I'd do FRA or MUC via ORD, whichever is cheaper. No reason to go out of your way for one vs the other.

It's MSN.

Funny enough, it's less of a flyover than MKE. We've quite literally went directly above MKE on flights to MSN.

I went to nuernberg for work every February 1994-2009 and I ate at different restaurants and visited many places in town when not working. If you fly out of muc you can take a train to nuernberg, stay and explore, and then fly muc - ord - msn. If the ord-msn part fails then maybe fly to mke or even consider a 1-way car rental.

I also visited Koeln / Aachen / Düsseldorf at different times of my past trips. Those are all great places. Never went to Heidelberg. So fra is another winner as I previously said; I just wanted to push for Nuremberg. Of course, NUE - FRA would be fun! Once you finalize your flight home I hope you’ll find time to investigate the places near both MUC / FRA or post in Germany forum.

I even invited my nuernberg friends to my wedding and in August my nuernberg friend that I’ve known since the 80s visited San Francisco with her family as part of their USA west coast vacation and it was great to regather with our spouses and children. Thus my nuernberg love is extremely biased

OP said it's a 6 hour connection at EWR. That's pretty long, IMHO.

I'm in the camp of BER-EWR-XXX based on the statement that you would leave BER earlier to do the FRA-ORD-XXX routing. I'm a huge fan of Heidelberg, having spend a lot of time there for work, but I don't see why you would tag that onto the trip at the expense of time in BER.

Of course, if you can talk your wife out of the 2 stop restriction, I think that BER-FRA-ORD-XXX is totally reasonable. You don't mention how you would get to FRA if you did FRA-ORD-XXX. Train? Flight? You could always do an afternoon BER-FRA flight, then spend the evening and night in FRA, then do FRA-ORD-XXX in the morning. That would really only cost you a half day in BER. No ned to spend two days in the area.

Nürnberg is definitely on the list, regardless of whichever route we take. We are planning to fly into MUC, and at worst, we'll make it a short stop on our train trip between München and Berlin.

I have to appreciate German kuchens (well, baumkuchen excepted), so perhaps it won't come as a surprise that I usually purchase a lot of lebkuchens every winter. I only very recently learned of their origins, and a chance to get even better versions definitely won't be passed up.

Isn't there a flight option for EWR-ORD that doesn't require a 6-hour wait after the BER flight arrives? There are lots of flights between those two hubs.

If I didn't like the connection options in EWR, I'd fly BER-FRA-ORD. I've connected in FRA dozens of times. It really isn't that bad. A 90-minute connection (or whatever it ends up being) isn't really a layover.

ORD is not the OP's destination.

Thank you Mayor! But DEN has far fewer options back from Germany (vs ORD/EWR) and it’s a huge back track to MSN.

One other option: fly to ORD from whichever, and drive to MSN. 135 miles, 2.5 hrs.

This is interesting to me as I will be returning to SFO on July 5th from Berlin. This is actually flexible, and we are sort of / kinda looking for the cheapest one way (or points, although I don't have any UA points right now).
I have been looking at a lot of "close" cities to see what I could fine.

Whats surprising to me is the lack of flights from BER to the States. I guess all the flights are in FRA and MUC....

To the OP, one thing that I am considering, that you may, or may not care about is MUC-DEN. Why? Its an A380 and I have never flown an A380 before. But that may not work for you..

That's ~4 flying hours of overflying and backtracking.

Lebkuchen are great. That said, I’ve bought them both at Trader Joe’s and a local German grocery. The German exports taste excellent - my nuernberg friends brought Elisen Lebkuechen and they’re great. The shop ones are still very nice.

if you like smoked beer (Rauchtbier), then Schlenkerla in Nuernberg / Bamberg has both great food and great smoked beer on tap that they brew. I briefly was able to get it in sf, around 2002!

Are you renting a car in Germany? If you drive from Berlin to Munich, you can hit Leipzig, Bamberg, and Nuremberg on the way. The departure taxes are less out of Munich than Frankfurt. While Heidelberg is nice, I wouldn’t necessarily go out of the way for it.

BER-ZRH-ORD?

ORD isn't the final destination and they want to avoid a double connection