Chicago -> Boston -> ?

I have driven from Boston to Indianapolis in one day (I did all 1000 miles of the driving, but someone else was in the car with me), so I consider Chicago to Boston in one day very doable with two drivers. I would advise you to stay on I-90 through Massachusetts rather than get on Route 2 for the scenic drive, though.

If you want to shotgun-it here, my suggestion would be to leave Chicago early in the morning after a solid 8-hour sleep, drive all day, arrive at your hotel, get something to eat, settle in for the night, and be bright-eyed and bushy-tailed to grab Boston by the reigns the following morning. If you drive overnight, you're just going to want to sleep-in in the morning, which won't make the most of your time here.

Personally I like driving at overnight because there is hardly anyone on the road besides truckers, and I have a CB in my car, so I can always strike up a conversation with the truckers anyhow. There's something about the sound of a turbodiesel spooling up at 2 A.M. that I love. =)

I'm surprised you didn't mention Durgin Park...though that atmosphere may not be for everyone. Walking around the North End for a place to eat, you can't go wrong. And as a rub to Darrel, most Bostonians think "Boston-128-California" ;-) I guess it's a good thing they have the Red Sox!

What day are you planning on leaving? Sunday night on the Pike is not the best day, even out in the boondocks of Western MA. If you get the chance, don't miss MA route 2, at least the section from NY State line to I-91. I find that to be the most enjoyable stretch of highway, as after that it gets congested. MA route 9 from NY line is nice as well. Basically anything West of I-91 is a good choice, with my choices being 2,23,9, and US-20.

I-90 in NY seems to take forever, though it is a much better option than the (partially non-existent) Southern Tier Expressway of I-86/88, which actually does take forever. I work with a former long-haul trucker, he said that sometimes going through PA was quicker...strange.

As for a turbodiesel at 2am...I admit it, that's another reason I bought my TDI, I always loved hearing that sound of a big Cummins engine spooling up. Now I get to emulate it --end corny statement--

Hope your trip is a great one!

Ah, Durgin Park. Yes, but I did mention Quincy Market and the Faneuil Hall area, which Durgin Park is technically a part of.

Guy, you should also play a few strings of candlepin bowling while you're here or maybe check out how the Mass Ave bidge is measured in "Smoots."

Anyone from outside of 128 is a tourist as far as we're concerned! Part of Route 128 is also I-95. Part of Route 128 South is also I-93 North. Confused yet? We've got plenty more for you when you get here! :)

Albeit I don't drive an oil-burner like you Timbo, but the turbo in my WRX wagon engine makes good spooling audio :)

Here's some content from http://www.masshole.com that I love.

When we say = We mean....

bzah = odd
flahwiz = roses, etc.
hahpahst = 30 minutes after the hour
Hahwahya? = How are you?
khakis = what we staht the cah with
pissa = superb
retahded = silly
shuah = of course
wikkid = extremely
yiz = you, plural


How we'll know you weren't bon heah:

You wear a Harvard sweatshirt.
You cross at a crosswalk.
You ask directions to "Cheers."
You order a grinder and a soda.
You follow soccer.
You eat at Durgin Park.
You pronounce it "Worchester."
You walk the Freedom Trail.
You call it "Copely" Square.
You go to BU.

Getting around:

Boston is a mishmosh of 17th-century cow paths and 19th-century landfill penned in by water. You know, "One if by land, two if by sea." Charlestown? Cahn't get theyah from heah. And which Warren Street do you want? We have three plus three Warren Avenues, three Warren Squares, a Warren Park, and a Warren Place. Pay no attention to the street names. There's no school on School Street, no court on Court street, no dock on Dock Square, no water on Water Street. Back Bay streets are in alphabetical odda. Arlington, Berkeley, Clarendon, Dartmouth. So are South Boston streets: A, B, C, D. If the streets are named after trees (Walnut,Chestnut,Cedar,)you're on Beacon Hill. If they're named after poets, you're in Wellesley. Dot is Dorchester, Rozzie is Roslindale, JP is Jamaica Plain. Readville doesn't exist.


The North-East-South-West thing:

Southie is South Boston. The South End is the South End. The North End is east of the West End. The West End is no more. A guy named Rappaport got rid of it one night. Eastie is East Boston. The East End is Boston Harbor.


About our "cuisine:"

Boston cream pie is a cake.
Frappes have ice cream; milk shakes don't.
Chowdah does not come with tomatoes.
Soda is club soda. Pop is Dad. If it's fizzy and flavored, it's tonic.
When we mean tonic water, we say tonic water.
Scrod is whatever they tell you it is, usually fish.
If you paid more than $6 a pound,you got scrod.
It ain't a water fountain, it's a bubblah.
Brown bread comes in a can. You open both ends, push it out, heat it and eat it with baked beans.
They're hot dogs. Franks were people who lived in France in the ninth century.