Cheap Vacation for 4 days [Chicago to New York]

[WheelPage]

I am meeting up with a bunch of friends at the end of this month and I am trying to keep it as cheap as possible. I am looking at a $235 plane ticket round trip Starting on a Friday and returning on a Monday. Housing will only cost me $70 all together and subway system should be what? 10 dollars a day? I will need counsel on the train fare. Food will be hard as most of us will want to get restaurant food, but I think if I budget for one meal out a day that won't be too bad and the rest will be groceries.

Plane Tickets: $235 roundtrip Chicago to New York
Housing: $70 in total
Transportation=Subway:  $40 in total [$10 for a day, maybe an one day pass?]
Food: $100 in total [eating out plus groceries] :/
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$445 This still sounds like a lot. :/

Other options:
Cheapoair $222
Hipmunk $262
Expedia $215
Travelocity $215

Any and all advice will be greatly appreciated.

[Lis]

Single rides on the subway in NYC are $2.50 and as long as you don't leave the station you probably will be able to transfer lines without paying again (break out that map!). The smallest unlimited ride card for 7 days, and while I don't know for sure, I'm going to go ahead and assume it's more than $40. You would probably be able to get away with $10 a day if you plan it right.

NYC doesn't have to be expensive meal-wise, but for the love of everything holy, STAY AWAY FROM THE TOURIST TRAPS. Go far far far away from Times Square. Go ahead and go see it, of course, but when it comes to finding a place to eat, don't stay there. There are a lot of really amazing small restaurants (think mom & pop shops) where you can get amazing food for not a lot. Well, not a lot in NYC terms. I personally love Little Italy... we Italians are known for cooking too much food and making sure everyone has had too much to eat :) You'll probably be able to take leftovers back for lunch the next day.

When it comes to restaurants and shops (and anyplace you spend money), the general rule of thumb is 'the more lights it has, the more expensive it'll be.' Try to stay away from bright flashy places and find those nice little places that are tucked away. They do exist, promise!

[Gerard]

Make sure you know how to get to and from the airport on public transport, because that can be a big hidden expense. EWR will cost a little more to get to/from, although if you're really pinching every penny, you can take a local bus between the airport and Newark Penn Station, which will save you about five bucks each way on the commuter train cost.

Speaking of pinching every penny... that's already a really cheap trip. More than half the cost is plane fare, and you're not going to get it much cheaper. For the rest, yeah, avoid paying for crap food, but treat yourself to a bagel or some Puerto Rican food or something.

Also, there's no budget line for activities. No liquor, museums, attractions, clubs, concerts, tours? Do you have four days' worth of free stuff lined up?  Or are you just gonna hang with your friends and talk?

[WheelPage]

Thanks Lis and actually, $2.50 doesn't sound too bad per-ride. I am familiar with Chicago public transit, so it shouldn't be too difficult to figure it out. Thanks for the tips on the restaurants. I know we will be eating Italian food for sure. :D I was hoping on spending less than 20 dollars on a meal a day. Meaning no alcohol, maybe soda-pop and the main entrée. This shouldn't be a problem with Mom & Pop shops, right? I don't want to do fast food nor could I convince anyone else to either. How dangerous is the area around JFK airport, maybe a 20 mile radius? Would it be safe to walk around at night?

Gerard, we are all meeting for sports related activities and a few of us are providing housing and then we will rent out a huge place for almost nothing. So, money-wise activities and housing is extremely low. Food & air flights are high. However, I have never bought a plane tight to New York and just tried to keep the cost down as low as possible with the flight prices. I would drive if I could split the cost with someone. Oh well.