CHI - KIN

$198 Find Cheap Flights from Chicago to Kingston - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$486
Typical prices: $523-$720
JetBlue
Sat 10/20Mon 10/22
ORD - KIN • 1 stop
Cheapest one-way
$198
Typical prices: $195-$340
American Airlines
Sat 12/1
ORD - KIN • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Chicago and Kingston. You'll need to take a connecting flight to reach the destination.
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Insights
Top routes
ORD - KIN
Cheapest • 2% average savings
MDW - KIN
Most popular
Insights
Insights
When to travel
August
Cheapest • 15% price drop
September
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Fort Lauderdale (FLL)
Cheapest • Avg $554 (round-trip)
Miami (MIA)
Shortest trip • 7h 38m (one-way)
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Insights
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Flight Deals

Cheap Flights from Chicago to Kingston (CHI-KIN)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Kingston

Sat, Nov 14 - Thu, Nov 19
Multiple Airlines Logo
10:27 am - 7:21 pmORD  Chicago O'Hare Intl-KIN Kingston Norman Manley
7h 54m1 stop Punta Cana
Multiple Airlines Logo
4:00 pm - 5:43 pmKIN  Kingston Norman Manley-ORD Chicago O'Hare Intl
26h 43m1 stop Toronto Pearson Intl
$472Multiple Airlines
Sat, Nov 14 - Thu, Nov 19
Multiple Airlines Logo
10:27 am - 7:21 pmORD  Chicago O'Hare Intl-KIN Kingston Norman Manley
7h 54m1 stop Punta Cana
Multiple Airlines Logo
4:00 pm - 2:52 pmKIN  Kingston Norman Manley-ORD Chicago O'Hare Intl
23h 52m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
$475Multiple Airlines
Tue, Oct 20 - Thu, Oct 22
JetBlue Logo
7:00 am - 12:43 pmORD  Chicago O'Hare Intl-KIN Kingston Norman Manley
5h 43m1 stop Fort Lauderdale
JetBlue Logo
4:10 pm - 11:30 pmKIN  Kingston Norman Manley-ORD Chicago O'Hare Intl
7h 20m1 stop Fort Lauderdale
$486JetBlue
Thu, Nov 5 - Mon, Nov 9
JetBlue Logo
7:00 am - 1:48 pmORD  Chicago O'Hare Intl-KIN Kingston Norman Manley
5h 48m1 stop Fort Lauderdale
JetBlue Logo
5:02 pm - 11:55 pmKIN  Kingston Norman Manley-ORD Chicago O'Hare Intl
7h 53m1 stop Fort Lauderdale
$486JetBlue
Mon, Nov 23 - Fri, Dec 4
American Airlines Logo
6:15 pm - 3:18 pmORD  Chicago O'Hare Intl-KIN Kingston Norman Manley
20h 03m1 stop Miami
American Airlines Logo
7:15 am - 7:49 pmKIN  Kingston Norman Manley-ORD Chicago O'Hare Intl
13h 34m1 stop Miami
$497American Airlines
Thu, Nov 19 - Tue, Nov 24
American Airlines Logo
2:38 pm - 10:23 pmORD  Chicago O'Hare Intl-KIN Kingston Norman Manley
6h 45m1 stop Miami
American Airlines Logo
7:00 am - 9:35 pmKIN  Kingston Norman Manley-ORD Chicago O'Hare Intl
15h 35m1 stop Miami
$555American Airlines
Mon, Nov 30 - Sat, Dec 12
Delta Logo
6:00 am - 8:00 pmMDW  Chicago Midway-KIN Kingston Norman Manley
13h 00m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:00 am - 10:55 pmKIN  Kingston Norman Manley-MDW Chicago Midway
14h 55m1 stop Atlanta Hartsfield-Jackson
$824Delta
Tue, Jan 5 - Mon, Jan 11
Delta Logo
10:35 am - 8:00 pmMDW  Chicago Midway-KIN Kingston Norman Manley
8h 25m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:00 am - 4:25 pmKIN  Kingston Norman Manley-MDW Chicago Midway
8h 25m1 stop Atlanta Hartsfield-Jackson
$824Delta
Mon, Nov 23 - Fri, Dec 4
Delta Logo
6:00 am - 8:00 pmMDW  Chicago Midway-KIN Kingston Norman Manley
13h 00m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:00 am - 4:17 pmKIN  Kingston Norman Manley-MDW Chicago Midway
8h 17m1 stop Atlanta Hartsfield-Jackson
$824Delta
Wed, Oct 7 - Sat, Oct 17
Delta Logo
6:04 am - 8:15 pmMDW  Chicago Midway-KIN Kingston Norman Manley
14h 11m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:15 am - 10:33 pmKIN  Kingston Norman Manley-MDW Chicago Midway
13h 18m1 stop Atlanta Hartsfield-Jackson
$824Delta
Booking Insights

Price, demand and travel trends for Chicago to Kingston flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Chicago to Kingston with more confidence.

How much is a round-trip flight from Chicago to Kingston?

Round-trip flights from Chicago to Kingston start at $486. Prices are below average for this route right now, with typical round-trip fares ranging from $523 to $720. The lowest price found in the past 5 days was $486 on JetBlue.

What is the cheapest Chicago to Kingston flight route?

There's little price difference between Chicago to Kingston routes. They average around $622 round-trip, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Chicago to Kingston?

Monday is the cheapest day of the week to fly from Chicago to Kingston, it is 9% cheaper than the average day. Thursday is the most expensive day with flight prices 9% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Chicago to Kingston?

  • August is the cheapest month to fly from Chicago to Kingston at $520 round-trip.
  • December ($883) and March ($699) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 69% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Find deals

Key details for Chicago to Kingston flights

Low season

December

Cheapest flight

$198
Best time to beat the crowds but there is an average 44% increase in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Chicago O'Hare Intl Airport to Kingston

When to book flights from Chicago to Kingston

Are your dates flexible? Find out the best times to travel from Chicago to Kingston based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago to Kingston flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airports can I use when flying from Chicago to Kingston?

    Flights from Chicago to Kingston may depart from several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Flights usually arrive at Kingston Norman Manley (KIN).

  • What cabin classes can I book on flights from Chicago to Kingston?

    Three cabin classes are available on flights from Chicago to Kingston:

    • Economy Class
    • Premium Economy Class
    • First Class

  • Which airports do connecting flights from Chicago to Kingston pass through?

    One-stop flights from Chicago to Kingston most commonly connect through:

    • Miami (MIA) - 59% of one-stop connections
    • Fort Lauderdale (FLL) - 21% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 17% of one-stop connections
    • New York John F Kennedy Intl (JFK) - 1% of one-stop connections

    Miami (MIA) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Chicago to Kingston?

    Yes. Being flexible with your travel dates can save you up to 17% on the Chicago to Kingston route. Monday is the cheapest departure day at $560 round-trip on average, while Thursday is the most expensive at $671, a difference of $111. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How long is a flight from Chicago to Kingston?

    A nonstop flight from Chicago to Kingston takes 0h 00m, covering 1,772 miles.

  • Do I need a passport to fly from Chicago to Kingston?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • Have flight prices from Chicago to Kingston changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $486 to $4,005. That means the highest observed fare was about 8x higher than the lowest one.

  • How are flight prices from Chicago to Kingston looking right now?

    One-way fares from Chicago to Kingston are currently in line with typical prices for this route. Average one-way fares are about $250.

  • How much time can I save by choosing a different layover airport from Chicago to Kingston?

    Flying via Miami (MIA) gives the shortest average 1-stop total travel time at 7h 38m, compared with 8h 29m via Fort Lauderdale (FLL) and 8h 36m via Atlanta Hartsfield-Jackson (ATL).

  • What car rental options are available at Kingston Norman Manley Airport (KIN)?

    Kingston Norman Manley Airport (KIN) hosts 5 major car rental companies, with daily rates starting from around $24 for economy cars. Top options include:
    · Island Car Rentals
    · U-Save
    · Avis
    · Budget
    · ACO Rent A Car

  • How much should I expect to pay for a Chicago to Kingston flight?

    Round-trip flights from Chicago to Kingston range from $523 to $720, with an average of $613 over the past 12 months. Anything below $523 counts as a good deal.

Your guide to booking Chicago to Kingston flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Monday departure instead of Thursday. On this route, Monday flights average $560 - about $111 less than Thursday (17% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Chicago to Kingston trip for August. Fares historically average $520 round-trip in that month - typically $363 less than the most expensive month, which is December (based on the last 12 months).

More options for your flight from Chicago to Kingston

Complete your trip to Kingston with a hotel stay or car rental

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