Is it better to fly or drive?

Flying is highly recommended due to the 14-hour drive time.

Which airport is closer to downtown?

Midway (MDW) is generally closer to the city center.

Are there direct flights?

Yes, from Newark (EWR) to Chicago (ORD/MDW).

Is Chicago expensive?

It is comparable to other major US cities in terms of cost.

Middletown

Chicago

Flight Driving

Middletown to Chicago

Updated: 28 May 2026

The distance from Middletown to Chicago is approximately 800 miles. Driving takes about 13-14 hours via I-80 West, making it a long two-day trip for most. Flying is the most practical option; you can fly out of Stewart International Airport (SWF) or Newark Liberty (EWR) directly into O'Hare or Midway. If you choose to drive, prepare for significant tolls across Pennsylvania, Ohio, and Indiana. Flying saves significant time and is often comparable in cost when factoring in fuel and lodging.

Total Distance: 1,300 km driving distance; 1,150 km straight-line air distance.

Fastest Way

Flying from Newark (EWR) is the fastest way to reach Chicago.

Cheapest Way

Flying is often cheaper than driving when accounting for gas, tolls, and hotels.

Compare Middletown to Chicago Routes

	Flight Direct	Driving Direct
Duration	2 hours 30 mins	14 hours
Avg Price	$150-$350	$200-$300 in fuel
Operator	United Airlines/American Airlines	Personal Vehicle
Route	EWR to ORD or MDW.	I-80 W through PA, OH, and IN.
Tip	Book flights from Newark for more direct options to Chicago.	Plan for an overnight stop in Cleveland or Toledo.

Travel Tips

Public Transit
Use the 'L' train system; it is the most efficient way to navigate the city.
Weather
Chicago is known as the 'Windy City'; dress in layers, especially in winter.
Dining
Try deep-dish pizza at a local institution like Lou Malnati's or Giordano's.
Airport Transit
Take the Blue Line from O'Hare to downtown for a cheap and fast commute.
Walking
The Chicago Riverwalk is a beautiful path for walking and sightseeing.

Safety Tips

Awareness
Stay in well-populated areas, especially at night.
Public Transit
Keep your belongings close while riding the 'L' trains.
Emergency
Know the location of your hotel and the nearest transit station.
Night Travel
Use rideshare services if traveling late at night in unfamiliar neighborhoods.