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 1/10. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$332
Overall average: $455
Spirit Airlines
Wed 1/21Mon 2/23
ORD - KIN • 1 stop
Cheapest one-way
$127
Typical prices: $178-$186
Arajet
Sat 1/10
ORD - KIN • 1 stop
Top airlines
Spirit Airlines
Cheapest • from $351 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
February
Cheapest • 33% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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!
Flight Deals
Booking Insights
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

Wed, Jan 21 - Mon, Feb 23
Spirit Airlines Logo
5:32 pm - 12:12 pm
ORD
-
KIN
17h 40m1 stop
Spirit Airlines Logo
1:17 pm - 11:47 pm
KIN
-
ORD
11h 30m1 stop
$332Spirit Airlines
Wed, Feb 4 - Thu, Feb 26
Multiple Airlines Logo
5:32 pm - 12:12 pm
ORD
-
KIN
17h 40m1 stop
Multiple Airlines Logo
1:17 pm - 11:05 pm
KIN
-
ORD
10h 48m1 stop
$343Multiple Airlines
Sun, Feb 1 - Thu, Feb 26
Multiple Airlines Logo
3:05 pm - 12:12 pm
ORD
-
KIN
20h 07m1 stop
Multiple Airlines Logo
1:17 pm - 11:05 pm
KIN
-
ORD
10h 48m1 stop
$347Multiple Airlines
Wed, Feb 4 - Sun, Feb 22
Spirit Airlines Logo
5:32 pm - 12:12 pm
ORD
-
KIN
17h 40m1 stop
Spirit Airlines Logo
1:17 pm - 11:22 am
KIN
-
ORD
23h 05m1 stop
$351Spirit Airlines
Sun, Feb 1 - Mon, Feb 23
Multiple Airlines Logo
3:05 pm - 12:12 pm
ORD
-
KIN
20h 07m1 stop
Multiple Airlines Logo
1:17 pm - 9:13 pm
KIN
-
ORD
8h 56m1 stop
$355Multiple Airlines
Thu, Feb 5 - Mon, Feb 23
Spirit Airlines Logo
8:43 pm - 12:12 pm
ORD
-
KIN
14h 29m1 stop
Spirit Airlines Logo
1:17 pm - 11:47 pm
KIN
-
ORD
11h 30m1 stop
$363Spirit Airlines
Wed, Jan 21 - Mon, Feb 23
Spirit Airlines Logo
12:42 pm - 12:12 pm
ORD
-
KIN
22h 30m2 stops
Spirit Airlines Logo
1:17 pm - 11:47 pm
KIN
-
ORD
11h 30m1 stop
$366Spirit Airlines
Sun, Feb 1 - Thu, Feb 26
Delta Logo
10:48 am - 8:00 pm
MDW
-
KIN
8h 12m1 stop
Delta Logo
9:00 am - 5:45 pm
KIN
-
MDW
9h 45m1 stop
$445Delta
Tue, Feb 3 - Fri, Feb 27
Delta Logo
6:35 pm - 8:00 pm
MDW
-
KIN
24h 25m2 stops
Delta Logo
9:00 am - 5:45 pm
KIN
-
MDW
9h 45m1 stop
$450Delta
Fri, Jan 16 - Thu, Jan 22
Delta Logo
6:30 pm - 8:00 pm
MDW
-
KIN
24h 30m2 stops
Delta Logo
9:00 am - 5:29 pm
KIN
-
MDW
9h 29m1 stop
$521Delta
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.

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Kingston departing in January.

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 November and December, where the average cost of round-trip tickets is $1,007 and $758 respectively.

Good to know

Low seasonJuly
Cheapest flight$127
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 1% 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 $332 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 $578 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 8014 reviews
7.9Entertainment
7.9Comfort
8.5Crew
8.1Boarding
7.3Food
Airline reviews

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

10.0 ExcellentNguyen, Dec 2025
DCA - SEA
Read more Delta reviews

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

The flight was delayed for about 2 hrs. Other than it, it was good.

Advertised fruit trays with cheese, but only snacks handed out!

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

Great. I had to modify a flight. That was easy and free. Thank You

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

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.

Awful!!! Spirit cancelled my flight just 4 hours before departure- with no alternative flights available. I ended up missing a huge family gathering because I wasn’t able to get out. Such An awful experience. And on top of that, all the buckle and dime-ing for bags. I will never book with Spirit EVER

Spirit has improved a lot since I flew with it in 2011. I give the airline a huge thumbs up!!

My flight was cancelled for “weather”. There was absolutely no bad weather along the course of my flight track. I missed my entire vacation with my family. I will never book a flight with spirit again

Flight was cancelled 2.5 before departure without warning. Staff was rude and lied to us pre-security.

I'd have like to check my bag and not toss my hair products.sears are very uncomfortable. And that even water isn't free really sucks. The ticket was almost $400

Terrible. They cancelled the flight at the last minute after I had checked in at the airport and then told me they could only put me on a flight after 7 days. Pathetic.

Terrible they canceled the flight very sheepishly and ended up costing me 1200 dollars and kayak and xcover are doing nothing

It’s Spirit need I say more? Thank this little airline because without it the other airlines would raise their prices so much I wouldn’t be able to fly anywhere. It’s affordable and gets you where you need to go! I’m not flying to get a free bag of chips, y’know?

Spirit cancelled the flight very late last night, I was on the way to the airport when I found out

First time in a decade I threw up on the flight, turbulence was terrible!! The staff were kinda rude at times.

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

Information on your arrival and departure airports