Going to Chicago, hralp

[Shannacore]

I'll be in Chicago in mid-April for a conference. I am having a HELL OF A TIME finding a hotel for 8 days that won't run me a total of like $1500+. This is probably because I am looking in the Downtown area. The conference is right in the middle of downtown (I think), so I'd reallllllly like to try to find a hotel that is within walking distance (2 miles at most-ish).

If I move 10-15 miles away, hotels are much more affordable. I know Chicago is pretty renown (In the US anyway) for its public transpo system. Just how user friendly is this? Especially for a nub that that never used public transpo in her life. I am not opposed to taking a bus/subway to the venue every day if it's not going to be ridiculous to figure out.

Also, any recommendations for sightseeing / good eateries? Conference is 5 days, but I'll be staying an additional 2 to roam the town.