Road Trips

New York to Chicago on Public Transport: Is it worth it?

chicago road trip
Written by Town & Tourist

New York City and Chicago have always had a rivalry. Some say New York is just Bigger & Badder, while others point out that the Chicago people are just more friendly & laid back!

Me & my girlfriend were having this same dispute…so to settle any arguments we decided to take a road trip be New York City & Chicago and of course head past some great cities on the way!

Then the debate came, shall we rent a car and take a traditional road trip or check out the public transport options?! Here is what we discovered.

How far is Chicago from New York?

There are 795 miles between New York & Chicago. Driving direct it would take you 13hr, 7 mins...but where is the fun in that!

Road Trips are about the journey and the amazing places to stop along the way!

Is it cheaper to fly or drive?

It’s not always cheaper to drive, but in many cases it be less than half the cost of flying to drive and alot more fun! 

New York to Chicago Road Trip Map

Dive into our interactive map below! 

User Guide:  Simply Click the +/- buttons to zoom in & out,  Click on a favourite attraction, and click directions symbol to give you the driving or walking route directly there!

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New York to Chicago Public Transport Comparison

Best Transport Methods between New York and Chicago
Transport Duration(Hr/mins) Cost($) Notes
Car/RV 13hr 8 mins 64 gallons. $100-$140 (depending upon mpg/route) An independent road trip where you can stop whenever you like!
Train 19hr  10 mins $95-$140

Lake Shore Limited/Cardinal  (Once Daily)

Bus 17hr 55mins $50-$120 Greyhound USA
Flight 5hr 4 mins $86-$406 American Airlines/Delta (Daily Flights)


Which is the best transport option from New York to Chicago?

From the Table above we evaluated which is the best transport option between New York and Chicago. Now this all depends on personal preference.

However, from the data it’s clear that the Bus is the cheapest method of transport between New York and Chicago.

So if your a real Backpacker and don’t want to rent a car then this is a great option for you. However, there are a couple of negatives against taking the Bus.

There is not as much comfort and space as a train and you can’t stop off as many times as you could in a car.

Train Between New York & Chicago:

The Amtrak train takes you up through Connecticut, Massachusetts before traveling along the coast of New York state.

This is a really Scenic train ride and an experience in itself. For more info see: Ultimate Guide to the USA by Amtrak Trains

Maple leaf express train usa niagara falls

Maple leaf express train heads via the Incredible niagara falls. Source:

Road Trip Between New York & Chicago:

Due to the amount of great cities along the way and the pure independence we decided on a classic all american Road Trip between New York & Chicago.

Enroute we stopped at some amazing cities and destinations!  See our Itinerary below:

  1. New York City 
  2. Philadelphia
  3. Baltimore
  4. Washington D.C
  5. Pittsburg
  6. Cleveland
  7. Detroit
  8. Chicago

For our Full Guide check out: New York City to Chicago Road Trip: Itinerary/Map

Why you should Travel to Chicago?

The Windy City, Chicago, Illinois is a large metropolis on the Scenic Lake Michigan. The Skyline is punctuated with vast skyscrapers, such as the Willis Tower (Former Sears Tower) and the Legendary John Hancock Center at over 1,451ft high.

Chicago is also known for Chicago style pizza (Deep dish) , and Chicago hot dogs in addition to Jazz and of course the Notorious 1920s gangster Al Capone.

chicago road trip


5 Unique Things to do in Chicago: 

1. Millennium Park – FREE! 

Millennium Park  is not just a public park, its a true expression of the Chicago experience! It is the largest public space inside the 319 acres of Chicagos Grant Park, located downtown. This area includes, gardens, sculptures and attractions.

Cloud Gate (The “Bean”)

A Large public sculpture weighing in at over 110tones and is over 66 feet long and 33 feet high. This is an astonishing sculpture to see and was designed by British Artist Anish Kapoor.

Cloudgate Chicago Bean

Cloudgate Chicago Bean

Crown Fountain: 

Crown Fountain was designed by Spanish artist Jaume Plensa the fountain is made up of two 50 foot glass block towers which of display rotating images of over 1000 Chicago residents.

The fountain fires water out of the giant mouth and is really popular with kids during the summer months.

Other highlights at Millennium Park include, Lure Garden and Maggie Daley Park. A large 20 acre adventure park which includes rock climbing, slides and mirror walks.

Crown Fountain Chicago

Crown Fountain Chicago

Where is it?

201 E Randolph St, Chicago, IL 60602, United States

2. Willis Tower (“Sears Tower”) 

The Willis Tower is a 110-story, 1,450-foot skyscraper in Chicago. When it was completed in 1973, it surpassed the World Trade Center in New York to become the tallest building in the world!

chicago-view from willis tower

chicago-view from willis tower

3. Green Mill Lounge – Can you spot Al Capone?? 

Head back to the 1940s at Chicagos Green Mill Lounge. Here you can find local Jazz Musicians, poets and was once a hangout for the Notorious Gangster Al Capone.

Green Mill Lounge Chicago Al Capones hangout

Green Mill Lounge Chicago Al Capones hangout

4. Relax at the Lakefront Promenade 

As Lake Michigan spans across the entire length of Chicago, you should really take advantage of these glistening waters! Head down to the The Lakefront Trail where you will find 18 miles of biking & walking with scenic lakefront views.

Best Summer Spot:

Beach? If you fancy a beach head to Oak Street Beach, which is on North Lake Shore Drive.

This is a hidden gem popular with the locals during the summer months. Relax on the sands, overlooking glistening lake Michigan, while admiring the Skyscrapers in the distance!

5. Navy Pier

Navy Pier is a 3,300-foot-long pier on the shoreline of Lake Michigan. Here you will find many fairground rides & attractions including a 360 Chicago, (A Premiere observation deck), Centennial Wheel (Observation Wheel)  Museum of Contemporary Art, the Childrens Museum, River Cruises and many more!

Navy Pier Chicago

Navy Pier Chicago

How much does it cost? 

It is FREE to enter Navy Pier, each attractions or  show has it’s own admission price.

Where to Stay in Chicago?

For a list of our recommended Hotels & latest deals, check out this link HERE. 

Road Trip Tips:

How to get the best car rental Deals?

Check out: Ultimate Car Rental Travel Hacks!

car rental travel hacks

Renting a Car is the perfect way to travel the USA!

Would you like to know the 3 secrets to get discounted hotel deals?

Check out: How to find the Best Hotel Deals??

About the author

Town & Tourist

A travel resource guide that has been carefully crafted and curated by travel bloggers to help you find the best places to travel to in the USA.