Central Europe Triangle Pass

http://www.raileurope.com/rail-tickets-passes/central-europe-triangle-pass/index.html

Not sure if this is a good fare, but could be an option. I'm also not sure if you saw this one already.

Changes

Things that could open up our itinerary:

1. Give up our boat trip from Budapest to Vienna (or vice versa). I think it will be cool, but the two trips each way per week are serious limiting with our 5/17 to 5/31 travel plans.
2. Skip Ceske Krumlov, I could live without it. I think the hiking would be cool, but that might be a poor attempt to re-live Bergen.
3. Do Ceske Krumlov in one night, arrive one morning, leave the next afternoon, not might have to give up the hiking
4. Adjust our departure/arrive dates
5. Stay an extra day - I'm open to either. With Memorial Day, we could stay for 14 nights with only 10 days off work

Itinerary Option 3: Krakow

So, if we fly round trip to Krakow, we're looking at this:

The schedule I can make work with the hydrofoil schedule is the same as Frankfurt, but sub in Krakow for Frankfurt:

Thursday, May 17: Depart Chicago
Friday, May 18: Arrive Krakow, Travel to Budapest
Monday, May 21: Depart Budapest, Arrive Vienna
Thursday, May 24: Depart Vienna, Arrive Ceske Krumlov
Saturday, May 26: Depart Ceske Krumlov, Arrive Prague
Tuesday, May 29, Depart Prague, Arrive Krakow
Thursday, May 31: Depart Krakow, Arrive Chicago

In addition to the baseline itinerary fares:

I've got round trip airfare to Krakow at $1,200.
One way from Kakow to Budapest is $235 by plane (2.5 hours, 1-stop) or $144 by train (8 hours, overnight train)
One way from Prague to Krakow is $275 by plane (2.5 hours, 1-stop) or $104 by train (11 hours, overnight train)
There may be some sort of Poland-Czech-Hungary-Austria rail pass

So, things seems expensive like Frankfurt, and those train travel times are longer than I anticipated.

Seems Warsaw might be a cheaper flight.

Itinerary Option 2: London

So, if we fly round trip to London, we're looking at this:

The schedule I can make work with the hydrofoil schedule is the same as Frankfurt, but sub in London for Frankfurt:

Thursday, May 17: Depart Chicago
Friday, May 18: Arrive London, Fly to Budapest
Monday, May 21: Depart Budapest, Arrive Vienna
Thursday, May 24: Depart Vienna, Arrive Ceske Krumlov
Saturday, May 26: Depart Ceske Krumlov, Arrive Prague
Tuesday, May 29, Depart Prague, Arrive London
Thursday, May 31: Depart London, Arrive Chicago

In addition to the baseline itinerary fares:

I've got round trip airfare to London at $950.
One way from London to Budapest is $110 by plane (2.5 hours non-stop).
One way from Prague to London is $60 by plane (2 hours, non-stop).
Kind of assume rail isn't an option.

So, our overall travel costs are probably about the same, but we get to see London. Not sure if you can use miles. I assume London is more expensive than the other cities in terms of lodging/food/booze.

Hold tight for my quick Krakow analysis!

Itinerary Option 1: Frankfort

So, if we fly round trip to Frankfort, we're looking at this:

The schedule I can make work with the hydrofoil schedule:

Thursday, May 17: Depart Chicago
Friday, May 18: Arrive Frankfort, Fly to Budapest

Monday, May 21: Depart Budapest, Arrive Vienna
Thursday, May 24: Depart Vienna, Arrive Ceske Krumlov
Saturday, May 26: Depart Ceske Krumlov, Arrive Prague
Tuesday, May 29, Depart Prague, Arrive Frankfort
Thursday, May 31: Depart Frankfort, Arrive Chicago

In addition to the baseline itinerary fares:

I've got round trip airfare to Frankfort at $1200/person, you can get $950 for different days.
One way from Frankfort to Budapest is $175 by plane (3.5 hours with a connection). Non-stop is over $800. We may be able to find something cheaper, I didn't put a ton of thought into it. Rail from Frankfurt to Budapest appears to be about $300 (16 hours).

So, even if we change travel dates to grab the $950 fare, I'm not sure our overall travel costs are any cheaper than $1,625.