To Chicago

Cheap Flights from Pittsburgh to Chicago

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Pittsburgh

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

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 Pittsburgh to Chicago

Explore current cheapest deals departing from Pittsburgh to Chicago

Round trip

Sort by: Cheapest

July 3 - July 7

Cheapest

Best

PIT - Chicago

$186

$137

Round trip

July 3 - July 4

Cheapest

Best

PIT - Chicago

$185

$137

Round trip

July 1 - July 8

Cheapest

Earliest

PIT - Chicago

$173

$137

Round trip

July 15 - July 21

Cheapest

PIT - Chicago

$170

$137

Round trip

July 7 - July 8

Cheapest

PIT - Chicago

$181

$137

Round trip

July 21 - July 22

Cheapest

PIT - Chicago

$171

$137

Round trip

July 1 - July 4

Cheapest

Best

Earliest

PIT - Chicago

$188

$137

Round trip

August 18 - August 19

Cheapest

PIT - Chicago

$163

$137

Round trip

August 4 - August 5

Cheapest

PIT - Chicago

$169

$137

Round trip

August 5 - August 11

Cheapest

PIT - Chicago

$159

$137

Round trip

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Route Intelligence — 486,190 Searches this Week

Insights for flights from Pittsburgh to Chicago

For cheap flights from Pittsburgh to Chicago, 17% of recent fares were classified as a good price. Right now, fares are below the typical level. Prices for this route typically range from $181–$326, with a median of $246.

When is the cheapest time to fly from Pittsburgh to Chicago? The most affordable months to fly are January, with a median fare of $172, followed by July and February, both with median fares of $183. New deals appear almost daily, offering frequent opportunities to find competitive prices.

A meaningful share of itineraries are non-stop, with 60.2% of recent fares being direct flights from Pittsburgh to Chicago. For the remaining itineraries that include connections, the typical number of stopovers is 2.

A typical journey from Pittsburgh to Chicago takes about 3h 11m, including connections. This duration accounts for both direct and connecting flights on this route.

The distance between Pittsburgh and Chicago is 646 kilometers, classifying this as a short-haul flight.

How much is a round trip from Pittsburgh to Chicago

Regular price: $146 - $286

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

The regular price range for flights from Pittsburgh to Chicago is between $146 and $286. The current lowest deal is $137 with American Airlines for travel from Jul 3-Jul 7.

now $137

Low $146

High $286

The cheapest time to fly from Pittsburgh to Chicago

Flights from Pittsburgh to Chicago are cheapest in January, with a median price of $172. The most expensive month to fly is March, with a median price of $899. Prices are generally lower from January to November.

January

Cheapest

Flights from $172

March

Most Expensive

Flights from $899

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Pittsburgh to Chicago

American Airlines

Southwest Airlines

Last-minute flights going from Pittsburgh to Chicago

Sun, Jun 21

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

Frontier Airlines

$480

$332

One-way

Mon, Jun 22

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

JetBlue Airways

$452

$337

One-way

Tue, Jun 30

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

United Airlines

$261

$137

One-way

Tue, Jun 30

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

$378

$167

One-way

Wed, Jul 1

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

United Airlines

$173

$137

One-way

Wed, Jul 1

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

United Airlines

$188

$137

One-way

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

3 nights

Sep 23 - Sep 26

$430 → $179

58%

4 nights

Sep 17 - Sep 21

$421 → $201

52%

3 nights

Jun 30 - Jul 3

$378 → $167

56%

7 nights

Sep 16 - Sep 23

$408 → $202

50%

Popular Airports to fly from Pittsburgh to Chicago

Pittsburgh - Chicago route insights

💸 Price insights

Recent fares are below the typical level.

Recent fares from Pittsburgh to Chicago are below the typical level, with deals around $137.

📅 Best time to fly

January is historically the cheapest month to fly.

Historically, January, July, and February are the cheapest months to fly from Pittsburgh to Chicago.

⏱️ Flight duration

Direct flights take 3h 11m on average.

The typical direct flight from Pittsburgh to Chicago takes 3 hours and 11 minutes.

✈️ Airlines & availability

Multiple airlines offer frequent deals.

Deals on flights from Pittsburgh to Chicago are frequent, with over 1 deal per day historically.

🏆 Airline highlight

American Airlines offers direct flights.

American Airlines is one of the airlines that historically offers direct flights on this route.

🎯 Booking tip

Consider booking 90 days in advance.

Historically, good prices for Pittsburgh to Chicago flights are found when booking 90 days out.

Pittsburgh main airports to depart from

Pittsburgh International (PIT)

Cheapest

Pittsburgh International is a good option for flights from Pittsburgh to Chicago.

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

💸 Flights from ~$137

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

Chicago Midway International is a good option for flights from Pittsburgh to Chicago, offering competitive prices.

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

💸 Flights from ~$137

Chicago Rockford International (RFD)

Chicago Rockford International serves the Chicago area for travelers flying from Pittsburgh.

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

💸 Flights from ~$230

O Hare International (ORD)

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

📍 ~30 km from Chicago city center (reachable by car or public transport)

💸 Flights from ~$137

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International Airport is an excellent alternative with high-frequency flight options to Chicago.

📍 ~135 km from Chicago (reachable by car or rail)

💸 Flights from ~$257

South Bend International (SBN)

South Bend International Airport is a close alternative to Chicago, offering easier security and parking.

📍 ~120 km from Chicago (reachable by car or rail)

💸 Flights from ~$246

Gerald R. Ford International (GRR)

Cheapest

Gerald R. Ford International Airport is a major regional hub, good for travelers on Chicago's eastern side.

📍 ~200 km from Chicago (reachable by car)

💸 Flights from ~$226

Dane County Regional (MSN)

Dane County Regional Airport is a reliable option, less congested than major Chicago airports.

📍 ~200 km from Chicago (reachable by car)

💸 Flights from ~$274

Fort Wayne International (FWA)

Fort Wayne International Airport offers stable regional service for travelers in Chicago's southeastern suburbs.

📍 ~240 km from Chicago (reachable by car)

💸 Flights from ~$278

Business & First Class Flight Deals to Chicago

45% AI deal score

$2,121

From PIT

Elite

Jul 14

Chicago, United States

45% AI deal score

Chicago, United States

42% AI deal score

Chicago, United States

34% AI deal score

$8,872

Frequently Asked Questions About Flights to Chicago

Historically, the lowest average prices for flights from Pittsburgh to Chicago are found when booking 14-27 days in advance. During this period, the average price was $217. Booking within 0-6 days of departure typically results in significantly higher prices, averaging around $457. For the trailing 90 days, prices generally increase closer to the departure date.

Across the trailing quarter, a good price for a flight from Pittsburgh to Chicago was $181 or less. The median price for this route was $246. About 75% of prices observed were $326 or less. These figures are based on data from the trailing 90 days.

Historically, January has been the cheapest month to fly from Pittsburgh to Chicago, with a median price of $172. February and July also offered relatively low median prices at $183. The annual median price for this route was $246. These insights are based on data collected over a 270-day period.

Related routes

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