I am travelling from SanFrancisco to Chicago and I will choose amongst following options :

1. hire a car and hit the road (kind of road trip)
2. take the Amtrak ( California Zephyr)

For options 1: If anyone is interested  to join me then please send me a private message. We will communicate through email.

• From San Francisco to Chicago
• Starting date: December 16 (Fridat night ) or December 17 ( Saturday Morning)
• Target Date: December  19 (Wedensday night) or December 20 (Thursday  mornining)
• Possible route: I 70 E and I 80 E
• I will drop you at your destination and will hit my own road after Chicago.

NOTE:

• The dates are fixed and are not flexible.
• This is ONLY possible raod trip and can be cancelled. However, I will finalize my decision by November 5 or November 12.
  
• If I cant make it for Option1 1, I will go for Option 2. That's final.
• About me: Sex - Male ; I have done couple of road trips before.

Thanks for taking time to read this post.
https://www.youtube.com/watch?v=wq-S8CIU7VA&ob=av2e

 I wouldn't do it if I were you, especially considering how inflexible your schedule is. The reason - The I-80 portion in Wyoming might get shut down if it snows. Also, since you're taking the trip during the winter, chances of snow delaying or disrupting your trips are high. 

I drove through I-80 on my way to Califonia too and I had an adventure of my life. 

P.S. If you're looking into a roadtrip to Alaska/Vancouver or Seattle from the Bay Area, hit me up. 

- As mentioned in my original post, the "dates && time" are fixed and are strictly in my terms and conditions (not others).
- I think am gonna take the Amtrak service as I have to overlap my time with my schedule.
- BTW, going from SFO --> Chicago is not an option for me its a necessity. I just wanted it to make a possible road trip

Alaska/Vancouver/Seattle sounds good from Bay Area.
Vancouver, being farthest around 1000 miles, is doable from  bay area. I can manage 4 day for that road trip and am looking forward to it. Since I'm also from Bay area, we can communicate regarding this some other time through email.

~Thanks