$388+ Cheap flights from Chicago (CHI) to Saint Kitts and Nevis
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SKB
Nov 12 — Nov 191
Round-trip
1 adult, Economy
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Best
Last-minute
One-way
Cheapest flights from Chicago to Saint Kitts and NevisExplore the most affordable flight options available from Chicago to Saint Kitts and Nevis. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 13, 2026.
Explore the most affordable flight options available from Chicago to Saint Kitts and Nevis. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 13, 2026.
This American Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:00 am -
1 stop7h 37m
Fri 12/113:38 pm -
1 stop11h 15m
Deal found 10/9![American Airlines logo]()
$765
This American Airlines deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/265:00 am -
1 stop7h 15m
Tue 12/13:31 pm -
1 stop10h 28m
Deal found 10/11![American Airlines logo]()
$767
This American Airlines deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:50 pm -
1 stop16h 40m
Tue 12/13:31 pm -
1 stop10h 28m
Deal found 10/10![American Airlines logo]()
$782
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:05 pm -
1 stop18h 28m
Fri 11/203:31 pm -
1 stop18h 39m
Deal found 10/8![American Airlines logo]()
$808
This American Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/226:59 am -
1 stop7h 30m
Sun 12/275:29 pm -
1 stop17h 54m
Deal found 10/12![American Airlines logo]()
$921
This Mytrip deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/265:40 am -
2 stops10h 50m
Thu 12/310:15 am -
3 stops31h 23m
Deal found 10/12![Multiple Airlines logo]()
$979
This American Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/35:00 am -
1 stop7h 33m
Mon 11/93:33 pm -
1 stop18h 27m
Deal found 10/9![American Airlines logo]()
$988
Best flights from Chicago to Saint Kitts and NevisDiscover carefully curated flight deals from Chicago to Saint Kitts and Nevis that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 13, 2026.
Discover carefully curated flight deals from Chicago to Saint Kitts and Nevis that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 13, 2026.
This American Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/265:00 am -
1 stop7h 15m
Thu 12/33:38 pm -
1 stop11h 15m
Deal found 10/12![American Airlines logo]()
$767
This American Airlines deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/28:29 pm -
1 stop16h 50m
Sat 1/92:31 pm -
1 stop10h 15m
Deal found 10/11![American Airlines logo]()
$767
This American Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:00 am -
1 stop7h 37m
Fri 12/113:38 pm -
2 stops17h 52m
Deal found 10/9![American Airlines logo]()
$769
This American Airlines deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/265:00 am -
1 stop7h 15m
Tue 12/13:31 pm -
2 stops17h 55m
Deal found 10/11![American Airlines logo]()
$771
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/276:00 am -
1 stop8h 25m
Sat 3/65:05 pm -
1 stop17h 11m
Deal found 10/8![American Airlines logo]()
$788
This American Airlines deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/255:00 am -
1 stop9h 25m
Mon 3/15:21 pm -
1 stop9h 38m
Deal found 10/10![American Airlines logo]()
$802
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:05 pm -
1 stop18h 28m
Fri 11/203:31 pm -
1 stop18h 39m
Deal found 10/8![American Airlines logo]()
$808
This American Airlines deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/267:50 pm -
1 stop18h 35m
Sat 4/34:21 pm -
1 stop16h 55m
Deal found 10/11![American Airlines logo]()
$878
Last-minute flights from Chicago to Saint Kitts and NevisDiscover last-minute flight deals from Chicago to Saint Kitts and Nevis. Data last updated October 13, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Saint Kitts and Nevis. Data last updated October 13, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/35:00 am -
1 stop7h 33m
Mon 11/93:33 pm -
1 stop18h 27m
Deal found 10/9![American Airlines logo]()
$988
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:05 pm -
1 stop18h 28m
Fri 11/203:31 pm -
1 stop18h 39m
Deal found 10/8![American Airlines logo]()
$808
This American Airlines deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:50 pm -
1 stop16h 40m
Tue 12/13:31 pm -
1 stop10h 28m
Deal found 10/10![American Airlines logo]()
$782
This American Airlines deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/265:00 am -
1 stop7h 15m
Tue 12/13:31 pm -
1 stop10h 28m
Deal found 10/11![American Airlines logo]()
$767
This Mytrip deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/265:40 am -
2 stops10h 50m
Thu 12/310:15 am -
3 stops31h 23m
Deal found 10/12![Multiple Airlines logo]()
$979
One-way flights from Chicago to Saint Kitts and NevisSearch for one-way flight options from Chicago to Saint Kitts and Nevis. Find affordable one-way fares based on user searches. Data last updated October 13, 2026.
Search for one-way flight options from Chicago to Saint Kitts and Nevis. Find affordable one-way fares based on user searches. Data last updated October 13, 2026.
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/35:21 am -
2 stops9h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![American Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/37:45 pm -
3 stops35h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$628
Find flight deals from Chicago to Saint Kitts and Nevis
Keep the following information in mind while searching for Chicago to Saint Kitts and Nevis flight deals. Data was last updated October 13, 2026.
Round-trip from | $728 (American Airlines) |
|---|---|
One-way from | $388 (American Airlines) |
Popular in | December |
Cheapest in | February |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Saint Kitts and Nevis that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 13, 2026.
Use the filters below to find and compare flights from Chicago to Saint Kitts and Nevis that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoBasseterre
ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl
ORDSKB
Chicago O'Hare Intl
Sun 1/3
5:21 am-4:29 pm
2 stops9h 08m
Basseterre Robert Bradshaw Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$388
ChicagoBasseterre
ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl
ORDSKB
Chicago O'Hare Intl
Sun 1/3
7:45 pm-9:10 am
3 stops35h 25m
Basseterre Robert Bradshaw Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$628
ChicagoBasseterre
ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl
ORDSKB
Chicago O'Hare Intl
Thu 11/26
5:00 am-2:15 pm
1 stop7h 15m
Basseterre Robert Bradshaw Intl
Thu 12/3
3:38 pm-12:53 am
1 stop11h 15m
$767
ChicagoBasseterre
ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl
ORDSKB
Chicago O'Hare Intl
Sat 1/2
8:29 pm-3:19 pm
1 stop16h 50m
Basseterre Robert Bradshaw Intl
Sat 1/9
2:31 pm-10:46 pm
1 stop10h 15m
$767
ChicagoBasseterre
ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl
ORDSKB
Chicago O'Hare Intl
Fri 12/4
5:00 am-2:37 pm
1 stop7h 37m
Basseterre Robert Bradshaw Intl
Fri 12/11
3:38 pm-7:30 am
2 stops17h 52m
$769
ChicagoBasseterre
ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl
ORDSKB
Chicago O'Hare Intl
Thu 11/26
5:00 am-2:15 pm
1 stop7h 15m
Basseterre Robert Bradshaw Intl
Tue 12/1
3:31 pm-7:26 am
2 stops17h 55m
$771
ChicagoBasseterre
ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl
ORDSKB
Chicago O'Hare Intl
Sat 2/27
6:00 am-4:25 pm
1 stop8h 25m
Basseterre Robert Bradshaw Intl
Sat 3/6
5:05 pm-8:16 am
1 stop17h 11m
$788
ChicagoBasseterre
ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl
ORDSKB
Chicago O'Hare Intl
Thu 2/25
5:00 am-4:25 pm
1 stop9h 25m
Basseterre Robert Bradshaw Intl
Mon 3/1
5:21 pm-12:59 am
1 stop9h 38m
$802
ChicagoBasseterre
ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl
ORDSKB
Chicago O'Hare Intl
Fri 11/13
6:05 pm-2:33 pm
1 stop18h 28m
Basseterre Robert Bradshaw Intl
Fri 11/20
3:31 pm-8:10 am
1 stop18h 39m
$808
ChicagoBasseterre
ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl
ORDSKB
Chicago O'Hare Intl
Fri 3/26
7:50 pm-3:25 pm
1 stop18h 35m
Basseterre Robert Bradshaw Intl
Sat 4/3
4:21 pm-8:16 am
1 stop16h 55m
$878
Sorted by cheapest first
Best time to book a flight from Chicago to Saint Kitts and Nevis
Have a flexible travel schedule? Discover the best time to fly to Saint Kitts and Nevis from Chicago with our price prediction graph.
ORD-SKB
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Saint Kitts and Nevis
CHI-KN0
ORD-SKB
What is the cheapest month to book a flight from Chicago to Saint Kitts and Nevis?
Currently, February is the cheapest month in which you can book a flight from Chicago to Saint Kitts and Nevis (average of $597). Flying from Chicago to Saint Kitts and Nevis in December is currently the most expensive (average of $1,798). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Saint Kitts and Nevis
Get insights into the airlines that provide service to Saint Kitts and Nevis. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Saint Kitts and Nevis. Reviews last updated October 13, 2026.
Read through reviews of airlines operating flights from Chicago to Saint Kitts and Nevis, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
7.9
Comfort
7.2
Food
6.4
Boarding
7.4
Overall
7.0
Entertainment
6.8
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Crew
7.9
Comfort
7.2
Food
6.4
Boarding
7.4
Overall
7.0
Entertainment
6.8
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Related info for your journey
Find useful and relevant information for your journey from Chicago to Saint Kitts and Nevis. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Saint Kitts and Nevis
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Saint Kitts and Nevis by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Saint Kitts and Nevis by cabin class
Find flights from Chicago to Saint Kitts and Nevis, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Saint Kitts and Nevis flights
Browse other Chicago and Saint Kitts and Nevis flight options. Last updated on October 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Saint Kitts and Nevis regions
Consider these flights traveling to Saint Kitts and Nevis regions.
Top airline flying from Chicago to Saint Kitts and Nevis
Discover the top airline that operate flights from Chicago to Saint Kitts and Nevis. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$603 | Average$804 | FlexibilityNo cancel fee | On-time71% |