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Crazy trip hack?

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ORD-TLV-ORD (through EWR) out 1/22 and in 1/28 is still selling for $644, over $300 less than EWR-TLV on the same dates. I want to park at EWR because the off-site parking is so cheap and because it might be tough to get rides both ways if I start and end at different airports.

So, I'm thinking of taking B6: EWR-BOS-ORD for $125 (best price according to Matrix) and then ORD-EWR-TLV and still come out almost $200 ahead of the game.

My first question is when and where is the earliest I can check for TLV. Can I do it at EWR in the morning before leaving for BOS at terminal C and then take the airtrain to terminal A to catch the B6 flt to BOS or is that too early to check (it would be about 15 hrs before EWR-TLV)? If not, can I check through to TLV at ORD or do I have to get the bag back at EWR and then check it to TLV?

My second question is more practical: Am I nuts? Is it a really stupid idea to do 3 segments and then an 11 hour redeye on the same day? Should I just suck it up and pay the extra $200 and stop trying to game the system?

Haven't booked anything so I'm just looking for some advice.

Thanks!

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