Trip from Chicago to and around Middle East and East Coast.

Well this is really my first experience of travelling, so any advice given would be really appreciated. Me and my friend are flying out to Chicago on the 28th June. We will being staying in his house in Chicago for a few days before setting off to go somewhere? I have no idea what direction to take but ideally would like to make it onto the east coast at some point. We obviously want to do alot of sight seeing as we are both self confessed culture geeks! Which states would you guys suggest travelling to and what sights are there to see and what exciting things are there to do. Ideally i would like to be home a few days before my flight on August 5th but i think we should have ample time to get pretty far and back? please help me i am clueless as of where to go?! Also what are hostels like, are they cheap? and has ever done or plans to couch surf? forms of travel as well?

You're gonna get a bucket of replies here to this one. I'll just start it off (but I'll be back it progresses).
If you're in Chicago, then you just 'Have' to do a little bit of Canada and the Great lakes. Chicago is on one of 'em (Lake Michigan) and once you've jaw dropped in awe at the size of it, go do another. They're all close by.
Now then, before I get carried away (I love it out there), I'll pass it over to others.
You're gonna have so much fun.

you have to go up and see niagara falls and don't stay on the US side!! and if your a culture geek head over to boston and walk the freedom trail! it has more than its fair share of US history!

Quoting Redpaddy

You're gonna get a bucket of replies here to this one. I'll just start it off (but I'll be back it progresses).
If you're in Chicago, then you just 'Have' to do a little bit of Canada and the Great lakes. Chicago is on one of 'em (Lake Michigan) and once you've jaw dropped in awe at the size of it, go do another. They're all close by.
Now then, before I get carried away (I love it out there), I'll pass it over to others.
You're gonna have so much fun.

thanks to both of you have you got any other suggestions could we make it down to florida and back do you think in 5 weeks? you guys obviously know of the sights and places to see! i really want to go back to new york? if either of you has a suggested route which allows us to cover the most ground but see everything in ample time that would be greatly appreciated!

I am curious where your flying from. My suggestion:

Chicago to Louisville, KY: Take in a horse race while there; if you party, 3rd Ave (I think is the night-spot to be)
Louisville to Nashville: Pop into ANY bar and enjoy some country music
Nashville to Atlanta: Never been to Atlanta....always wanted to go!
Atlanta to New Orleans, LA: Tour the cemetery, have a hurricane (or two) and beat the hangover with coffee and Beniegt's at Cafe du Monde. Any place for dinner will be wonderful.
New Orleans to Jacksonville, FL: Relax on the beach
Jacksonville to Charleston, SC: The suggery sweet pralines are to-die for! Tour some of the grand old plantations
Charleston to Outter Banks, NC
Outter Banks to Washington DC: Spend a couple days touring our countries capitol and exploring the Smithsonian
Washington DC to Philedelphia, PA: Explore more US history
Philedelphia to NYC
NYC to Boston:
Boston to Montreal Canada
Montreal to Niagara Falls
Niagara Falls to Sault Ste Marie, MI: Rent bikes and cycle the Island
Sault Ste Marie to Chicago.....

If I had 5 weeks to travel, these are the places that I would go and the route that I would take. Some I have been to and others not yet. I am excited for you....can I go!!! haha

Enjoy and happy planning!!

In 5 weeks, you can get to anywhere you want - and back. I have family in Manitoba and Florida. Awhile ago we all met up for a reunion in Winnipeg. The folks from Florida (Miami) took 5 days to get there. I think it's about 1,400 miles by road. I've driven from Winnipeg to Golden (B.C.) and back in 4 days. It was a round trip (not on the same route both ways) of some 1,700 miles. The roads in North America are easy - especially in Canada, where they are so unpopulated compared to in Europe. When I drove across Saskatchewan on Highway 1, sometimes I didn't see another vehicle for 1/2 an hour or more.
Chicago to New York.... There are so many routes you can take. I would suggest (just as an opinion) a bit of a dog-leg and do Chicago, Toronto (a meal up The CN Tower is a must), Niagara, Buffalo, New York. Once you're in N.Y., you'll have good idea of how long it'll take you to get to Florida - as you'll be about 1/3rd of the way there. From the restaurant up the CN Tower, you can see Niagara Falls through it's amazing telescopes - some 70 miles away - plus it's the best view you'll ever see of Lake Ontario, apart from a plane!!
Over to others for their ideas.
What a great trip you're gonna have.