KIN - ORD

$284 Find Cheap Flights from Kingston to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Kingston to O'Hare Intl departing on 8/28. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Kingston to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Kingston to Chicago, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Kingston to Chicago (KIN-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Kingston to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Kingston to O'Hare Intl

Tue, Sep 30 - Tue, Oct 7
Spirit Airlines Logo
12:08 pm - 10:48 pmKIN-ORD
10h 40m1 stop
Spirit Airlines Logo
7:29 pm - 11:09 amORD-KIN
15h 40m1 stop
$301Spirit Airlines
Find Deal
Wed, Sep 17 - Wed, Sep 24
Spirit Airlines Logo
12:08 pm - 10:48 pmKIN-ORD
10h 40m1 stop
Spirit Airlines Logo
6:44 pm - 11:02 amORD-KIN
16h 18m1 stop
$323Spirit Airlines
Find Deal
Wed, Sep 17 - Wed, Sep 24
Spirit Airlines Logo
12:08 pm - 10:48 pmKIN-ORD
10h 40m1 stop
Spirit Airlines Logo
5:46 pm - 11:02 amORD-KIN
17h 16m2 stops
$334Spirit Airlines
Find Deal
Thu, Oct 2 - Thu, Oct 9
Spirit Airlines Logo
12:08 pm - 10:48 pmKIN-ORD
10h 40m1 stop
Spirit Airlines Logo
5:05 am - 11:09 amORD-KIN
6h 04m1 stop
$369Spirit Airlines
Find Deal
Thu, Oct 2 - Thu, Oct 9
Spirit Airlines Logo
12:08 pm - 10:48 pmKIN-ORD
10h 40m1 stop
Spirit Airlines Logo
1:26 pm - 11:09 amORD-KIN
21h 43m2 stops
$382Spirit Airlines
Find Deal
Sat, Dec 27 - Sat, Jan 3
Delta Logo
9:00 am - 9:27 pmKIN-ORD
13h 27m1 stop
Delta Logo
7:05 am - 8:00 pmORD-KIN
11h 55m1 stop
$456Delta
Find Deal
Wed, Oct 1 - Thu, Oct 9
JetBlue Logo
2:47 am - 12:21 pmKIN-ORD
9h 34m1 stop
JetBlue Logo
1:36 pm - 12:39 amORD-KIN
11h 03m1 stop
$538JetBlue
Find Deal
Thu, Dec 11 - Sat, Jan 3
Delta Logo
9:00 am - 8:36 pmKIN-ORD
12h 36m2 stops
Delta Logo
7:00 am - 8:00 pmORD-KIN
12h 00m2 stops
$562Delta
Find Deal
Thu, Dec 11 - Tue, Dec 30
 Logo
1:28 pm - 9:00 pmKIN-ORD
8h 32m1 stop
 Logo
4:35 am - 8:53 amORD-KIN
27h 18m1 stop
Thu, Dec 11 - Tue, Dec 30
 Logo
3:30 pm - 2:06 pmKIN-ORD
23h 36m2 stops
 Logo
4:35 am - 8:53 amORD-KIN
27h 18m1 stop
Booking Insights

KAYAK's insights & trends for Kingston to O'Hare Intl flights

Get data-powered insights and trends into flights from Kingston to O'Hare Intl to help you find the cheapest flights, the best time to fly and much more.

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

The average price of all round-trip flights from Kingston to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago on a Saturday, as we generally find the cheapest rates on that day for this route. On the other hand, Tuesday is the most expensive day to fly from Kingston to Chicago. For your return ticket, we recommend flying on a Thursday and avoiding Sundays for the best deals.

What is the cheapest month to fly from Kingston to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Kingston to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Kingston to Chicago O'Hare Intl Airport is September, where tickets cost $331 (return) on average. On the other hand, the most expensive months are April and July, where the average cost of round-trip tickets is $845 and $564 respectively.

Good to know

Low seasonApril
Cheapest flight$284
Best time to beat the crowds but there is an average 67% increase in price.
Most popular time to fly and prices are also 20% lower on average.
Flight from Kingston to Chicago

When to book flights from Kingston to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Kingston to O'Hare Intl based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Kingston to Chicago flights

  • What is the cheapest flight from Kingston to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Kingston to Chicago O'Hare Intl Airport was $284 for a one-way ticket and $301 for a round-trip.

  • Do I need a passport to fly between Kingston and Chicago?

    A passport is required to fly from Kingston to Chicago.

  • Which airports will I be using when flying from Kingston to Chicago?

    Kingston and Chicago are both served by 1 main airport. You will leave Kingston from Kingston Norman Manley and will be arriving at Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Kingston to Chicago?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Kingston to Chicago?

    SkyTeam is the only airline alliance operating flights between Kingston and Chicago.

  • Which is the best airline for flights from Kingston to Chicago, Delta or Spirit Airlines?

    The two airlines most popular with KAYAK users for flights from Kingston to Chicago are Delta and Spirit Airlines. With an average price for the route of $489 and an overall rating of 8.0, Delta is the most popular choice. Spirit Airlines is also a great choice for the route, with an average price of $406 and an overall rating of 6.3.

  • How does KAYAK find such low prices on flights from Kingston to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Kingston to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Kingston to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Kingston is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Kingston to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Kingston with another airline. Booking your flights between Kingston and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Kingston to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Kingston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Kingston to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying from Kingston to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Kingston to O'Hare Intl? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 7981 reviews
7.9Comfort
7.9Entertainment
7.3Food
8.5Crew
8.2Boarding
Airline reviews

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

10.0 ExcellentLee, Aug 2025ATL - PHL
Read more Delta reviews

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

Our seats were comfortable with adequate room to stretch out and recline. The food was tasty and served it just the right intervals. Our flight attendant was extra attentive and friendly. Flight arrived early. And the most turbulence. Overall that’s good and experience for an 11 hour flight as can be hoped for

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.

There was supposed to be a meal served, but there wasn’t and the major toilet was out of order

They made us board and then deboard due to mechanical issue which delayed the departure by almost 2 hours and we barely made our connecting flight. These quality checks should've been done before boarding not after.

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

They should have MSNBC available on board. A 4- hour flight should provide more than a cookie.

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

As expected. Nothing jumps out at me as bad or wrong, but the flight was fine. No complaints with pilot or crew. The flight left on time and arrived earlier than stated. Overall, I will continue to plan on flying with Spirit.

I didnt take the flight because your company booked it through a scam agency called airline assist. There was no flight. You guys suck.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

Everything you need to know for your flight from Kingston to O'Hare Intl

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