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Cheap flight deals from Kingston to Chicago Starting at $235

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

  • One way
  • Round-trip
      • KIN09:54
        12h 8m
        1 stop
        ORD21:02
        Wed, Dec 4|Kingston - Chicago|Spirit Airlines
        $235$395
        41% OFF
        41% OFF
        $395$235

        Choose Spirit Airlines flights from Kingston to Chicago. The one-way connecting flight with Spirit Airlines departs from Norman Manley International Airport on Wed, Dec 4, arriving at O'Hare International Airport. One-way Prices start from $235 including taxes and charges.

      • KIN06:11
        13h 20m
        1 stop
        ORD18:31
        Thu, Nov 28|Kingston - Chicago|Jetblue Airways
        $294$395
        26% OFF
        26% OFF
        $395$294

        Choose Jetblue Airways flights from Kingston to Chicago. The one-way connecting flight with Jetblue Airways departs from Norman Manley International Airport on Thu, Nov 28, arriving at O'Hare International Airport. One-way Prices start from $294 including taxes and charges.

      • KIN20:20
        13h 58m
        1 stop
        ORD09:18
        Fri, Dec 6|Kingston - Chicago|Jetblue Airways
        $306$395
        23% OFF
        23% OFF
        $395$306

        Choose Jetblue Airways flights from Kingston to Chicago. The one-way connecting flight with Jetblue Airways departs from Norman Manley International Airport on Fri, Dec 6, arriving at O'Hare International Airport. One-way Prices start from $306 including taxes and charges.

      • KIN15:30
        19h 50m
        1 stop
        MDW10:20
        Mon, Dec 23|Kingston - Chicago|Flair Airlines
        $312
        $312

        Choose Flair Airlines flights from Kingston to Chicago. The one-way connecting flight with Flair Airlines departs from Norman Manley International Airport on Mon, Dec 23, arriving at Midway International Airport. One-way Prices start from $312 including taxes and charges.

      • KIN01:30
        8h 48m
        1 stop
        ORD09:18
        Wed, Dec 11|Kingston - Chicago|Jetblue Airways
        $313
        $313

        Choose Jetblue Airways flights from Kingston to Chicago. The one-way connecting flight with Jetblue Airways departs from Norman Manley International Airport on Wed, Dec 11, arriving at O'Hare International Airport. One-way Prices start from $313 including taxes and charges.

      • KIN20:08
        13h 55m
        1 stop
        ORD09:03
        Mon, Dec 9|Kingston - Chicago|Jetblue Airways
        $316
        $316

        Choose Jetblue Airways flights from Kingston to Chicago. The one-way connecting flight with Jetblue Airways departs from Norman Manley International Airport on Mon, Dec 9, arriving at O'Hare International Airport. One-way Prices start from $316 including taxes and charges.

      • KIN04:03
        12h 13m
        1 stop
        ORD15:16
        Fri, Nov 22|Kingston - Chicago|Jetblue Airways
        $327
        $327

        Choose Jetblue Airways flights from Kingston to Chicago. The one-way connecting flight with Jetblue Airways departs from Norman Manley International Airport on Fri, Nov 22, arriving at O'Hare International Airport. One-way Prices start from $327 including taxes and charges.

      • KIN07:30
        14h 47m
        1 stop
        ORD21:17
        Tue, Dec 17|Kingston - Chicago|Caribbean Airlines
        $328
        $328

        Choose Caribbean Airlines flights from Kingston to Chicago. The one-way connecting flight with Caribbean Airlines departs from Norman Manley International Airport on Tue, Dec 17, arriving at O'Hare International Airport. One-way Prices start from $328 including taxes and charges.

      • KIN07:30
        11h 12m
        1 stop
        ORD17:42
        Tue, Dec 10|Kingston - Chicago|Caribbean Airlines
        $330
        $330

        Choose Caribbean Airlines flights from Kingston to Chicago. The one-way connecting flight with Caribbean Airlines departs from Norman Manley International Airport on Tue, Dec 10, arriving at O'Hare International Airport. One-way Prices start from $330 including taxes and charges.

      • KIN00:35
        9h 51m
        1 stop
        ORD09:26
        Wed, Dec 25|Kingston - Chicago|Jetblue Airways
        $334
        $334

        Choose Jetblue Airways flights from Kingston to Chicago. The one-way connecting flight with Jetblue Airways departs from Norman Manley International Airport on Wed, Dec 25, arriving at O'Hare International Airport. One-way Prices start from $334 including taxes and charges.

      • KIN13:00
        3h 5m
        Nonstop
        CHI14:00
        Fri, Nov 29|Kingston - Chicago|Spirit 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 Kingston to Chicago?

Explore the best time to buy affordable tickets to Chicago 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.

Find cheap airlines flights from Kingston to Chicago

Which airline provides the cheapest flights from Kingston to Chicago? Discover the option that best suits your travel needs before embarking on your journey.

Spirit Airlines
From $235
Jetblue Airways
From $294
American Airlines
From $306
Flair Airlines
From $312
Caribbean Airlines
From $328
Air Canada
From $340
WestJet
From $355
Delta Air Lines
From $413
Arajet Airline
From $467
Copa Airlines
From $503

Find more flights and airlines

Alternative Cheap Routes from Kingston to Chicago

Did you know that you can save money and time on an alternative route from Kingston to Chicago? Check out some of the different available routes below.

  • Cheapest
    Spirit Airlines
    KIN
    09:54
    12h 8m
    1 transfer
    ORD
    21:02
    Norman Manley International Airport - O'Hare International Airport
    Wed, Dec 4Spirit Airlines
    $235
  • Flair Airlines
    KIN
    15:30
    19h 50m
    1 transfer
    MDW
    10:20
    Norman Manley International Airport - Midway International Airport
    Mon, Dec 23Flair Airlines
    $312
  • Flair Airlines
    KIN
    15:30
    19h 50m
    1 transfer
    MDW
    10:20
    Norman Manley International Airport - Midway International Airport
    Mon, Dec 23Flair Airlines
    $312
    Find More Flights

Frequently Asked Questions

  • When are flight tickets from Kingston (KIN) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Kingston to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Kingston (KIN) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around $487.

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

How to find a cheap flight from Kingston to Chicago

Understanding the common pitfalls when booking your flight tickets can help you save massively when it comes time to fly. We’ve listed our six essential steps to keep in mind when you’re booking flight tickets to help you find the best price.
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 Info | Kingston to Chicago

Cheapest nonstop flight price$234
Off-season for travelOctober
Peak season for travelAugust
Flight distance2,854.66 km
Popular airlineCaribbean Airlines

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