Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

Cheap Flight Deals From Pittsburgh (PIT) to Chicago (CHI) Starting at $40

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This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Airfares from $40 One Way, $100 Round Trip from Pittsburgh to Chicago

Prices starting at $100 for return flights and $40 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Chicago economy flight packages

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More About Flying To Chicago from Pittsburgh

Route Information for Flights from Pittsburgh to Chicago

Origin Airport IATA Code PIT
Destination Airport IATA Code CHI
Distance 410 mi
Direct Flight Airlines American Airlines, Qatar Airways, JAL, Air Canada, Aer Lingus, Copa Airlines, Air New Zealand, United Airlines, Alaska Airlines, Qantas, Southwest Airlines, Royal Jordanian, SAS, ANA, Lufthansa, Gulf Air, British Airways
Earliest Flight Arrival 10:31AM UTC
Latest Flight Arrival 1:14AM UTC

Book Your Flight from Pittsburgh to Chicago

Pittsburgh International Airport

The Pittsburgh International Airport is located just twenty miles west of downtown on Airport Boulevard. Twelve airlines service the airport, including Midwest, Northwest, JetBlue, Delta, Continental and American Airlines. Orbitz.com can locate both domestic and international flights from Pittsburgh for the budget traveler.

Parking at the Airport

Short-term, long-term and extended parking lots are available at the airport. Rates are charged by the hour or by the day. Valet parking is also available for an additional fee. The short-term lot is perfect for people who are dropping off or picking up travelers. Long-term lots are ideal for travelers going on short vacations, and the extended lots are most economical for long business trips. Shuttle services are available to and from the parking lots.

Transportation to the Airport

Getting to the airport can often be a challenge. Orbitz.com can help you select a car rental service if you want to rent a car during your stay. Most hotels offer their guests free shuttle service to and from the airport. Limos are available for rent, and fees are usually charged by the hour. Other transportation options include metered taxi services and the city bus system, which charges a flat rate.

Pittsburgh International Airport Restaurants

Travelers can enjoy a meal or a snack in the airport terminals before they board their plane. Restaurant choices include McDonald's, which offers a variety of breakfast items and coffee, and Mayorga Coffee Roasters, which offers a selection of gourmet coffees and pastries. Orbitz.com can help with dining options while providing low-fare flights from Pittsburgh for people traveling on a budget.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

Flights from Pittsburgh to Chicago - Frequently Asked Questions

Am I able to catch a flight from Pittsburgh to Chicago now?

If you're worried about travel restrictions and quarantine requirements when flying from Pittsburgh to Chicago, check out our Covid-19 Travel Advisor.

Are there non-stop flights from Pittsburgh to Chicago?

There most certainly are, which is terrific news if you're not a big fan of swapping planes en route. American Airlines and United Airlines offer direct flights from Pittsburgh, PA Airport (PIT-Pittsburgh Intl.) to Chicago, IL Airport (ORD-O'Hare Intl.).

What is the shortest flight from Pittsburgh to Chicago?

Keep that movie marathon for some other time, because the journey from Pittsburgh Intl. Airport (PIT) to Midway Intl. Airport (MDW) can be as quick as 2 hours and 17 minutes.

What airlines fly from Pittsburgh to Chicago most frequently?

There are two airlines offering frequent flights from Pittsburgh Intl. Airport (PIT) to O'Hare Airport, including American Airlines (AA). The preferred choice of many travelers, it operates 156 flights on this route each month. If you want to broaden your options, check out the cost of tickets with United Airlines (UA), which offers 117 flights from Pittsburgh to Chicago every month.

If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?

We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to Chicago with flexible change policies?

In most cases you'll have the option to reschedule your flight to Chicago without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.

What is the cheapest day of the week to fly?

Consider flying out early in the week to save on your airfare. Orbitz data from 2020 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.

What is the cheapest month to fly?

We won't keep you guessing, according to Orbitz data the cheapest month to fly is August. Perfect for those who need a weekend getaway, or just a break from it all before the weather changes. Be aware that the most expensive time to fly is the height of summer, with ticket prices peaking in the month of June.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2020 saved up to 45% on their airfares. Get mixing and matching today!

*According to flight demand on Orbitz.com from January to December 2020. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.