Flight deals from Chicago to Jamestown

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

Round-trip
One way

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

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Cheapest flights

From price

13 20
20 27
May

27 4
4 11
11 18
18 25
Jun

25 1
1 8
8 15
15 22
22 29
Jul

29 6

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

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 £388.
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.

Be flexible with your travel dates to get the cheapest flight from Chicago to Jamestown.

Simply tap "Date" on the flight search bar to browse through the calendar and check out airfare from Chicago to Jamestown over the next 6 months in 2025. If you're planning to fly within the next three months, it looks like the most affordable option is on Sun, Apr 27, with one-way flights priced at just £168.

Compare cheap flight deals from Chicago to Jamestown across hundreds of airlines.

With our extensive search, you can compare prices from over 500 airlines to find the cheapest flight tickets from Chicago to Jamestown. The cheapest airline for this route is United Airlines.

Set up a Price Alert

By setting up a Price Alert for your journey from Chicago to Jamestown, you can easily keep an eye on ticket prices without having to check every day.

Don't miss out on cheap flight deals and promo codes from Chicago to Jamestown.

You can always find the latest offers through Trip.com Deals and Promo Codes for cheap flights. By signing up for a free membership, you'll get access to even more deals for your flights.

Book early or wait until the last minute.

It's usually best to book early. Flight tickets are often cheapest when they're first released, typically about a year before the departure date. So, have a look online as soon as the flights you're interested in become available. If you miss the cheapest time, you might still find some good deals as the departure date gets closer.

Search for flights on the go.

For the best travel flight booking experience, download the Trip.com app. You can search for cheap flights from Chicago to Jamestown and snag some exclusive deals just for you.

Flight Information from Chicago to Jamestown

Cheapest one-way flight price	£167
Off-season travel month	April
Peak season for travel	March
Flight distance	1,040.16km
Popular airline	United Airlines