I almost didn’t book the trip. I’d been staring at flight prices between London and Delhi for two weeks straight, watching the numbers fluctuate like some kind of cruel game, and honestly? I was starting to think everyone who said “India is so affordable” had forgotten to account for the part where you actually have…

I remember standing outside Soldier Field before a Bears game a couple of years ago, watching people stream in from every direction, and thinking — okay, where exactly did all these people stay last night? Because I’d just spent about two hours the week before trying to figure out the same thing, and let me…

Last summer I spent four days in Chicago’s Wrigleyville neighborhood, and I’m genuinely still thinking about it — not just because the Cubs won that Friday night game, but because I managed to find a really solid hotel two blocks from the stadium for under $110 a night. During baseball season. In Chicago. Yeah, I…

Last spring, I had a four-day window between freelance projects and I did something I almost never do — I decided to treat myself to a proper city trip. No couch surfing, no shared hostel dorms, no Airbnb in a neighborhood that requires three transfers and some optimism. I wanted to be downtown, close to…

I’ll be honest — when I first heard “boutique lifestyle hotel in the heart of Chicago,” my brain immediately translated that to “way outside your budget, Ava.” I’ve been doing this budget travel thing for eight years now, and I’ve learned to be appropriately skeptical of anything that sounds too polished. But the Cambria Hotel…

My first time hearing about the Hoxton Hotel Chicago, I kind of rolled my eyes a little. I’d seen the Hoxton brand pop up in London and Amsterdam and Paris, always with that effortlessly cool aesthetic and the kind of lobby that makes you want to sit there for four hours drinking coffee and pretending…

Fairmont Chicago Millennium Park: How I Scored a Luxury Stay Without Paying Full Price I’ll be real with you — I’m not usually the person recommending five-star hotels. My whole thing is stretching a dollar until it screams. But last spring, I ended up at the Fairmont Chicago Millennium Park for two nights, and I…

I almost didn’t stay at the Kinzie Hotel Chicago. When I first pulled it up during a trip-planning session at my kitchen table in Austin — back before I fully committed to the nomad life — the nightly rate made me close the tab pretty quickly and go back to scrolling through hostels. But then…

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…