CHI - KIN

$147 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 3/8. 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
$382
Overall average: $398
Spirit Airlines
Thu 4/16Tue 4/21
ORD - KIN • 1 stop
Cheapest one-way
$147
Typical prices: $183-$352
Spirit Airlines
Sun 3/8
ORD - KIN • 1 stop
Top airlines
Spirit Airlines
Cheapest • from $382 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
April
Cheapest • 23% price drop
October
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, Apr 16 - Tue, Apr 21
Spirit Airlines Logo
5:05 am - 11:06 am
ORD
-
KIN
6h 01m
1 stop
Spirit Airlines Logo
12:11 pm - 12:14 am
KIN
-
ORD
12h 03m
1 stop
$382Spirit Airlines
Thu, Apr 16 - Tue, Apr 21
Spirit Airlines Logo
5:34 pm - 11:06 am
ORD
-
KIN
17h 32m
1 stop
Spirit Airlines Logo
12:11 pm - 7:47 pm
KIN
-
ORD
7h 36m
1 stop
$387Spirit Airlines
Sun, Mar 8 - Mon, Mar 9
Spirit Airlines Logo
5:15 am - 11:15 am
ORD
-
KIN
6h 00m
1 stop
Spirit Airlines Logo
12:17 pm - 11:22 am
KIN
-
ORD
23h 05m
1 stop
$389Spirit Airlines
Fri, Mar 6 - Wed, Mar 18
Spirit Airlines Logo
5:15 am - 12:15 pm
ORD
-
KIN
6h 00m
1 stop
Spirit Airlines Logo
12:32 pm - 11:17 pm
KIN
-
ORD
10h 45m
1 stop
$391Spirit Airlines
Tue, Mar 17 - Tue, Mar 24
Spirit Airlines Logo
5:05 am - 11:35 am
ORD
-
KIN
6h 30m
1 stop
Spirit Airlines Logo
12:32 pm - 11:17 pm
KIN
-
ORD
10h 45m
1 stop
$395Spirit Airlines
Thu, May 28 - Wed, Jun 3
Air Canada Logo
1:55 pm - 1:55 pm
ORD
-
KIN
24h 00m
2 stops
Air Canada Logo
3:05 pm - 9:05 am
KIN
-
ORD
18h 00m
1 stop
$429Air Canada
Fri, Mar 6 - Wed, Mar 11
Delta Logo
6:00 am - 8:00 pm
MDW
-
KIN
13h 00m
1 stop
Delta Logo
9:00 am - 10:31 pm
KIN
-
MDW
13h 31m
1 stop
$476Delta
Fri, Mar 6 - Mon, Mar 9
Delta Logo
6:00 am - 8:00 pm
MDW
-
KIN
13h 00m
1 stop
Delta Logo
9:00 am - 5:22 pm
KIN
-
MDW
8h 22m
1 stop
$560Delta
Fri, Mar 6 - Wed, Mar 11
Delta Logo
6:00 am - 8:00 pm
MDW
-
KIN
13h 00m
1 stop
Delta Logo
9:00 am - 5:54 pm
KIN
-
MDW
8h 54m
2 stops
$565Delta
Fri, Mar 6 - Wed, Mar 11
Delta Logo
6:00 am - 8:00 pm
MDW
-
KIN
13h 00m
1 stop
Delta Logo
9:00 am - 5:54 pm
KIN
-
MDW
8h 54m
2 stops
$609Delta
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 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 April, where tickets cost $440 (return) on average. On the other hand, the most expensive months are November and February, where the average cost of round-trip tickets is $1,007 and $719 respectively.

Good to know

Low seasonJuly
Cheapest flight$147
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 7% lower on average.
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 $147 for a one-way ticket and $382 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 $485 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 $589 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 8204 reviews
7.9Comfort
7.8Entertainment
8.5Crew
7.2Food
8.1Boarding
Airline reviews

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

10.0 ExcellentSoosnata, Feb 2026
LAX - HNL
Read more Delta reviews

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Good experience and the flight landed early. There was no food I had or entertainment.

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

Flight was delayed. No information on why it was delayed. After we boarded the flight, , the crew made announcement that the captain hs not arrived and he will take 15 mins more to arrive. Passengers were just sitting patiently for the captain to arrive and start, Terrible experience.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Smallest leg room I've ever had on a plane.

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Excellent!!! Aeromexico is a great airline. What was not that good is the service provided by Kayak. It is never clear and not easy to manage.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

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.

Terrible. Spirit cancelled the flight with 3 hours notice and were absolutely no help getting another flight. Had to make my own reservation on another airline and arrived in Dallas 12 hours later.

The flight itself was great except for an air traffic controller delay. We left 30 min late but they made up most of the time in flight. The booking was frustrating, as we chose a certain flight and it was changed four times. We got to Orlando several hours later than the original flight we chose.

Crew was very nice. Take off and landing were great. Economy seats are not comfortable. Extra cost for snacks.

Less than acceptable. Family members had flights cancelled with no reason. Multiple hour delay, gate changes, poor communication, less than satisfactory. I will never fly with spirit again, which is a shame because it’s a budget friendly option but quite frankly with all of the hassle and hoops that come with flying spirit. Completely unacceptable.

Everything was terrible. Flight was delayed several hours, crew was abrasive. Stuck on runway for over a hour. There was an argument between passengers that nearly turned into a fight while waiting to exit plane, crew did nothing. Took nearly 3 hours to retrieve luggage at baggage claim. Lost an entire day of vacation. Will never fly spirit again under any circumstance

There absolutely needs to be WiFi on flights. Not sure why this new aircraft did not have the capability, but it made for a very frustrating flight. I honestly would have paid twice as much for another airline to have WiFi as an option, especially as a mom with kids who have disabilities.

More comfortable seats, free snacks and soft drinks, some sort of entertainment or WiFi.

All of our flights were canceled, though every other airline was flying out and in

it was terrible. flight was cancelled hours before the flight without a given reason and no other booking available .

Spirit Airlines has a reputation for being a terrible, cheap airline, this is why. I took a gamble on them, having never flown with them before, and the flight got cancelled. First they delayed the flight about 4 times before finally canceling it because a flight attendant didn’t show up to work that day. That’s so stupid. When I asked a ticketing agent she said that’s “company policy”. A company policy that inconveniences hundreds of passengers because a single flight attendant didn’t show is ridiculous and inefficient. I will never, ever try flying Spirit Airlines again.

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

Information on your arrival and departure airports