Labor Day in Iceland

It's not prudent, nor financially smart, so I doubt it's going to happen, but I want to give it one last pitch.
We can fly Chicago to Reykjavik on Iceland Air for $1,000. Leave Saturday August 31, return Saturday September 7.

I swear this same flight was $900 last night, so that's not good.

$724 for the same dates from Boston to Reykjavik. Again, that was like $100 cheaper last night. Probably cost $250-$275 to get to Boston, unless we use your miles.

Could rent something like this for $700 for the week. Or one of these for $500.

My work travel agent claims it can rent the Grand Hotel Reykjavik for $150/night, which is way cheaper than I'm finding on the hotel website.

Or Reykjavik Lights hotel for about $150/night.

Frommer's has mixed info on when is best to go. Both May and September are considered the "shoulder" seasons. Less crowded, cheaper, some stuff open, other stuff closed. A lot seems to depend on the weather, was it a bad winter, i.e. stuff is still inaccessible in May, or it could be an early winter, i.e. stuff may be inaccessible in September. For the record, it's currently 48 and raining in Reykjavik.

Looks like average temps in May and September are similar. More daylight in May.

So, there it it. It's probably not financially responsible to go to Iceland in September and Spain in October. But it would be super cool. I wish flights were a little cheaper. I'd love to find a way to use $5k and pull off both Spain and Iceland.