Cheap Flights from Chicago (CHI) to Philadelphia (PHL)

You need to fly 665 miles east from Chicago to reach Philadelphia. A journey from the Windy City to the City of Brotherly love will take you just over two hours in the air on a direct flight.

American, US Airways and United Airlines each have more than 40 weekly nonstop flights between Chicago O’Hare (ORD) and Philadelphia International Airport (PHL). Another option is to fly from Chicago Midway (MDW), where Southwest offers a full weekly schedule of direct flights to Philadelphia.

Making your way to Chicago’s airports

Chicago O’Hare is the city’s biggest airport and one of the busiest transit hubs in the world. There’s no getting away from the fact that navigation through the four enormous terminals can feel a little overwhelming, but the layout is good and there’s a fast Automated People Mover to help things along.

To avoid too much stress, we recommend that you get to the airport a full two hours before your flight. One traditionally difficult part of travel (airport parking!) can be totally avoided by using public transportation. The CTA Blue Line train can get you from the Loop to O’Hare in about half an hour. The train runs every 15 minutes, 24/7.

Chicago Midway is the city’s little sister airport, and it’s well-liked by many who appreciate the simple one-terminal layout and the proximity to the city center (it’s just 8 miles away).

Public transit to MDW is straightforward. Just catch the CTA Orange Line. The trip from the Loop to Midway takes about 25 minutes. However, there is a 10-15 minute walk through a tunnel from the airport stop to the terminal, so allow a bit of extra time for that.

Arriving in Philadelphia

History is one of Philly’s great draws. Colonial architecture and important revolutionary sites are everywhere you look, and many of the most popular historical attractions (like Independence Hall and the Liberty Bell Center) are free to the public. If you want to totally immerse yourself in that pivotal time, Valley Forge National Park (about an hour outside the city) is home to George Washington’s headquarters, and is populated by talented reenactors.

Back in the city, don’t miss the great museums. The Franklin Institute Science Museum and the Academy of Natural Sciences will get your brain going, while the Philadelphia Museum of Art holds enough treasures to keep you marveling for weeks.

After all that sightseeing, you’re going to be hungry. The city has a booming culinary scene, but save room for a cheesesteak from a legend like Pat’s King of Steaks!

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