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Latest Flight Deals from Pittsburgh to Chicago

Book one-way or return flights from Pittsburgh to Chicago from as little as £37. Choose from the popular airlines below and book your flight today!

  • One way
  • Round-trip
      • PIT13:30
        1h 38m
        Direct
        ORD14:08
        Sun, May 26|Pittsburgh - Chicago|American Airlines
        £37£54
        31% OFF
        31% OFF
        £54£37
      • PIT06:29
        1h 41m
        Direct
        ORD07:10
        Wed, Jul 3|Pittsburgh - Chicago|American Airlines
        £38£54
        30% OFF
        30% OFF
        £54£38
      • PIT08:21
        1h 42m
        Direct
        ORD09:03
        Sat, Apr 27|Pittsburgh - Chicago|American Airlines
        £39£54
        28% OFF
        28% OFF
        £54£39
      • PIT13:41
        9h 24m
        1 stop
        MDW22:05
        Tue, May 7|Pittsburgh - Chicago|Frontier Airlines
        £39
        £39
      • PIT12:58
        1h 42m
        Direct
        ORD13:40
        Tue, Apr 30|Pittsburgh - Chicago|American Airlines
        £40
        £40
      • PIT13:30
        1h 38m
        Direct
        ORD14:08
        Sat, May 18|Pittsburgh - Chicago|American Airlines
        £40
        £40
      • PIT12:58
        1h 42m
        Direct
        ORD13:40
        Sat, May 4|Pittsburgh - Chicago|American Airlines
        £40
        £40
      • PIT17:05
        1h 40m
        Direct
        ORD17:45
        Wed, Jun 19|Pittsburgh - Chicago|American Airlines
        £40
        £40
      • PIT06:29
        1h 41m
        Direct
        ORD07:10
        Wed, Jun 12|Pittsburgh - Chicago|American Airlines
        £40
        £40
      • PIT13:30
        1h 38m
        Direct
        ORD14:08
        Sat, May 25|Pittsburgh - Chicago|American Airlines
        £40
        £40
      • PIT13:00
        3h 5m
        Direct
        CHI14:00
        Fri, May 3|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.

Searching for the best last minute flight from Pittsburgh to Chicago? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Pittsburgh to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Airlines Flying from Pittsburgh to Chicago

View airlines operating flights from Pittsburgh to Chicago. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

American Airlines
From £37
Frontier Airlines
From £39
Spirit Airlines
From £42
Delta Air Lines
From £49
Southwest Airlines
From £49
United Airlines
From £59
Sun Country Airlines
From £61
Breeze Airways
From £162
Alaska Airlines
From £167
ANA airlines

Find more flights and airlines

Alternative Routes from Pittsburgh to Chicago

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Pittsburgh to Chicago.

  • Cheapest
    American Airlines
    PIT
    13:30
    1h 38m
    Direct
    ORD
    14:08
    Pittsburgh International Airport - O'Hare International Airport
    Sun, May 26American Airlines
    £37
  • Frontier Airlines
    PIT
    13:41
    9h 24m
    1 transfer
    MDW
    22:05
    Pittsburgh International Airport - Midway International Airport
    Tue, May 7Frontier Airlines
    £39
  • Frontier Airlines
    PIT
    13:41
    9h 24m
    1 transfer
    MDW
    22:05
    Pittsburgh International Airport - Midway International Airport
    Tue, May 7Frontier Airlines
    £39
    Find More Flights

How do I find the cheapest flights?

  • 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 cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.

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

    According to Trip.com's data, the lowest price is around £208.

  • How long is the flight from Pittsburgh (PIT) to Chicago (CHI)?

    It takes about 1 hour 36 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 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, 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, Southwest Airlines, Alaska Airlines, Royal Jordanian, All Nippon Airways, Air New Zealand, Air Canada and Qantas Airways.

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

    American Airlines operates 1 direct flights from Pittsburgh (PIT) to Chicago (CHI).

  • How many airports in Chicago (CHI)?

How to find a cheap flight from Pittsburgh to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Pittsburgh to Chicago. Book your flights at the right time and save more.
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 Information from Pittsburgh to Chicago

Cheapest direct flight price

£37

Cheapest return ticket price

£74

Cheapest month

February

Peak season for travel

October

Flight distance

660.47km

Average flight time

1 hour 36 minutes

Popular airline

United Airlines

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