I have utilized the Groome shuttle service from DIA to Colorado Springs many, many times. They have scheduled rides leaving DIA every hour to one of many of the popular hotels in Colorado Springs. Catch the shuttle there (fee is approximately $50), be dropped off at a hotel, and uber to whereever you're staying! Here is the link to the shuttle service: https://groometransportation.com/colorado-springs/?&sd_client_id=7b301c39-4840-4127-b122-e273c585872d

Yes you can! Most of the time you might need to layover at another major airport hub - sometimes Denver - and fly in. Colorado Springs is a smaller airport but has increased its number of connections over the years.