So last week I tried booking this crazy international trip from Chicago to Bangkok with two layovers – total nightmare fuel. Thought I could wing it like old times typing airline websites into my browser one by one. Big mistake.

The Disaster First Attempt
Started with airline sites directly. United’s calendar showed Bangkok flights but wouldn’t display layover details until payment page. Got to checkout – boom! Five hour layover in Tokyo but only 45 mins in Taipei. Missed that connection and I’d be sleeping on airport floors. Closed that tab so fast.
Hopped over to Kayak next. Found a sweet Qatar Airways deal but wait – hidden city ticketing alert popped up. Screenshot that nonsense and ran. Ain’t risking getting stranded because some algorithm got creative.
App Armor to the Rescue
Grabbed my phone and rage-downloaded everything:
- Hopper: Predictions said “wait 2 weeks” for price drop. Set alerts. Ghosted me when prices actually spiked. Uninstalled.
- Skyscanner: Flights looked cheap until filter added “minimum connection time.” Options disappeared like magic tricks. Useless.
- Google Flights: Finally! The map view showed all layover cities clearly. Could sort by total trip duration AND baggage fees. Jackpot moment.
Saw Swiss Air routing through Zurich with 2 hour layovers both ways. Google Flights flagged the short connection but showed on-time stats – 90% historical reliability. Booked right there feeling like a genius.
Epic App Failures (Rant Time)
Delta’s app? LOL. Tried avoiding checked bag fees by specifying Bangkok as destination. Still charged me $200 anyway because first leg was domestic. Their chatbot responded with yoga emojis when I complained. Actual nightmare.

Momondo’s app kept crashing when selecting multi-city. Restarted three times before I threw phone on sofa. Cheap flights don’t matter if you can’t freaking book them!
What Actually Saved My Sanity
- Google Flights for visualizing routes like airport Tetris
- Airline apps AFTER booking to set alerts (United’s gate change push notifications saved me in Tokyo)
- Screenshoting every damn step – argued $75 fee away with Expedia using timestamped booking flow pics
Bonus level unlocked: Downloaded LoungeBuddy day-of-flight realizing my credit card gave free lounge access during layovers. Ate free ramen instead of $25 airport sandwiches. Felt like hacking the matrix.
Moral of the story? Modern flight booking needs like four apps minimum. And always pack snacks – your app might forget to remind you that layover’s in a food desert terminal.