CHI - KIN

$127 Find Cheap Flights from Chicago to Kingston

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Kingston departing on 8/20. 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 Kingston

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

Cheap Flights from Chicago to Kingston (CHI-KIN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Kingston 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 Chicago to Kingston

Wed, Aug 20 - Thu, Aug 21
Spirit Airlines Logo
5:05 am - 11:27 amORD-KIN
6h 22m1 stop
Spirit Airlines Logo
9:47 am - 7:07 pmKIN-ORD
9h 20m1 stop
$322Spirit Airlines
Find Deal
Tue, Aug 26 - Tue, Sep 2
Spirit Airlines Logo
5:05 am - 11:27 amORD-KIN
6h 22m1 stop
Spirit Airlines Logo
12:32 pm - 11:59 pmKIN-ORD
11h 27m1 stop
$328Spirit Airlines
Find Deal
Wed, Aug 20 - Thu, Aug 21
Spirit Airlines Logo
11:21 am - 8:42 amORD-KIN
21h 21m2 stops
Spirit Airlines Logo
12:32 pm - 11:59 pmKIN-ORD
11h 27m1 stop
$333Spirit Airlines
Find Deal
Tue, Aug 19 - Mon, Aug 25
Spirit Airlines Logo
5:05 am - 11:27 amORD-KIN
6h 22m1 stop
Spirit Airlines Logo
9:47 am - 11:59 pmKIN-ORD
14h 12m1 stop
$355Spirit Airlines
Find Deal
Tue, Aug 19 - Mon, Aug 25
Spirit Airlines Logo
8:12 pm - 11:27 amORD-KIN
15h 15m1 stop
Spirit Airlines Logo
12:32 pm - 11:59 pmKIN-ORD
11h 27m1 stop
$359Spirit Airlines
Find Deal
Thu, Sep 11 - Sat, Sep 20
Spirit Airlines Logo
6:44 pm - 11:02 amORD-KIN
16h 18m1 stop
Spirit Airlines Logo
12:08 pm - 10:48 pmKIN-ORD
10h 40m1 stop
$360Spirit Airlines
Find Deal
Wed, Aug 13 - Wed, Aug 27
Spirit Airlines Logo
8:12 pm - 11:27 amORD-KIN
15h 15m1 stop
Spirit Airlines Logo
12:32 pm - 11:59 pmKIN-ORD
11h 27m1 stop
$362Spirit Airlines
Find Deal
Thu, Aug 28 - Thu, Sep 4
Spirit Airlines Logo
5:05 am - 11:27 amORD-KIN
6h 22m1 stop
Spirit Airlines Logo
12:08 pm - 10:48 pmKIN-ORD
10h 40m1 stop
$363Spirit Airlines
Find Deal
Wed, Sep 24 - Tue, Sep 30
Delta Logo
10:35 am - 8:00 pmMDW-KIN
9h 25m1 stop
Delta Logo
9:00 am - 9:36 pmKIN-MDW
12h 36m1 stop
$381Delta
Find Deal
Sun, Oct 26 - Fri, Oct 31
Delta Logo
7:10 am - 8:00 pmORD-KIN
12h 50m1 stop
Delta Logo
9:00 am - 11:53 pmKIN-ORD
14h 53m1 stop
$381Delta
Find Deal
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KAYAK's insights & trends for Chicago to Kingston flights

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

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

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

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

If you are looking for a flight deal from Chicago to Kingston, look for departures on Thursdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Kingston, Saturday is the cheapest day to fly and Tuesday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Kingston, 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 Chicago to Kingston is February, where tickets cost $380 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $1,041 and $761 respectively.

Good to know

Low seasonJuly
High seasonMarch
Cheapest flight$127
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 33% increase in price.
Flight from Chicago O'Hare 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
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 flights from Chicago to Kingston

  • What is the cheapest flight from Chicago to Kingston?

    In the last 3 days, the lowest price for a flight from Chicago to Kingston was $127 for a one-way ticket and $322 for a round-trip.

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

    A passport is required to fly from Chicago to Kingston.

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

    Chicago has 2 major airports: Chicago Midway and Chicago O'Hare Intl. Kingston Norman Manley is the only airport in Kingston. You’ll usually find the cheapest deals if you fly from Chicago O'Hare Airport.

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

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

  • Which airline alliances offer flights from Chicago to Kingston?

    SkyTeam, and Star Alliance are the airline alliances operating flights between Chicago and Kingston, with SkyTeam being the most commonly used for this route.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Kingston are Delta and Spirit Airlines. With an average price for the route of $690 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 $407 and an overall rating of 6.3.

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

    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 Chicago to Kingston.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Kingston from Chicago 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 Chicago to Kingston?

    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 Kingston with an airline and back to Chicago with another airline.

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

    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 Kingston from Chicago 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 Chicago to Kingston

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Kingston. 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 Chicago to Kingston? 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 7953 reviews
7.3Food
7.9Entertainment
8.2Boarding
8.5Crew
7.9Comfort
Airline reviews

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

4.0 OkayAnonymous, Jul 2025ATL - ROC
Read more Delta reviews

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Food was surprisingly good but the WiFi was not great

this crew didn't care much. bumping carts into seats more times than i care to remember

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

Great. Very smooth. Plenty of information. However, wish they would give out a menu in advance of making a dinner choice like other international airlines. The flight attendant says chicken or pasta and there are details about ingredients or spices requiring the passenger to ask which requires the flight attendant to answer many times. So easy to solve this problem. P

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I've flown Spirit many times. However, they seem to be getting worse. I don't understand how the contracts with the gates at the airport works, but Spirit never seems to have a gate ready when we land. This happened again on this flight. And once again, baggage took forever to arrive at the baggage claim belt. This time it was about 45 minutes to an hour, late at night, when the airport was not crowded. On a previous trip, they lost the luggage cart and we were all waiting for about 3 hours for our luggage. Plus, I did get a deal through Kayak on a flight that was shown sold out on Spirit's site. However, by the time I added all the luggage, and didn't even pick seats, I could have taken any direct flight I wanted through Delta. I'm about done with Spirit.

I enjoyed my flight, it was pretty smooth and we landed earlier than eta.

Booked through kayak, everything seemed normal but when it came time to go, my flight ticket didn’t exist, so I had to purchase another set of tickets at the airport the day of the flight, for about double. When I reached kayaks customer service, they claimed no responsibility, and pushed me onto another 3rd party booking service, airfare assist, where I have had no luck getting any kind of help or refund. I’ve used kayak many times, but I’ll never again after I’ve been burned by this.

The flight was delayed four and half hours for paperwork on a maintenance issue. Very frustrating.

It was okay delay was long but I made it

Flight was cancelled. No reason given. No apologies. Next available flight is two days later. Ruined our 4th of July plans.

The air fares are good, Charging me for every single thing 😩

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

Flight delayed over 3 or 4 hours because no captain to fly plane. I couldn’t make a connection and had to wait 9 hours for another flight. Had to fly red eye flight. Sucks

it was a quick trip. seats aren't that comfortable but because it was a quick trip it was ok. You need to have an N/A in your rating as I didn't have any food or entertainment so the only thing I could do was score low.

Everything you need to know for your flight from Chicago to Kingston

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