$59 Cheap flights from Pittsfield, IL

View $59 flight on Wed, Dec 16, 2026

Popular airlines from Pittsfield

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our OneKeyCash

    Learn about One Key

  • Cheapest flights from Pittsfield

    Prices were available within the past 7 days and start at $59 for one-way flights and $118 for roundtrip, for the period specified. Prices and availability are subject to change.

    All deals

    One way

    Roundtrip

    Select Contour Airlines flight, departing Thu, Dec 3 from Quincy to Chicago, returning Sun, Dec 6, priced at $118 Found 6 hours ago

    Thu, Dec 3 - Sun, Dec 6 · UIN · ORD · Roundtrip

    Select Contour Airlines flight, departing Wed, Dec 16 from Quincy to Chicago, returning Sat, Dec 19, priced at $128 Found 9 hours ago

    Wed, Dec 16 - Sat, Dec 19 · UIN · ORD · Roundtrip

    Select Contour Airlines flight, departing Sat, Dec 19 from Quincy to Chicago, returning Tue, Dec 22, priced at $138 Found 7 hours ago

    Sat, Dec 19 - Tue, Dec 22 · UIN · ORD · Roundtrip

    Select Contour Airlines flight, departing Fri, Jan 15 from Quincy to Chicago, returning Sat, Jan 16, priced at $144 Found 16 hours ago

    Fri, Jan 15 - Sat, Jan 16 · UIN · ORD · Roundtrip

    Select Contour Airlines flight, departing Sat, Nov 28 from Quincy to Chicago, returning Sat, Dec 5, priced at $148 Found 17 hours ago

    Sat, Nov 28 - Sat, Dec 5 · UIN · ORD · Roundtrip

    Select Contour Airlines flight, departing Mon, Nov 30 from Quincy to Chicago, returning Fri, Dec 4, priced at $158 Found 9 hours ago

    Mon, Nov 30 - Fri, Dec 4 · UIN · ORD · Roundtrip

    Select Contour Airlines flight, departing Mon, Jun 7 from Quincy to Chicago, returning Mon, Jun 21, priced at $165 Found 1 day ago

    Mon, Jun 7 - Mon, Jun 21 · UIN · ORD · Roundtrip

    Select Contour Airlines flight, departing Thu, Nov 19 from Quincy to Chicago, returning Sat, Nov 28, priced at $168 Found 15 hours ago

    Thu, Nov 19 - Sat, Nov 28 · UIN · ORD · Roundtrip

    Select Contour Airlines flight, departing Fri, Dec 11 from Quincy to Nashville, returning Mon, Dec 14, priced at $178 Found 10 hours ago

    Fri, Dec 11 - Mon, Dec 14 · UIN · BNA · Roundtrip

    Select Contour Airlines flight, departing Sat, Nov 28 from Quincy to Chicago, returning Sun, Nov 29, priced at $188 Found 1 day ago

    Sat, Nov 28 - Sun, Nov 29 · UIN · ORD · Roundtrip

    How to Find Cheap Flights from Pittsfield, IL

    How much is a flight from Pittsfield?

    This week, flights from Pittsfield are available between $118 – $188.

    How to find cheap flights from Pittsfield?

    Expedia makes it easy to compare cheap flights from Pittsfield to many destinations. Check out excellent deals on domestic and international flights from Pittsfield. Once you select an offer, use our filters and sort by “Price (Lowest)” to see some of the cheapest and suitable options.

    How can I get the best deal on flights from Pittsfield?

    On Expedia, you have some of best airline ticket deals at your fingertips. Whether it’s a beach escape with your partner, a family vacation with your kids, or business trip with colleagues, these low airline ticket prices mean more savings for you. An excellent strategy for finding some of the best deals on flights from Pittsfield is to be flexible with your dates. Within each offer, you can compare prices for similar timeframes using our “Show flexible dates” feature. Depending on your destination, direct flights from Pittsfield may be more expensive. Airlines with strict bag policies or fees can also impact your costs.

    What is the best airline to fly from Pittsfield?

    At Expedia, we give you all the available options from our reputable partners. Select the airline that best suits your preferences and membership loyalties. You can fly from Pittsfield with: Contour Airlines.

    What is the best month to fly from Pittsfield?

    One of the cheapest times to fly from Pittsfield airport(s) is December, based on the current list of flights available now. Prices on plane tickets vary considerably throughout the year due to availability and seasonal demand.

    Are there any last-minute flights from Pittsfield?

    Expedia is the place to find last-minute flights from Pittsfield, making it easy for you to compare prices on flights in the near future for different combinations of travel dates and from multiple airlines. We source some of the best deals for you and display some of the best offers available over the next 2 weeks.

    Why book your ticket with Expedia?

    Booking flights from Pittsfield with Expedia is the obvious choice to get low prices, save money, and see more value from every dollar spent. We show you some of the best deals happening right now and provide a vast inventory of airlines and flight routes to choose from, so you can find some of the cheapest flights from Pittsfield. You can customize your journey to your timeline, route preferences, budget, rewards programs, and more.

    Can I change/cancel my flight?

    Some flights can be changed or canceled, but fees and refunds will depend on the unique terms of your flight agreement. Airlines have different rules and restrictions for exchanging or refunding flights. For more information, go to your itinerary or visit our customer service portal. We recommend choosing flights with no change fees for the most flexibility. Filter by “Flexible change policies” to see flights with no change fees.

    Travel information

    Origin city nameQuincy
    Origin airportQuincy, IL
    Origin airport IATA codeUIN
    Airlines servingContour Airlines
    Popular airlineContour Airlines
    Roundtrip price$118

    Explore a world of travel with Expedia

    *Available to One Key members.