£103 Cheap Flights from Pittsburgh (PIT) to Chicago (ORD)

You can find one-way and return flights from Pittsburgh, PA (PIT) to Chicago, IL (ORD) with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when PIT to ORD ticket fares go up or down.

If you're looking for the cheapest time to fly from Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (ORD-O'Hare Intl.), September is typically your best bet. You can expect average return flight prices around £164 during this month. Other budget-friendly months for this route include August and October.

Enter PIT to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.

Sun Country Airlines offers one of the cheapest connecting return flights on this route, starting from £192. United is one of the cheapest airlines offering nonstop return flights from Pittsburgh, PA (PIT-Pittsburgh Intl.) to Chicago, IL (ORD-O'Hare Intl.), with tickets starting from around £234 for flights that can be booked for departure within the next year. These prices are per adult, for economy/coach class. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.

To find a cheap flight from Pittsburgh, PA (PIT) to Chicago, IL (ORD), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.

The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.

Sort flights by "Departure (earliest)" on Expedia to find the earliest flight from Pittsburgh, PA (PIT) to Chicago, IL (ORD). To compare more early flights, use the "Early Morning" and "Morning" filters in your search.

Direct flights from PIT to ORD usually take about 2 hours, traveling roughly 660 kilometers. If you opt for a connecting flight, expect to add around 3 hours 50 minutes to your journey. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.

Select the "Business class" and "First class" filters when looking for Pittsburgh, PA (PIT) to Chicago, IL (ORD) flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.

It's easy to earn miles on a Pittsburgh, PA (PIT) to Chicago, IL (ORD) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Typically, booking a last minute flight from Pittsburgh, PA (PIT) to Chicago, IL (ORD) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.

Securing a Pittsburgh, PA (PIT) to Chicago, IL (ORD) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.

If you booked your Pittsburgh, PA (PIT) to Chicago, IL (ORD) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.