Cheap Flights from Chicago to Jamestown starting at S$ 327

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.

Cheapest time to fly from Chicago to Jamestown

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

Cheapest flights

From price

16 23
23 30
Apr

30 6
6 13
13 20
20 27
May

27 4
4 11
11 18
18 25
Jun

25 1
1 8

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

Frequently Asked Questions

When to buy 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 is a flight from Chicago (CHI) to Jamestown (JMS) cost?

According to Trip.com's data, the lowest price is around S$ 693.
How many airports in Jamestown?

There are 1 airports near Jamestown: 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.

Choose your dates flexibly and get the best deals on flights from Chicago to Jamestown.

Tap 'Date' on the flight search bar to browse the calendar for Chicago to Jamestown airfare over the next 6 months in 2025. If you're looking to fly within the next 3 months, the cheapest date seems to be Thu, Apr 10, with one-way flights starting at S$ 327.

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

Our extensive search lets you compare prices from over 500 airlines to find the cheapest flights from Chicago to Jamestown. The cheapest flight at the moment is with United Airlines.

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Don't miss out on cheap deals and promo codes for Chicago to Jamestown flights.

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Book early or wait for last-minute deals.

It's always better to book early. Flight tickets are often at their lowest when first released, usually a year ahead of departure. Keep an eye out as soon as your desired flights open for booking. If you miss the early deals, you may still find lower prices closer to your travel date.

Search for flights on the go.

For the best flight booking experience on the go, download Trip.com and search for cheap flights from Chicago to Jamestown to get your exclusive deals.

Find cheapest flight ticket from Chicago to Jamestown

Cheapest one-way flight price	S$ 326
Off-season for travel	April
Peak season for travel	December
Flight distance	1,040.16km
Popular airline	Frontier Airlines