Originally Posted by Phoenixtinct

Yes, you can. As long as all the flights are available on the day you want/need. Also, keep in mind that you're not limited to AA on the PDX-ORD segment. You can also use AS if there's availability as they are also a partner of AA.

I would use the Multi-City feature and pick the flights one by one if the AA website doesn't produce the results you're looking for. Once you've put it together, put the reservation on hold and if it doesn't price out correctly, call AA to refresh it and you should see the correct amount of miles. And yes, this can all be ticketed as 1 award as long as your layover in ORD is not longer than 4 hours. Once you get to TXL, you can have up to 24 hours before your flight to MUC but domestically, the connection needs to be within 4 hours of arrival. Good Luck!