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Flights from Chicago to Jamestown
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Flights from Chicago to Jamestown Starting at £185

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

  • One way
  • Round-trip
      • ORD08:45
        7h 37m
        1 stop
        JMS16:22
        Sat, Dec 14|Chicago - Jamestown|United Airlines
        £185£389
        52% OFF
        52% OFF
        £389£185

        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 £185 including taxes and charges.

      • ORD10:35
        5h 47m
        1 stop
        JMS16:22
        Sun, Dec 15|Chicago - Jamestown|United Airlines
        £218£389
        44% OFF
        44% OFF
        £389£218

        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 £218 including taxes and charges.

      • MDW07:15
        9h 7m
        1 stop
        JMS16:22
        Sun, Dec 15|Chicago - Jamestown|Frontier Airlines
        £267£389
        31% OFF
        31% OFF
        £389£267

        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 £267 including taxes and charges.

      • ORD07:25
        8h 57m
        1 stop
        JMS16:22
        Mon, Dec 16|Chicago - Jamestown|Frontier Airlines
        £267
        £267

        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 £267 including taxes and charges.

      • ORD10:35
        5h 47m
        1 stop
        JMS16:22
        Wed, Dec 11|Chicago - Jamestown|United Airlines
        £294
        £294

        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 £294 including taxes and charges.

      • ORD08:30
        7h 52m
        1 stop
        JMS16:22
        Wed, Dec 11|Chicago - Jamestown|American Airlines
        £300
        £300

        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 £300 including taxes and charges.

      • ORD11:40
        25h 6m
        1 stop
        JMS12:46
        Sun, Dec 15|Chicago - Jamestown|American Airlines
        £315
        £315

        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 £315 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.

Find the best time to fly from Chicago to Jamestown

Explore the best time to buy affordable tickets to Jamestown with our price trend chart, which predicts how flight prices will change in the coming weeks from previous data.

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

Airlines Flying from Chicago to Jamestown

Compare prices from various providers below to understand which option best suits your travel needs, before enjoying a comfortable journey with a trusted airline from Chicago to Jamestown.

United Airlines
From £185
Frontier Airlines
From £267
American Airlines
From £300

Find more flights and airlines

Alternative Routes from Chicago to Jamestown

Searching for potential routes that might be cheaper and faster? There are a few alternative ways to get to Jamestown from Chicago which could help you save money and time.

  • Cheapest
    United Airlines
    ORD
    08:45
    7h 37m
    1 transfer
    JMS
    16:22
    O'Hare International Airport - Jamestown Regional Airport
    Sat, Dec 14United Airlines
    £185
  • Frontier Airlines
    MDW
    07:15
    9h 7m
    1 transfer
    JMS
    16:22
    Midway International Airport - Jamestown Regional Airport
    Sun, Dec 15Frontier Airlines
    £267
  • Frontier Airlines
    MDW
    07:15
    9h 7m
    1 transfer
    JMS
    16:22
    Midway International Airport - Jamestown Regional Airport
    Sun, Dec 15Frontier Airlines
    £267
    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 £348.

  • 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

If you leave it until the last minute and forget to check some of the key information when booking tickets, prices can often end up skyrocketing. Below, you can find our top tips for getting the best value flights – from changing dates to chasing deals, there are plenty ways to keep your next trip affordable.
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 Chicago to Jamestown

Cheapest direct flight price£185
Off-season travel monthDecember
Peak season for travelNovember
Flight distance1,040.16km
Popular airlineAmerican Airlines

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