Tuesday Flight Update

I know Tuesday afternoon is supposedly the best time to buy. Maybe I'm a little ahead of myself. Quick flight update:



Roundtrip Chicago to Madrid
Friday 10/18 - Sunday 11/3:

• $1,031 on Iberia
• Not available using your miles/me booking alone. There are United flights that go through New York, so shorter flight time, they are available to book as a single ticket, but 55,000 miles for you. I wonder if you can use your miles NYC to Madrid on those days? Find a different way to get to NYC? Something to look into.

Saturday 10/19 - Sunday 11/3:

•  $1,031 on Iberia
• Can't get it to work. There's a 6:10 flight with a connection to Munich, but it's 55,000 miles for you.

Sunday 10/20 - Sunday 11/3:

• $996 on Iberia
• There's a 6:25 pm to Munich. Fly back at 6:25 AM from Madrid, connect in Frankfort. $120 for you with miles. $1,060 for me.

Into Lisbon, out of Barcelona
Friday 10/18 - Sunday 11/3:

• There's a 4 PM to London, Arrive Lisbon 10:55 AM. There's a 7:20 AM flight from Barcelona to Frankfort that we can both take, but for some reason you can fly Lufthansa home at 10:35 AM. I have to fly United home at 12:45 PM. That would be $1,050 for me. However, we can both take the 6:10 AM from Barcelona and the 12:45 PM from Frankfort. That would be $1,215 for me. Ironically, the 10:35 flight home from Frankfort is available to me, but not you when we combo with the 6:10 AM from Barcelona. Strange.
• Not that it matters, but its $1,150 to do that itinerary on Iberia. Connect in London on the way there, Madrid on the way home. $1,115 if we get ourselves back to Madrid.

Saturday 10/19 - Sunday 11/3

• Exact same flights/prices as flying Friday on United.

Sunday 10/20 - Sunday 11/3

• We have to take a 9:10 PM flight to London, don't get to Lisbon until 4:20 PM. Same flight home. Cost is $1,180 for me, so only $35 cheaper than flying out Friday or Saturday.

Seems to me that 10/18 to Lisbon; 11/3 home from Barcelona is a pretty good option. Now, last week that flight seemed to be a little cheaper if we booked on Thursday. However, our options seem to be dwindling, so I'd be ok locking this trip in. We can figure out the rest of the trip from there. What do you think?