$287 Find Cheap Flights from Chicago to St Kitts

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 St Kitts departing on 4/4. 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 St Kitts

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to St Kitts, 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 St Kitts, as well as popular online travel agencies
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Flight Deals

Book Cheap Chicago to St Kitts Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to St Kitts 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 St Kitts

Tue, Mar 3 - Tue, Mar 10
American Airlines Logo
6:59 pm - 2:22 pm
ORD
-
SKB
17h 23m
1 stop
American Airlines Logo
2:24 pm - 11:17 pm
SKB
-
ORD
9h 53m
1 stop
$543American Airlines
Tue, Mar 3 - Tue, Mar 10
American Airlines Logo
8:58 pm - 2:22 pm
ORD
-
SKB
15h 24m
2 stops
American Airlines Logo
2:24 pm - 7:25 am
SKB
-
ORD
18h 01m
2 stops
$548American Airlines
Sat, Apr 4 - Sat, Apr 11
American Airlines Logo
6:59 pm - 1:21 pm
ORD
-
SKB
17h 22m
1 stop
American Airlines Logo
4:50 pm - 12:25 am
SKB
-
ORD
8h 35m
1 stop
$573American Airlines
Sat, May 16 - Thu, May 21
American Airlines Logo
7:00 pm - 1:30 pm
ORD
-
SKB
17h 30m
1 stop
American Airlines Logo
2:40 pm - 10:19 pm
SKB
-
ORD
8h 39m
1 stop
$587American Airlines
Sat, May 16 - Thu, May 21
American Airlines Logo
9:01 pm - 1:30 pm
ORD
-
SKB
15h 29m
2 stops
American Airlines Logo
2:40 pm - 7:28 am
SKB
-
ORD
17h 48m
2 stops
$592American Airlines
Sat, Apr 18 - Sat, Apr 25
Delta Logo
5:10 am - 2:10 pm
ORD
-
SKB
8h 00m
1 stop
Delta Logo
1:55 pm - 11:59 pm
SKB
-
ORD
11h 04m
1 stop
$603Delta
Sat, Apr 18 - Sat, Apr 25
Delta Logo
6:00 am - 2:10 pm
MDW
-
SKB
7h 10m
1 stop
Delta Logo
1:55 pm - 10:28 pm
SKB
-
MDW
9h 33m
1 stop
$603Delta
Fri, Mar 6 - Sat, Mar 14
Delta Logo
12:29 pm - 1:33 pm
ORD
-
SKB
23h 04m
2 stops
Delta Logo
1:50 pm - 11:54 pm
SKB
-
ORD
11h 04m
1 stop
$608Delta
Sat, Apr 18 - Sat, Apr 25
American Airlines Logo
8:46 pm - 1:30 pm
ORD
-
SKB
15h 44m
2 stops
American Airlines Logo
4:50 pm - 12:25 am
SKB
-
ORD
8h 35m
1 stop
$618American Airlines
Thu, Apr 16 - Mon, Apr 20
American Airlines Logo
8:46 pm - 1:30 pm
ORD
-
SKB
15h 44m
2 stops
American Airlines Logo
2:32 pm - 1:22 pm
SKB
-
ORD
23h 50m
1 stop
$622American Airlines
Booking Insights

KAYAK's insights & trends for Chicago to St Kitts flights

Get data-powered insights and trends into flights from Chicago to St Kitts to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Chicago to St Kitts?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $412, prices are generally cheapest when you fly direct.

Good to know

Low seasonJuly
Cheapest flight$287
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly and prices are also 30% lower on average.
Flight from Chicago to Basseterre

FAQs - booking St Kitts flights

  • How does KAYAK find such low prices on flights from Chicago to St Kitts?

    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 St Kitts.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to St Kitts?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to St Kitts 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 St Kitts?

    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 from Chicago to St Kitts with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to St Kitts?

    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 from Chicago to St Kitts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Chicago to St Kitts

 
See real verified KAYAK customer reviews for airlines flying from Chicago to St Kitts. 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 St Kitts? 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.
7.2
American AirlinesOverall score based on 11212 reviews
6.9Entertainment
6.4Food
7.2Comfort
8.0Crew
7.5Boarding
Airline reviews

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.

2.0 MediocreAndrew, Feb 2026
ORD - LGA
Read more American Airlines reviews

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.

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

Everything you need to know for your flight to St Kitts

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.