Travel

Flight options:
For those that want direct flights -
Chicago has direct flights to and from Aspen and Denver. The options are limited.
Milwaukee has direct flights to and from Denver. This is the cheapest route and is overall less travel time, even including the 3 hour drive to Snowmass.
You do save money flying out of Chicago to Denver.
Flying directly into Aspen is more expensive, but you are 30 minutes away from the wedding rather than driving 3 hours from Denver. So it is up to you if you want to pay extra, or if you want to save money and don't mind having a lovely scenic drive! I did the drive and it went by quickly, and was breathtaking. I would book flights asap.
Hotel Options:
Aspen/Snowmass are ski towns, so there are a lot of condo style options that have either a studio apartment layout or multi room layouts if you share with others.