Cheap Flights from Kingston to Chicago starting at S$ 334

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 Kingston to Chicago

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 Kingston (KIN) to Chicago (CHI) the cheapest?

Airlines adjust prices for flights from Kingston to Chicago 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 Kingston (KIN) to Chicago (CHI) cost?

According to Trip.com's data, the lowest price is around S$ 866.
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
- The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
How many airports in Chicago?

There are 3 airports near Chicago: O'Hare International Airport, Midway International Airport and Chicago Rockford International Airport.

How to find a cheap flight from Kingston to Chicago

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 Kingston to Chicago. Book your flights at the right time and save more.

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

Tap 'Date' on the flight search bar to browse the calendar for Kingston to Chicago 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 Wed, Apr 2, with one-way flights starting at S$ 334.

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

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

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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.

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

Find cheapest flight ticket from Kingston to Chicago

Cheapest one-way flight price	S$ 333
Off-season for travel	March
Peak season for travel	December
Flight distance	2,854.66km
Popular airline	Jetblue Airways