Are there direct flights from Pittsburgh to Chicago?

Yes, direct flights are a common option for the Pittsburgh to Chicago route. Historically, approximately 70.6% of flights on this route have been direct. For flights that include stopovers, the median number of stopovers is typically one. This indicates that travelers have a strong likelihood of finding a non-stop option for their journey.

How many hours is the flight from Pittsburgh to Chicago?

The direct flight from Pittsburgh to Chicago typically takes about 1 hour and 49 minutes. This covers a distance of approximately 646 kilometers. If your journey includes one stop, the median flight time increases to about 4 hours and 52 minutes. Travelers should account for these differences when planning their trip, depending on whether they choose a direct or connecting flight.

Should I set a price alert for Pittsburgh to Chicago flights?

Historically, deals for flights from Pittsburgh to Chicago have been frequent. This suggests that setting a price alert could be beneficial for travelers looking to secure a good fare. Given the frequent availability of deals, an alert can help you monitor price changes and potentially catch a lower price as it becomes available. This route has consistently shown opportunities for price fluctuations over the trailing quarter.

Flights From Pittsburgh

To Chicago

Cheap Flights from Pittsburgh to Chicago

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Pittsburgh

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Prices updated 5 days ago

402 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Jul 12, 2026.)

Today’s best flight deals from Pittsburgh to Chicago

Explore current cheapest deals departing from Pittsburgh to Chicago

Round trip

Sort by: Cheapest

August 25 - August 29

Cheapest

PIT - Chicago

$161

$137

Round trip

August 22 - August 25

Cheapest

PIT - Chicago

$162

$137

Round trip

August 12 - August 15

Cheapest

PIT - Chicago

$166

$137

Round trip

August 27 - August 31

Cheapest

PIT - Chicago

$161

$137

Round trip

August 5 - August 8

Cheapest

Best

Earliest

PIT - Chicago

$167

$137

Round trip

August 8 - August 11

Cheapest

PIT - Chicago

$166

$137

Round trip

August 8 - August 12

Cheapest

PIT - Chicago

$166

$137

Round trip

August 26 - August 29

Cheapest

PIT - Chicago

$162

$137

Round trip

August 15 - August 17

Cheapest

PIT - Chicago

$163

$137

Round trip

August 17 - August 19

Cheapest

PIT - Chicago

$170

$137

Round trip

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Pittsburgh to Chicago: Overview

Insights for flights from Pittsburgh to Chicago

Right now, fares for cheap flights from Pittsburgh to Chicago are below the typical level. Over the last 90 days, prices for this route typically ranged from $207–$356, with a median of $250. Only 9% of recent fares were classified as a good price, indicating that finding exceptional value can be challenging.

When is the cheapest time to fly from Pittsburgh to Chicago? You'll find the most affordable fares in January, with a median price of $172. July and February also offer competitive prices, both with a median of $183.

For flights from Pittsburgh to Chicago, almost all itineraries are non-stop, with 70.6% of recent fares being direct. For the remaining itineraries that do include connections, the typical number of stopovers is 1.

A typical journey from Pittsburgh to Chicago takes about 3h 11m, including connections. This duration accounts for the median travel time across all observed itineraries on this route.

The distance between Pittsburgh and Chicago is 646 kilometers, classifying this as a short-haul route. This means you can expect a relatively quick flight, making it a convenient option for travelers.

How much is a round trip from Pittsburgh to Chicago

Regular price: $120 - $276

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

The regular price range for flights from Pittsburgh to Chicago is between $120 and $276. The current lowest deal is $137 with American Airlines for travel from August 25 to August 29.

now $137

Low $120

High $276

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

Wed, Jul 22

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

JetBlue Airways

$315

$248

One-way

Sat, Jul 25

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

JetBlue Airways

$303

$218

One-way

Tue, Aug 4

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

$273

$157

One-way

Wed, Aug 5

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (MDW)

Southwest Airlines

$165

$137

One-way

Wed, Aug 5

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

Frontier Airlines

$275

$224

One-way

Thu, Aug 6

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (MDW)

Southwest Airlines

$173

$137

One-way

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

3 nights

Sep 23 - Sep 26

$409 → $157

62%

3 nights

Sep 2 - Sep 5

$404 → $157

61%

4 nights

Sep 19 - Sep 23

$403 → $201

50%

4 nights

Sep 2 - Sep 6

$403 → $203

50%

Popular Airports to fly from Pittsburgh to Chicago

Pittsburgh - Chicago route insights

💸 Price insights

Recent fares are below the typical level

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

📅 Best time to fly

January is historically cheapest at $172

Historically, January is the cheapest month to fly from Pittsburgh to Chicago at $172.

⏱️ Flight duration

Flights typically take 3h 11m

Flights from Pittsburgh to Chicago typically take 3 hours and 11 minutes.

✈️ Airlines & availability

Direct flights are dominant on this route

Direct flights are dominant on this route, making up 70.6% of recent availability.

🏆 Airline highlight

American Airlines offers a recent deal for $137

American Airlines recently offered a flight from Pittsburgh to Chicago for $137.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Pittsburgh to Chicago are frequent, appearing often over 30 days.

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 offers significant carrier presence and direct flight options for Chicago travelers.

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

💸 Flights from ~$214

Gerald R. Ford International (GRR)

Cheapest

Gerald R. Ford International provides a robust domestic network with legacy and low-cost airlines.

📍 ~250 km from Chicago (reachable by car)

💸 Flights from ~$211

Dane County Regional (MSN)

Dane County Regional is a reliable regional hub with efficient operations and good amenities for travelers.

📍 ~205 km from Chicago (reachable by car)

💸 Flights from ~$284

South Bend International (SBN)

South Bend International is the closest alternative airport to the Chicago metro area.

📍 ~120 km from Chicago (reachable by train)

💸 Flights from ~$265

Fort Wayne International (FWA)

Fort Wayne International offers multiple cabin classes and solid connectivity for eastern domestic destinations.

📍 ~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 best time to book flights from Pittsburgh to Chicago for the cheapest prices is typically 14-27 days before departure. During this window, the average price for a flight has been around $217. Booking within 0-6 days of departure usually sees prices rise significantly, with an average of $457. Even booking 60+ days out tends to be slightly more expensive at an average of $239, indicating that last-minute deals are generally not the most economical option for this route.

Based on historical data from the trailing 90 days, a good price for a flight from Pittsburgh to Chicago is considered to be $207 or less. The median price for this route has been $250. Prices can go up to $356 or more for the higher end of the market. Travelers aiming for a budget-friendly trip should target fares at or below the $207 threshold.

Historically, the cheapest months to fly from Pittsburgh to Chicago include January, with a median price of $172, and July and February, both with a median price of $183. The annual median price for this route is $250, making these months notably more affordable. Travelers looking for the best value on this route should consider planning their trips during these periods to potentially save on airfare.

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