Hitchhiking from Connecticut to Illinois

Well I tried Yahoo Answers and ppl were just kinda close minded and not very helpful. I know the community here is more open minded to different styles of living so hopefully I'll be able to figure out a bit before just doing it haha. Well so basically I want to get to a town a couple miles from Chicago to visit a friend. There's no real reason other than I think it would be a hilarious surprise and I've always wanted to Hitchhike, hopefully Hitchhiking with my broskies all the way to Cali in a summer or two. But yeaa first question is what is the best place to hitch a ride? I was thinking, and have read, that rest stops or truckstops might be my best bets. How should I approach it? Like if youve ever done it, what was the way you found your ride, or how would you recommend me approaching a random trucker.

I'm expecting to do this sometime in February or March, what shoudl I pack up? I have a basic idea, but open to recommendations. There's definately not a best way to approach it but there are probably a couple tips I could benefit from.

Also forgot to mention I'm close to NYC part of Connecticut. If you can get specific and recommend what interstate or whatever is a good one that can take me close to Chicago that would be great. I know there are a couple laws against walking on the highway and what not, if you want to give them to me great if not i can always do the extra research

Thank you all

updated by @jimmy-dc: 01/13/15 10:01:16PM

if u cant hitch the highway you can hitch the onramp worse case they will tell ya to go a hundred feet thataway

truck stops are ok to try but mosty have policies against riders ..doesnt mean they wont still give ua a ride tho a sign helps if people headin to there see ya and want company for the long trip or if they see your going a long long way they are more likely to pick ya up

pack light...

umm i couldnt tell u the best rout as las time i hitched wass from colorodo springs to mount shasdta 1st went up through laramue wyoi=min g for some reason then down through vegas (boith sicked horibly) then down to southern calu to go back up sometimes its easiest to go where the rides take you and not worry so much bout going straight to the goal

oh yea ended up o]in portland for 6 months then to my idah ark (crystal mining) then to chicago...all while trying to get to philly from new mexico

(took a year to get home)

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