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Cheap Flights from Chicago to Pittsburgh

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RatePunk searches hundreds of travel sites at once for deals on flights to Pittsburgh

Prices updated 24 days ago

486,190 searches this week

171 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)

Today’s best flight deals from Chicago to Pittsburgh

Explore current cheapest deals departing from Chicago to Pittsburgh

Round trip

Sort by: Cheapest

July 1 - July 7

Cheapest

ORD - Pittsburgh

$162

$137

Round trip

July 4 - July 8

Cheapest

MDW - Pittsburgh

$426

$137

Round trip

July 1 - July 8

Cheapest

ORD - Pittsburgh

$162

$137

Round trip

July 14 - July 15

Cheapest

MDW - Pittsburgh

$408

$137

Round trip

July 14 - July 21

Cheapest

MDW - Pittsburgh

$394

$137

Round trip

August 4 - August 11

MDW - Pittsburgh

$162

$138

Round trip

July 1 - July 4

Best

MDW - Pittsburgh

$658

$157

Round trip

June 30 - July 1

Earliest

MDW - Pittsburgh

$347

$157

Round trip

June 30 - July 3

Earliest

MDW - Pittsburgh

$350

$157

Round trip

June 30 - July 4

Earliest

MDW - Pittsburgh

$349

$157

Round trip

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Route Intelligence — 486,190 Searches this Week

Insights for flights from Chicago to Pittsburgh

For travelers looking for cheap flights from Chicago to Pittsburgh, the cheapest month to fly is typically May, with a median fare of $142. Other cost-effective options include September and November, both showing a median fare of $207. These months present the most favorable pricing for this route.

Fares for flights from Chicago to Pittsburgh typically range from $296–$940, with a median of $549. Right now, current fares are below the typical level for this route. Only 1% of recent fares were classified as a good price, indicating that finding exceptionally low prices can be challenging, though new deals show up several times a week.

Most itineraries for this route connect at least once, with only 25.8% of recent fares being direct flights from Chicago to Pittsburgh. For connecting itineraries, the typical number of connections is 4. This suggests that travelers should anticipate layovers when planning their journey.

A typical journey from Chicago to Pittsburgh takes approximately 25h 45m, including connections. This duration accounts for both direct and connecting flights, reflecting the overall travel time you can expect for this route.

The distance between Chicago and Pittsburgh is 662 kilometers, classifying this as a short-haul route. This relatively short distance typically means quicker travel times, though the prevalence of connecting flights on this route can extend the overall journey.

How much is a round trip from Chicago to Pittsburgh

Regular price: $128 - $309

Prices are currently within the regular range for flights from Chicago to Pittsburgh.

The regular price range for this route is between $128 and $309. The current lowest deal is $137 with American Airlines. This deal is for travel from July 1 to July 7.

now $137

Low $128

High $309

The cheapest time to fly from Chicago to Pittsburgh

The cheapest month to fly from Chicago to Pittsburgh is May, with a median price of $142. The most expensive month is March, with a median price of $863. Prices are generally lower from January to December.

May

Cheapest

Flights from $142

March

Most Expensive

Flights from $863

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Pittsburgh

Southwest Airlines

Last-minute flights going from Chicago to Pittsburgh

Mon, Jun 29

⌛ Last-Minute

MDW - Pittsburgh

Chicago (MDW) - Pittsburgh (PIT)

Deutsche Luft Hansa

$364

$337

One-way

Tue, Jun 30

⌛ Last-Minute

MDW - Pittsburgh

Chicago (MDW) - Pittsburgh (PIT)

$347

$157

One-way

Tue, Jun 30

⌛ Last-Minute

MDW - Pittsburgh

Chicago (MDW) - Pittsburgh (PIT)

$350

$157

One-way

Tue, Jun 30

⌛ Last-Minute

MDW - Pittsburgh

Chicago (MDW) - Pittsburgh (PIT)

$349

$157

One-way

Wed, Jul 1

⌛ Last-Minute

ORD - Pittsburgh

Chicago (ORD) - Pittsburgh (PIT)

American Airlines

$162

$137

One-way

Wed, Jul 1

⌛ Last-Minute

ORD - Pittsburgh

Chicago (ORD) - Pittsburgh (PIT)

American Airlines

$162

$137

One-way

Biggest price drops on these dates for flights from Chicago to Pittsburgh

3 nights

Jul 1 - Jul 4

$658 → $157

76%

2 nights

Jul 1 - Jul 3

$657 → $157

76%

7 nights

Jul 1 - Jul 8

$611 → $167

73%

4 nights

Jul 1 - Jul 5

$657 → $298

55%

Popular Airports to fly from Chicago to Pittsburgh

Chicago - Pittsburgh route insights

💸 Price insights

Recent fares are below the typical level.

Recent fares from Chicago to Pittsburgh are below the typical level at $137.

📅 Best time to fly

Fly in May for the best prices.

Historically, May is the cheapest month to fly, with a median price of $142.

⏱️ Flight duration

Connecting flights typically take 25h 45m.

The median flight duration for connecting flights from Chicago to Pittsburgh is 25 hours and 45 minutes.

✈️ Airlines & availability

Connecting flights are dominant on this route.

Connecting flights make up 25.8% of deals, with a median of 4 stopovers.

🏆 Airline highlight

Southwest Airlines offers direct flights.

Southwest Airlines is one of the carriers offering direct flights on this route.

🎯 Booking tip

Deals appear regularly for this route.

Historically, deals for flights from Chicago to Pittsburgh appear regularly, with 0.37 deals per day.

Chicago main airports to depart from

Chicago Midway International (MDW)

Cheapest

Consider Chicago Midway International for flights to Pittsburgh, offering competitive prices from Chicago.

📍 ~15 km from Chicago city center (reachable by car or public transport)

💸 Flights from ~$137

Chicago Rockford International (RFD)

Chicago Rockford International is an alternative departure option for your trip to Pittsburgh from Chicago.

📍 ~120 km from Chicago city center (reachable by car)

💸 Flights from ~$212

O Hare International (ORD)

O Hare International is a major airport for flights to Pittsburgh, providing options from Chicago.

📍 ~25 km from Chicago city center (reachable by car or public transport)

💸 Flights from ~$137

Pittsburgh main airports to arrive at

Pittsburgh International (PIT)

Cheapest

Pittsburgh International Airport is a convenient arrival choice for flights from Chicago to Pittsburgh.

📍 ~20 km from Pittsburgh city center (reachable by car)

💸 Flights from ~$137

Airports nearby Pittsburgh used as alternative

Cleveland Hopkins International (CLE)

Cheapest

Consider Cleveland Hopkins for a major international hub with extensive route variety and broad carrier selection.

📍 ~190 km from Pittsburgh (reachable by car)

💸 Flights from ~$109

Akron–Canton (CAK)

Akron–Canton offers easier navigation and parking, with good domestic connectivity for low-cost travelers.

📍 ~150 km from Pittsburgh (reachable by car)

💸 Flights from ~$188

University Park (SCE)

University Park provides reliable regional connections to major airline hubs, despite a significant driving distance.

📍 ~200 km from Pittsburgh (reachable by car)

💸 Flights from ~$271

Erie International (ERI)

Erie International offers alternative access for travelers in the northern corridor, though with limited departures.

📍 ~150 km from Pittsburgh (reachable by car)

💸 Flights from ~$278

Business & First Class Flight Deals to Pittsburgh

Pittsburgh, United States

37% AI deal score

$2,669

From ORD

Elite

Jun 21

Pittsburgh, United States

34% AI deal score

$4,161

Frequently Asked Questions About Flights to Pittsburgh

Historically, the best time to purchase tickets for flights from Chicago to Pittsburgh is typically 14-27 days before departure. During this window, the average price for a ticket is around $214. Prices tend to be higher for last-minute bookings, with flights purchased 7-13 days out averaging $930. For those planning further ahead, tickets bought 60+ days in advance have historically averaged $582.

Across the trailing quarter, a good price for a flight from Chicago to Pittsburgh is considered to be $296 or less. The median price for this route over the same period was $549. Prices can range significantly, with 75% of fares historically being $940 or less. Travelers aiming for a budget-friendly trip should target prices at or below the $296 threshold.

Historically, May, September, and November have offered the cheapest flights from Chicago to Pittsburgh. The median price in May was $142, while both September and November had a median price of $207. These months are significantly more affordable than the annual median price of $549 for this route. Travelers looking for the best value should consider flying during these periods.

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Cheap Flights from Chicago to Pittsburgh

Today’s best flight deals from Chicago to Pittsburgh

Unlock all 500+ flight deals to Pittsburgh and get alerts when great deals appear

Route Intelligence — 486,190 Searches this Week

Insights for flights from Chicago to Pittsburgh

How much is a round trip from Chicago to Pittsburgh

The cheapest time to fly from Chicago to Pittsburgh

Direct flights from Chicago to Pittsburgh

Last-minute flights going from Chicago to Pittsburgh

Biggest price drops on these dates for flights from Chicago to Pittsburgh

Popular Airports to fly from Chicago to Pittsburgh

Chicago - Pittsburgh route insights

Recent fares are below the typical level.

Fly in May for the best prices.

Connecting flights typically take 25h 45m.

Connecting flights are dominant on this route.

Southwest Airlines offers direct flights.

Deals appear regularly for this route.

Chicago main airports to depart from

Pittsburgh main airports to arrive at

Airports nearby Pittsburgh used as alternative

Business & First Class Flight Deals to Pittsburgh

Best Elite deals to Pittsburgh

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Frequently Asked Questions About Flights to Pittsburgh

When should I buy Chicago to Pittsburgh tickets?

When should I buy Chicago to Pittsburgh tickets?

What's a cheap fare from Chicago to Pittsburgh?

What's a cheap fare from Chicago to Pittsburgh?

Which months have the cheapest flights from Chicago to Pittsburgh?

Which months have the cheapest flights from Chicago to Pittsburgh?

Are there direct flights from Chicago to Pittsburgh?

Are there direct flights from Chicago to Pittsburgh?

How long does it take to fly from Chicago to Pittsburgh?

How long does it take to fly from Chicago to Pittsburgh?

How often do Chicago to Pittsburgh flight prices drop?

How often do Chicago to Pittsburgh flight prices drop?

Related routes

Consider alternative routes from Chicago