$628 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 8/17. 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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Cheap Flights from Chicago to St Kitts

 
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

Sun, Aug 17 - Thu, Aug 21
American Airlines Logo
7:05 pm - 1:22 pmORD-SKB
17h 17m1 stop
American Airlines Logo
2:30 pm - 10:41 pmSKB-ORD
9h 11m1 stop
$628American Airlines
Find Deal
Sun, Aug 17 - Thu, Aug 21
American Airlines Logo
8:41 pm - 1:22 pmORD-SKB
15h 41m2 stops
American Airlines Logo
2:30 pm - 10:41 pmSKB-ORD
9h 11m1 stop
$632American Airlines
Find Deal
Fri, Aug 8 - Tue, Aug 12
American Airlines Logo
7:05 pm - 1:35 pmORD-SKB
17h 30m1 stop
American Airlines Logo
2:30 pm - 10:41 pmSKB-ORD
9h 11m1 stop
$653American Airlines
Find Deal
Fri, Aug 8 - Tue, Aug 12
American Airlines Logo
4:57 pm - 12:25 pmORD-SKB
18h 28m1 stop
American Airlines Logo
2:30 pm - 7:24 amSKB-ORD
17h 54m2 stops
$657American Airlines
Find Deal
Fri, Sep 5 - Mon, Sep 8
American Airlines Logo
7:15 pm - 1:40 pmORD-SKB
17h 25m1 stop
American Airlines Logo
2:42 pm - 11:48 pmSKB-ORD
10h 06m1 stop
$678American Airlines
Find Deal
Sun, Jul 27 - Sun, Aug 3
American Airlines Logo
8:45 pm - 1:35 pmORD-SKB
15h 50m2 stops
American Airlines Logo
2:35 pm - 7:23 amSKB-ORD
17h 48m2 stops
$680American Airlines
Find Deal
Sun, Sep 7 - Fri, Sep 12
United Airlines Logo
8:52 am - 11:20 amORD-SKB
25h 28m1 stop
United Airlines Logo
2:35 pm - 7:38 amSKB-ORD
18h 03m2 stops
$714United Airlines
Find Deal
Sat, Jul 26 - Sat, Aug 2
 Logo
5:05 am - 5:45 pmORD-SKB
11h 40m2 stops
 Logo
1:00 pm - 11:53 pmSKB-ORD
11h 53m2 stops
Sun, Jun 29 - Thu, Jul 3
United Airlines Logo
8:49 am - 11:20 amORD-SKB
25h 31m1 stop
United Airlines Logo
9:40 am - 7:49 amSKB-ORD
23h 09m2 stops
$2,270United Airlines
Find Deal
Sun, Jun 29 - Thu, Jul 3
United Airlines Logo
9:31 pm - 5:49 pmORD-SKB
19h 18m2 stops
United Airlines Logo
9:40 am - 11:30 pmSKB-ORD
14h 50m2 stops
$3,610United Airlines
Find Deal
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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 $907, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to St Kitts?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to St Kitts, 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 St Kitts is July, when tickets cost $642 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $1,645 and $1,169 respectively.


Good to know

Low seasonJuly
High seasonApril
Cheapest flight$628
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 11% 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.

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 10000 reviews
6.5Food
7.5Boarding
7.2Comfort
6.9Entertainment
8.0Crew
Airline reviews

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

6.0 GoodAnonymous, Mar 2025ORD - CLT
Read more American Airlines reviews

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.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

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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