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Flights from Chicago to Jamestown
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Find Chicago to Jamestown flights starting at CAD 330.

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • One way
  • Round-trip
      • ORD08:45
        7h 37m
        1 stop
        JMS16:22
        Sat, Dec 14|Chicago - Jamestown|United Airlines
        CAD 330CAD 694
        52% OFF
        52% OFF
        CAD 694CAD 330

        Choose United Airlines flights from Chicago to Jamestown. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Sat, Dec 14, arriving at Jamestown Regional Airport. One-way Prices start from CAD 330 including taxes and charges.

      • ORD10:35
        5h 47m
        1 stop
        JMS16:22
        Sun, Dec 15|Chicago - Jamestown|United Airlines
        CAD 388CAD 694
        44% OFF
        44% OFF
        CAD 694CAD 388

        Choose United Airlines flights from Chicago to Jamestown. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Sun, Dec 15, arriving at Jamestown Regional Airport. One-way Prices start from CAD 388 including taxes and charges.

      • MDW07:15
        9h 7m
        1 stop
        JMS16:22
        Sun, Dec 15|Chicago - Jamestown|Frontier Airlines
        CAD 475CAD 694
        31% OFF
        31% OFF
        CAD 694CAD 475

        Choose Frontier Airlines flights from Chicago to Jamestown. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Sun, Dec 15, arriving at Jamestown Regional Airport. One-way Prices start from CAD 475 including taxes and charges.

      • ORD07:25
        8h 57m
        1 stop
        JMS16:22
        Mon, Dec 16|Chicago - Jamestown|Frontier Airlines
        CAD 476
        CAD 476

        Choose Frontier Airlines flights from Chicago to Jamestown. The one-way connecting flight with Frontier Airlines departs from O'Hare International Airport on Mon, Dec 16, arriving at Jamestown Regional Airport. One-way Prices start from CAD 476 including taxes and charges.

      • ORD10:35
        5h 47m
        1 stop
        JMS16:22
        Wed, Dec 11|Chicago - Jamestown|United Airlines
        CAD 523
        CAD 523

        Choose United Airlines flights from Chicago to Jamestown. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Wed, Dec 11, arriving at Jamestown Regional Airport. One-way Prices start from CAD 523 including taxes and charges.

      • ORD08:30
        7h 52m
        1 stop
        JMS16:22
        Wed, Dec 11|Chicago - Jamestown|American Airlines
        CAD 534
        CAD 534

        Choose American Airlines flights from Chicago to Jamestown. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Wed, Dec 11, arriving at Jamestown Regional Airport. One-way Prices start from CAD 534 including taxes and charges.

      • ORD11:40
        25h 6m
        1 stop
        JMS12:46
        Sun, Dec 15|Chicago - Jamestown|American Airlines
        CAD 562
        CAD 562

        Choose American Airlines flights from Chicago to Jamestown. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Sun, Dec 15, arriving at Jamestown Regional Airport. One-way Prices start from CAD 562 including taxes and charges.

      • CHI13:00
        3h 5m
        Nonstop
        JMS14:00
        Sat, Dec 7|Chicago - Jamestown|United Airlines
        Find More Flights
        Find More Flights

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

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

We monitor flight fares to help you find the best deals effortlessly

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

Find Cheapest Airlines Flying from Chicago to Jamestown

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

United Airlines
From CAD 330
Frontier Airlines
From CAD 475
American Airlines
From CAD 534

Find more flights and airlines

Alternative Routes for Chicago to Jamestown Flights

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Chicago to Jamestown.

  • Cheapest
    United Airlines
    ORD
    08:45
    7h 37m
    1 transfer
    JMS
    16:22
    O'Hare International Airport - Jamestown Regional Airport
    Sat, Dec 14United Airlines
    CAD 330
  • Frontier Airlines
    MDW
    07:15
    9h 7m
    1 transfer
    JMS
    16:22
    Midway International Airport - Jamestown Regional Airport
    Sun, Dec 15Frontier Airlines
    CAD 475
  • Frontier Airlines
    MDW
    07:15
    9h 7m
    1 transfer
    JMS
    16:22
    Midway International Airport - Jamestown Regional Airport
    Sun, Dec 15Frontier Airlines
    CAD 475
    Find More Flights

FAQ

  • When are flight tickets from Chicago (CHI) to Jamestown (JMS) the cheapest?

    Airlines adjust prices for flights from Chicago to Jamestown 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 Chicago (CHI) to Jamestown (JMS) cost?

    According to Trip.com's data, the lowest price is around CAD 621.

  • How many airports in Jamestown (JMS)?

    There are 1 airport(s) in Jamestown (JMS): Jamestown Regional Airport.

How to find a cheap flight from Chicago to Jamestown

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 Chicago to Jamestown. 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 for Chicago to Jamestown Flights

Cheapest direct flight priceCAD 330
Off-season travel monthDecember
Peak season for travelNovember
Flight distance1,040.16km
Popular airlineAmerican Airlines

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