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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 3/21. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SKB
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
1 adult, Economy
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Cheap 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 January 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$582
(American Airlines)

One-way from

$313
(American Airlines)

Popular in

December

Cheapest in

October

Average price

$880
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. 16% potential increase in price ($159 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($29 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find 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 January 15, 2026.

This American Airlines deal was found by Cheapflights users on 1/14. 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.
Wed 1/215:00 am
ORD
-
SKB
1 stop7h 47m
American Airlines
Wed 1/283:47 pm
SKB
-
ORD
1 stop10h 43m
American Airlines
Deal found 1/14$507
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Wed 1/215:00 am
ORD
-
SKB
1 stop7h 47m
American Airlines
Wed 2/113:47 pm
SKB
-
ORD
2 stops17h 38m
American Airlines
Deal found 1/14$512
This Expedia deal was found by Cheapflights users on 1/15. 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.
Wed 2/49:40 am
ORD
-
SKB
1 stop26h 32m
JetBlue
Sun 2/83:20 pm
SKB
-
ORD
1 stop30h 11m
JetBlue
Deal found 1/15$523
This American Airlines deal was found by Cheapflights users on 1/15. 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.
Wed 2/47:59 pm
ORD
-
SKB
2 stops16h 48m
American Airlines
Sun 2/83:47 pm
SKB
-
ORD
2 stops18h 03m
American Airlines
Deal found 1/15$537
This American Airlines deal was found by Cheapflights users on 1/15. 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.
Thu 2/265:00 am
ORD
-
SKB
1 stop7h 22m
American Airlines
Mon 3/23:24 pm
SKB
-
ORD
1 stop11h 13m
American Airlines
Deal found 1/15$582
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Sat 1/247:30 pm
ORD
-
SKB
1 stop17h 17m
American Airlines
Fri 1/303:47 pm
SKB
-
ORD
1 stop10h 43m
American Airlines
Deal found 1/14$591
This American Airlines deal was found by Cheapflights users on 1/13. 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 1/208:50 pm
ORD
-
SKB
2 stops15h 57m
American Airlines
Sat 1/242:15 pm
SKB
-
ORD
1 stop22h 36m
American Airlines
Deal found 1/13$592
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/225:15 am
ORD
-
SKB
2 stops11h 15m
Multiple Airlines
Fri 1/238:30 am
SKB
-
ORD
1 stop10h 07m
Multiple Airlines
Deal found 1/14$595
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Sat 1/249:10 pm
ORD
-
SKB
2 stops15h 37m
American Airlines
Tue 2/103:47 pm
SKB
-
ORD
1 stop10h 43m
American Airlines
Deal found 1/14$596
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/2112:17 pm
ORD
-
SKB
1 stop28h 13m
Multiple Airlines
Fri 1/238:30 am
SKB
-
ORD
1 stop10h 07m
Multiple Airlines
Deal found 1/14$603

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 January 15, 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

Wed 2/4

7:59 pm-2:47 pm

2 stops16h 48m

Basseterre Robert Bradshaw Intl

Sun 2/8

3:47 pm-7:50 am

2 stops18h 03m

$537

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Thu 2/26

5:00 am-2:22 pm

1 stop7h 22m

Basseterre Robert Bradshaw Intl

Mon 3/2

3:24 pm-12:37 am

1 stop11h 13m

$582

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Fri 3/6

6:59 pm-2:22 pm

1 stop17h 23m

Basseterre Robert Bradshaw Intl

Thu 3/12

2:24 pm-11:17 pm

1 stop9h 53m

$612

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 4/18

8:44 pm-1:30 pm

2 stops15h 46m

Basseterre Robert Bradshaw Intl

Sat 4/25

2:00 pm-11:57 pm

1 stop10h 57m

$617

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 2/14

6:01 am-4:30 pm

1 stop8h 29m

Basseterre Robert Bradshaw Intl

Tue 2/17

3:24 pm-7:24 am

2 stops18h 00m

$647

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Mon 3/9

6:59 pm-1:24 pm

1 stop17h 25m

Basseterre Robert Bradshaw Intl

Sat 3/14

2:23 pm-11:17 pm

1 stop9h 54m

$674

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 3/21

6:59 pm-1:21 pm

1 stop17h 22m

$313

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Fri 3/20

6:35 pm-1:23 pm

1 stop17h 48m

$338

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Fri 3/20

3:59 pm-12:32 pm

2 stops19h 33m

$383

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Fri 3/20

4:51 pm-6:30 pm

3 stops48h 39m

$387

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

Showing 1-10 of 11 results
1
2

Compare providers for flights from O'Hare Intl to Basseterre

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Basseterre in January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Basseterre flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago O'Hare Intl Airport-Basseterre flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 $793). 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 January 15, 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
11,136 reviews

Boarding

7.5

Crew

8.0

Overall

7.2

Food

6.4

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,136 reviews
American Airlines
7.2
Good
11,136 reviews

Boarding

7.5

Crew

8.0

Overall

7.2

Food

6.4

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

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 16h 48m. 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 37% 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 $793). 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 January 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$488Average$737FlexibilityNo cancel feeOn-time71%

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