Is it better to fly or take the train to Chicago?

Flying is much faster, but the train offers a unique, scenic experience.

How do I get from O'Hare to downtown?

The Blue Line train is the most efficient way to reach the city center.

Are there direct flights from JFK to Chicago?

Yes, multiple airlines offer daily non-stop flights.

What is the best time to visit Chicago?

Late spring and summer offer the best weather for outdoor activities.

Do I need a car in Chicago?

No, the public transit system is excellent and covers the entire city.

Massapequa

Chicago

Train Flight

Massapequa to Chicago

Updated: 28 May 2026

The distance from Massapequa to Chicago is roughly 800 miles. The most practical way to travel is by flying from JFK or LaGuardia Airport to O'Hare or Midway. Alternatively, you can take the LIRR to Penn Station and board the Amtrak Lake Shore Limited for a scenic, overnight train journey. Driving is a long-haul trip taking approximately 13 to 15 hours via I-80 West. This route takes you from the Atlantic coast to the shores of Lake Michigan.

Total Distance: 1,250 km driving, 1,150 km air distance.

Fastest Way

Flying is the fastest, taking about 2.5 hours in the air plus airport transit time.

Cheapest Way

Flying is often the cheapest if booked well in advance, compared to the cost of a sleeper train.

Compare Massapequa to Chicago Routes

	Train Direct	Flight Direct
Duration	19 hours	2 hours 30 mins
Avg Price	$120-$300	$150-$400
Operator	Amtrak Lake Shore Limited	United Airlines
Route	Penn Station to Union Station Chicago.	JFK/LGA to ORD/MDW.
Tip	Consider a sleeper car for the overnight portion of the trip.	Book flights early to secure non-stop routes.

Travel Tips

Airport Transit
Use the 'L' train Blue Line from O'Hare to reach downtown Chicago quickly.
Weather
Chicago is known as the Windy City; dress in layers regardless of the season.
Pizza
Try the famous Chicago-style deep-dish pizza at a local institution like Lou Malnati's.
Walking
The downtown area is very walkable, but use the 'L' for longer distances.
Booking
Use the Ventra app for all public transportation in Chicago.

Safety Tips

Urban Awareness
Stick to well-populated areas in the Loop and River North.
Public Transit
The 'L' is safe, but be mindful of your belongings during peak hours.
Night Travel
Use ride-sharing apps if traveling late at night in unfamiliar areas.
Emergency
Dial 911 for any emergency situations.