Driving from Chicago to New York City (and the other way around) sounds like the ultimate American road trip — two iconic cities, your best playlists, and maybe a few pit stops along the way. But the fantasy fades fast when every toll booth feels like a personal attack on your bank account. No matter how cleverly you plan your road trip (even with AI’s help) or how careful you are about gas mileage, this route is basically a pay-to-drive experience. Tolls alone can cost up to $143.63, as of this writing — that’s about 17 cents for every single mile. And if you’re driving a truck? You’re looking at a jaw-dropping $440 just to hit the road.
It’s not just your bank account taking a hit if you opt for a road trip between the Windy City and the Big Apple. The route is roughly a 13-hour marathon — longer if you hit some traffic or decide to stop for food or sleep. Splitting the trip into two or more days and crashing at a roadside motel? While that’s convenient, it only adds even more to your running tab.
So, what’s a road-weary traveler to do? If you value your time and money, flying might be the smarter move. But if you’re still craving scenic views for the trip, you can always do what most Americans want to do — hop on a train and let someone else deal with the driving. It’s also what the locals recommend, anyway.
Consider flying or taking the train instead
Sure, you could avoid some tolls by taking the long way — but unless you’ve got time to burn and a love for uninspiring highways, it’s probably not worth it. Not only do the alternative roads not make it on the list of the most stunning routes in the U.S., they’ll also cost you precious hours of your life you’ll never get back. Chicago locals on Reddit sure aren’t sugarcoating it. “The drive sucks, it’s long and boring. Nothing but farms from NWI to Cleveland, then like nothing for all of Pennsylvania until NYC. Flights are cheap/plentiful/and relatively quick,” u/jabbs72 advised. “However, another option is Amtrak? That might be a fun experience.”
Another user corroborated this but suggested padding the journey with detours to make it worthwhile, especially if you’re doing the New York to Chicago route. “Much of the area between NYC and Chicago is not destination worthy; however, you can certainly make a trip out of it. You go through upstate NY and stop at Mohonk Preserve, Kaaterskill Falls, Watkins Glen, Letchworth State Park, Niagara Falls (Canadian Side), Presque Isle State Park, then down to Pittsburgh,” u/kemba_sitter noted. If you’re considering taking the train, however, the Amtrak Lake Shore Limited 49 may be your best bet. As the name implies, it hugs some of the most picturesque lake shorelines, including the Mohawk River, Erie Canal, and Lake Michigan. Yes, it takes 19 hours — but at least you’ll have views and legroom.
Or you can just skip all that and fly. After all, flights between Chicago and NYC often dip below $50 on budget airlines like Spirit, or come in at around $85 with Delta or United. It’s much faster, cheaper, and doesn’t come with spending an eternity on 500 miles of farmland.
