$104 Cheap Flights from Pittsburgh (PIT) to Chicago (ORD)

Pittsburgh (PIT) to Chicago (ORD) at a glance

Travel conveniently from Pittsburgh International Airport (PIT) to O'Hare International Airport (ORD) with a range of airlines servicing this domestic short-haul route. Whether you prefer full-service or low-cost carriers, you can explore options that align with your budget and schedule. Discover the latest deals on flights from Pittsburgh to Chicago as you plan your visit to the city’s iconic attractions and neighborhoods. Your next flight to Chicago awaits!

• Fastest flight duration: around 1h 45m non-stop
• Route distance: roughly 400 miles (645 km)
• Flights per week: around 35+ flights with multiple daily departures on average
• Typical fares (one-way): economy tickets often range from $45–$335, depending on seasonality and how far ahead you book

Flights from Pittsburgh International Airport (PIT) to O'Hare International Airport (ORD)

Based on recent traveler bookings, here are the top airlines flying from Pittsburgh to Chicago, popular for both non-stop and one-stop options. Common layover spots include Logan International Airport (BOS) with a layover of about 3 hours and 30 minutes, John F. Kennedy International Airport (JFK) at around 2 hours and 15 minutes, and Orlando International Airport (MCO) with a 1 hour and 15-minute layover. These choices offer you the flexibility to combine price, travel time, and cabin class to create your ideal itinerary.

• United: As a full-service airline, United provides both non-stop and one-stop options, with one-way ticket prices generally falling between $45 and $345. This carrier represents around 53% of the departures on this route, with a standard non-stop flight taking approximately 1 hour and 45 minutes.
• American Airlines: Another full-service option, American Airlines offers non-stop and one-stop flights, with one-way fares usually ranging from $45 to $360. It accounts for roughly 44% of departures on this route, featuring a typical non-stop flight duration of 1 hour and 45 minutes.
• JetBlue Airways: This low-cost carrier provides one-stop services, with one-way fares typically between $95 and $195. JetBlue comprises about 1% of departures on this route, with an in-flight time of 4 hours and 30 minutes and an overall journey time of approximately 6 hours and 30 minutes, including layover.
• Frontier Airlines: As a budget airline, Frontier offers one-stop services, with one-way fares generally ranging from $85 to $185. Frontier contributes to around 1% of the departures on this route, featuring an in-flight duration of 4 hours and 30 minutes and a total travel time of about 6 hours and 30 minutes, including layover.
• Delta: Delta operates as a full-service airline providing one-stop service, with one-way fares typically between $100 and $360. It represents about 1% of departures on this route, with an in-flight time of 4 hours and 30 minutes, and a complete journey duration of roughly 6 hours and 30 minutes, including layover.

Travelers flying from Pittsburgh to Chicago have the option to upgrade to first class with either United or American Airlines for a more luxurious journey.

Best time to fly from Pittsburgh (PIT) to Chicago (ORD)

The most popular months for travelers flying from Pittsburgh to Chicago are March, April, and August, when peak temperatures in Chicago reach up to 73°F in August. If you prefer quieter travel, consider December, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 33.1°F. For better deals, August usually offers the lowest average one-way fare around $137. Flight availability peaks in October, with approximately 48 flights per week, making it easier to find convenient departure times. January has the fewest flights, with approximately 27 flights per week.

• Cheapest time to fly: August usually offers good deals with average one-way fare around $137, roughly 23% cheaper than the yearly average.
• More budget-friendly months to fly: October and September typically offer average one-way fares of around $149.
• Most flight options: October has the highest number of flights from Pittsburgh to Chicago, with approximately 48 flights per week, giving you more flexibility in scheduling your trip.

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

Alternative route from Pittsburgh (PIT) to Chicago (ORD)

• Pittsburgh to Chicago (PIT-MDW): Midway International Airport (MDW) is located approximately 16 miles from O'Hare International Airport (ORD). One-way economy ticket prices for this journey generally fall between $40 and $360, varying with the time of year and how early you book. Travelers can choose from both non-stop and one-stop flight options on this route. Leading airlines providing service here include low-cost carrier Southwest Airlines and Delta. Additionally, first-class service is offered on this route.

How to find the best prices for flights from Pittsburgh (PIT) to Chicago (ORD)

Getting some of the best deals on flights from Pittsburgh to Chicago is all about timing and flexibility. Here are some key tips to help you save:

1. Best times to book and fly: cheaper fares are usually available when booking 2-8 weeks in advance, which aligns with when most travelers make their reservations. Morning departures, between 5 AM and 12 PM, often feature lower prices and are the most popular flight times. Additionally, flying on Wednesday tends to be cheaper, while Friday remains the busiest travel day.
2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at O'Hare International Airport from Pittsburgh International Airport

Chicago welcomes travelers from Pittsburgh with a range of transport options based on price, convenience, and proximity. Here's how to reach Chicago efficiently:

• Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
• Car rental: Renting a car from O'Hare International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at O'Hare International Airport on Expedia.
• Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
• Public transportation: From O'Hare International Airport, O'Hare Station, a metro station, is located about 0.1 miles away on foot, while Rosemont Station, a train station, is situated approximately 2.2 miles from the airport by car.

Pittsburgh to Chicago Flights

The cheapest times to fly from Pittsburgh to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Pittsburgh to Chicago are during the month of October. You can find some of the cheapest flights from Pittsburgh to Chicago with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Pittsburgh to Chicago

Sunday is one of the best days to book for cheap flights from Pittsburgh to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Pittsburgh to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Pittsburgh to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $104 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Pittsburgh to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Pittsburgh to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.