CHI - KIN

$155 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 11/7. 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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Flight 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

Tue, Nov 4 - Fri, Nov 7
Spirit Airlines Logo
10:52 am - 12:01 pmORD-KIN
24h 09m1 stop
Spirit Airlines Logo
1:06 pm - 11:12 amKIN-ORD
23h 06m1 stop
$348Spirit Airlines
Find Deal
Wed, Dec 3 - Thu, Dec 11
Multiple Airlines Logo
3:43 pm - 12:14 pmORD-KIN
19h 31m1 stop
Multiple Airlines Logo
1:19 pm - 7:21 pmKIN-ORD
7h 02m1 stop
$356Multiple Airlines
Find Deal
Wed, Dec 3 - Mon, Dec 15
Spirit Airlines Logo
3:43 pm - 12:14 pmORD-KIN
19h 31m1 stop
Spirit Airlines Logo
1:19 pm - 11:14 amKIN-ORD
22h 55m1 stop
$365Spirit Airlines
Find Deal
Tue, Nov 4 - Fri, Nov 7
Spirit Airlines Logo
1:48 pm - 12:01 pmORD-KIN
21h 13m2 stops
Spirit Airlines Logo
1:06 pm - 12:27 amKIN-ORD
12h 21m1 stop
$368Spirit Airlines
Find Deal
Thu, Dec 4 - Thu, Dec 11
Multiple Airlines Logo
4:21 pm - 12:14 pmORD-KIN
18h 53m1 stop
Multiple Airlines Logo
1:19 pm - 7:21 pmKIN-ORD
7h 02m1 stop
$374Multiple Airlines
Find Deal
Tue, Feb 17 - Fri, Feb 27
Delta Logo
5:50 am - 8:00 pmORD-KIN
13h 10m1 stop
Delta Logo
9:00 am - 6:57 pmKIN-ORD
10h 57m1 stop
$413Delta
Find Deal
Tue, Feb 17 - Tue, Feb 24
Delta Logo
6:00 am - 8:00 pmMDW-KIN
13h 00m1 stop
Delta Logo
9:00 am - 6:34 pmKIN-MDW
10h 34m2 stops
$418Delta
Find Deal
Sat, Dec 6 - Sat, Dec 13
American Airlines Logo
10:06 am - 10:34 pmORD-KIN
11h 28m2 stops
American Airlines Logo
1:42 pm - 11:51 pmKIN-ORD
11h 09m2 stops
$438American Airlines
Find Deal
Tue, Nov 4 - Fri, Nov 7
WestJet Logo
1:48 pm - 3:33 pmMDW-KIN
24h 45m2 stops
WestJet Logo
4:30 pm - 5:43 pmKIN-MDW
26h 13m2 stops
$722WestJet
Find Deal
Tue, Nov 4 - Fri, Nov 7
WestJet Logo
9:20 am - 3:33 pmMDW-KIN
29h 13m2 stops
WestJet Logo
4:30 pm - 10:30 amKIN-MDW
19h 00m3 stops
$1,296WestJet
Find Deal

Everything you should know

Top airlines
Spirit Airlines
Cheapest • from $348 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
February
Cheapest • 30% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$348
Overall average: $582
Spirit Airlines
Tue 11/4Fri 11/7
ORD - KIN • 1 stop
Cheapest one-way
$155
Typical prices: $161-$261
Spirit Airlines
Fri 11/7
ORD - KIN • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Kingston!
Booking Insights

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.

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 June, where the average cost of round-trip tickets is $916 and $590 respectively.

Good to know

Low seasonJuly
Cheapest flight$155
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 6% 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 $155 for a one-way ticket and $348 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 oneworld 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 American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Kingston are Delta and American Airlines. With an average price for the route of $572 and an overall rating of 7.9, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $567 and an overall rating of 7.2.

  • 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.
7.9
DeltaOverall score based on 7984 reviews
8.2Boarding
7.3Food
7.9Comfort
8.5Crew
7.9Entertainment
Airline reviews

Old plane and old configuration/seats but still comfortable for a morning flight

10.0 ExcellentBraulio, Oct 2025ATL - SDQ
Read more Delta reviews

Old plane and old configuration/seats but still comfortable for a morning flight

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

On time flight. Seat comfort could be better in the Comfort section.

My issue was with TSA agents for delta airlines. My luggage got flagged. The agent was going thru another persons first. He took 20 min to go thru hers. I asked them to bring mine closer so I could sit down . They said you can go sit it will be fine. I said I am supposed to keep my eyes on my bags at all times. The agent was meticulously unwrapping 2 gifts that the lady had and then tried to re warp it. He was trying to be kind i get it but 20 min for me to stand watching him do that was ridiculous. It was 6 am and there were a ton of travelers. Mine was flagged for some air packed tea that I bought in Turkey. My previous delta flight and 2 others before didn’t flag it. Consistency would be nice. Also on the flight the window shades were down for take off and landing - I thought that was very odd I thought they had to remain open for take off and landing.

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

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!

Very sad about what Spirit has become, because the flights I had with them were delayed between an hour and a half and two, terrible service

Vegas is such a quick flight that amenities aren’t the important part, in my opinion. Just get me there efficiently and safely, and that’s exactly what they did!

The flight was severely delayed due to the missing flight attendants.

Absolutely horrible. Usually pay $40-$50 to check luggage in. I tried to check my suitcase in and the price is raised to $70. That's ridiculously greedy c'mon. I had to leave my suitcase with all my clothes and hygiene products and repurchase once i landed in Atlanta. You guys make it really stressful to travel. Don't even want to travel anymore.

They cancelled the flight 3 hours prior departure. Had to spend $400 for a ne way flight with Delta Airlines! Spirit Airlines are not serios!

My luggage didn’t arrive at LAX, so that wasn’t a good experience.

Terrible seat, no in flight entertainment. No complimentary food or drinks. Seats really hurt my back after flying spirit for the day.

Plastic seat really hurt my back. Cannot even recline on the flight. Very hard to sleep on the plane due to terrible seats . Food and drinks were expensive and not very good. There were like 2 open exit rows behind me. My isle was full so I asked flight attendants if I could sit there. They told me it was a safety issue??? I think it more unsafe to have no one sitting there. In case of emergency, you’d want someone there to help.

The delays and the lack of communication and organization within the airport itself for Staffing this flight and coordinating the paper log necessary to depart was ridiculous and deplorable

It was a no show, so we got put in hotels for a nite. The A320 plane was very modern and flite and crew (if a pilot shows up were fine). Price was very good.

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

Information on your arrival and departure airports

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