$303 Find Cheap Flights from Chicago to Saint Kitts and Nevis

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 Saint Kitts and Nevis departing on 11/25. 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

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Book Cheap Chicago to Saint Kitts and Nevis 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 Saint Kitts and Nevis 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 Saint Kitts and Nevis

Thu, Oct 30 - Wed, Nov 12
American Airlines Logo
5:00 am - 1:35 pmORD-SKB
7h 35m1 stop
American Airlines Logo
3:39 pm - 12:07 pmSKB-ORD
22h 28m1 stop
$589American Airlines
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Sat, Sep 27 - Sat, Oct 4
American Airlines Logo
7:15 pm - 1:40 pmORD-SKB
17h 25m1 stop
American Airlines Logo
2:42 pm - 11:49 pmSKB-ORD
10h 07m1 stop
$591American Airlines
Find Deal
Sat, Sep 27 - Sat, Oct 4
American Airlines Logo
8:47 pm - 1:40 pmORD-SKB
15h 53m2 stops
American Airlines Logo
2:42 pm - 11:49 pmSKB-ORD
10h 07m1 stop
$595American Airlines
Find Deal
Tue, Sep 9 - Sun, Sep 14
American Airlines Logo
8:29 pm - 1:40 pmORD-SKB
16h 11m2 stops
American Airlines Logo
2:42 pm - 7:47 amSKB-ORD
18h 05m2 stops
$600American Airlines
Find Deal
Tue, Sep 9 - Sun, Sep 14
American Airlines Logo
7:15 pm - 1:40 pmORD-SKB
17h 25m1 stop
American Airlines Logo
2:42 pm - 8:40 amSKB-ORD
18h 58m1 stop
$610American Airlines
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Sat, Dec 13 - Sat, Dec 20
American Airlines Logo
7:00 am - 4:15 pmORD-SKB
7h 15m1 stop
American Airlines Logo
5:25 pm - 9:02 amSKB-ORD
17h 37m1 stop
$616American Airlines
Find Deal
Sat, Dec 13 - Sat, Dec 20
American Airlines Logo
5:10 am - 4:15 pmORD-SKB
9h 05m2 stops
American Airlines Logo
5:25 pm - 12:18 amSKB-ORD
8h 53m1 stop
$620American Airlines
Find Deal
Wed, Sep 10 - Sun, Sep 14
American Airlines Logo
8:20 pm - 1:40 pmORD-SKB
16h 20m2 stops
American Airlines Logo
2:42 pm - 7:47 amSKB-ORD
18h 05m2 stops
$625American Airlines
Find Deal
Sun, Aug 31 - Sun, Sep 7
 Logo
8:12 pm - 5:45 pmORD-SKB
20h 33m2 stops
 Logo
3:25 pm - 4:51 pmSKB-ORD
26h 26m3 stops
Sat, Dec 27 - Sat, Jan 3
United Airlines Logo
2:30 pm - 5:49 pmORD-SKB
49h 19m2 stops
United Airlines Logo
9:40 am - 6:52 pmSKB-ORD
11h 12m2 stops
$3,647United Airlines
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Booking Insights

KAYAK's insights & trends for Chicago to Saint Kitts and Nevis flights

Get data-powered insights and trends into flights from Chicago to Saint Kitts and Nevis 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 Saint Kitts and Nevis?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Saint Kitts and Nevis, 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 Saint Kitts and Nevis 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 $1,196 and $1,169 respectively.


Good to know

Low seasonJuly
Cheapest flight$303
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Chicago to Basseterre

FAQs - booking Saint Kitts and Nevis flights

  • How does KAYAK find such low prices on flights from Chicago to Saint Kitts and Nevis?

    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 Saint Kitts and Nevis.

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

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

    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 Saint Kitts and Nevis 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 Saint Kitts and Nevis?

    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 Saint Kitts and Nevis 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 Saint Kitts and Nevis?

    The cheapest time of day to fly to Saint Kitts and Nevis 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 Saint Kitts and Nevis 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 Saint Kitts and Nevis

 
Need help choosing which airline to fly with from Chicago to Saint Kitts and Nevis? 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
6.9Entertainment
7.2Comfort
7.5Boarding
8.0Crew
6.5Food
Airline reviews

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

2.0 MediocreAnonymous, Jul 2025ORD - RIC
Read more American Airlines reviews

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 you need to know for your flight from Chicago to Saint Kitts and Nevis

Cabin class types available on flights to Saint Kitts and Nevis

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

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