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  1. Default New York to Chicago

    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,
    Thomas

  2. #2
    Join Date
    Mar 2005
    Location
    Western/Central Massachusetts
    Posts
    1,703

    Default Welcome!

    Welcome to the RoadTrip America Forum!

    I imagine you meant to say you live East of NYC! Somewhere in the Coram area?

    Our first suggestion for saving money whilst on the road would be in this article written by some of our intrepid road warriors. The problem with most of the popular cities is one of cost, though if you look hard enough, you can avoid big expenditures and still have a great time.

    I tend towards mass transit to get around cities mostly because it alleviates much of the stress of driving through those areas. An added bonus is not paying ludicrous amounts of cash to park my car. You may be able to find a hotel that offers a shuttle into the city if you search a bit.

    It is good that you have been able to get out and drive to some other locations, too. That should give you some foresight into what you can expect on the road.

    I think you would be better off focusing on getting to Western Ohio and a place to stay the first day, rather than in Illinois, since Illinois appears to be about a 15 hour drive from your hometown. 1600 miles round trip is, in the opinion of many of us here, a three-day journey, not two, especially if you want it to be a comfortable trip. Sure, it is possible, but you will be hard pressed to stop for any of the interesting side attractions you may see along the way.

  3. #3
    Join Date
    Jan 1998
    Location
    Las Vegas, Nevada
    Posts
    10,060

    Default You drove to Miami from NYC as a novice?

    Quote Originally Posted by Ascythopicism View Post
    Hello there, RoadTrip America Forum!
    Welcome to the Great American RoadTrip Forum! Yes, I have seen you start a couple of threads but never quite complete them -- so nice to "see" you here.
    I am a freshman in college (I live in a suburb on Long Island,
    How did you like that rainstorm a week or so ago -- one of the RTA audiobook reviewers lived for several years (close to where you must be living now) and he was amazed with the flooding out there this year!
    ...have only been driving for a little over a year. I have, however, made driving trips to Hershey, PA, Boston, MA, and Miami, FL.
    Wow, that is an impressive amount of driving for only a year of having a license!
    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.
    That seems reasonable.
    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,
    Spoken like a true New Yorker -- it is pretty tough to find anyplace that even remotely resembles "the middle of nowhere" when one is east of the Mississippi River! As you probably know, by the most direct route, it is about 815 miles from NY to Chicago, so it is good day and 1/2 drive one-way to Chicago (there is no safe way you could drive this distance in one day !) There are several side trips you can take on this trip.

    But probably the first thing you ought to think about is what expectations and /or goals you have for this trip. Both you and your companion should take this quiz and make sure you are both "up" for the same kind of trip. Also, read this article about speed runs and your road trip gear kit. Here is another set of guidelines about budgeting for your trip.

    Midwest Michael often posts about Chicago and lodging choices, so I will leave that to him.

    Mark

  4. Default

    Thanks for your kind responses (and welcomes) thus far.

    Aye, Mass Tim, I did mean East. Medford to be specific.

    Editor: The storm wasn't too bad in my area. At least, I think it wasn't. My room is situated in a basement (read dungeon) so it's easy to forget there's a "surface world" out there (a big reason why I love to travel). Also, to be fair, I made the Miami trip with my father and younger brother. He started off in New York, and stopped in a town near the middle of South Carolina (Lafayette?). I continued the next day down to Jacksonville, stayed with family for a few days, then I finished up the rest of our land trip to Miami. We then took a short cruise to Nassau. After our four days of complete luxury (and gambling), I made the ride back to Jacksonville (from Miami), he continued the drive to the same town in South Carolina (we stayed in a hotel across the street from our initial visit) and I finished the complete trip back to Long Island, New York. So I didn't complete the trip solo, but it was the most I've ever driven before in succession. I've found driving for long periods of time doesn't bother me as long as I have some Penn Jillette radio show to listen to (which has since been cancelled, I guess I need to make the switch to audio books now).

    Apologies for the almost-off-topic ramblings (I've gotten pretty good at 'em). I look forward to someone (who knows the city and surrounding areas well) enlightening me as to what there is to do on any given mid-summer night in Chicago. Another question:

    Have you guys found any websites that offer better deals / are more informative than the stereotypical hotels.com / priceline / et cetera when it comes to researching and booking hotels?

  5. #5
    Join Date
    Jan 1998
    Location
    Las Vegas, Nevada
    Posts
    10,060

    Default My colleagues at Tripso

    Quote Originally Posted by Ascythopicism View Post
    Have you guys found any websites that offer better deals / are more informative than the stereotypical hotels.com / priceline / et cetera when it comes to researching and booking hotels?
    My colleagues at Tripso.com have kind of made that an art form.

    Mark

  6. Default

    Chicago in the summer is wonderful. I adore things like free tuesday evenings at the art institute, downtown, which has one of the best exhibits of impressionism in America. Butterfly Haven in lincoln park is cool, too. Dig a little on the internet, you'll find free nights for things and tons of festivals around the city.

    Sorry, I'm obsessed with chicago right now - and trying to plan my own trip to new york (!) so I'm totally mooching tips off your thread.

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