$324+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SKB
Jun 12 — Jun 191
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Saint Kitts and Nevis 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 Saint Kitts and Nevis
Cheapest
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 May 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 May 13, 2026.
This Mytrip deal was found by Cheapflights users on 5/12. 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.
Fri 11/62:00 pm
ORD
- SKB
1 stop24h 00m
Air Canada
Sat 11/145:00 pm
SKB
- ORD
1 stop21h 56m
Air Canada
Deal found 5/12![Air Canada logo]()
$658
This American Airlines deal was found by Cheapflights users on 5/9. 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.
Sun 10/117:05 pm
ORD
- SKB
1 stop17h 10m
American Airlines
Fri 10/162:50 pm
SKB
- ORD
1 stop8h 41m
American Airlines
Deal found 5/9![American Airlines logo]()
$659
This Gotogate deal was found by Cheapflights users on 5/9. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2512:50 pm
ORD
- SKB
2 stops46h 25m
Multiple Airlines
Sat 10/315:00 pm
SKB
- ORD
1 stop21h 56m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$663
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Sat 8/228:53 pm
ORD
- SKB
2 stops15h 45m
American Airlines
Mon 8/242:40 pm
SKB
- ORD
2 stops17h 48m
American Airlines
Deal found 5/12![American Airlines logo]()
$699
This American Airlines deal was found by Cheapflights users on 5/11. 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.
Tue 12/157:07 pm
ORD
- SKB
1 stop17h 13m
American Airlines
Tue 12/225:29 pm
SKB
- ORD
1 stop17h 18m
American Airlines
Deal found 5/11![American Airlines logo]()
$719
This Gotogate deal was found by Cheapflights users on 5/11. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/223:55 pm
ORD
- SKB
2 stops42h 20m
Multiple Airlines
Sat 11/285:00 pm
SKB
- ORD
1 stop21h 56m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$726
This American Airlines deal was found by Cheapflights users on 5/8. 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 10/97:05 pm
ORD
- SKB
1 stop17h 10m
American Airlines
Mon 10/122:50 pm
SKB
- ORD
1 stop8h 41m
American Airlines
Deal found 5/8![American Airlines logo]()
$729
This Delta deal was found by Cheapflights users on 5/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/276:00 am
MDW
- SKB
1 stop7h 03m
Delta
Sat 7/43:18 pm
SKB
- MDW
1 stop7h 59m
Delta
Deal found 5/9![Delta logo]()
$789
This Delta deal was found by Cheapflights users on 5/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:45 pm
MDW
- SKB
2 stops18h 25m
Delta
Sat 12/262:55 pm
SKB
- MDW
1 stop8h 50m
Delta
Deal found 5/12![Delta logo]()
$1,744
This Delta deal was found by Cheapflights users on 5/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/196:00 am
MDW
- SKB
1 stop7h 10m
Delta
Sat 12/262:55 pm
SKB
- MDW
1 stop8h 50m
Delta
Deal found 5/12![Delta logo]()
$1,789
This Delta deal was found by Cheapflights users on 5/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/176:45 pm
MDW
- SKB
2 stops42h 25m
Delta
Sat 12/264:25 pm
SKB
- MDW
2 stops25h 57m
Delta
Deal found 5/12![Delta logo]()
$1,987
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 May 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 May 13, 2026.
This American Airlines deal was found by Cheapflights users on 5/9. 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.
Sun 10/118:46 pm
ORD
- SKB
2 stops15h 29m
American Airlines
Fri 10/162:50 pm
SKB
- ORD
2 stops17h 46m
American Airlines
Deal found 5/9![American Airlines logo]()
$664
This Mytrip deal was found by Cheapflights users on 5/12. 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.
Fri 11/63:55 pm
ORD
- SKB
2 stops22h 05m
Air Canada
Sat 11/145:00 pm
SKB
- ORD
2 stops20h 10m
Air Canada
Deal found 5/12![Air Canada logo]()
$665
This JetBlue deal was found by Cheapflights users on 5/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/295:22 pm
ORD
- SKB
1 stop20h 27m
JetBlue
Tue 7/73:38 pm
SKB
- ORD
1 stop26h 42m
JetBlue
Deal found 5/10![JetBlue logo]()
$783
This Delta deal was found by Cheapflights users on 5/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/276:00 am
MDW
- SKB
1 stop7h 03m
Delta
Sat 7/43:18 pm
SKB
- MDW
1 stop7h 59m
Delta
Deal found 5/9![Delta logo]()
$789
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Sun 10/48:44 pm
ORD
- SKB
2 stops15h 31m
American Airlines
Sat 10/102:50 pm
SKB
- ORD
1 stop9h 52m
American Airlines
Deal found 5/12![American Airlines logo]()
$699
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Sat 8/228:53 pm
ORD
- SKB
2 stops15h 45m
American Airlines
Mon 8/242:40 pm
SKB
- ORD
1 stop9h 20m
American Airlines
Deal found 5/12![American Airlines logo]()
$699
This American Airlines deal was found by Cheapflights users on 5/10. 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.
Sat 7/255:59 pm
ORD
- SKB
1 stop18h 44m
American Airlines
Sun 8/22:43 pm
SKB
- ORD
1 stop9h 47m
American Airlines
Deal found 5/10![American Airlines logo]()
$699
This American Airlines deal was found by Cheapflights users on 5/8. 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 6/75:00 am
ORD
- SKB
1 stop7h 39m
American Airlines
Sat 6/132:13 pm
SKB
- ORD
1 stop10h 45m
American Airlines
Deal found 5/8![American Airlines logo]()
$754
This American Airlines deal was found by Cheapflights users on 5/12. 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 6/115:00 am
ORD
- SKB
1 stop7h 39m
American Airlines
Wed 6/172:41 pm
SKB
- ORD
2 stops17h 16m
American Airlines
Deal found 5/12![American Airlines logo]()
$759
This American Airlines deal was found by Cheapflights users on 5/10. 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.
Mon 6/85:00 am
ORD
- SKB
1 stop7h 39m
American Airlines
Sun 6/142:41 pm
SKB
- ORD
1 stop19h 28m
American Airlines
Deal found 5/10![American Airlines logo]()
$777
Last-minute flights from Chicago to Saint Kitts and NevisDiscover last-minute flight deals from Chicago to Saint Kitts and Nevis. Data last updated May 13, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Saint Kitts and Nevis. Data last updated May 13, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 5/11. 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 5/298:52 pm
ORD
- SKB
1 stop15h 15m
American Airlines
Fri 6/52:41 pm
SKB
- ORD
1 stop9h 49m
American Airlines
Deal found 5/11![American Airlines logo]()
$864
This American Airlines deal was found by Cheapflights users on 5/10. 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.
Mon 6/15:00 am
ORD
- SKB
1 stop7h 40m
American Airlines
Fri 6/52:41 pm
SKB
- ORD
1 stop9h 49m
American Airlines
Deal found 5/10![American Airlines logo]()
$779
This American Airlines deal was found by Cheapflights users on 5/11. 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 6/48:56 pm
ORD
- SKB
2 stops15h 43m
American Airlines
Thu 6/112:41 pm
SKB
- ORD
1 stop9h 49m
American Airlines
Deal found 5/11![American Airlines logo]()
$789
This FlightHub deal was found by Cheapflights users on 5/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:30 pm
ORD
- SKB
2 stops41h 05m
JetBlue
Sun 6/143:55 pm
SKB
- ORD
1 stop17h 50m
JetBlue
Deal found 5/9![JetBlue logo]()
$782
This American Airlines deal was found by Cheapflights users on 5/9. 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 6/56:47 pm
ORD
- SKB
1 stop17h 17m
American Airlines
Sun 6/142:41 pm
SKB
- ORD
1 stop19h 28m
American Airlines
Deal found 5/9![American Airlines logo]()
$842
This American Airlines deal was found by Cheapflights users on 5/8. 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 6/75:00 am
ORD
- SKB
1 stop7h 39m
American Airlines
Sat 6/132:13 pm
SKB
- ORD
1 stop10h 45m
American Airlines
Deal found 5/8![American Airlines logo]()
$754
This American Airlines deal was found by Cheapflights users on 5/10. 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.
Mon 6/85:00 am
ORD
- SKB
1 stop7h 39m
American Airlines
Sun 6/142:41 pm
SKB
- ORD
1 stop19h 28m
American Airlines
Deal found 5/10![American Airlines logo]()
$777
This American Airlines deal was found by Cheapflights users on 5/12. 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 6/118:52 pm
ORD
- SKB
2 stops15h 47m
American Airlines
Wed 6/172:41 pm
SKB
- ORD
2 stops17h 16m
American Airlines
Deal found 5/12![American Airlines logo]()
$759
This American Airlines deal was found by Cheapflights users on 5/8. 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 6/206:00 pm
ORD
- SKB
1 stop18h 39m
American Airlines
Sat 6/272:13 pm
SKB
- ORD
1 stop10h 45m
American Airlines
Deal found 5/8![American Airlines logo]()
$740
This Delta deal was found by Cheapflights users on 5/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/276:00 am
MDW
- SKB
1 stop7h 03m
Delta
Sat 7/43:18 pm
SKB
- MDW
1 stop7h 59m
Delta
Deal found 5/9![Delta logo]()
$789
This JetBlue deal was found by Cheapflights users on 5/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/295:22 pm
ORD
- SKB
1 stop20h 27m
JetBlue
Tue 7/73:38 pm
SKB
- ORD
1 stop26h 42m
JetBlue
Deal found 5/10![JetBlue logo]()
$783
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 May 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 May 13, 2026.
This Justfly.com deal was found by Cheapflights users on 5/8. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:00 am
ORD
- SKB
1 stop7h 33m
JetBlue
Deal found 5/8![JetBlue logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 5/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:44 am
ORD
- SKB
1 stop16h 46m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 5/8. 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.
Tue 9/15:30 pm
ORD
- SKB
2 stops48h 00m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$348
This Justfly.com deal was found by Cheapflights users on 5/8. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:27 pm
ORD
- SKB
1 stop20h 06m
JetBlue
Deal found 5/8![JetBlue logo]()
$389
This American Airlines deal was found by Cheapflights users on 5/10. 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.
Sun 6/75:00 am
ORD
- SKB
1 stop7h 39m
American Airlines
Deal found 5/10![American Airlines logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 5/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/96:00 am
MDW
- SKB
2 stops11h 30m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$465
This Kiwi.com deal was found by Cheapflights users on 5/8. 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.
Mon 8/317:55 am
ORD
- SKB
3 stops23h 10m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$494
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Wed 6/242:24 pm
ORD
- SKB
1 stop22h 15m
American Airlines
Deal found 5/12![American Airlines logo]()
$516
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 May 13, 2026.
Round-trip from | $658 (Mytrip) |
|---|---|
One-way from | $324 (Justfly.com) |
Popular in | March |
Cheapest in | February |
Average price | $699 |
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 May 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
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Sun 10/11
8:46 pm-1:15 pm
2 stops15h 29m
Basseterre Robert Bradshaw Intl
Fri 10/16
2:50 pm-7:36 am
2 stops17h 46m
$664
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Fri 11/6
3:55 pm-4:00 pm
2 stops22h 05m
Basseterre Robert Bradshaw Intl
Sat 11/14
5:00 pm-11:10 am
2 stops20h 10m
$665
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Sun 10/4
8:44 pm-1:15 pm
2 stops15h 31m
Basseterre Robert Bradshaw Intl
Sat 10/10
2:50 pm-11:42 pm
1 stop9h 52m
$699
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Sat 8/22
8:53 pm-1:38 pm
2 stops15h 45m
Basseterre Robert Bradshaw Intl
Mon 8/24
2:40 pm-11:00 pm
1 stop9h 20m
$699
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Sat 7/25
5:59 pm-1:43 pm
1 stop18h 44m
Basseterre Robert Bradshaw Intl
Sun 8/2
2:43 pm-11:30 pm
1 stop9h 47m
$699
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Sun 6/7
5:00 am-1:39 pm
1 stop7h 39m
Basseterre Robert Bradshaw Intl
Sat 6/13
2:13 pm-11:58 pm
1 stop10h 45m
$754
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Thu 6/11
5:00 am-1:39 pm
1 stop7h 39m
Basseterre Robert Bradshaw Intl
Wed 6/17
2:41 pm-6:57 am
2 stops17h 16m
$759
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Mon 6/8
5:00 am-1:39 pm
1 stop7h 39m
Basseterre Robert Bradshaw Intl
Sun 6/14
2:41 pm-9:09 am
1 stop19h 28m
$777
ChicagoBasseterre
ORD - SKB
ORDSKB
Chicago O'Hare Intl
Mon 6/29
5:22 pm-2:49 pm
1 stop20h 27m
Basseterre Robert Bradshaw Intl
Tue 7/7
3:38 pm-5:20 pm
1 stop26h 42m
$783
Quickest round-trip
ChicagoBasseterre
MDW - SKB
MDWSKB
Chicago Midway
Sat 6/27
6:00 am-2:03 pm
1 stop7h 03m
Basseterre Robert Bradshaw Intl
Sat 7/4
3:18 pm-10:17 pm
1 stop7h 59m
$789
Showing 1-10 of 20 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
No data available for this route at this time. Please check back soon.
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 May 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.
Boarding
7.5
Comfort
7.2
Crew
7.9
Food
6.4
Entertainment
6.9
Overall
7.1
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
Boarding
7.5
Comfort
7.2
Crew
7.9
Food
6.4
Entertainment
6.9
Overall
7.1
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$488 | Average$784 | FlexibilityNo cancel fee | On-time71% |