Are there direct flights from Pittsburgh to Chicago?

Yes, direct flights are commonly available from Pittsburgh to Chicago. Historically, approximately 70.6% of flights on this route have been direct. For journeys that do include a stopover, travelers typically experience one stop between the two cities. This data reflects trends observed across the trailing 90 days.

How many hours is the flight from Pittsburgh to Chicago?

The median flight time for a direct flight from Pittsburgh to Chicago is approximately 1 hour and 49 minutes, covering a distance of 646 kilometers. Flights with one stop typically take longer, with a median duration of 4 hours and 52 minutes. Travelers can expect a relatively short journey when flying directly between these two cities.

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

Yes, setting a price alert for flights from Pittsburgh to Chicago is recommended. Historically, deals on this route have been frequent across the trailing 30 days. This suggests that prices can fluctuate, and an alert could help you secure a favorable fare for your travel.

Flights From Pittsburgh

To Chicago

Cheap Flights from Pittsburgh to Chicago

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Deals from

Pittsburgh

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

Prices updated 2 days ago

444 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Aug 9, 2026.)

Today’s best flight deals from Pittsburgh to Chicago

Explore current cheapest deals departing from Pittsburgh to Chicago

2026-08-24 – 2026-08-29
PIT - Chicago
50% AI deal score
$163
$137
Round trip
2026-09-05 – 2026-09-06
PIT - Chicago
75% AI deal score
$250
$137
Round trip
2026-10-01 – 2026-10-03
PIT - Chicago
49% AI deal score
$159
$137
Round trip
2026-10-14 – 2026-10-19
PIT - Chicago
49% AI deal score
$158
$137
Round trip
2026-11-11 – 2026-11-14
PIT - Chicago
66% AI deal score
$177
$137
Round trip
2026-09-14 – 2026-09-21
PIT - Chicago
76% AI deal score
$379
$137
Round trip
2026-10-08 – 2026-10-12
PIT - Chicago
46% AI deal score
$164
$137
Round trip
2026-10-21 – 2026-10-24
PIT - Chicago
49% AI deal score
$160
$138
Round trip
2026-10-08 – 2026-10-10
PIT - Chicago
48% AI deal score
$164
$138
Round trip
2026-11-19 – 2026-11-26
PIT - Chicago
65% AI deal score
$180
$138
Round trip

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 to $356, with a median of $250. Only 9% of recent fares were classified as a good price, indicating that finding deals can be competitive.

If you are looking for the cheapest time to fly from Pittsburgh to Chicago, the data indicates that January is typically the most affordable month, with a median fare of $172. July and February also offer lower median fares, both at $183, making them strong contenders for budget-conscious travel.

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

A typical journey from Pittsburgh to Chicago, including any connections, takes approximately 3h 11m. This duration reflects the overall travel time you can expect for this route.

The distance between Pittsburgh and Chicago is 646 kilometers. This classifies the route as a short-haul flight, meaning it is a relatively brief journey.

How much is a round trip from Pittsburgh to Chicago

Regular price: $133 - $348

Prices are currently within the regular range.

The regular price range for flights from Pittsburgh to Chicago is $133 to $348. The current lowest deal is $137 with Southwest Airlines for travel from Sep 5-Sep 11.

now $137

Low $133

High $348

The cheapest time to fly from Pittsburgh to Chicago

The cheapest month to fly from Pittsburgh to Chicago is January, with a median price of $172. The most expensive month 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

Mon, Aug 24

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

Frontier Airlines

$289

$189

One-way

Thu, Aug 27

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

Frontier Airlines

$282

$172

One-way

Thu, Aug 27

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (RFD)

Allegiant Air

$243

$184

One-way

Thu, Aug 27

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (MDW)

Southwest Airlines

$180

$191

One-way

Thu, Aug 27

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (MDW)

Southwest Airlines

$182

$191

One-way

Thu, Aug 27

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

$284

$191

One-way

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

1 night

Sep 5 - Sep 6

$405 → $137

66%

2 nights

Sep 5 - Sep 7

$406 → $164

60%

2 nights

Sep 7 - Sep 9

$406 → $172

58%

4 nights

Sep 10 - Sep 14

$402 → $172

57%

Popular Airports to fly from Pittsburgh to Chicago

Pittsburgh - Chicago route insights

💸 Price insights

Recent fares below the typical level

Recent fares from 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, with a median price of $172.

⏱️ Flight duration

Short-haul flights average 3h 11m

Flights from Pittsburgh to Chicago typically average 3 hours 11 minutes, classifying as a short-haul route.

✈️ Airlines & availability

Direct flights are dominant

Direct flights are dominant on this route, accounting for 70.6% of recent fares.

🏆 Airline highlight

Southwest Airlines offers a $137 deal

Southwest Airlines offers a recent deal for $137 from Pittsburgh to Chicago (PIT to MDW).

🎯 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 convenient option for flights from Pittsburgh to Chicago, offering competitive prices.

📍 ~25 km from Pittsburgh city center (reachable by car)

💸 Flights from ~$137

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

Chicago Midway International is a convenient arrival airport for flights to Chicago from Pittsburgh.

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

💸 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 Amtrak Hiawatha line or car)

💸 Flights from ~$259

Business & First Class Flight Deals to Chicago

76% AI deal score

$513

$351

Save $162

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 is 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, averaging $239.

Across the trailing quarter, a good price for a flight from Pittsburgh to Chicago is considered to be $207 or less. The median price for this route has historically been around $250. Prices can go up to $356 or more for the higher end of fares in the trailing 90 days.

Historically, January, July, and February have been the cheapest months to fly from Pittsburgh to Chicago. The median price in January was $172, while both July and February saw a median of $183. The annual median price for this route is typically around $250, indicating potential savings during these months.

Related routes

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Pittsburgh to Chicago: Overview

Insights for flights from Pittsburgh to Chicago

A typical journey from Pittsburgh to Chicago, including any connections, takes approximately 3h 11m. This duration reflects the overall travel time you can expect for this route.

The distance between Pittsburgh and Chicago is 646 kilometers. This classifies the route as a short-haul flight, meaning it is a relatively brief journey.

How much is a round trip from Pittsburgh to Chicago

Regular price: $133 - $348

Prices are currently within the regular range.

The regular price range for flights from Pittsburgh to Chicago is $133 to $348. The current lowest deal is $137 with Southwest Airlines for travel from Sep 5-Sep 11.

now $137

Low $133

High $348

The cheapest time to fly from Pittsburgh to Chicago

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

Mon, Aug 24

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

Frontier Airlines

$289

$189

One-way

Thu, Aug 27

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

Frontier Airlines

$282

$172

One-way

Thu, Aug 27

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (RFD)

Allegiant Air

$243

$184

One-way

Thu, Aug 27

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (MDW)

Southwest Airlines

$180

$191

One-way

Thu, Aug 27

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (MDW)

Southwest Airlines

$182

$191

One-way

Thu, Aug 27

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

$284

$191

One-way

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

1 night

Sep 5 - Sep 6

$405 → $137

66%

2 nights

Sep 5 - Sep 7

$406 → $164

60%

2 nights

Sep 7 - Sep 9

$406 → $172

58%

4 nights

Sep 10 - Sep 14

$402 → $172

57%

Popular Airports to fly from Pittsburgh to Chicago