Chicago
Chicago
Train Flight

New Paltz to Chicago

Updated: 28 May 2026

The trip from New Paltz to Chicago covers over 800 miles. The most practical method is to drive to Stewart International Airport (SWF) for a flight or take a train to NYC to catch the Lake Shore Limited. Driving is a long two-day journey across Pennsylvania and Indiana. Chicago is a major hub, making it accessible via multiple transport modes.

Total Distance: 1,300 km driving distance; 1,150 km straight-line air distance.
Fastest Way
Direct flight from Newark (EWR) to O'Hare (ORD).
Cheapest Way
Budget airlines from Newark (EWR) are usually the cheapest.
Compare New Paltz to Chicago Routes
Train
Direct from NYC
Flight
Direct from SWF or EWR
Duration 19 hours 2 hours 30 mins
Avg Price $120 - $300 $150 - $350
Operator Amtrak American Airlines/United
Route Lake Shore Limited from Penn Station to Union Station. Flight from Stewart (SWF) or Newark (EWR) to O'Hare (ORD).
Tip Book a roomette for a comfortable overnight journey. Flying from Newark often provides more direct flight options.
Travel Tips
  • Airport Choice
    Newark (EWR) is easier to reach from New Paltz than JFK or LaGuardia.
  • Train Booking
    Amtrak tickets for the Lake Shore Limited sell out fast; book early.
  • Public Transit
    Use the 'L' train system to get around Chicago cheaply.
  • Weather Prep
    Chicago is known as the Windy City; pack layers regardless of the season.
  • Dining
    Try the deep-dish pizza at local institutions like Lou Malnati's.
Safety Tips
  • General Safety
    Stay in well-populated tourist areas like the Loop and Magnificent Mile.
  • Public Transit
    Keep your belongings secure while riding the 'L' trains.
  • Night Travel
    Avoid walking alone in unfamiliar neighborhoods at night.
  • Emergency Prep
    Keep the number for local taxi services saved in your phone.
People Also Ask
  • How do I get to Newark Airport?
    You can drive or take a shuttle service from New Paltz.
  • Is the train ride scenic?
    Yes, especially the stretch along the Erie Canal and Lake Erie.
  • What is the best way to get around Chicago?
    The CTA 'L' train and bus system is very efficient.
  • Are there direct flights from Stewart?
    Yes, but they are limited; check schedules frequently.
  • How long is the flight?
    Approximately 2.5 hours in the air.
Quick Info
  • From New Paltz, New York, United States
  • To Chicago, Illinois, United States
  • Modes
Best Time to Travel

Summer for festivals or late spring for pleasant walking weather.

Things to Do in Chicago
1
Millennium Park
See the famous Cloud Gate sculpture, also known as 'The Bean'. It is a must-visit photo spot.
2
Art Institute of Chicago
Explore one of the oldest and largest art museums in the country. It houses iconic works.
3
Navy Pier
Enjoy the lakefront with rides, restaurants, and boat tours. It is great for families.
4
Willis Tower
Visit the Skydeck for panoramic views of the city. The glass floor is a thrilling experience.
Tags
New Paltz to Chicago flights to Chicago Amtrak to Chicago travel from NY to Chicago Chicago travel guide Stewart Airport to Chicago train to Chicago Midwest travel New Paltz travel