New York to Chicago, and back

Hello everyone. I'm traveling to USA in March, and I planning do it this way:
- New York 10 days
- Road trip to Chicago 2 days
- Chicago 5 days
- Milwaukee 5 days
- Road trip to New York 2 days

The trip will be with my wife and my daugther ( 2 years old).
I'm thinking rent a car un NY travel to Chicago, and return it in Chicago.
And then, after 10 days, rent another car to go back to NY.

Traveling with a baby, i'm thinking in make the trip in 2 days, sleeping in the middle.
Maybe some nice place to stop and sleep, and I need some opinions here. Is our first travel to USA and I don't know if is safe sleep in some route hotel.
I like to know information about the route too.

Thank you very much.

Welcome to the RTA Forum!

The biggest problem with your plan is that it's likely going to be very expensive, because of the car rentals. One way rentals typically include a surcharge that can cost hundreds of dollars. If you rent a car in NY drop in in Chicago, then pick a car up again in Chicago to drive back to New York, you could easily be looking at an extra $1000 for car rental fees!

I will also say that while Chicago is a city you can easily get around without a car - Milwaukee is very much a car city, and if you don't have a rental, you'll pretty much have to rely on taxi's or uber, if you want to do more than just see the immediate downtown area.

NYC to Chicago is 800 miles, so 2 days each way would only give you a very limited chance to stop and explore. I think you might be better off taking the train from NYC to Chicago and from Chicago to Milwaukee, and possibly renting a car for your days in Milwaukee.

Thanks Michael.
Is true, in 2 days I can't stop and explore. But that is not the idea. The only stop I plan to do is for rest, and sleep.
In Milwaukee I have a friend with car, so that is not a problem either.
Related with the car cost, I'm seeing in Hertz, picking up the car in NY, and returning the car in Chicago, in the Hertz website give me this price: $253.18
Will it be correct?

Sleeping in hotels along the Interstate highways is very safe. That's what they are there for, catering to travelers. There is no need to go into cities to find hotels, they are conveniently located right near the exits.

Note that the fastest way to Chicago from NYC involves toll roads. I would take I-80 (free except for the bridge between NJ and PA) to OH, then follow the Ohio Turnpike and Indiana Toll Road to Chicago. I would probably look at the area around Toledo OH for an overnight, there are several hotels at Exit 59. This would get you into Chicago before evening rush hour.

To find the best price on car rental, we have a search function here.

Thanks, I'm seeing that is almost the same cost, rent a car one way (returning the car in Chicago) for 2 days, that renting it 10 days and picking and dropping of in NY. So ...

Are you sure that you are looking at the total costs, including taxes and fees?

When I searched, I was finding rates of about $400-500 for a two day, one way car rental from NYC to v Chicago, after looking at total costs.

Keep in mind, if you have to rent from airport locations, you'll probably want to go from Newark to Midway, otherwise you'll be on the wrong sides of NYC and Chicago, and will have to drive across traffic in both cities.

I still think that taking the train, or maybe even flying, would be quite a bit cheaper and easier based on the goals of your trip.