Flights from Pittsburgh to Chicago from $71

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Flights Schedule Cheap Tickets Airlines Airports

Airfare Deals Pittsburgh to Chicago

On HolidayPrice.com you will find 3 direct and 0 connecting flights from Pittsburgh to Chicago at a price of from $71. You can compare airfare deals from airlines and multiple travel sites, book and save on cheap plane tickets and last minute offers. Also check out PIT - CHI flight schedule to find best flight time, convenient departure and arrival airports.

Sun

The cost of airline tickets from Pittsburgh to Chicago (United States) and back without transfers can be found with the help of the calendar. Specify the search parameters: one way or round-trip, payment currency, click on the month/day you need and we will search for flights to Chicago.

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Cheap flights from Pittsburgh
Cheap flights to Chicago
Airline tickets to United States

One way flight from Pittsburgh to Chicago

Below are the prices of tickets for direct one-way flights from Pittsburgh to Chicago. The cheapest flight from Pittsburgh to Chicago starts from $71 – the departure date for this flight is 14 December 2025.

*Prices include: baggage, hand luggage, airline fees and charges.

Round trip from Pittsburgh to Chicago

You can buy a round-trip ticket from Pittsburgh to Chicago (United States) and back using the table below. The best offer starts from $89, the flight dates are: there on 09 December 2025 year and back on 09 December 2025 year.

Sort by: Departure date Cheap flights Trip time Direct flights

American Airlines AA 2511 Day flight

Departure 30.12.25 13:15, Tu

Direct Trip 3 days

Return 03.01.26 00:30, Sa

Find Flights from $320

*Prices include: baggage, hand luggage, airline fees and charges.

Not found promotions and sales.

Flight Schedule Pittsburgh to Chicago 2025

The current flight schedule for the route from Pittsburgh to Chicago for today, tomorrow and the next few days. This schedule will help you decide on the time of departure and arrival, the airline, the flight number and the day of the week.

More than 7 flights every day, from 1hours 25min. Local departure and arrival times are indicated.

05:45 → 06:28

United Airlines UA2074

PIT → ORD

- - - - Fr Sa Su

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05:45 → 06:28

United Airlines UA2034

PIT → ORD

- - - Th - - -

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06:25 → 06:50

Southwest Airlines WN2593

PIT → MDW

Mo - - Th Fr - Su

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06:55 → 07:20

Southwest Airlines WN2593

PIT → MDW

- - - - - Sa -

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07:00 → 07:42

United Airlines UA1848

PIT → ORD

- - We - - - -

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07:00 → 07:25

Southwest Airlines WN4132

PIT → MDW

- Tu We - - - -

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07:05 → 07:48

United Airlines UA1848

PIT → ORD

Mo Tu We Th Fr - Su

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07:05 → 07:48

United Airlines UA2008

PIT → ORD

Mo Tu - Th Fr Sa Su

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10:10 → 10:35

Southwest Airlines WN836

PIT → MDW

Mo - - Th Fr - -

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10:15 → 10:40

Southwest Airlines WN836

PIT → MDW

- - - - - - Su

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10:59 → 11:42

United Airlines UA2683

PIT → ORD

Mo Tu We - Fr - Su

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11:04 → 11:47

United Airlines UA2683

PIT → ORD

Mo - We Th Fr Sa Su

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Show all

*Schedule is indicated only for direct scheduled flights and low-cost airlines.

Flight Information

Flying to Chicago from Pittsburgh takes 01:23 minutes (excluding transfers). The distance between Pittsburgh and Chicago is 408 miles (657 kilometers). Planes depart from Pittsburgh between 00:00 and 23:55. The fastest flight from the company Southwest Airlines with flight number WN 280. Flies for just 01:20 minutes with departure from Pittsburgh and arrival in Chicago Midway.

Airlines

Direct flight

There are 3 airlines that fly directly from Pittsburgh to Chicago. The most popular company carrying out non-stop flights is American Airlines.

American Airlines: AA 3544, AA 2894, AA 2897
Southwest Airlines: WN 2296, WN 2204, WN 1507
United Airlines: UA 3975, UA 3726, UA 1925

*Flight number

Flights with Transfers

Flights with transfers from Pittsburgh to Chicago can be bought from 0 airlines:

*Transit cities

Airports

Airports serving the air communication between Pittsburgh and Chicago. You can fly to Chicago from 1 Pittsburgh airports. Planes arrive at 2 airport in Chicago.

Pittsburgh airports:

Pittsburgh ~ 21 km*

Chicago airports:

O'Hare ~ 25 km* from $ 90Chicago Midway ~ 14 km* from $ 101

*Distance from the airport to the city center

Aircraft

You can fly from Pittsburgh to Chicago on board of 3 airlines that utilize 13 aircraft models.

Airbus A319
Airbus A320
Boeing 737
Boeing 737-700
Boeing 737-800

Boeing 737-900
Canadair reg jet 700
Canadair regional jet
Embraer 170
Embraer 175

Embraer EMB 175
Embraer ERJ-135/140/145 Regional Jet
Embraer RJ145

Connecting cities

The list of cities on transfer flights to Chicago from Pittsburgh. The best options are to fly through: .

Cheap airline tickets from Pittsburgh to United States

Here is a list of flights from Pittsburgh to United States purchased on HolidayPrice.com in the past 48 hours. If you find an interesting offer for cheap tickets, do not delay your purchase, prices change every 15 minutes.

Pittsburgh - New York AA 3871 American Airlines Embraer RJ140

19:55 Pittsburgh

in a way 1 hours 5 min Direct

21:00 LaGuardia

Flights
from $62 17 January 2026

Pittsburgh - Los Angeles NK 653 Spirit Airlines Airbus A319

14:30 Pittsburgh

in a way 4 hours 56 min Direct

19:26 Los Angeles

Flights
from $99 07 March 2026

Pittsburgh - Miami NK 577 Spirit Airlines Airbus A319

13:45 Pittsburgh

in a way 2 hours 15 min Direct

16:00 Fort Lauderdale Executive Airport

Flights
from $122 17 April 2026

Pittsburgh - Chicago WN 280 Southwest Airlines Boeing 737-700

00:20 Pittsburgh

in a way 1 hours 20 min Direct

01:40 Chicago Midway

Flights
from $71 14 December 2025

Pittsburgh - San Francisco UA 2228 United Airlines Boeing 737-900

01:10 Pittsburgh

in a way 5 hours 18 min Direct

06:28 San Francisco

Flights
from $120 17 January 2026

All flights from Pittsburgh

Flights from United States to Chicago

Here are the cheapest flight bookings from United States to Chicago made by users of our website. If you didn’t find your flight destination, use the search bar at the top of the page.

New York - Chicago UA 761 United Airlines Boeing 737-800

13:00 LaGuardia

in a way 2 hours 0 min Direct

15:00 O'Hare

Flights
from $30 13 January 2026

Los Angeles - Chicago UA 910 United Airlines Boeing 737-800

10:23 Los Angeles

in a way 3 hours 37 min Direct

14:00 O'Hare

Flights
from $47 25 February 2026

Miami - Chicago AA 2796 American Airlines Boeing 767-300

17:05 Miami

in a way 2 hours 55 min Direct

20:00 O'Hare

Flights
from $24 11 December 2025

Miami - Chicago WN 1626 Southwest Airlines Boeing 737

13:35 Fort Lauderdale Executive Airport

in a way 3 hours 0 min Direct

16:35 Chicago Midway

Flights
from $24 11 December 2025

San Francisco - Chicago UA 1800 United Airlines Airbus A319

04:15 San Francisco

in a way 3 hours 45 min Direct

08:00 O'Hare

Flights
from $70 23 January 2026

All flights to Chicago

Tips for buying a ticket

Pittsburgh – Chicago – Pittsburgh round-trip route are always cheaper than tickets purchased there and back separately.

Cheap flights from Pittsburgh to Chicago — Chicago city

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