somewheresomeday.com *
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This is something I have wanted for a while and haven’t found, but it feels like something that current AI systems ought to be able to do, so I’m hoping there’s a website I can go to to do what I want. And maybe it’s just ChatGPT.
What I’m looking for is the ability to search for travel/vacation options where there is a range of destinations and dates that would be acceptable. Like right now I’d like to know what options there are for 4 day Caribbean vacations from Baltimore in February with direct flights.
But all the normal travel sites want you to enter exact values for the two things I am flexible on, date and destination. So to actually do my search above would require many hours of clicking through individual searches.
Surely this is a common enough situation that somebody has solved the problem, right?
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Message Thread | This response ↓
 Flexible travel searches—any recommendations? - DT January 15, 2026, 9:55:24
- I tried to get Perplexity to give me the cheapest flights to Croatia on an airline that would earn - ATL January 15, 2026, 13:44:41
- Google flights - Carl Spackler January 15, 2026, 10:07:25
- Agreed. I frequently try to do what you are asking DT - memyselfandillini January 15, 2026, 10:16:05
- Awesome. Thanks!* - DT January 15, 2026, 10:39:06
- And just like that, we are paying a pet ER bill instead of going to Jamaica. - DT January 15, 2026, 12:08:24
- Oh man, sorry. - memyselfandillini January 15, 2026, 18:33:41
- Sorry to hear! Coworker has dropped $8k this week on his dog - Dilbert January 15, 2026, 15:08:26
- Yikes, best of luck* - Tortillini January 15, 2026, 14:28:22
- Oh wow...just so this. So sorry, hope things go well.* - ATL January 15, 2026, 13:45:16
- Oof. Sorry.* - DocWalk20 January 15, 2026, 12:13:02
- Damn, sorry buddy* - reggiedunlop January 15, 2026, 12:10:20
- sounds like a great idea for a new company* - Gene Parmesan January 15, 2026, 10:05:16
- somewheresomeday.com * - doubledown January 15, 2026, 10:34:17
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on January 15, 2026, 10:34:17, in reply to "sounds like a great idea for a new company*"