$311+ Cheap flights from Chicago (CHI) to St Kitts
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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SKB
May 19 — May 261
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to St Kitts with Cheapflights
1. Tell us where you want to go
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to St Kitts
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to St KittsExplore the most affordable flight options available from Chicago to St Kitts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 19, 2026.
Explore the most affordable flight options available from Chicago to St Kitts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 19, 2026.
This American Airlines deal was found by Cheapflights users on 4/18. 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.
Sat 7/116:00 pm
ORD
- SKB
1 stop18h 43m
American Airlines
Thu 7/162:43 pm
SKB
- ORD
1 stop10h 41m
American Airlines
Deal found 4/18![American Airlines logo]()
$719
This American Airlines deal was found by Cheapflights users on 4/14. 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 9/215:00 am
ORD
- SKB
1 stop7h 20m
American Airlines
Sat 9/262:45 pm
SKB
- ORD
1 stop8h 43m
American Airlines
Deal found 4/14![American Airlines logo]()
$754
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2312:59 pm
ORD
- SKB
1 stop28h 31m
Multiple Airlines
Sat 5/303:35 pm
SKB
- ORD
2 stops41h 47m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$794
This American Airlines deal was found by Cheapflights users on 4/18. 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.
Fri 6/56:47 pm
ORD
- SKB
1 stop17h 20m
American Airlines
Sun 6/72:40 pm
SKB
- ORD
1 stop10h 39m
American Airlines
Deal found 4/18![American Airlines logo]()
$819
This American Airlines deal was found by Cheapflights users on 4/19. 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 5/99:01 pm
ORD
- SKB
2 stops15h 34m
American Airlines
Sat 5/162:00 pm
SKB
- ORD
1 stop10h 54m
American Airlines
Deal found 4/19![American Airlines logo]()
$849
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 5/114:44 pm
ORD
- SKB
2 stops24h 11m
Multiple Airlines
Fri 5/158:30 am
SKB
- ORD
1 stop8h 19m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$860
This American Airlines deal was found by Cheapflights users on 4/18. 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.
Sat 5/232:19 pm
ORD
- SKB
1 stop22h 21m
American Airlines
Sat 5/302:40 pm
SKB
- ORD
1 stop8h 59m
American Airlines
Deal found 4/18![American Airlines logo]()
$883
Best flights from Chicago to St KittsDiscover carefully curated flight deals from Chicago to St Kitts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 19, 2026.
Discover carefully curated flight deals from Chicago to St Kitts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 19, 2026.
This American Airlines deal was found by Cheapflights users on 4/14. 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 9/218:44 pm
ORD
- SKB
2 stops15h 36m
American Airlines
Sat 9/262:45 pm
SKB
- ORD
1 stop8h 43m
American Airlines
Deal found 4/14![American Airlines logo]()
$759
This FlightHub deal was found by Cheapflights users on 4/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/117:20 am
ORD
- SKB
2 stops28h 49m
Multiple Airlines
Fri 5/158:30 am
SKB
- ORD
2 stops24h 14m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$990
This FlightHub deal was found by Cheapflights users on 4/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/18:20 pm
ORD
- SKB
2 stops17h 29m
JetBlue
Sun 7/53:55 pm
SKB
- ORD
2 stops19h 11m
JetBlue
Deal found 4/17![JetBlue logo]()
$1,203
This United Airlines deal was found by Cheapflights users on 4/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/308:53 am
ORD
- SKB
1 stop7h 56m
United Airlines
Wed 6/39:40 am
SKB
- ORD
2 stops14h 46m
United Airlines
Deal found 4/14![United Airlines logo]()
$1,315
This American Airlines deal was found by Cheapflights users on 4/18. 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.
Fri 6/58:52 pm
ORD
- SKB
1 stop15h 15m
American Airlines
Sun 6/72:40 pm
SKB
- ORD
2 stops17h 20m
American Airlines
Deal found 4/18![American Airlines logo]()
$824
This American Airlines deal was found by Cheapflights users on 4/19. 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 5/99:01 pm
ORD
- SKB
2 stops15h 34m
American Airlines
Sat 5/162:00 pm
SKB
- ORD
1 stop10h 54m
American Airlines
Deal found 4/19![American Airlines logo]()
$849
This American Airlines deal was found by Cheapflights users on 4/18. 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.
Sat 5/232:19 pm
ORD
- SKB
1 stop22h 21m
American Airlines
Sat 5/302:40 pm
SKB
- ORD
1 stop8h 59m
American Airlines
Deal found 4/18![American Airlines logo]()
$883
This Mytrip deal was found by Cheapflights users on 4/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/57:33 pm
ORD
- SKB
2 stops21h 22m
Multiple Airlines
Sun 6/72:20 pm
SKB
- ORD
3 stops30h 56m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$1,242
This American Airlines deal was found by Cheapflights users on 4/17. 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.
Wed 7/14:05 pm
ORD
- SKB
1 stop20h 38m
American Airlines
Sun 7/52:43 pm
SKB
- ORD
1 stop8h 55m
American Airlines
Deal found 4/17![American Airlines logo]()
$1,211
Last-minute flights from Chicago to St KittsDiscover last-minute flight deals from Chicago to St Kitts. Data last updated April 19, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to St Kitts. Data last updated April 19, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/17. 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.
Tue 4/215:00 am
ORD
- SKB
1 stop7h 26m
American Airlines
Thu 4/232:35 pm
SKB
- ORD
1 stop10h 50m
American Airlines
Deal found 4/17![American Airlines logo]()
$1,139
This American Airlines deal was found by Cheapflights users on 4/19. 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 5/99:01 pm
ORD
- SKB
2 stops15h 34m
American Airlines
Sat 5/162:00 pm
SKB
- ORD
1 stop10h 54m
American Airlines
Deal found 4/19![American Airlines logo]()
$849
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 5/114:44 pm
ORD
- SKB
2 stops24h 11m
Multiple Airlines
Fri 5/158:30 am
SKB
- ORD
1 stop8h 19m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$860
This American Airlines deal was found by Cheapflights users on 4/16. 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 5/117:00 pm
ORD
- SKB
1 stop17h 35m
American Airlines
Fri 5/152:35 pm
SKB
- ORD
1 stop10h 50m
American Airlines
Deal found 4/16![American Airlines logo]()
$1,327
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2312:59 pm
ORD
- SKB
1 stop28h 31m
Multiple Airlines
Sat 5/303:35 pm
SKB
- ORD
2 stops41h 47m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$794
This American Airlines deal was found by Cheapflights users on 4/18. 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.
Sat 5/232:19 pm
ORD
- SKB
1 stop22h 21m
American Airlines
Sat 5/302:40 pm
SKB
- ORD
1 stop8h 59m
American Airlines
Deal found 4/18![American Airlines logo]()
$883
This United Airlines deal was found by Cheapflights users on 4/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:30 am
ORD
- SKB
2 stops11h 19m
United Airlines
Wed 6/39:40 am
SKB
- ORD
2 stops14h 46m
United Airlines
Deal found 4/15![United Airlines logo]()
$1,315
One-way flights from Chicago to St KittsSearch for one-way flight options from Chicago to St Kitts. Find affordable one-way fares based on user searches. Data last updated April 19, 2026.
Search for one-way flight options from Chicago to St Kitts. Find affordable one-way fares based on user searches. Data last updated April 19, 2026.
This Justfly.com deal was found by Cheapflights users on 4/18. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/188:35 am
ORD
- SKB
1 stop27h 34m
JetBlue
Deal found 4/18![JetBlue logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/207:15 am
ORD
- SKB
3 stops34h 15m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:00 am
MDW
- SKB
3 stops35h 30m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/185:30 pm
ORD
- SKB
3 stops37h 35m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$441
This American Airlines deal was found by Cheapflights users on 4/18. 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.
Tue 5/195:00 am
ORD
- SKB
1 stop7h 35m
American Airlines
Deal found 4/18![American Airlines logo]()
$449
This Expedia deal was found by Cheapflights users on 4/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/199:55 am
ORD
- SKB
2 stops49h 20m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$451
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 am
MDW
- SKB
3 stops25h 05m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$551
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1810:30 am
MDW
- SKB
3 stops54h 15m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$567
Find flight deals from Chicago to St Kitts
Keep the following information in mind while searching for Chicago to St Kitts flight deals. Data was last updated April 19, 2026.
Round-trip from | $719 (American Airlines) |
|---|---|
One-way from | $311 (Justfly.com) |
Popular in | March |
Cheapest in | February |
Average price | $788 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to St Kitts 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 April 19, 2026.
Use the filters below to find and compare flights from Chicago to St Kitts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Mon 9/21
8:44 pm-1:20 pm
2 stops15h 36m
Basseterre Robert Bradshaw Intl
Sat 9/26
2:45 pm-10:28 pm
1 stop8h 43m
$759
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Fri 6/5
8:52 pm-1:07 pm
1 stop15h 15m
Basseterre Robert Bradshaw Intl
Sun 6/7
2:40 pm-7:00 am
2 stops17h 20m
$824
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Sat 5/9
9:01 pm-1:35 pm
2 stops15h 34m
Basseterre Robert Bradshaw Intl
Sat 5/16
2:00 pm-11:54 pm
1 stop10h 54m
$849
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Sat 5/23
2:19 pm-1:40 pm
1 stop22h 21m
Basseterre Robert Bradshaw Intl
Sat 5/30
2:40 pm-10:39 pm
1 stop8h 59m
$883
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Mon 5/11
7:20 am-1:09 pm
2 stops28h 49m
Basseterre Robert Bradshaw Intl
Fri 5/15
8:30 am-7:44 am
2 stops24h 14m
$990
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Wed 7/1
8:20 pm-2:49 pm
2 stops17h 29m
Basseterre Robert Bradshaw Intl
Sun 7/5
3:55 pm-10:06 am
2 stops19h 11m
$1,203
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Wed 7/1
4:05 pm-1:43 pm
1 stop20h 38m
Basseterre Robert Bradshaw Intl
Sun 7/5
2:43 pm-10:38 pm
1 stop8h 55m
$1,211
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Fri 6/5
7:33 pm-5:55 pm
2 stops21h 22m
Basseterre Robert Bradshaw Intl
Sun 6/7
2:20 pm-8:16 pm
3 stops30h 56m
$1,242
Quickest round-trip
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Sat 5/30
8:53 am-5:49 pm
1 stop7h 56m
Basseterre Robert Bradshaw Intl
Wed 6/3
9:40 am-11:26 pm
2 stops14h 46m
$1,315
Cheapest one-way
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Mon 5/18
8:35 am-1:09 pm
1 stop27h 34m
$311
Showing 1-10 of 15 resultsSorted by cheapest first
Best time to book a flight from Chicago to St Kitts
Have a flexible travel schedule? Discover the best time to fly to St Kitts 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 St Kitts
CHI-zzLXK
ORD-SKB
MDW-SKB
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing St Kitts
Get insights into the airlines that provide service to St Kitts. 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 St Kitts. Reviews last updated April 19, 2026.
See what other customers who have flown with American Airlines from Chicago to St Kitts have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.4
Entertainment
6.9
Crew
7.9
Comfort
7.2
Boarding
7.5
Overall
7.1
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Food
6.4
Entertainment
6.9
Crew
7.9
Comfort
7.2
Boarding
7.5
Overall
7.1
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 St Kitts. 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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Chicago and St Kitts flights
Browse other Chicago and St Kitts flight options. Last updated on April 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Chicago to St Kitts
Discover the top airline that operate flights from Chicago to St Kitts. 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 April 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$488 | Average$733 | FlexibilityNo cancel fee | On-time71% |