Is there a direct flight?

Yes, there are direct flights from PVD to Chicago.

Which airport is better?

Midway is closer to downtown, while O'Hare has more flight options.

How do I get to downtown?

The CTA 'L' train is the most efficient way from both airports.

Is Chicago expensive?

It can be, but there are many free attractions like the parks and museums.

What is the best time to visit?

Summer offers the best weather for lakefront activities.

Wakefield

Chicago

Flight

Wakefield to Chicago

Updated: 28 May 2026

The distance from Wakefield to Chicago is approximately 1,000 miles. The most practical way to travel is by flying from T.F. Green Airport (PVD) to either O'Hare (ORD) or Midway (MDW). The flight takes about 2.5 hours, with total travel time around 5 hours including airport transit. Driving is possible but takes over 16 hours, making it less practical for most travelers. This route connects the Atlantic coast to the Midwest's largest city.

Total Distance: 1,600 km driving, 1,400 km air distance.

Fastest Way

Direct flight from PVD to ORD is the fastest, taking roughly 2.5 hours in the air.

Cheapest Way

Flying from PVD to MDW is usually the most cost-effective option.

Compare Wakefield to Chicago Routes

Flight

Direct

Duration

5 hours

Avg Price

$150 - $400

Operator

United Airlines

Route

PVD to ORD.

Book a flight to Midway (MDW) if you want easier access to the downtown area via the Orange Line.

Travel Tips

Airport Transit
Use the 'L' train system to get from O'Hare or Midway to downtown Chicago.
Weather
Chicago weather changes quickly; pack layers regardless of the season.
Dining
You must try deep-dish pizza at one of the local iconic pizzerias.
Booking
Use flight comparison sites to find the best deals from PVD.
Walking
Chicago is very walkable, especially in the Loop and along the river.

Safety Tips

Stay Aware
Like any major city, stay alert in crowded areas and on public transit.
Stick to Main Streets
When walking at night, stick to well-lit, busy streets.
Emergency
Keep your phone charged and have a backup power bank.
Public Transit
The 'L' is safe, but be mindful of your belongings during rush hour.