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

Direct flights offer convenience and save travel time, but they are not always the cheapest option. Flights with layovers can sometimes be more affordable, especially if you are willing to spend extra time in transit. Consider your budget and schedule when deciding between direct and connecting flights.

Can flexible travel dates help on Pittsburgh to Chicago flights?

Yes, being flexible with your travel dates can significantly impact the price of flights. Shifting your departure or return by a few days, especially to travel during off-peak times, often leads to lower fares. Weekday travel is usually less expensive than weekend travel.

What extra costs should I check before booking Pittsburgh to Chicago 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. Being aware of these additional fees can help you accurately budget for your trip.

Flights From Pittsburgh

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 4 days ago

476 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 12, 2026.)

Today’s best flight deals from Pittsburgh to Chicago

Explore current cheapest deals departing from Pittsburgh to Chicago

2026-10-26 – 2026-10-31
PIT - Chicago
44% AI deal score
$255
$241
Round trip
2026-12-06 – 2026-12-09
PIT - Chicago
45% AI deal score
$266
$241
Round trip
2026-11-05 – 2026-11-09
PIT - Chicago
39% AI deal score
$154
$247
Round trip
2026-11-09 – 2026-11-10
PIT - Chicago
38% AI deal score
$154
$247
Round trip
2026-11-24 – 2026-11-25
PIT - Chicago
40% AI deal score
$152
$247
Round trip
2026-12-02 – 2026-12-07
PIT - Chicago
39% AI deal score
$153
$247
Round trip
2026-12-05 – 2026-12-07
PIT - Chicago
41% AI deal score
$158
$247
Round trip
2026-12-04 – 2026-12-09
PIT - Chicago
44% AI deal score
$263
$249
Round trip
2027-01-12 – 2027-01-20
PIT - Chicago
40% AI deal score
$217
$255
Round trip
2027-01-12 – 2027-01-27
PIT - Chicago
39% AI deal score
$201
$256
Round trip

Pittsburgh to Chicago: Overview

Insights for flights from Pittsburgh to Chicago

Right now, the cheapest fares from Pittsburgh to Chicago start at $423 and typically range up to $888, with a median price of $625. Current fares are significantly below the typical level, making it a favorable time to find cheap flights from Pittsburgh to Chicago. Approximately 13% of recent fares on this route were classified as a good price.

If you are looking for the cheapest time to fly from Pittsburgh to Chicago, June stands out with a median fare of $177. Other affordable months include December and January, both with median fares of $207. These months offer more budget-friendly options compared to the overall median.

Most itineraries for flights from Pittsburgh to Chicago connect at least once, with only 24.2% of recent fares being non-stop. For connecting itineraries, the typical number of connections is 2. This means you will likely encounter layovers when flying this route.

A typical journey from Pittsburgh to Chicago takes 1h 46m, including connections. For non-stop flights, the median flight time is also 1h 46m. However, connecting itineraries can extend significantly, with a median connecting journey time of 70h 44m.

The distance between Pittsburgh and Chicago is 646 kilometers. This classifies the route as a short-haul flight, indicating a relatively brief travel duration.

How much is a round trip from Pittsburgh to Chicago

Regular price: $174 - $334

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

The regular price range for flights from Pittsburgh to Chicago is between $174 and $334. The current lowest deal is $219 with Breeze Airways for travel from Jan 26-Feb 22.

now $219

Low $174

High $334

The cheapest time to fly from Pittsburgh to Chicago

Flights from Pittsburgh to Chicago are cheapest in June, with a median price of $177. The most expensive month to fly is March, with a median price of $881. Generally, prices are lower from January to December.

June

Cheapest

Flights from $177

March

Most Expensive

Flights from $881

Jan

Feb

Mar

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Pittsburgh to Chicago

United Airlines

Last-minute flights going from Pittsburgh to Chicago

Fri, Oct 9

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

Frontier Airlines

$367

$418

One-way

Fri, Oct 9

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

Frontier Airlines

$450

$419

One-way

Fri, Oct 9

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

Frontier Airlines

$457

$434

One-way

Mon, Oct 12

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

Frontier Airlines

$432

$419

One-way

Tue, Oct 13

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

Frontier Airlines

$356

$398

One-way

Tue, Oct 13

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

Frontier Airlines

$435

$409

One-way

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

3 nights

Dec 6 - Dec 9

$266 → $232

13%

2 nights

Nov 22 - Nov 24

$280 → $258

3 nights

Nov 21 - Nov 24

$279 → $258

3 nights

Oct 12 - Oct 15

$435 → $418

Popular Airports to fly from Pittsburgh to Chicago

Pittsburgh - Chicago route insights

💸 Price insights

Fares are below the typical level

Recent fares from Pittsburgh to Chicago are below the typical level of $625.

📅 Best time to fly

Fly in June for the best prices

Historically, June offers the lowest median prices at $177 for this route.

⏱️ Flight duration

Direct flights take 1h 46m

The typical direct flight from Pittsburgh to Chicago takes 1 hour and 46 minutes.

✈️ Airlines & availability

Connecting flights are more common

Only 24.2% of recent flights on this route are direct, with connecting flights having 2 stopovers.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines is one carrier providing direct flight options from Pittsburgh to Chicago.

🎯 Booking tip

Deals are rare for this route

Deals on flights from Pittsburgh to Chicago are historically rare, appearing infrequently.

Pittsburgh main airports to depart from

Pittsburgh International (PIT)

Cheapest

Pittsburgh International Airport is a convenient departure point for flights from Pittsburgh to Chicago.

📍 ~21 km from city center (reachable by car)

💸 Flights from ~$224

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering extensive connections for your trip to Chicago.

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

💸 Flights from ~$218

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 ~$311

Business & First Class Flight Deals to Chicago

49% AI deal score

$2,993

$2,218

Save $775

Air Canada, +1

Business Class

From PIT

Elite

Nov 16

Chicago, United States

48% AI deal score

$2,905

$2,384

Save $521

Air Canada, +1

Business Class

From PIT

Elite

Oct 30

Chicago, United States

47% AI deal score

$2,549

$2,216

Save $333

Air Canada, +1

Business Class

From PIT

Elite

Oct 30

Chicago, United States

47% AI deal score

$2,644

$2,334

Save $310

Air Canada, +1

Business Class

From PIT

Elite

Nov 16

Chicago, United States

47% AI deal score

$2,926

$2,440

Save $486

Air Canada, +1

Business Class

From PIT

Elite

Nov 16

Chicago, United States

47% AI deal score

$2,944

$2,525

Save $419

Air Canada, +1

Business Class

From PIT

Elite

Nov 16

Chicago, United States

47% AI deal score

$2,976

$2,548

Save $428

Air Canada, +1

Business Class

From PIT

Elite

Nov 16

Chicago, United States

47% AI deal score

$2,908

$2,548

Save $360

Air Canada, +1

Business Class

Frequently Asked Questions About Flights to Chicago

To find more affordable flights, consider being flexible with your travel dates and times. Comparing prices across different airlines and booking sites can also help you discover better deals. Setting up price alerts may notify you when fares drop for your desired route.

Booking flights in advance, often several weeks or months before your trip, can sometimes result in lower prices. However, prices can fluctuate, so monitoring fares over time may help you identify a good booking window. Weekday travel might also offer more competitive rates.

Comparing nearby airports for both your origin and destination can sometimes reveal more economical flight options. While it may add to your ground travel time, the potential savings on airfare can be significant. Always factor in the total cost and convenience when considering this option.

Related routes

More routes from Pittsburgh

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Flights to Chicago from other cities

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Pittsburgh to Chicago: Overview

Insights for flights from Pittsburgh to Chicago

The distance between Pittsburgh and Chicago is 646 kilometers. This classifies the route as a short-haul flight, indicating a relatively brief travel duration.

How much is a round trip from Pittsburgh to Chicago

Regular price: $174 - $334

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

The regular price range for flights from Pittsburgh to Chicago is between $174 and $334. The current lowest deal is $219 with Breeze Airways for travel from Jan 26-Feb 22.

now $219

Low $174

High $334

The cheapest time to fly from Pittsburgh to Chicago

June

Cheapest

Flights from $177

March

Most Expensive

Flights from $881

Jan

Feb

Mar

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Pittsburgh to Chicago

United Airlines

Last-minute flights going from Pittsburgh to Chicago

Fri, Oct 9

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

Frontier Airlines

$367

$418

One-way

Fri, Oct 9

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

Frontier Airlines

$450

$419

One-way

Fri, Oct 9

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

Frontier Airlines

$457

$434

One-way

Mon, Oct 12

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

Frontier Airlines

$432

$419

One-way

Tue, Oct 13

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

Frontier Airlines

$356

$398

One-way

Tue, Oct 13

⌛ Last-Minute

PIT - Chicago

Pittsburgh (PIT) - Chicago (ORD)

Frontier Airlines

$435

$409

One-way

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

3 nights

Dec 6 - Dec 9

$266 → $232

13%

2 nights

Nov 22 - Nov 24

$280 → $258

3 nights

Nov 21 - Nov 24

$279 → $258

3 nights

Oct 12 - Oct 15

$435 → $418

Popular Airports to fly from Pittsburgh to Chicago

Pittsburgh - Chicago route insights

💸 Price insights

Fares are below the typical level

Recent fares from Pittsburgh to Chicago are below the typical level of $625.

📅 Best time to fly

Fly in June for the best prices

Historically, June offers the lowest median prices at $177 for this route.

⏱️ Flight duration

Direct flights take 1h 46m

The typical direct flight from Pittsburgh to Chicago takes 1 hour and 46 minutes.

✈️ Airlines & availability

Connecting flights are more common

Only 24.2% of recent flights on this route are direct, with connecting flights having 2 stopovers.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines is one carrier providing direct flight options from Pittsburgh to Chicago.

🎯 Booking tip

Deals are rare for this route

Deals on flights from Pittsburgh to Chicago are historically rare, appearing infrequently.

Pittsburgh main airports to depart from

Pittsburgh International (PIT)

Cheapest

Pittsburgh International Airport is a convenient departure point for flights from Pittsburgh to Chicago.

📍 ~21 km from city center (reachable by car)

💸 Flights from ~$224

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering extensive connections for your trip to Chicago.

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

💸 Flights from ~$218

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 ~$311

Chicago, United States

47% AI deal score

$2,908

$2,548

Save $360

Air Canada, +1

Business Class

Frequently Asked Questions About Flights to Chicago

Cheap Flights from Pittsburgh to Chicago

Today’s best flight deals from Pittsburgh to Chicago

Pittsburgh to Chicago: Overview

Insights for flights from Pittsburgh to Chicago

How much is a round trip from Pittsburgh to Chicago

The cheapest time to fly from Pittsburgh to Chicago

Direct flights from Pittsburgh to Chicago

Last-minute flights going from Pittsburgh to Chicago

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

Popular Airports to fly from Pittsburgh to Chicago

Pittsburgh - Chicago route insights

Fares are below the typical level

Fly in June for the best prices

Direct flights take 1h 46m

Connecting flights are more common

United Airlines offers direct flights

Deals are rare for this route

Pittsburgh main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Dec 08

Dec 04

Nov 21

Nov 15

Nov 16

Nov 16

Oct 30

Oct 30

Nov 16

Nov 16

Nov 16

Nov 16

Frequently Asked Questions About Flights to Chicago

How can I find cheap flights from Pittsburgh to Chicago?

When should I book flights from Pittsburgh to Chicago?

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

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

Can flexible travel dates help on Pittsburgh to Chicago flights?

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

Related routes

More routes from Pittsburgh

Flights to Chicago from other cities

Pittsburgh to Chicago: Overview

Insights for flights from Pittsburgh to Chicago

How much is a round trip from Pittsburgh to Chicago

The cheapest time to fly from Pittsburgh to Chicago

Direct flights from Pittsburgh to Chicago

Last-minute flights going from Pittsburgh to Chicago

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

Popular Airports to fly from Pittsburgh to Chicago

Pittsburgh - Chicago route insights

Fares are below the typical level

Fly in June for the best prices

Direct flights take 1h 46m

Connecting flights are more common

United Airlines offers direct flights

Deals are rare for this route

Pittsburgh main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Dec 08

Dec 04

Nov 21

Nov 15

Nov 16

Nov 16

Oct 30

Oct 30

Nov 16

Nov 16

Nov 16

Nov 16

Frequently Asked Questions About Flights to Chicago

How can I find cheap flights from Pittsburgh to Chicago?

When should I book flights from Pittsburgh to Chicago?

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