Are direct flights from Chicago to Pittsburgh always the best option?

Direct flights are often the most convenient, saving time and avoiding potential connection issues. However, connecting flights can sometimes be more affordable, especially if you are willing to accept a longer travel time. The 'best' option depends on your priorities for cost versus convenience.

Can flexible travel dates help on Chicago to Pittsburgh flights?

Yes, being flexible with your travel dates can significantly impact flight prices. Flying on weekdays or during off-peak seasons often results in lower fares. Even shifting your departure or return by a day or two may lead to savings.

What extra costs should I check before booking Chicago to Pittsburgh flights?

Before booking, always check for potential extra costs such as baggage fees, seat selection charges, and in-flight services. Some airlines may also charge for printing boarding passes at the airport. Factoring these into your total budget is important.

Flights From Chicago

To Pittsburgh

Cheap Flights from Chicago to Pittsburgh

Browse current best options from Chicago. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Chicago

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

Prices updated 7 days ago

483 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Oct 26, 2026.)

Today’s best flight deals from Chicago to Pittsburgh

Explore current cheapest deals departing from Chicago to Pittsburgh

2027-01-13 – 2027-01-19
CHI - Pittsburgh
39% AI deal score
$199
$238
Round trip
2027-01-13 – 2027-01-25
CHI - Pittsburgh
38% AI deal score
$181
$243
Round trip
2027-01-11 – 2027-01-19
CHI - Pittsburgh
39% AI deal score
$191
$244
Round trip
2027-01-13 – 2027-01-18
CHI - Pittsburgh
38% AI deal score
$204
$244
Round trip
2027-01-13 – 2027-01-21
CHI - Pittsburgh
38% AI deal score
$192
$248
Round trip
2027-01-11 – 2027-01-25
CHI - Pittsburgh
37% AI deal score
$180
$249
Round trip
2027-01-13 – 2027-01-31
CHI - Pittsburgh
38% AI deal score
$176
$249
Round trip
2027-01-11 – 2027-01-18
CHI - Pittsburgh
38% AI deal score
$198
$250
Round trip
2026-12-11 – 2026-12-13
CHI - Pittsburgh
45% AI deal score
$305
$258
Round trip
2026-12-09 – 2026-12-16
CHI - Pittsburgh
40% AI deal score
$253
$262
Round trip

Chicago to Pittsburgh: Overview

Insights for flights from Chicago to Pittsburgh

For those looking for cheap flights from Chicago to Pittsburgh, October stands out as the most affordable month, with a median fare of $495. Other budget-friendly options include August, where the median fare is $529, and December, with a median fare of $589. Planning your trip during these months could lead to more favorable prices.

Fares for flights from Chicago to Pittsburgh typically range from $466–$848, with a median of $631. Right now, current fares are below the typical level, which may present an opportunity for savings. However, the share of recent fares classified as a good price is 0%, indicating that truly exceptional deals are not currently common.

Most itineraries for this route are connecting flights, with only 13.1% of recent fares being direct flights from Chicago to Pittsburgh. For itineraries that include connections, the typical number of stopovers is 3. This suggests that travelers should prepare for journeys that involve at least one stop.

A typical journey from Chicago to Pittsburgh takes approximately 1h 42m, including connections. While the non-stop flight time is also 1h 42m, connecting itineraries have a significantly longer median duration of 17h 59m. This difference highlights the impact of stopovers on overall travel time.

The distance between Chicago and Pittsburgh is 662 kilometers, classifying this as a short-haul route. This relatively short distance means that flights are generally brief, making it a convenient option for quick trips.

How much is a round trip from Chicago to Pittsburgh

Regular price: $107 - $258

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

The regular price range for flights from Chicago to Pittsburgh is between $107 and $258. The current lowest deal is $243 with Southwest Airlines for travel from Nov 19-Nov 23.

now $243

Low $107

High $258

The cheapest time to fly from Chicago to Pittsburgh

The cheapest month to fly from Chicago to Pittsburgh is October, with a median price of $495. The most expensive month is November, with a median price of $722. Prices are generally lower from January to December.

October

Cheapest

Flights from $495

November

Most Expensive

Flights from $722

Jan

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Pittsburgh

Frontier Airlines

Allegiant Air

JetBlue Airways

Breeze Airways

Last-minute flights going from Chicago to Pittsburgh

Tue, Oct 27

⌛ Last-Minute

ORD - Pittsburgh

Chicago (ORD) - Pittsburgh (PIT)

JetBlue Airways

$420

$519

One-way

Fri, Oct 30

⌛ Last-Minute

ORD - Pittsburgh

Chicago (ORD) - Pittsburgh (PIT)

Frontier Airlines

$412

$441

One-way

Sat, Oct 31

⌛ Last-Minute

ORD - Pittsburgh

Chicago (ORD) - Pittsburgh (PIT)

Frontier Airlines, Allegiant Air

$286

$313

One-way

Sat, Oct 31

⌛ Last-Minute

ORD - Pittsburgh

Chicago (ORD) - Pittsburgh (PIT)

Frontier Airlines, Allegiant Air

$292

$313

One-way

Sat, Oct 31

⌛ Last-Minute

ORD - Pittsburgh

Chicago (ORD) - Pittsburgh (PIT)

Frontier Airlines, Allegiant Air

$275

$353

One-way

Sun, Nov 1

⌛ Last-Minute

RFD - Pittsburgh

Chicago (RFD) - Pittsburgh (PIT)

Allegiant Air

$341

$283

One-way

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

3 nights

Nov 1 - Nov 4

$436 → $314

28%

6 nights

Nov 1 - Nov 7

$379 → $314

17%

10 nights

Nov 1 - Nov 11

$341 → $292

14%

13 nights

Nov 1 - Nov 14

$332 → $292

12%

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 $243.

📅 Best time to fly

October is historically cheapest

Historically, October has the cheapest median prices at $495 for flights from Chicago to Pittsburgh.

⏱️ Flight duration

Direct flights take 1h 42m

Direct flights from Chicago to Pittsburgh typically take 1 hour 42 minutes.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights make up 86.9% of routes, with a median of 3 stopovers.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines has 1 direct deal available for flights from Chicago to Pittsburgh.

🎯 Booking tip

Deals appear regularly

Deals for flights from Chicago to Pittsburgh appear regularly within a 30-day window.

Chicago main airports to depart from

Chicago Midway International (MDW)

Cheapest

Chicago Midway International offers a convenient departure point for flights to Pittsburgh.

📍 ~14 km from Chicago city center (reachable by car or public transport)

💸 Flights from ~$277

Chicago Rockford International (RFD)

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

📍 ~126 km from Chicago city center (reachable by car)

💸 Flights from ~$319

O Hare International (ORD)

O Hare International provides another major airport choice for your journey to Pittsburgh.

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

💸 Flights from ~$277

Pittsburgh main airports to arrive at

Pittsburgh International (PIT)

Cheapest

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

📍 ~21 km from Pittsburgh (reachable by car)

💸 Flights from ~$208

Airports nearby Pittsburgh used as alternative

Cleveland Hopkins International (CLE)

Cheapest

Cleveland Hopkins International offers significantly more direct flight options and broad carrier selection if Pittsburgh is unavailable.

📍 ~135 km from Pittsburgh (reachable by car)

💸 Flights from ~$171

Business & First Class Flight Deals to Pittsburgh

66% AI deal score

$3,988

$2,649

Save $1,339

Aeroméxico, +1

Business Class

From ORD

Elite

Oct 29

Pittsburgh, United States

45% AI deal score

$960

$813

Save $147

From ORD

Elite

Dec 04

Pittsburgh, United States

39% AI deal score

$2,287

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 08

Pittsburgh, United States

39% AI deal score

$2,357

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Nov 27

Pittsburgh, United States

38% AI deal score

$2,280

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 08

Pittsburgh, United States

38% AI deal score

$2,311

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 25

Pittsburgh, United States

38% AI deal score

$2,330

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 11

Pittsburgh, United States

38% AI deal score

$2,403

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Pittsburgh

To find more affordable flights, consider being flexible with your travel dates and times. Comparing prices across different airlines and booking sites can often reveal better deals. Setting up price alerts may also help you catch drops in fares.

Booking flights in advance, typically several weeks to a few months before your departure, often yields better prices. However, prices can fluctuate, so monitoring fares is usually a good strategy. Last-minute bookings may sometimes be more expensive.

Comparing nearby airports can sometimes offer more flight options or different price points. While it may add to your ground travel, the potential savings could make it worthwhile. Always consider the total cost and convenience when choosing.

Related routes

More routes from Chicago

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Flights to Pittsburgh from other cities

Flights from Charlotte to Pittsburgh Flights from Dallas to Pittsburgh Flights from Denver to Pittsburgh Flights from Fort Myers to Pittsburgh Flights from Frankfurt to Pittsburgh Flights from Houston to Pittsburgh Flights from Las Vegas to Pittsburgh Flights from London to Pittsburgh Flights from Melbourne to Pittsburgh Flights from Miami to Pittsburgh Flights from Milan to Pittsburgh Flights from Minneapolis to Pittsburgh

Chicago to Pittsburgh: Overview

Insights for flights from Chicago to Pittsburgh

How much is a round trip from Chicago to Pittsburgh

Regular price: $107 - $258

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

The regular price range for flights from Chicago to Pittsburgh is between $107 and $258. The current lowest deal is $243 with Southwest Airlines for travel from Nov 19-Nov 23.

now $243

Low $107

High $258

The cheapest time to fly from Chicago to Pittsburgh

October

Cheapest

Flights from $495

November

Most Expensive

Flights from $722

Jan

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Pittsburgh

Frontier Airlines

Allegiant Air

JetBlue Airways

Breeze Airways

Last-minute flights going from Chicago to Pittsburgh

Tue, Oct 27

⌛ Last-Minute

ORD - Pittsburgh

Chicago (ORD) - Pittsburgh (PIT)

JetBlue Airways

$420

$519

One-way

Fri, Oct 30

⌛ Last-Minute

ORD - Pittsburgh

Chicago (ORD) - Pittsburgh (PIT)

Frontier Airlines

$412

$441

One-way

Sat, Oct 31

⌛ Last-Minute

ORD - Pittsburgh

Chicago (ORD) - Pittsburgh (PIT)

Frontier Airlines, Allegiant Air

$286

$313

One-way

Sat, Oct 31

⌛ Last-Minute

ORD - Pittsburgh

Chicago (ORD) - Pittsburgh (PIT)

Frontier Airlines, Allegiant Air

$292

$313

One-way

Sat, Oct 31

⌛ Last-Minute

ORD - Pittsburgh

Chicago (ORD) - Pittsburgh (PIT)

Frontier Airlines, Allegiant Air

$275

$353

One-way

Sun, Nov 1

⌛ Last-Minute

RFD - Pittsburgh

Chicago (RFD) - Pittsburgh (PIT)

Allegiant Air

$341

$283

One-way

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

3 nights

Nov 1 - Nov 4

$436 → $314

28%

6 nights

Nov 1 - Nov 7

$379 → $314

17%

10 nights

Nov 1 - Nov 11

$341 → $292

14%

13 nights

Nov 1 - Nov 14

$332 → $292

12%

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 $243.

📅 Best time to fly

October is historically cheapest

Historically, October has the cheapest median prices at $495 for flights from Chicago to Pittsburgh.

⏱️ Flight duration

Direct flights take 1h 42m

Direct flights from Chicago to Pittsburgh typically take 1 hour 42 minutes.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights make up 86.9% of routes, with a median of 3 stopovers.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines has 1 direct deal available for flights from Chicago to Pittsburgh.

🎯 Booking tip

Deals appear regularly

Deals for flights from Chicago to Pittsburgh appear regularly within a 30-day window.

Chicago main airports to depart from

Chicago Midway International (MDW)

Cheapest

Chicago Midway International offers a convenient departure point for flights to Pittsburgh.

📍 ~14 km from Chicago city center (reachable by car or public transport)

💸 Flights from ~$277

Chicago Rockford International (RFD)

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

📍 ~126 km from Chicago city center (reachable by car)

💸 Flights from ~$319

O Hare International (ORD)

O Hare International provides another major airport choice for your journey to Pittsburgh.

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

💸 Flights from ~$277

Pittsburgh main airports to arrive at

Pittsburgh International (PIT)

Cheapest

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

📍 ~21 km from Pittsburgh (reachable by car)

💸 Flights from ~$208

Airports nearby Pittsburgh used as alternative

Cleveland Hopkins International (CLE)

Cheapest

Cleveland Hopkins International offers significantly more direct flight options and broad carrier selection if Pittsburgh is unavailable.

📍 ~135 km from Pittsburgh (reachable by car)

💸 Flights from ~$171

Pittsburgh, United States

66% AI deal score

$3,988

$2,649

Save $1,339

Aeroméxico, +1

Business Class

From ORD

Elite

Oct 29

Pittsburgh, United States

45% AI deal score

$960

$813

Save $147

From ORD

Elite

Dec 04

Pittsburgh, United States

39% AI deal score

$2,287

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 08

Pittsburgh, United States

39% AI deal score

$2,357

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Nov 27

Pittsburgh, United States

38% AI deal score

$2,280

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 08

Pittsburgh, United States

38% AI deal score

$2,311

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 25

Pittsburgh, United States

38% AI deal score

$2,330

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Dec 11

Pittsburgh, United States

38% AI deal score

$2,403

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Pittsburgh

Cheap Flights from Chicago to Pittsburgh

Today’s best flight deals from Chicago to Pittsburgh

Chicago to Pittsburgh: Overview

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

October is historically cheapest

Direct flights take 1h 42m

Connecting flights are dominant

United Airlines offers direct flights

Deals appear regularly

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

Oct 29

Dec 08

Oct 31

Nov 11

Dec 04

Oct 29

Dec 04

Dec 08

Nov 27

Dec 08

Dec 25

Dec 11

Frequently Asked Questions About Flights to Pittsburgh

How can I find cheap flights from Chicago to Pittsburgh?

When should I book flights from Chicago to Pittsburgh?

Should I compare nearby airports for flights from Chicago to Pittsburgh?

Are direct flights from Chicago to Pittsburgh always the best option?

Can flexible travel dates help on Chicago to Pittsburgh flights?

What extra costs should I check before booking Chicago to Pittsburgh flights?

Related routes

More routes from Chicago

Flights to Pittsburgh from other cities

Chicago to Pittsburgh: Overview

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

October is historically cheapest

Direct flights take 1h 42m

Connecting flights are dominant

United Airlines offers direct flights

Deals appear regularly

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

Oct 29

Dec 08

Oct 31

Nov 11

Dec 04

Oct 29

Dec 04

Dec 08

Nov 27

Dec 08

Dec 25

Dec 11

Frequently Asked Questions About Flights to Pittsburgh

How can I find cheap flights from Chicago to Pittsburgh?

When should I book flights from Chicago to Pittsburgh?

Should I compare nearby airports for flights from Chicago to Pittsburgh?