive, and trust me, my family thinks I’m slightly unhinged. But here’s the thing: I’ve got friends in Chicago, the food scene there is absolutely insane, and honestly? When you…

Look, I’m just gonna say it upfront – Mexico City has completely ruined me for other destinations. After my first trip there three years ago (a spontaneous decision fueled by a ridiculously cheap flight alert), I’ve been back seven times. Yeah, seven. And every single time, I’ve flown direct from Chicago because honestly? Life’s too…

Three years ago, I paid $340 for a roundtrip flight from Chicago to Orlando because I needed to visit my best friend who’d just moved there. I remember sitting on that plane thinking “this is fine, flights to Florida are just expensive” while simultaneously watching someone next to me talk about how they’d paid $87…