Cheap flights from Pittsburgh to Chicago

Pittsburgh
PIT
Chicago FSS
CHI

Flight deals from Pittsburgh to Chicago

Below you can see the best deals on flights Pittsburgh — Chicago for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 5 September, from $69.

Top 10 cheap flights from Pittsburgh to Chicago

DL
DL
$ 69

Pittsburgh — Chicago

17:15—20:30
8 Sep 2026
4 h 15 m
1 stop
DL
DL
$ 69

Pittsburgh — Chicago

19:45—23:59
8 Sep 2026
5 h 14 m
1 stop
DL
DL
$ 69

Pittsburgh — Chicago

17:40—22:44
8 Sep 2026
6 h 4 m
1 stop
DL
DL
$ 69

Pittsburgh — Chicago

15:19—20:31
8 Sep 2026
6 h 12 m
1 stop
DL
DL
$ 69

Pittsburgh — Chicago

17:40—23:59
8 Sep 2026
7 h 19 m
1 stop
DL
DL
$ 69

Pittsburgh — Chicago

15:19—22:18
8 Sep 2026
7 h 59 m
1 stop
DL
DL
$ 69

Pittsburgh — Chicago

10:25—12:59
9 Sep 2026
3 h 34 m
1 stop
DL
DL
$ 69

Pittsburgh — Chicago

06:00—09:07
9 Sep 2026
4 h 7 m
1 stop
DL
DL
$ 69

Pittsburgh — Chicago

12:18—16:57
9 Sep 2026
5 h 39 m
1 stop
DL
DL
$ 69

Pittsburgh — Chicago

19:45—23:59
9 Sep 2026
5 h 14 m
1 stop

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Pittsburgh — Chicago flight

Looking for cheap flights from Pittsburgh to Chicago? Compare fares from different airlines, check the flight schedule and travel time — and book your Pittsburgh — Chicago ticket online at the best price.

The route has direct flights — around 197 flights per week, flights are operated by United Airlines, American Airlines, Alaska Airlines, Japan Airlines and 5 more airlines, a nonstop flight takes about 1 h 45 min, the distance between the cities is around 660 km.

Planning your trip? You may find our Chicago travel guide, how to get from the airport into town and Chicago weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $67Min. price
OctoberCheapest
AugustPeak season
YesDirect flights
660 kmDistance
1 h 45 minTravel time
9Airlines
197 / wkFlights

Flight schedule from Pittsburgh to Chicago

The table shows direct flights from Pittsburgh to Chicago on the selected date. The flight takes approximately 1 h 45 min. Regular flights are operated by United Airlines, American Airlines, Alaska Airlines and Japan Airlines. Departures from Pittsburgh International Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today
Any time
Last update: 16 Aug 2026

Flight ticket prices by day: Pittsburgh — Chicago

Below is a calendar of the lowest flight ticket prices for Pittsburgh — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $67 in October, and the most expensive are around $207 in August. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Average one-way fares from Pittsburgh to Chicago by month. Tickets are usually cheapest in January (around $98) and priciest in December (about $139) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$98lowMay$126highSep$102low
Feb$102lowJun$130highOct$112medium
Mar$112mediumJul$135highNov$130high
Apr$107lowAug$121mediumDec$139high

Some values are estimated based on seasonality.

When to fly

Weather in Chicago: it is warmest in July (up to 27 °C on average) and coolest in January (around 0 °C). The driest month is November.

Tickets are usually cheapest in October and most expensive in August. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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How to get the best deal on a Pittsburgh — Chicago ticket

  • Book ahead: fares for Pittsburgh — Chicago are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • The cheapest month to fly to Chicago is usually October — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the Pittsburgh — Chicago route are operated by 9 airlines; United Airlines runs the most flights (around 42% of all flights). Compare carriers, flight shares and schedules below.

  • United AirlinesUA
    28x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight PIT → ORD28x/week
      Duration
      1h 51m
      Days
      MTWTFSS
    42.1%Open →
  • American AirlinesAA
    26x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight PIT → ORD26x/week
      Duration
      1h 52m
      Days
      MTWTFSS
    39.1%Open →
  • Alaska AirlinesAS
    7x/week
    WebsiteFleet: 31545M pax/year
    • Direct flight PIT → ORD7x/week
      Duration
      1h 46m
      Days
      MTWTFSS
    10.2%Open →
  • Japan AirlinesJL
    2x/week
    WebsiteFleet: 14540M pax/year
    • Direct flight PIT → ORD2x/week
    3.0%Open →
  • All Nippon AirwaysNH
    1x/week
    WebsiteFleet: 21648M pax/year
    • Direct flight PIT → ORD1x/week
    1.5%Open →
  • Air CanadaAC
    1x/week
    WebsiteFleet: 20346M pax/year
    • Direct flight PIT → ORD1x/week
    1.5%Open →
  • IberiaIB
    1x/week
    WebsiteFleet: 9224M pax/year
    • Direct flight PIT → ORD1x/week
      Duration
      1h 46m
      Days
      MTWTFSS
    1.0%Open →
  • British AirwaysBA
    1x/week
    WebsiteFleet: 29243M pax/year
    • Direct flight PIT → ORD1x/week
    1.0%Open →
  • LufthansaLH
    1x/week
    WebsiteFleet: 38764.5M pax/year
    • Direct flight PIT → ORD1x/week
    0.5%Open →

Cities and airports on the Pittsburgh — Chicago route

Flights Pittsburgh — Chicago depart from Pittsburgh International Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Pittsburgh

PIT
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the Pittsburgh — Chicago flight

How long is the flight from Pittsburgh to Chicago?

A nonstop Pittsburgh — Chicago flight takes about 1 h 45 min — the distance between the cities is around 660 km.

How far is it from Pittsburgh to Chicago?

The distance from Pittsburgh to Chicago is about 660 km, which a nonstop flight covers in around 1 h 45 min.

Are there direct flights from Pittsburgh to Chicago?

Yes, there are nonstop flights Pittsburgh — Chicago — around 197 flights per week.

Which airlines fly from Pittsburgh to Chicago?

Airlines operating Pittsburgh — Chicago include United Airlines, American Airlines, Alaska Airlines, Japan Airlines, All Nippon Airways. See the full list with schedules in the "Airlines" section on this page.

Which airports do Pittsburgh — Chicago flights use?

Flights from Pittsburgh depart from Pittsburgh International Airport, and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Pittsburgh to Chicago?

The price of a Pittsburgh — Chicago ticket depends on your travel date, season and demand: it is usually cheapest to fly in October, and most expensive in August. Tickets typically cost between $67 and $207. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Pittsburgh — Chicago?

Flights Pittsburgh — Chicago are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is October. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Pittsburgh to Chicago?

To catch a low fare Pittsburgh — Chicago, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually October.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from Pittsburgh

See all
New York CityWashington, D.C.BostonDetroitPhiladelphiaMinneapolisOrlandoAtlantaTorontoFort LauderdaleCharlotteDallasMontrealSeattleTampaMiamiDenverHoustonRaleighLos AngelesBradfordPhoenixLondonReykjavikSan FranciscoDublinMyrtle BeachLas VegasSalt Lake CityDu BoisLancasterNashvilleSouth PortlandFort MyersHartfordCancunPunta CanaNorth CharlestonNew OrleansSan Diego

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverNashvilleLondonIndianapolisSan DiegoMontrealSt. LouisMilwaukeeCharlottePhiladelphiaColumbusKansas CityPhoenixMiamiLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaLouisvilleKnoxvilleRochesterCleveland

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