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Flexible travel searches—any recommendations?

Posted by DT <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DT' width='330' height='300' border=0 style='border:none;'> on January 15, 2026, 9:55:24

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?

I tried to get Perplexity to give me the cheapest flights to Croatia on an airline that would earn

Posted by ATL <iframe src='https://mb.boardhost.com/TheDeuce/info/user=ATL' width='330' height='300' border=0 style='border:none;'> on January 15, 2026, 13:44:41, in reply to "Flexible travel searches—any recommendations?"

me Skymiles and it did not do very well at all.

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“We are old and tired and just want to be taken care of.” - Republican voter, Dec. 2024.

Google flights

Posted by Carl Spackler <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Carl+Spackler' width='330' height='300' border=0 style='border:none;'> on January 15, 2026, 10:07:25, in reply to "Flexible travel searches—any recommendations?"

Go to explore
Put in Bal
Tell it your month

The only limiting factor is it stupidly has “weekend” and “1 week” options. But putting in “weekend” returns 4 day trips.

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Agreed. I frequently try to do what you are asking DT

Posted by memyselfandillini <iframe src='https://mb.boardhost.com/TheDeuce/info/user=memyselfandillini' width='330' height='300' border=0 style='border:none;'> on January 15, 2026, 10:16:05, in reply to "Google flights"

and, unless you want a cruise , Google flights Explore tab seems to give the most info on various options ina. given time window and region
and the most ability to tailor a
search result (eg direct flights only)

I have used the AI tools to generate sample itineraries around different destinations and it seems to come up with reasonable suggestions, though I am Walter-Mittying things so far and have yet to take any of those trips!

Awesome. Thanks!*

Posted by DT <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DT' width='330' height='300' border=0 style='border:none;'> on January 15, 2026, 10:39:06, in reply to "Agreed. I frequently try to do what you are asking DT"

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And just like that, we are paying a pet ER bill instead of going to Jamaica.

Posted by DT <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DT' width='330' height='300' border=0 style='border:none;'> on January 15, 2026, 12:08:24, in reply to "Awesome. Thanks!*"

Depending on what the tests show, Sprout might not be going to college next year either.

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Oh man, sorry.

hope it turns out.

where do you take them? We’ve been using Rocky Gorge Animal Hospital. It’s up north of the beltway so a PIA, but I feel slightly less gouged.

We live up north of Baltimore, and have a vet we really like, Chadwell Animal Hospital

Posted by DT <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DT' width='330' height='300' border=0 style='border:none;'> on January 15, 2026, 20:25:53, in reply to "Oh man, sorry. "

But when I called this morning and described the symptoms, they told me to take him to a pet ER right away. They didn’t have any openings and it was potentially life threatening, although it doesn’t seem like it was.

Not sure exactly how much extra we are paying for the ER/no appointment service, but I’m sure it’s adding a fair bit to the already high medical costs.

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hope it turns out.

where do you take them? We’ve been using Rocky Gorge Animal Hospital. It’s up north of the beltway so a PIA, but I feel slightly less gouged.

Sorry to hear! Coworker has dropped $8k this week on his dog

Posted by Dilbert <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Dilbert' width='330' height='300' border=0 style='border:none;'> on January 15, 2026, 15:08:26, in reply to "And just like that, we are paying a pet ER bill instead of going to Jamaica."

An after hours visit, ER visit, labs.

With no real diagnosis.

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Depending on what the tests show, Sprout might not be going to college next year either.

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We’re not there yet. X-ray showed no blockage anywhere in digestive tract.

Posted by DT <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DT' width='330' height='300' border=0 style='border:none;'> on January 15, 2026, 17:41:04, in reply to "Sorry to hear! Coworker has dropped $8k this week on his dog"

And bloodwork was all pretty much within normal ranges or close to it. So no surgery needed.

Given some past issues he’s had the vet is guessing it was some sort of congenital bowel irritation or inflammation that flared up really bad for some reason. Doing an ultrasound tomorrow to diagnoses/corroborate. Fingers crossed that’s it, in which case it seems pretty manageable.

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An after hours visit, ER visit, labs.

With no real diagnosis.

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Depending on what the tests show, Sprout might not be going to college next year either.

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Yikes, best of luck*

Posted by Tortillini <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Tortillini' width='330' height='300' border=0 style='border:none;'> on January 15, 2026, 14:28:22, in reply to "And just like that, we are paying a pet ER bill instead of going to Jamaica."

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Depending on what the tests show, Sprout might not be going to college next year either.

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Oh wow...just so this. So sorry, hope things go well.*

Posted by ATL <iframe src='https://mb.boardhost.com/TheDeuce/info/user=ATL' width='330' height='300' border=0 style='border:none;'> on January 15, 2026, 13:45:16, in reply to "And just like that, we are paying a pet ER bill instead of going to Jamaica."

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Depending on what the tests show, Sprout might not be going to college next year either.

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“We are old and tired and just want to be taken care of.” - Republican voter, Dec. 2024.

Oof. Sorry.*

Posted by DocWalk20 <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DocWalk20' width='330' height='300' border=0 style='border:none;'> on January 15, 2026, 12:13:02, in reply to "And just like that, we are paying a pet ER bill instead of going to Jamaica."

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Depending on what the tests show, Sprout might not be going to college next year either.

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Damn, sorry buddy*

Posted by reggiedunlop <iframe src='https://mb.boardhost.com/TheDeuce/info/user=reggiedunlop' width='330' height='300' border=0 style='border:none;'> on January 15, 2026, 12:10:20, in reply to "And just like that, we are paying a pet ER bill instead of going to Jamaica."

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Depending on what the tests show, Sprout might not be going to college next year either.

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sounds like a great idea for a new company*

Posted by Gene Parmesan <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Gene+Parmesan' width='330' height='300' border=0 style='border:none;'> on January 15, 2026, 10:05:16, in reply to "Flexible travel searches—any recommendations?"

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somewheresomeday.com *

Posted by doubledown <iframe src='https://mb.boardhost.com/TheDeuce/info/user=doubledown' width='330' height='300' border=0 style='border:none;'> on January 15, 2026, 10:34:17, in reply to "sounds like a great idea for a new company*"

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