Cheap Flights from Pittsburgh International (PIT) to Chicago (CHI)

To get from Pittsburgh to Chicago, you need to travel 410 miles northwest. The journey shouldn’t take more than an hour and a half in the air, if you’re flying direct.

American and United are your go-to airlines for nonstop flights from Pittsburgh International Airport (PIT) to Chicago O’Hare (ORD). For anyone who prefers to fly into Chicago’s smaller airport, Midway (MDW), Southwest offers multiple daily direct flights on their PIT - MDW route.

Making your way to Pittsburgh International Airport

The airport has one main terminal building, which consists of a large ticketing, baggage and security hall connected to a central Skymall building with four radiating concourses. A rapid people mover provides transport from the ticketing hall to the Skymall. There’s free wifi throughout the terminal, and the airport’s website helpfully lists the current security line wait times and various parking lot capacities.

If you’re driving, there’s a range of parking to choose from, costing between $8 and $24 per day. A taxi from downtown generally costs about $35, or $50 in rush hour traffic. You can also take public transportation to PIT: the 28X Airport Flyer runs approximately every 30 minutes from 5:30 am until 12 am, and tickets cost $3.75, and exact change is required.

Arriving in Chicago

Although there are skyscrapers all over the world, there’s something about Chicago’s buildings which keeps everyone craning their necks for a better view. Some of the country’s most beautiful architecture stands tall on the streets of the Windy City, including the magnificent Willis Tower. If you have a stomach for heights, you can travel the 103 floors to the building’s Skydeck.

If you’d rather admire things from below, hop on the Chicago Architecture Foundation River Cruise. Then, if the weather is great, head over to Grant Park, where acres of grass, flowers, and elegant walkways surround the famous Buckingham Fountain. This centerpiece is one of the world’s largest fountains, and it puts on marvelous 20-minute choreographed displays every hour between 9am and 10:35pm. If the weather turns rotten, don’t worry. Just duck into one of the park’s world-class indoor attractions, which include the Field Museum, the Shedd Aquarium, and the Art Institute of Chicago.

And of course, while you’re in the neighborhood, you might as well indulge your tastebuds with some of the city’s signature eats: deep dish pizza or red-hot hot dogs. Debates rage across households (and the internet) about where you’ll find the best specimens of each, so we’ll leave that decision up to you.

Skyscanner offers a fast, easy, and totally free way to find the cheapest flights from Pittsburgh to Chicago. Our airfare comparison service digs through the internet to bring you the best deals from every major airline.