ORD - SKB

$207 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 10/22. 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

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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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

Wed, Nov 5 - Tue, Nov 11
American Airlines Logo
5:00 am - 3:18 pmORD-SKB
8h 18m1 stop
American Airlines Logo
4:28 pm - 10:59 pmSKB-ORD
8h 31m1 stop
$480American Airlines
Find Deal
Wed, Nov 5 - Tue, Nov 11
American Airlines Logo
5:00 am - 3:18 pmORD-SKB
8h 18m1 stop
American Airlines Logo
4:28 pm - 7:21 amSKB-ORD
16h 53m2 stops
$484American Airlines
Find Deal
Sat, Nov 29 - Sat, Dec 6
American Airlines Logo
7:30 pm - 3:18 pmORD-SKB
17h 48m1 stop
American Airlines Logo
3:21 pm - 10:57 pmSKB-ORD
9h 36m1 stop
$505American Airlines
Find Deal
Wed, Nov 5 - Tue, Nov 11
American Airlines Logo
9:02 pm - 3:18 pmORD-SKB
16h 16m2 stops
American Airlines Logo
4:28 pm - 7:45 amSKB-ORD
17h 17m2 stops
$509American Airlines
Find Deal
Thu, Dec 4 - Mon, Dec 8
American Airlines Logo
7:07 pm - 2:20 pmORD-SKB
17h 13m1 stop
American Airlines Logo
3:21 pm - 12:37 amSKB-ORD
11h 16m1 stop
$530American Airlines
Find Deal
Thu, Dec 4 - Mon, Dec 8
American Airlines Logo
5:00 am - 2:20 pmORD-SKB
7h 20m1 stop
American Airlines Logo
3:21 pm - 7:19 amSKB-ORD
17h 58m2 stops
$534American Airlines
Find Deal
Sat, Dec 13 - Fri, Dec 19
American Airlines Logo
5:00 am - 4:19 pmORD-SKB
9h 19m2 stops
American Airlines Logo
5:29 pm - 8:25 amSKB-ORD
16h 56m2 stops
$552American Airlines
Find Deal
Sat, Dec 13 - Sat, Dec 20
American Airlines Logo
5:00 am - 4:19 pmORD-SKB
9h 19m2 stops
American Airlines Logo
5:29 pm - 7:29 amSKB-ORD
16h 00m2 stops
$577American Airlines
Find Deal
Sat, Nov 29 - Fri, Dec 5
American Airlines Logo
7:30 pm - 3:18 pmORD-SKB
17h 48m1 stop
American Airlines Logo
3:21 pm - 12:37 amSKB-ORD
11h 16m1 stop
$590American Airlines
Find Deal
Mon, Oct 13 - Mon, Oct 20
Multiple Airlines Logo
5:05 am - 4:50 pmORD-SKB
10h 45m2 stops
Multiple Airlines Logo
1:55 pm - 5:13 pmSKB-ORD
28h 18m3 stops
$860Multiple Airlines
Find Deal

Everything you should know

When to travel
October
Cheapest • 32% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$480
Overall average: $891
American Airlines
Wed 11/5Tue 11/11
ORD - SKB • 1 stop
Cheapest one-way
$207
JetBlue
Wed 10/22
ORD - SKB • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Basseterre!
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 October, where tickets cost $527 (return) on average. On the other hand, the most expensive months are March and July, where the average cost of round-trip tickets is $1,195 and $1,038 respectively.

Good to know

Low seasonAugust
Cheapest flight$207
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 9% 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 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Basseterre was $207 for a one-way ticket and $480 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.

  • Which is the best airline for flights from Chicago to Basseterre, Delta or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Basseterre are Delta and American Airlines. With an average price for the route of $615 and an overall rating of 7.9, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $766 and an overall rating of 7.2.

  • 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 airlines 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.
7.9
DeltaOverall score based on 7957 reviews
7.9Comfort
8.2Boarding
7.3Food
8.5Crew
7.9Entertainment
Airline reviews

The staff and the boarding procedure were all amazing . The one flight was not equipped with WIFI which now adays seems odd. All in all the experience was good

8.0 ExcellentAnonymous, Sep 2025GFK - MSP
Read more Delta reviews

The staff and the boarding procedure were all amazing . The one flight was not equipped with WIFI which now adays seems odd. All in all the experience was good

Passengers need to check in big baggage instead of bringing on the plane. That cause inconvenience for everyone. Otherwise flight was good.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Same as before being upgraded to business class made it perfect

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

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

Information on your arrival and departure airports

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