CHI - KIN

$145 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 10/19. 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

Sat, Nov 8 - Thu, Nov 13
Spirit Airlines Logo
5:59 pm - 12:13 pmORD-KIN
17h 14m1 stop
Spirit Airlines Logo
1:28 pm - 11:42 pmKIN-ORD
11h 14m1 stop
$342Spirit Airlines
Find Deal
Sat, Oct 11 - Sun, Oct 19
Spirit Airlines Logo
6:00 pm - 11:09 amORD-KIN
17h 09m2 stops
Spirit Airlines Logo
12:14 pm - 11:45 pmKIN-ORD
11h 31m1 stop
$373Spirit Airlines
Find Deal
Sat, Oct 11 - Sun, Oct 19
Spirit Airlines Logo
7:43 pm - 11:09 amORD-KIN
15h 26m1 stop
Spirit Airlines Logo
12:14 pm - 11:45 pmKIN-ORD
11h 31m1 stop
$376Spirit Airlines
Find Deal
Wed, Oct 29 - Wed, Nov 5
Spirit Airlines Logo
7:43 pm - 11:09 amORD-KIN
15h 26m1 stop
Spirit Airlines Logo
1:28 pm - 9:00 pmKIN-ORD
8h 32m1 stop
$381Spirit Airlines
Find Deal
Thu, Oct 16 - Mon, Oct 20
Spirit Airlines Logo
7:43 pm - 11:09 amORD-KIN
15h 26m1 stop
Spirit Airlines Logo
12:14 pm - 11:45 pmKIN-ORD
11h 31m1 stop
$382Spirit Airlines
Find Deal
Wed, Oct 15 - Sun, Oct 26
Spirit Airlines Logo
7:43 pm - 11:09 amORD-KIN
15h 26m1 stop
Spirit Airlines Logo
12:14 pm - 1:03 amKIN-ORD
12h 49m1 stop
$386Spirit Airlines
Find Deal
Wed, Oct 22 - Sat, Oct 25
 Logo
7:43 pm - 11:09 amORD-KIN
15h 26m1 stop
 Logo
7:55 am - 6:38 pmKIN-ORD
10h 43m1 stop
Sun, Oct 12 - Sun, Oct 19
Delta Logo
12:48 pm - 8:00 pmMDW-KIN
7h 12m1 stop
Delta Logo
9:00 am - 10:14 pmKIN-MDW
13h 14m1 stop
$433Delta
Find Deal
Sat, Oct 11 - Sun, Oct 19
Delta Logo
1:18 pm - 8:00 pmORD-KIN
6h 42m1 stop
Delta Logo
9:00 am - 11:59 pmKIN-ORD
14h 59m1 stop
$433Delta
Find Deal
Wed, Oct 29 - Wed, Nov 5
Delta Logo
6:00 am - 8:00 pmMDW-KIN
14h 00m1 stop
Delta Logo
10:00 am - 6:25 pmKIN-MDW
9h 25m2 stops
$438Delta
Find Deal

Everything you should know

Top airlines
Spirit Airlines
Cheapest • from $342 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
February
Cheapest • 29% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$342
Overall average: $621
Spirit Airlines
Sat 11/8Thu 11/13
ORD - KIN • 1 stop
Cheapest one-way
$145
Typical prices: $216-375
Spirit Airlines
Sun 10/19
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.

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 June, where the average cost of round-trip tickets is $1,015 and $590 respectively.

Good to know

Low seasonJuly
Cheapest flight$145
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 1% 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 $145 for a one-way ticket and $342 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, Star Alliance, 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 $638 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 7954 reviews
8.5Crew
7.3Food
7.9Comfort
7.9Entertainment
8.2Boarding
Airline reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

10.0 ExcellentAnonymous, Sep 2025CLT - BOS
Read more Delta reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

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!

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.

Everything was fine. I'm average height and I pack light. I'm ready for my Spirit flight.

Changing the flight time to 6:15 am on the return flight is extremely inconvenient. The flight was okay. It was on time. The crew was friendly. The seats were uncomfortable. All the upsells are annoying, and I would prefer paying a single higher fee and not have to purchase so much extra.

Spirit Airlines was ok but TRAVELHELPDESK, the 3rd party travel agent IS A JOKE! VERY RUDE CUSTOMER AGENTS ont he phone. NO HELP AT ALL. But the airlines was ok.

No Tumberlence smooth flight. Try to change the menu on Snacks.

Cancelled my flight last minute and did not help me rebook. It was a horrible experience.

No frills - because you get what you pay for. The crew was amazing!! I had plenty of room to spread out because the flight was half full. Which made it easy to sleep.

The terminal crew is so rude cabin crew is extremely rude flight is very good

Spirit is low fare air line. Food also cost you. No free food.

The flight was delayed twice with minimal explanation. The terminal and airplane were filthy. The food voucher didn’t even cover a tiny pizza from a kiosk in the terminal. All in all, a pretty miserable experience for a flight to attend a funeral

I will use spirit more New clean aircraft Excellent crew ! Quick boarding process !

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

Information on your arrival and departure airports

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