$459+ Cheap flights from Chicago (CHI) to Saint Kitts and Nevis
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SKB
Sep 18 — Sep 251
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Saint Kitts and Nevis with Cheapflights
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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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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 August 19, 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 August 19, 2026.
This Expedia deal was found by Cheapflights users on 8/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:30 pm -
1 stop21h 55m
Sat 11/145:25 pm -
1 stop24h 13m
Deal found 8/17![Air Canada logo]()
$566
This Air Canada deal was found by Cheapflights users on 8/16. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/208:50 pm -
1 stop17h 35m
Sat 11/285:25 pm -
1 stop24h 13m
Deal found 8/16![Air Canada logo]()
$635
This Travelocity deal was found by Cheapflights users on 8/18. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/251:55 pm -
2 stops45h 20m
Sat 10/314:25 pm -
1 stop22h 48m
Deal found 8/18![Multiple Airlines logo]()
$672
This Travelocity deal was found by Cheapflights users on 8/18. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:05 am -
2 stops52h 10m
Fri 10/304:20 pm -
2 stops49h 18m
Deal found 8/18![Multiple Airlines logo]()
$734
This American Airlines deal was found by Cheapflights users on 8/18. 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 10/257:29 pm -
1 stop17h 10m
Fri 10/302:39 pm -
1 stop9h 54m
Deal found 8/18![American Airlines logo]()
$739
This Expedia deal was found by Cheapflights users on 8/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/293:45 pm -
2 stops43h 30m
Tue 10/612:45 pm -
2 stops21h 15m
Deal found 8/15![Multiple Airlines logo]()
$757
This Delta deal was found by Cheapflights users on 8/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/196:00 am -
1 stop7h 10m
Sat 12/262:55 pm -
1 stop9h 15m
Deal found 8/16![Delta logo]()
$1,150
This Delta deal was found by Cheapflights users on 8/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1811:28 am -
2 stops24h 12m
Sat 12/262:55 pm -
1 stop9h 15m
Deal found 8/16![Delta logo]()
$1,367
This Delta deal was found by Cheapflights users on 8/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/176:44 pm -
2 stops40h 56m
Sat 12/262:55 pm -
1 stop9h 15m
Deal found 8/16![Delta logo]()
$1,385
This Delta deal was found by Cheapflights users on 8/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2511:20 am -
2 stops24h 20m
Sat 1/22:55 pm -
1 stop9h 15m
Deal found 8/16![Delta logo]()
$2,006
This Delta deal was found by Cheapflights users on 8/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/266:00 am -
1 stop7h 10m
Sat 1/22:55 pm -
1 stop9h 15m
Deal found 8/16![Delta logo]()
$2,173
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 August 19, 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 August 19, 2026.
This Delta deal was found by Cheapflights users on 8/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/65:30 am -
1 stop7h 30m
Sat 2/132:50 pm -
1 stop11h 00m
Deal found 8/19![Delta logo]()
$739
This American Airlines deal was found by Cheapflights users on 8/15. 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 2/97:10 pm -
1 stop17h 37m
Tue 2/233:15 pm -
2 stops18h 12m
Deal found 8/15![American Airlines logo]()
$744
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Wed 9/305:00 am -
1 stop7h 40m
Wed 10/72:39 pm -
2 stops17h 48m
Deal found 8/16![American Airlines logo]()
$769
This American Airlines deal was found by Cheapflights users on 8/18. 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 12/108:57 pm -
2 stops15h 36m
Thu 12/175:29 pm -
2 stops16h 36m
Deal found 8/18![American Airlines logo]()
$779
This American Airlines deal was found by Cheapflights users on 8/19. 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 11/78:57 pm -
2 stops15h 36m
Sat 11/144:56 pm -
1 stop18h 05m
Deal found 8/19![American Airlines logo]()
$779
This American Airlines deal was found by Cheapflights users on 8/15. 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.
Mon 1/188:55 pm -
2 stops15h 52m
Sun 1/245:23 pm -
2 stops16h 02m
Deal found 8/15![American Airlines logo]()
$784
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Mon 9/285:00 am -
1 stop7h 40m
Mon 10/52:39 pm -
1 stop10h 59m
Deal found 8/14![American Airlines logo]()
$796
This American Airlines deal was found by Cheapflights users on 8/17. 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 10/17:00 pm -
1 stop17h 40m
Thu 10/82:39 pm -
1 stop9h 54m
Deal found 8/17![American Airlines logo]()
$807
This Delta deal was found by Cheapflights users on 8/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/196:00 am -
1 stop7h 10m
Sat 12/264:25 pm -
2 stops21h 31m
Deal found 8/16![Delta logo]()
$1,347
This Delta deal was found by Cheapflights users on 8/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1811:28 am -
2 stops24h 12m
Sat 12/262:55 pm -
1 stop9h 15m
Deal found 8/16![Delta logo]()
$1,367
This Delta deal was found by Cheapflights users on 8/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2511:20 am -
2 stops24h 20m
Sat 1/22:55 pm -
1 stop9h 15m
Deal found 8/16![Delta logo]()
$2,006
This Delta deal was found by Cheapflights users on 8/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/266:00 am -
1 stop7h 10m
Sat 1/22:55 pm -
1 stop9h 15m
Deal found 8/16![Delta logo]()
$2,173
Last-minute flights from Chicago to Saint Kitts and NevisDiscover last-minute flight deals from Chicago to Saint Kitts and Nevis. Data last updated August 19, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Saint Kitts and Nevis. Data last updated August 19, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Mon 9/285:00 am -
1 stop7h 40m
Mon 10/52:39 pm -
1 stop10h 59m
Deal found 8/14![American Airlines logo]()
$796
This Expedia deal was found by Cheapflights users on 8/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/293:45 pm -
2 stops43h 30m
Tue 10/612:45 pm -
2 stops21h 15m
Deal found 8/15![Multiple Airlines logo]()
$757
This American Airlines deal was found by Cheapflights users on 8/15. 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 9/297:00 pm -
1 stop17h 40m
Tue 10/62:39 pm -
1 stop19h 51m
Deal found 8/15![American Airlines logo]()
$771
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Wed 9/305:00 am -
1 stop7h 40m
Wed 10/72:39 pm -
2 stops17h 48m
Deal found 8/16![American Airlines logo]()
$767
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 August 19, 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 August 19, 2026.
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Mon 9/215:00 am -
1 stop7h 40m
Deal found 8/16![American Airlines logo]()
$459
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Mon 9/217:11 am -
3 stops28h 04m
Deal found 8/16![Multiple Airlines logo]()
$566
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Mon 9/216:25 am -
3 stops24h 40m
Deal found 8/17![Multiple Airlines logo]()
$625
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 August 19, 2026.
Round-trip from | $566 (Expedia) |
|---|---|
One-way from | $459 (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 2,558,603 searches. Data last updated August 19, 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
ChicagoBasseterre
ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl
ORDSKB
Chicago O'Hare Intl
Sat 2/6
5:30 am-3:00 pm
1 stop7h 30m
Basseterre Robert Bradshaw Intl
Sat 2/13
2:50 pm-11:50 pm
1 stop11h 00m
$739
ChicagoBasseterre
ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl
ORDSKB
Chicago O'Hare Intl
Tue 2/9
7:10 pm-2:47 pm
1 stop17h 37m
Basseterre Robert Bradshaw Intl
Tue 2/23
3:15 pm-7:27 am
2 stops18h 12m
$744
ChicagoBasseterre
ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl
ORDSKB
Chicago O'Hare Intl
Wed 9/30
5:00 am-1:40 pm
1 stop7h 40m
Basseterre Robert Bradshaw Intl
Wed 10/7
2:39 pm-7:27 am
2 stops17h 48m
$769
ChicagoBasseterre
ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl
ORDSKB
Chicago O'Hare Intl
Thu 12/10
8:57 pm-2:33 pm
2 stops15h 36m
Basseterre Robert Bradshaw Intl
Thu 12/17
5:29 pm-8:05 am
2 stops16h 36m
$779
ChicagoBasseterre
ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl
ORDSKB
Chicago O'Hare Intl
Sat 11/7
8:57 pm-2:33 pm
2 stops15h 36m
Basseterre Robert Bradshaw Intl
Sat 11/14
4:56 pm-9:01 am
1 stop18h 05m
$779
ChicagoBasseterre
ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl
ORDSKB
Chicago O'Hare Intl
Mon 1/18
8:55 pm-2:47 pm
2 stops15h 52m
Basseterre Robert Bradshaw Intl
Sun 1/24
5:23 pm-7:25 am
2 stops16h 02m
$784
ChicagoBasseterre
ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl
ORDSKB
Chicago O'Hare Intl
Mon 9/28
5:00 am-1:40 pm
1 stop7h 40m
Basseterre Robert Bradshaw Intl
Mon 10/5
2:39 pm-12:38 am
1 stop10h 59m
$796
ChicagoBasseterre
ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl
ORDSKB
Chicago O'Hare Intl
Thu 10/1
7:00 pm-1:40 pm
1 stop17h 40m
Basseterre Robert Bradshaw Intl
Thu 10/8
2:39 pm-11:33 pm
1 stop9h 54m
$807
ChicagoBasseterre
MDW Chicago Midway - SKB Basseterre Robert Bradshaw Intl
MDWSKB
Chicago Midway
Sat 12/19
6:00 am-3:10 pm
1 stop7h 10m
Basseterre Robert Bradshaw Intl
Sat 12/26
4:25 pm-11:56 am
2 stops21h 31m
$1,347
ChicagoBasseterre
MDW Chicago Midway - SKB Basseterre Robert Bradshaw Intl
MDWSKB
Chicago Midway
Fri 12/18
11:28 am-1:40 pm
2 stops24h 12m
Basseterre Robert Bradshaw Intl
Sat 12/26
2:55 pm-10:10 pm
1 stop9h 15m
$1,367
Showing 1-10 of 14 resultsSorted 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
MDW-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
MDW-SKB
What is the cheapest month to book a flight from Chicago to Saint Kitts and Nevis?
Currently, October is the cheapest month in which you can book a flight from Chicago to Saint Kitts and Nevis (average of $565). Flying from Chicago to Saint Kitts and Nevis in December is currently the most expensive (average of $1,000). 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 August 19, 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
Overall
7.1
Boarding
7.5
Food
6.4
Entertainment
6.8
Comfort
7.2
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Crew
7.9
Overall
7.1
Boarding
7.5
Food
6.4
Entertainment
6.8
Comfort
7.2
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
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Complete your trip
Complete your trip to Saint Kitts and Nevis by adding a car rental and/or hotel reservation to your travel itinerary.
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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 August 19, 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 2,558,603 searches. Data last updated August 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$590 | Average$804 | FlexibilityNo cancel fee | On-time71% |