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Cheap flight deals from Pittsburgh to Chicago Starting at MYR 263

Discover our range of affordable one-way and round-trip flights from Pittsburgh to Chicago and kick-start your next adventure today!

  • One way
  • Round-trip
      • Cheapest nonstop
        PIT06:35
        1h 52m
        Nonstop
        ORD07:27
        Thu, Mar 20|Pittsburgh - Chicago|American Airlines
        MYR 263MYR 430
        39% OFF
        39% OFF
        MYR 430MYR 263

        Choose American Airlines flights from Pittsburgh to Chicago. The one-way direct flight with American Airlines departs from Pittsburgh International Airport on Thu, Mar 20, arriving at O'Hare International Airport. One-way Prices start from MYR 263 including taxes and charges.

      • PIT11:38
        1h 51m
        Nonstop
        ORD12:29
        Tue, Mar 18|Pittsburgh - Chicago|American Airlines
        MYR 273MYR 430
        36% OFF
        36% OFF
        MYR 430MYR 273

        Choose American Airlines flights from Pittsburgh to Chicago. The one-way direct flight with American Airlines departs from Pittsburgh International Airport on Tue, Mar 18, arriving at O'Hare International Airport. One-way Prices start from MYR 273 including taxes and charges.

      • PIT11:38
        1h 42m
        Nonstop
        ORD12:20
        Thu, Mar 6|Pittsburgh - Chicago|American Airlines
        MYR 313MYR 430
        27% OFF
        27% OFF
        MYR 430MYR 313

        Choose American Airlines flights from Pittsburgh to Chicago. The one-way direct flight with American Airlines departs from Pittsburgh International Airport on Thu, Mar 6, arriving at O'Hare International Airport. One-way Prices start from MYR 313 including taxes and charges.

      • PIT15:58
        1h 51m
        Nonstop
        ORD16:49
        Tue, Apr 29|Pittsburgh - Chicago|American Airlines
        MYR 319
        MYR 319

        Choose American Airlines flights from Pittsburgh to Chicago. The one-way direct flight with American Airlines departs from Pittsburgh International Airport on Tue, Apr 29, arriving at O'Hare International Airport. One-way Prices start from MYR 319 including taxes and charges.

      • PIT16:33
        1h 42m
        Nonstop
        ORD17:15
        Fri, Feb 21|Pittsburgh - Chicago|American Airlines
        MYR 353
        MYR 353

        Choose American Airlines flights from Pittsburgh to Chicago. The one-way direct flight with American Airlines departs from Pittsburgh International Airport on Fri, Feb 21, arriving at O'Hare International Airport. One-way Prices start from MYR 353 including taxes and charges.

      • PIT16:33
        1h 42m
        Nonstop
        ORD17:15
        Sat, Feb 22|Pittsburgh - Chicago|American Airlines
        MYR 353
        MYR 353

        Choose American Airlines flights from Pittsburgh to Chicago. The one-way direct flight with American Airlines departs from Pittsburgh International Airport on Sat, Feb 22, arriving at O'Hare International Airport. One-way Prices start from MYR 353 including taxes and charges.

      • PIT19:55
        1h 30m
        Nonstop
        MDW20:25
        Mon, Mar 3|Pittsburgh - Chicago|Southwest Airlines
        MYR 361
        MYR 361

        Choose Southwest Airlines flights from Pittsburgh to Chicago. The one-way direct flight with Southwest Airlines departs from Pittsburgh International Airport on Mon, Mar 3, arriving at Midway International Airport. One-way Prices start from MYR 361 including taxes and charges.

      • PIT07:05
        1h 35m
        Nonstop
        MDW07:40
        Tue, Mar 4|Pittsburgh - Chicago|Southwest Airlines
        MYR 361
        MYR 361

        Choose Southwest Airlines flights from Pittsburgh to Chicago. The one-way direct flight with Southwest Airlines departs from Pittsburgh International Airport on Tue, Mar 4, arriving at Midway International Airport. One-way Prices start from MYR 361 including taxes and charges.

      • PIT19:15
        1h 30m
        Nonstop
        MDW19:45
        Wed, Mar 5|Pittsburgh - Chicago|Southwest Airlines
        MYR 361
        MYR 361

        Choose Southwest Airlines flights from Pittsburgh to Chicago. The one-way direct flight with Southwest Airlines departs from Pittsburgh International Airport on Wed, Mar 5, arriving at Midway International Airport. One-way Prices start from MYR 361 including taxes and charges.

      • PIT12:25
        27h 47m
        1 stop
        MDW15:12
        Mon, Feb 24|Pittsburgh - Chicago|Frontier Airlines
        MYR 289
        MYR 289

        Choose Frontier Airlines flights from Pittsburgh to Chicago. The one-way connecting flight with Frontier Airlines departs from Pittsburgh International Airport on Mon, Feb 24, arriving at Midway International Airport. One-way Prices start from MYR 289 including taxes and charges.

      • PIT01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Fri, Feb 21|Pittsburgh - Chicago|American Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Pittsburgh to Chicago flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule

  1. UA708

    United Airlines

    07:00

    PIT

    1.8h

    Nonstop

    07:50

    ORD

    SMTWTFS
    Search

  2. WN611

    Southwest Airlines

    07:05

    PIT

    1.6h

    Nonstop

    07:40

    MDW

    S-T-TFS
    Search

  3. UA1617

    United Airlines

    11:18

    PIT

    1.8h

    Nonstop

    12:06

    ORD

    SM-WTFS
    Search

  4. AA4547

    American Airlines

    11:38

    PIT

    1.9h

    Nonstop

    12:29

    ORD

    SM-WT-S
    Search

  5. WN1522

    Southwest Airlines

    12:50

    PIT

    1.5h

    Nonstop

    13:20

    MDW

    --T----
    Search

  6. WN3286

    Southwest Airlines

    13:50

    PIT

    1.5h

    Nonstop

    14:20

    MDW

    SM-WT-S
    Search

  7. UA1669

    United Airlines

    14:06

    PIT

    1.8h

    Nonstop

    14:55

    ORD

    SMTWTFS
    Search

  8. WN3122

    Southwest Airlines

    17:50

    PIT

    1.5h

    Nonstop

    18:20

    MDW

    SMTWTFS
    Search

  9. UA1398

    United Airlines

    17:52

    PIT

    1.8h

    Nonstop

    18:41

    ORD

    SMTWTFS
    Search

  10. AA3707

    American Airlines

    20:00

    PIT

    1.8h

    Nonstop

    20:49

    ORD

    SMTWTFS
    Search
Find more flights and airlines

When is the cheapest time to fly from Pittsburgh to Chicago?

Price trend charts are a great way of tracking how much your flights cost in the lead up to departure and can help you choose when to book your tickets. See how prices to Chicago from Pittsburgh have changed and are set to move below.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

  • When are flight tickets from Pittsburgh (PIT) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Pittsburgh to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Pittsburgh (PIT) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around MYR 1,144.

  • How long does it take to fly from Pittsburgh (PIT) to Chicago (CHI)?

    It takes about 4 hours 28 minutes to fly from Pittsburgh (PIT) to Chicago (CHI).

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25 km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14 km, by taxi about 30 minutes.

  • What are the most popular airlines that fly from Pittsburgh (PIT) to Chicago (CHI)?

    Airlines with flights from Pittsburgh (PIT) to Chicago (CHI): United Airlines, Qantas Airways, Gulf Air, American Airlines, Qatar Airways and Southwest Airlines.

  • What's the most popular airline for non-stop flights from Pittsburgh (PIT) to Chicago (CHI)?

    American Airlines operates 1 non-stop flights from Pittsburgh (PIT) to Chicago (CHI).

  • How many airports are there in Chicago (CHI)?

How to find a cheap flight from Pittsburgh to Chicago

Understanding the common pitfalls when booking your flight tickets can help you save massively when it comes time to fly. We’ve listed our six essential steps to keep in mind when you’re booking flight tickets to help you find the best price.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Info | Pittsburgh to Chicago

Cheapest direct flight priceMYR 262
Cheapest return ticket priceMYR 533
Off-season for travelJanuary
Peak season for travelNovember
Flight distance660.47 km
Average flight time4 hours 28 minutes
Popular airlineAmerican Airlines

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