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Cheap Flights from Pittsburgh International to Chicago

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Compare Pittsburgh International to Chicago flight deals

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Flight deals from Pittsburgh International to Chicago

Looking for a cheap last-minute deal or the best return flight from Pittsburgh International to Chicago? Find the lowest prices on one-way and return tickets right here.
Chicago.R 969 per passenger.Departing Sat, 26 Jul.One-way flight with United.Outbound direct flight with United departs from Pittsburgh International on Sat, 26 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 969, select.
Chicago.R 969 per passenger.Departing Wed, 11 Jun.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pittsburgh International on Wed, 11 Jun, arriving in Chicago Midway.Price includes taxes and charges.From R 969, select.
Chicago.R 1,321 per passenger.Departing Thu, 14 Aug.One-way flight with United.Outbound direct flight with United departs from Pittsburgh International on Thu, 14 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,321, select.
Chicago.R 1,634 per passenger.Departing Fri, 30 May.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Pittsburgh International on Fri, 30 May, arriving in Chicago Midway.Price includes taxes and charges.From R 1,634, select.
Chicago.R 2,400 per passenger.Departing Sat, 31 May.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pittsburgh International on Sat, 31 May, arriving in Chicago Midway.Price includes taxes and charges.From R 2,400, select.
Chicago.R 2,402 per passenger.Departing Tue, 23 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pittsburgh International on Tue, 23 Sep, arriving in Chicago Midway.Price includes taxes and charges.From R 2,402, select.
Chicago.R 2,944 per passenger.Departing Thu, 9 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pittsburgh International on Thu, 9 Oct, arriving in Chicago Midway.Price includes taxes and charges.From R 2,944, select.
Chicago.R 2,951 per passenger.Departing Fri, 21 Nov.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pittsburgh International on Fri, 21 Nov, arriving in Chicago Midway.Price includes taxes and charges.From R 2,951, select.

Find the cheapest month to fly from Pittsburgh International to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Pittsburgh International to Chicago flights are currently cheapest in June.
May
from R 1,634
Jun
from R 969
Jul
from R 969
Aug
from R 1,321
Sep
from R 2,402
Oct
from R 2,944
Nov
from R 2,951
Dec
Find prices
Jan
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Feb
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Mar
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Apr
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Direct flights from Pittsburgh International to Chicago

Alternative Pittsburgh International to Chicago routes

Looking for the cheapest, fastest or easiest route from Pittsburgh International to Chicago? You could fly into the following airports instead.

Pittsburgh to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 969
Cheapest month to flyJune
Average flight time1 hr, 39 mins
Most popular airlineAmerican Airlines
Average flights per week352

Finding cheap flights from Pittsburgh International to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Pittsburgh International to Chicago is R 2,282. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
1 hour and 38 minutes is the average flight time from Pittsburgh International to Chicago.
Alaska Airlines, American Airlines and Qatar Airways fly direct from Pittsburgh International to Chicago.
As of May 2025, there are 486 flights per week flying from Pittsburgh International to Chicago.
The cheapest month to fly from Pittsburgh International to Chicago is usually May 2025.
If you're flying from Pittsburgh International Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from R 2,282.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Pittsburgh International Airport to Chicago on Saturday, 31 May 2025.
Yes – the average flight time is 1 hour and 38 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In May, the average temperature is usually around 13°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, American Airlines offers the cheapest flight tickets to Chicago.

Travelling from Pittsburgh International Airport (PIT) to Chicago: what you need to know

  • The average duration of a direct flight from Pittsburgh International Airport to Chicago is 1 hour 35 minutes.

  • Pittsburgh International Airport is located in Pittsburgh. Based in the UTC-5 timezone, Chicago is one hour behind Pittsburgh.

  • With 70 flights a week between the two airports, Pittsburgh International Airport (PIT) to O'Hare International Airport (ORD) is the busiest route. American Airlines operates the earliest flight at 05:25. If you're eager to make the most of your day before jetting off, the last flight from PIT to ORD is with American Airlines at 20:31.

  • For a stress-free journey, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This will give you enough time to catch your PIT to Chicago flight.

  • Delays at security and check-in are more likely if you're flying during high season, so allow some extra breathing room. A good rule for peak periods? Get there up to four hours ahead for international flights and two hours for domestic departures.

  • You can book a direct Pittsburgh International Airport to Chicago ticket. Begin your trip at PIT and end it at O'Hare International Airport (ORD).

  • Well-known airlines that operate direct flights from Pittsburgh International Airport to Chicago include:

  • To get to PIT from central Pittsburgh, it'll take around 25 minutes by car. It's roughly 21 kilometres from the airport to the city centre.

  • Planning to catch an early flight from Pittsburgh International Airport to Chicago? Avoid the last-minute rush to the airport (and catch some extra z's) by choosing one of these hotels close to PIT:

  • 76.88% of flights taking off from Pittsburgh International Airport reach their destination on time.

  • PIT is located at 1000 Airport Boulevard.

How to find the cheapest flights from Pittsburgh International Airport (PIT) to Chicago

  • The lowest price we've seen for a one-way Pittsburgh International Airport to Chicago flight is R 969. The cheapest price for a return flight is R 2,282. Keep in mind fares can change due to availability at the time of booking.

  • Score cheap flights from PIT to Chicago by booking one month ahead. According to our research, that's the sweet spot for finding a bargain.

  • Organise your trip for May. That's the best month for scoring the biggest deals on Pittsburgh International Airport to Chicago tickets. If you're flexible with your dates, use the 'Whole month' tool to access the cheapest price across each month.

  • There's no need to check back constantly to find out if fares have dropped when you set up a Price Alert. We'll let you know when there's an updated deal for cheap flights from PIT to Chicago.

  • Save money on your flight from Pittsburgh International Airport to Chicago with the help of our filters. Select your ideal times, number of stops and airlines, then sort the results by 'Cheapest' to see the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) to central Chicago takes about 35 minutes to reach by car. The centre is roughly 40 kilometres away.

  • Getting to the centre on public transport will take you around 55 minutes.

  • If you have a late flight from Pittsburgh International Airport to Chicago, few things beat the convenience of staying close to the terminal. Grab your bags from the carousel and then be showered and sleeping soon after at one of these hotels near ORD:

  • Pick up an O'Hare International Airport rental car and discover Chicago and beyond with your own wheels. Routes Car Rentals, Dollar and Budget are leading providers you can book with here.

  • To get the lowest price, book your vehicle from O'Hare International Airport around four weeks ahead of your flight from PIT to Chicago.

  • The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Central Chicago is about 19 kilometres from Chicago Midway International Airport (MDW). After your flight from Pittsburgh International Airport to Chicago has landed and you've made your way to arrivals, expect a drive of about 20 minutes.

  • If you're travelling on public transport, it'll take about 45 minutes.

  • Following your PIT to Chicago flight, tuck yourself in at a hotel near MDW. These are some comfortable accommodation options that'll help you sink into relaxation mode:

  • Forget about inconvenient public transport schedules or waiting forever for a cab. Pick up a Chicago Midway International Airport rental car and let your trip unfold on your terms. Compare offers from Dollar, Hertz and Budget.

  • Avoid potential price surges. Securing your ride four weeks before your arrival at MDW will save you money.

  • Chicago Midway International Airport can be found at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is about 137 kilometres from central Chicago. It'll take you about 1 hour 25 minutes to get to the city centre by car once you've stepped off your flight from Pittsburgh International Airport to Chicago.

  • If you're using public transport, the journey will take you around 4 hours 15 minutes.

  • If you don't want to travel to the centre, find a hotel near RFD. Get comfortable at one of these options after your PIT to Chicago flight:

  • Whether you're after a zippy compact for solo travel or a roomy SUV to transport your group, you'll find the ideal Chicago Rockford International Airport rental car for you. Browse the range of wheels available from providers such as Budget, Alamo and National.

  • Booking a couple of weeks in advance of your flight from Pittsburgh International Airport to Chicago is always a good idea. Along with more affordable prices, you might find it easier to get the make and model you prefer at RFD.

  • Chicago Rockford International Airport's street address is 2 Airport Cir.

Best time to go to Chicago

  • Carefully consider your travel dates before locking in your flight from Pittsburgh International Airport to Chicago. The city comes alive in peak season, but prices are typically higher and attractions can get crowded. Visit Chicago in the low season if you prefer a more relaxed vibe.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Book your Pittsburgh International Airport to Chicago flight ticket then if that's your definition of good weather.

  • Look for cheap tickets from PIT to Chicago in January if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

Explore more of United States

  • You've visited Chicago, now it's time to explore other parts of United States. Travel around 451 kilometres south-east to Columbus to tick off its leading sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, you've got a jam-packed schedule ahead.

  • Indianapolis is another well-known destination in United States and is around 257 kilometres south-east of Chicago. No journey is complete without experiencing The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from Pittsburgh to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.