Hello there, RoadTrip America Forum! I've been lurking the forums for a while now, as I am a novice roadtripper, but this is (obviously) my first post. I am a freshman in college (I live in a suburb on Long Island, about 60 miles west of New York City) and have only been driving for a little over a year. I have, however, made driving trips to Hershey, PA, Boston, MA, and Miami, FL. As a wee lad, my family rarely went on vacation; we once went to the Thousand Islands in Canada and drove to Florida two or three times. I have this great desire to experience that which is not in my immediate sphere, but have only seen the far east coast. In my nineteen years of existence, the farthest west I have been is Key West, Florida (not very far west, I know). Because of this, I had set my (hopefully) annual summer-roadtrip sights to San Francisco. However, this dream was shortly shot down when I realized the amount of time and money this trip would require (again, poor college student who will be working a "full-time" job over the summer).
After figuring out the max amount of days I could be out of work (nine days), calculating the amount of money my girlfriend and I could (most likely) raise before we set out (roughly $2000), the most practical (and farthest west) city seemed to be Chicago. Now, this will be my first trip in which I do not have relatives with whom I can stay with, and this brings me to my first problem / question:
Where should I stay?
Now, as I see it, I have two options: a cheap, but geographically distant (from the city) hotel, or a more expensive, closer-to-the-city hotel. What makes this decision even more difficult is that I am unsure what to do with my car when I get to the city. Say I do find a hotel in a suburb outside of the city, do I leave my car there and use mass transit to get to and to travel within the city? Or would it be wiser to drive the car into the city, and find (presumably more expensive) parking wherever we wish to stop? Same questions with a hotel located centrally in Chicago.
Also, I was thinking of a way to perhaps save money by driving ten to twelve hours toward Illinois, staying in a cheap hotel in the middle of nowhere, and then using the whole of the next day to finish the trip to Chicago, spending the day in the city, then finally checking into the (presumably) more expensive hotel (in either the surrounding suburbs or the city itself). The idea is that this plan will give us the same amount of time in the city, but be cheaper because we would not have checked into the hotel at our destination on day one, but at a hotel a couple of hours away.
My girlfriend and I (as I'm sure most of you are as well) enjoy active vacations. As I have it planned out so far, we will have two days of travel time (around 1600 miles round-trip, costing us around $200) and anywhere from four to seven days for everything else. Now, seven days in a city seems quite expensive (and may get tiring) so I'm shooting for four to five days. So far all I have (loosely) planned is either a White Sox or a Cubs game, and a visit to the planetarium; hardly enough activities for "four to five days." So next question:
What can two college kids who have up to five days in Chicago do to occupy themselves (that isn't too insanely expensive)?
I'm aware that this thread is gargantuanly huge, but I was hoping that anyone knowledgable could lend some good advice. Any and all help is appreciated.
Thanks for taking the time to read,