CHI - KIN

$161 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 2/15. 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
$389
Overall average: $427
Spirit Airlines
Thu 2/19Mon 2/23
ORD - KIN • 1 stop
Cheapest one-way
$161
Overall average: $272
Multiple Airlines
Sun 2/15
ORD - KIN • 1 stop
Top airlines
Spirit Airlines
Cheapest • from $389 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
February
Cheapest • 31% 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

Thu, Feb 19 - Mon, Feb 23
Spirit Airlines Logo
5:15 am - 12:15 pm
ORD
-
KIN
6h 00m
1 stop
Spirit Airlines Logo
1:17 pm - 11:22 am
KIN
-
ORD
23h 05m
1 stop
$389Spirit Airlines
Thu, Feb 5 - Thu, Feb 12
Spirit Airlines Logo
8:43 pm - 12:12 pm
ORD
-
KIN
14h 29m
1 stop
Spirit Airlines Logo
1:17 pm - 11:47 pm
KIN
-
ORD
11h 30m
1 stop
$411Spirit Airlines
Thu, Feb 19 - Mon, Feb 23
Multiple Airlines Logo
3:40 pm - 12:15 pm
ORD
-
KIN
19h 35m
1 stop
Multiple Airlines Logo
1:17 pm - 11:22 am
KIN
-
ORD
23h 05m
1 stop
$419Multiple Airlines
Mon, Apr 13 - Wed, Apr 22
Spirit Airlines Logo
5:05 am - 11:00 am
ORD
-
KIN
5h 55m
1 stop
Spirit Airlines Logo
12:00 pm - 11:41 pm
KIN
-
ORD
11h 41m
1 stop
$431Spirit Airlines
Thu, Feb 19 - Mon, Feb 23
Multiple Airlines Logo
3:40 pm - 12:15 pm
ORD
-
KIN
19h 35m
1 stop
Multiple Airlines Logo
1:17 pm - 4:52 pm
KIN
-
ORD
28h 35m
2 stops
$435Multiple Airlines
Mon, Mar 16 - Wed, Mar 25
Spirit Airlines Logo
8:41 pm - 11:00 am
ORD
-
KIN
14h 19m
1 stop
Spirit Airlines Logo
12:17 pm - 7:46 pm
KIN
-
ORD
7h 29m
1 stop
$437Spirit Airlines
Thu, Feb 5 - Thu, Feb 12
Spirit Airlines Logo
8:43 pm - 12:12 pm
ORD
-
KIN
14h 29m
1 stop
Spirit Airlines Logo
1:17 pm - 9:13 pm
KIN
-
ORD
8h 56m
1 stop
$444Spirit Airlines
Wed, Feb 18 - Wed, Feb 25
Delta Logo
10:49 am - 8:00 pm
MDW
-
KIN
8h 11m
1 stop
Delta Logo
9:00 am - 10:31 pm
KIN
-
MDW
14h 31m
1 stop
$466Delta
Wed, Feb 18 - Wed, Feb 25
Delta Logo
9:34 am - 8:00 pm
MDW
-
KIN
9h 26m
2 stops
Delta Logo
9:00 am - 5:45 pm
KIN
-
MDW
9h 45m
1 stop
$471Delta
Fri, Apr 17 - Wed, Apr 22
Delta Logo
6:30 am - 8:05 pm
MDW
-
KIN
13h 35m
1 stop
Delta Logo
9:00 am - 10:29 pm
KIN
-
MDW
13h 29m
1 stop
$550Delta
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 February.

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 $589 respectively.

Good to know

Low seasonJuly
Cheapest flight$161
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 4% 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 $161 for a one-way ticket and $389 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 $547 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 $582 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 8088 reviews
7.9Comfort
7.2Food
8.5Crew
7.8Entertainment
8.1Boarding
Airline reviews

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

4.0 OkayJohn, Jan 2026
DAL - ATL
Read more Delta reviews

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

Good seat comfort ORF to ATL. Bad seat ATL to SEA (terrible lumbar support, hard, ouch)..

Because I was moved to an exit row, the snacks in economy comfort, the selection of snacks was better.

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

Easiest airport experience ever in my life at MSP with Delta check-in and flight attendant gave us a bottle of champagne in celebration of our 10-year wedding anniversary, so overall amazing!

No in flight service, no explanation - FC got service, C+ did not, unsure about Economy. No turbulence to speak of, so I guess another way to cut cost, or promote health and well being of Delta employees? Also, boarding in MEM combined zones, and with overhead space already full on both flights after Zone 2/ Diamond, presents a huge challenge to find a space for a bag. Delta, other than point A to B, is no longer reasonable to fly - very poor experiences, not even taking into account the chastising at the gate and rude crews, across the board.

It would have been better if the flight wasn't delayed by 2.5 hours

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

Delta flight Delay for ,more that two hours i.e original flight was 6.30 PM and it starts at 8.45 PM, When we connect Delta team for meal vouchers as it is late arrival in designation,But we did not get it as per delta policy , which is not good for mid night arrival,

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

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.

Extra legroom with my upgrade bundle. Clean aircraft, on-time departure, early arrival. Good value for the price.

I didn't have a flight because of a ticking problem that was discovered at the airport at checkin for the initial flight of the round trip.

Even though the plane was delayed from the previous airport, the staff recognized this and kept us informed. The flight crew was absolutely awesome from on my flight from Ft. Meyers to AC. Great experience all around!

Flight was delayed would have liked it to have been on time. I didn't experience the food or entertainment but the boarding process was smooth and the flight crew worked well together and did a great job!

Not seat assigned because overbooking. We could go because some people decided to give their seats.

Spirit loves to pick and choose when to harass you about your personal item. I’ve flown numerous times with the same bag with no problem yet flying out of Orlando they forced me to pay $99 for a carry on and then ran out of overhead space. Do better!

For the price of the fare, there really isn’t much to complain about.

didn't order food on board. there's no way to hold a water botton on the way. otherwise it was a pleasant flight, thanks to the crew.

Even though there was a delay the crew was exceptional.

Cheap, only one short delay. No issues despite bad weather. Able to take a big backpack for free.

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

Information on your arrival and departure airports