Chicago to New York road trip

[MyBoysHaveDogsNames]

Hi

I've booked flight to Chicago in early July to see some friends for a few days. We are returning from New York three weeks later.

We will be in Chicago for approx 4 days and will spend about the same in New York so have nearly 2 weeks to fill. We are keen to drive and I definitely want to go to Nashville. Maybe New Orleans and fancy The Keys and Disney. I don't want to cram too much in and be driving too much though.

Grateful for any recommendations!

Maybe Virginia mountains too?

I would consider flying or using Amtrak to Nashville from Chicago then onto New York again by air. If you do drive get some decent scale road maps and using this and the internet work out distances and timings thoroughly. You do not want to be spending your holiday time stuck behind the wheel all the time looking at uninteresting highways.

I would check all terms and conditions re car hire very carefully before committing yourself; some companies do not allow returning a car in another state.

You are proposing far too many places and in too short a period of time. New Orleans is too far for the time you have as is Disney and the Keys; those need to be ideally visited on another occasion and separately.

Chicago-Nashville isn’t that bad of a drive especially if you split it into two days but it’s isn’t a particularly interesting drive either.

Florida keys makes no sense - it’s like driving from Paris to Amsterdam via Moscow.

I’ve driven from Chicago to upstate NY via Toronto and it was one of the best holidays I’ve had - loads of amazing places to visit if you take a more direct route - you don’t need to try and see everything in the US is one trip!

Why not fly down to the Keys from Chicago then drive up to NY?

Have you thought about putting all those places on a map and working out how long the drive will be between them?

That’s a pretty random selection of places.

Chicago-Nashville-New York looks feasible on google maps, and would pick up Virginia and Washington DC en route to NYC.

Or have a look at internal flights (Skyscanner is helpful) and Amtrak.

Thanks All. I realise that is a lot of places and wasn't intending on trying to fit them all in, but get some ideas as to what's the best plan.

ArfArfBarf. The original plan was Canada so your trip sounds interesting. Would it be fun for a 10 and 13 year old? I'm keen to actually have a holiday and not be stuck in the car too much and also would rather s scenic route.

We went with younger kids but I’d have thought so, especially Toronto.

Hi, I drive round the states quite a lot, the distances you propose are doable but you won't see very much! I would suggest a few routes :
Drive via Detroit, the Henry Ford museum is quite good and I like Detroit but it is definitely run down, to Canada, dip down to to Niagara falls, a couple of days in Toronto, then on to Montreal ( I will warn you though, the drive Toronto to Montreal is soooo boring unless you are in a snowstorm in which case it's terrifying!) . Then drive south which will be beautiful, via vermont, Ben and Jerrys factory, Stowe ( see the Von trapps!) there are a few riding ranches in that part of the world. Then into NYC. Two: fly from Chicago midway (which is much closer to downtown Chicago) to Nashville. Then do a Nashville appalachia trail through the blue mountains WV. It is stunning. It will be hot in july! We stayed in a tiny house in Maryland which was gorgeous, the deer outside the cabin in the morning were lovely.

I would either fly from Chicago to the Keys as pp suggested than drive up the i95 over a week or so stopping off a Savannah, Charleston, maybe the Outer Banks

Or

Drive from Chicago via Louisville to Nashville the either continue South to New Orleans if you desperately want to go there or just head to NY from there via the Smoky Mountains. You can always go to Dollywood instead of Disney 😉

You need to think carefully about how much driving you want to do. I will happily drive for many hours in the States to get where I want to go but obviously not every day!

Have a look at Roadtrippers.com, you can put various routes in, work out times and get an estimate of fuel costs.

I think three weeks is a bit of a push for seeing Chicago, NY and driving from the Keys to NYC even if you fly down there in the first place.
Obviously it’s possible but you’d be driving past so much cool stuff that you wouldn’t have time to stop at.