I'm from the Chicago area, and it seems I'll get to take my first trip to Asia sometime this August, with a 1-week business trip to Singapore. I'll be pretty flexible with extending a few days either side if I want to, or maybe hanging out at a layover stop for a few days. Anyway, I've been researching the flight options, and aaaaa, so many options! I'm feeling pretty overwhelmed. I'll very likely continue on from Singapore to Germany for a couple weeks at the end too, and then back to Chicago.

I fly to Europe a lot (usually Lufthansa), but I'm really not at all familiar with the Asia-based airlines, routes, schedules, practical travel issues, anything.

I'd greatly appreciate if anyone could share their advice or experiences with this kind of itinerary, or share what you would try to do or try to avoid regarding travel arrangements, like what's the best or most comfortable airline for this in your opinion, or best route and schedule, or good layover city to explore, how to best handle the jetlag, or any bit of gained wisdom you think could be useful to share.

Feel free to add any must-sees in any free days in Singapore.

A little more info ... I presently have about 90000 miles saved on United, and would love to be able to upgrade to business or first (do you know if upgrades are possible on these routes?), or I'd consider buying a straight business ticket, since 22 hours crammed in econ seems pretty awful. I also am terrible at sleeping on planes, and have yet to manage it even once on 30+ overnight flights to Europe sitting in economy. So, a decent lie-flat seat-bed would be wonderful.

Thanks for any advice you can share!