$541 Find Cheap Flights from Chicago to St Kitts

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to St Kitts departing on 11/29. 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 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

Sat, Nov 29 - Fri, Dec 5
American Airlines Logo
5:00 am - 3:40 pmORD-SKB
8h 40m1 stop
American Airlines Logo
3:21 pm - 12:37 amSKB-ORD
11h 16m1 stop
$541American Airlines
Find Deal
Sat, Dec 13 - Thu, Dec 18
American Airlines Logo
5:00 am - 2:07 pmORD-SKB
7h 07m1 stop
American Airlines Logo
3:27 pm - 10:59 pmSKB-ORD
9h 32m1 stop
$549American Airlines
Find Deal
Sat, Dec 13 - Thu, Dec 18
American Airlines Logo
7:00 am - 4:19 pmORD-SKB
7h 19m1 stop
American Airlines Logo
5:29 pm - 8:26 amSKB-ORD
16h 57m2 stops
$554American Airlines
Find Deal
Sat, Dec 13 - Thu, Dec 18
American Airlines Logo
8:50 pm - 2:27 pmORD-SKB
15h 37m2 stops
American Airlines Logo
5:29 pm - 8:26 amSKB-ORD
16h 57m2 stops
$564American Airlines
Find Deal
Thu, Dec 4 - Mon, Dec 8
American Airlines Logo
7:07 pm - 2:20 pmORD-SKB
17h 13m1 stop
American Airlines Logo
3:27 pm - 10:57 pmSKB-ORD
9h 30m1 stop
$574American Airlines
Find Deal
Thu, Dec 4 - Mon, Dec 8
American Airlines Logo
7:07 pm - 2:20 pmORD-SKB
17h 13m1 stop
American Airlines Logo
3:27 pm - 7:19 amSKB-ORD
17h 52m2 stops
$579American Airlines
Find Deal
Sat, Mar 14 - Sat, Mar 21
Delta Logo
6:00 am - 2:08 pmMDW-SKB
7h 08m1 stop
Delta Logo
1:53 pm - 9:46 pmSKB-MDW
8h 53m1 stop
$788Delta
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Thu, Nov 27 - Thu, Dec 4
Multiple Airlines Logo
11:40 am - 10:55 amORD-SKB
21h 15m3 stops
Multiple Airlines Logo
4:58 pm - 12:19 amSKB-ORD
33h 21m3 stops
$858Multiple Airlines
Find Deal
Fri, Dec 19 - Sat, Jan 3
Delta Logo
6:40 pm - 3:13 pmMDW-SKB
18h 33m2 stops
Delta Logo
2:53 pm - 10:22 pmSKB-MDW
9h 29m1 stop
$2,214Delta
Find Deal
Fri, Dec 19 - Sat, Jan 3
Delta Logo
5:26 pm - 3:13 pmMDW-SKB
19h 47m1 stop
Delta Logo
2:53 pm - 10:22 pmSKB-MDW
9h 29m1 stop
$2,434Delta
Find Deal
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 $386, prices are generally cheapest when you fly direct.

Good to know

Low seasonJuly
Cheapest flight$541
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly and prices are also 22% 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.

  • What is the cheapest time of day to fly to St Kitts?

    The cheapest time of day to fly to St Kitts is generally in the evening, when round-trip flights cost $611 on average. Morning departures are around 30% more expensive than evening flights, on average. The most expensive time of day to fly to St Kitts is generally at night, which is peak travel time and where the average cost of a ticket is $826.

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 11045 reviews
7.5Boarding
8.0Crew
6.9Entertainment
6.4Food
7.2Comfort
Airline reviews

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.

2.0 MediocreAnonymous, Oct 2025ORD - PDX
Read more American Airlines reviews

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.

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!

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.

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