ORD - SKB

$338 Find Cheap Flights from Chicago to Basseterre

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Basseterre departing on 7/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Basseterre

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Basseterre, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Basseterre, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$637
American Airlines
Sat 8/15Sat 8/22
ORD - SKB • 1 stop
Cheapest one-way
$338
American Airlines
Sun 7/12
ORD - SKB • 1 stop
Top airlines
Cheapest • from $637 (round-trip)
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Basseterre. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $929 (round-trip)
Shortest trip • 7h 07m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Basseterre!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Basseterre (ORD-SKB)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Basseterre that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Basseterre

Sat, Aug 15 - Sat, Aug 22
American Airlines Logo
5:00 am - 1:44 pm
ORD
-
SKB
7h 44m
1 stop
American Airlines Logo
3:46 pm - 9:05 am
SKB
-
ORD
18h 19m
1 stop
$637American Airlines
Sat, Oct 10 - Sat, Oct 17
American Airlines Logo
8:46 pm - 1:15 pm
ORD
-
SKB
15h 29m
2 stops
American Airlines Logo
2:50 pm - 7:30 am
SKB
-
ORD
17h 40m
2 stops
$642American Airlines
Thu, Nov 12 - Thu, Nov 19
American Airlines Logo
5:00 am - 2:39 pm
ORD
-
SKB
7h 39m
1 stop
American Airlines Logo
3:39 pm - 9:25 am
SKB
-
ORD
19h 46m
1 stop
$646American Airlines
Sat, Aug 1 - Thu, Aug 6
American Airlines Logo
5:00 am - 1:43 pm
ORD
-
SKB
7h 43m
1 stop
American Airlines Logo
2:44 pm - 12:35 am
SKB
-
ORD
10h 51m
1 stop
$647American Airlines
Sat, Aug 1 - Thu, Aug 6
American Airlines Logo
8:55 pm - 1:43 pm
ORD
-
SKB
15h 48m
2 stops
American Airlines Logo
2:44 pm - 7:30 am
SKB
-
ORD
17h 46m
2 stops
$652American Airlines
Sat, Oct 10 - Sun, Oct 18
JetBlue Logo
6:30 am - 1:03 pm
ORD
-
SKB
29h 33m
1 stop
JetBlue Logo
2:10 pm - 11:47 am
SKB
-
ORD
22h 37m
1 stop
$665JetBlue
Sat, Oct 10 - Sat, Oct 17
American Airlines Logo
5:00 am - 1:15 pm
ORD
-
SKB
7h 15m
1 stop
American Airlines Logo
2:50 pm - 11:42 pm
SKB
-
ORD
9h 52m
1 stop
$732American Airlines
Sun, Nov 29 - Thu, Dec 3
Multiple Airlines Logo
3:55 pm - 12:15 pm
ORD
-
SKB
42h 20m
2 stops
Multiple Airlines Logo
12:45 pm - 2:55 pm
SKB
-
ORD
28h 10m
2 stops
$750Multiple Airlines
Thu, Oct 8 - Fri, Oct 16
American Airlines Logo
5:00 am - 1:15 pm
ORD
-
SKB
7h 15m
1 stop
American Airlines Logo
2:50 pm - 10:31 pm
SKB
-
ORD
8h 41m
1 stop
$757American Airlines
Wed, Oct 7 - Wed, Oct 14
American Airlines Logo
7:05 pm - 1:15 pm
ORD
-
SKB
17h 10m
1 stop
American Airlines Logo
2:50 pm - 10:31 pm
SKB
-
ORD
8h 41m
1 stop
$762American Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Basseterre flights

Get data-powered insights and trends into flights from Chicago to Basseterre to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Basseterre?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Basseterre, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Basseterre is January, where tickets cost $0 (return) on average. On the other hand, the most expensive months are June and December, where the average cost of round-trip tickets is $1,225 and $1,186 respectively.

Good to know

Low seasonOctober
Cheapest flight$338
Best time to beat the crowds with an average 44% drop in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from Chicago to Basseterre

When to book flights from Chicago to Basseterre

Are your dates flexible? Find out the best times to travel from Chicago to Basseterre based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Basseterre flights

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

    In the last 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Basseterre was $338 for a one-way ticket and $637 for a round-trip.

  • Do I need a passport to fly between Chicago and Basseterre?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Chicago and on arrival in Basseterre.

  • Which aircraft models fly most regularly from Chicago to Basseterre?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Basseterre?

    oneworld is the only airline alliance operating flights between Chicago and Basseterre.

  • How does KAYAK find such low prices on flights from Chicago to Basseterre?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Basseterre.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Basseterre?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Basseterre from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Basseterre?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Basseterre with an airline and back to Chicago with another airline. Booking your flights between Chicago and SKB can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Basseterre?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Basseterre from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Chicago to Basseterre

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Basseterre. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Basseterre? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11670 reviews
7.5Boarding
6.8Entertainment
7.2Comfort
6.4Food
7.9Crew
Airline reviews

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

2.0 MediocreGirish, Jun 2026
ORD - DFW
Read more American Airlines reviews

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Everything you need to know for your flight from Chicago to Basseterre

Information on your arrival and departure airports