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Basseterre

$313+ Cheap flights from O'Hare Intl (ORD) to Basseterre (SKB)

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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SKB
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Basseterre

Cheapest flights from O'Hare Intl to Basseterre
Explore the most affordable flight options available from O'Hare Intl to Basseterre. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.

This American Airlines deal was found by Cheapflights users on 2/11. 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.
Mon 3/95:00 am
ORD
-
SKB
1 stop7h 24m
American Airlines
Thu 3/122:24 pm
SKB
-
ORD
1 stop11h 14m
American Airlines
Deal found 2/11$553
This American Airlines deal was found by Cheapflights users on 2/11. 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 5/168:46 pm
ORD
-
SKB
2 stops15h 49m
American Airlines
Thu 5/212:41 pm
SKB
-
ORD
2 stops17h 29m
American Airlines
Deal found 2/11$558
This American Airlines deal was found by Cheapflights users on 2/9. 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.
Wed 3/186:59 pm
ORD
-
SKB
1 stop17h 25m
American Airlines
Wed 3/252:24 pm
SKB
-
ORD
1 stop9h 53m
American Airlines
Deal found 2/9$573
This American Airlines deal was found by Cheapflights users on 2/11. 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 4/187:00 pm
ORD
-
SKB
1 stop17h 26m
American Airlines
Sat 4/254:50 pm
SKB
-
ORD
1 stop8h 35m
American Airlines
Deal found 2/11$583
This American Airlines deal was found by Cheapflights users on 2/9. 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.
Sat 3/218:55 pm
ORD
-
SKB
2 stops15h 26m
American Airlines
Sat 3/283:40 pm
SKB
-
ORD
1 stop20h 17m
American Airlines
Deal found 2/9$598
This Delta deal was found by Cheapflights users on 2/9. 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 3/215:30 am
ORD
-
SKB
1 stop7h 40m
Delta
Sat 3/281:50 pm
SKB
-
ORD
1 stop11h 04m
Delta
Deal found 2/9$603
This American Airlines deal was found by Cheapflights users on 2/10. 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 5/255:00 am
ORD
-
SKB
1 stop7h 38m
American Airlines
Fri 5/292:41 pm
SKB
-
ORD
1 stop8h 52m
American Airlines
Deal found 2/10$606
This American Airlines deal was found by Cheapflights users on 2/10. 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 5/148:46 pm
ORD
-
SKB
2 stops15h 49m
American Airlines
Mon 5/182:35 pm
SKB
-
ORD
2 stops17h 54m
American Airlines
Deal found 2/10$618

Find flight deals from O'Hare Intl to Basseterre

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Basseterre (SKB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$543
(American Airlines)

One-way from

$313
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$770
Provider with most accurate pricing for Chicago O'Hare Intl-Basseterre Robert Bradshaw Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Basseterre Robert Bradshaw Intl flights.
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From Chicago O'Hare Intl to Basseterre Robert Bradshaw Intl
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One-way flight from Chicago O'Hare Intl to Basseterre Robert Bradshaw Intl
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Highest demand for flights based on searches. 12% potential increase in price ($109 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Basseterre 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 February 12, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Basseterre that are best for you.

Fly from

O'Hare Intl

Fly to

Basseterre

Route

Depart

Return

Price

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Mon 3/9

8:55 pm-1:24 pm

2 stops15h 29m

Basseterre Robert Bradshaw Intl

Thu 3/12

2:24 pm-11:17 pm

1 stop9h 53m

$558

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 5/16

8:46 pm-1:35 pm

2 stops15h 49m

Basseterre Robert Bradshaw Intl

Thu 5/21

2:41 pm-7:10 am

2 stops17h 29m

$558

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 4/18

7:00 pm-1:26 pm

1 stop17h 26m

Basseterre Robert Bradshaw Intl

Sat 4/25

2:00 pm-11:54 pm

1 stop10h 54m

$573

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Wed 3/18

8:58 pm-1:24 pm

2 stops15h 26m

Basseterre Robert Bradshaw Intl

Wed 3/25

2:24 pm-12:38 am

1 stop11h 14m

$578

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 3/21

8:55 pm-1:21 pm

2 stops15h 26m

Basseterre Robert Bradshaw Intl

Sat 3/28

4:30 pm-7:25 am

2 stops15h 55m

$588

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Wed 3/25

9:28 am-6:30 pm

2 stops32h 02m

$313

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Thu 4/2

2:57 pm-1:24 pm

1 stop21h 27m

$322

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Mon 4/6

6:59 pm-1:35 pm

1 stop17h 36m

$363

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 3/14

6:10 pm-6:30 pm

2 stops23h 20m

$426

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Mon 4/6

7:31 pm-9:40 am

3 stops37h 09m

$444

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

  • Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Basseterre flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-Basseterre flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Basseterre flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Basseterre flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Basseterre flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from O'Hare Intl to Basseterre

Have a flexible travel schedule? Discover the best time to fly to Basseterre from O'Hare Intl with our price prediction graph.
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 O'Hare Intl Airport to Basseterre

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Basseterre?

Currently, May is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Basseterre (average of $465). Flying from Chicago O'Hare Intl Airport to Basseterre in March is currently the most expensive (average of $780). 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 Basseterre

Get insights into the airlines that provide service to Basseterre. 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 Basseterre. Reviews last updated February 12, 2026.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Basseterre, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,267 reviews

Entertainment

6.9

Overall

7.2

Boarding

7.5

Crew

8.0

Food

6.4

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,267 reviews
American Airlines
7.2
Good
11,267 reviews

Entertainment

6.9

Overall

7.2

Boarding

7.5

Crew

8.0

Food

6.4

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Basseterre. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Basseterre from Chicago O'Hare Intl?

    Located just 1.1 mi from the city center, Basseterre Robert Bradshaw Intl is the airport most travelers will use when flying to Basseterre from Chicago O'Hare Intl. Booking flights from Chicago O'Hare Intl to Robert Bradshaw Intl (SKB) should be relatively easy as there are 0 daily inbound flights from Chicago O'Hare Intl from 1 airline.

  • How long is the flight from Chicago O'Hare Intl Airport to Basseterre?

    American Airlines can get you from Chicago O'Hare Intl Airport to Basseterre in just under 15h 29m. Your travel time can differ by up to . The distance from Chicago O'Hare Intl Airport to Basseterre is about 2260 mi.

  • What is the cheapest airline to fly from Chicago O'Hare Intl Airport to Basseterre round-trip?

    Flying on American Airlines is currently your cheapest option to Basseterre, with prices starting at $488. This flight start at 35% lower than the current average price 3 months from now.

  • Can I find deals for flights from O'Hare Intl to Basseterre that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Basseterre flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Basseterre?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Basseterre.

  • Can I find deals for business class flights from O'Hare Intl to Basseterre?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Basseterre by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Basseterre?

    Currently, May is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Basseterre (average of $465). Flying from Chicago O'Hare Intl Airport to Basseterre in March is currently the most expensive (average of $780). 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.

See more FAQs

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Top airline flying from O'Hare Intl to Basseterre

Discover the top airline that operate flights from O'Hare Intl to Basseterre. 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 February 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$488Average$737FlexibilityNo cancel feeOn-time71%

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