ORD - SKB

$516 Find Cheap Flights from Chicago to Basseterre

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Basseterre departing on 11/28. 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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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

Fri, Nov 28 - Thu, Dec 4
American Airlines Logo
5:00 am - 3:18 pmORD-SKB
8h 18m1 stop
American Airlines Logo
3:27 pm - 7:19 amSKB-ORD
17h 52m2 stops
$516American Airlines
Find Deal
Sat, Dec 13 - Thu, Dec 18
American Airlines Logo
5:00 am - 2:07 pmORD-SKB
7h 07m1 stop
American Airlines Logo
3:27 pm - 10:59 pmSKB-ORD
9h 32m1 stop
$524American Airlines
Find Deal
Sat, Dec 13 - Thu, Dec 18
American Airlines Logo
5:00 am - 4:19 pmORD-SKB
9h 19m2 stops
American Airlines Logo
5:29 pm - 8:26 amSKB-ORD
16h 57m2 stops
$529American 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
3:27 pm - 11:07 amSKB-ORD
21h 40m1 stop
$536American Airlines
Find Deal
Thu, Dec 4 - Mon, Dec 8
American Airlines Logo
8:55 pm - 2:20 pmORD-SKB
15h 25m2 stops
American Airlines Logo
3:27 pm - 11:07 amSKB-ORD
21h 40m1 stop
$541American Airlines
Find Deal
Mon, Dec 15 - Sat, Dec 20
American Airlines Logo
7:07 pm - 2:27 pmORD-SKB
17h 20m1 stop
American Airlines Logo
3:27 pm - 12:43 amSKB-ORD
11h 16m1 stop
$564American Airlines
Find Deal
Mon, Dec 15 - Sat, Dec 20
American Airlines Logo
8:50 pm - 2:27 pmORD-SKB
15h 37m2 stops
American Airlines Logo
5:29 pm - 7:29 amSKB-ORD
16h 00m2 stops
$569American Airlines
Find Deal
Fri, Nov 28 - Thu, Dec 4
American Airlines Logo
5:34 pm - 2:25 pmORD-SKB
18h 51m2 stops
American Airlines Logo
3:27 pm - 7:19 amSKB-ORD
17h 52m2 stops
$607American Airlines
Find Deal
Fri, Nov 28 - Thu, Dec 4
British Airways Logo
6:45 pm - 1:50 pmORD-SKB
17h 05m1 stop
British Airways Logo
3:27 pm - 10:57 pmSKB-ORD
9h 30m1 stop
$620British Airways
Find Deal
Fri, Nov 28 - Thu, Dec 4
Multiple Airlines Logo
9:10 pm - 5:45 pmORD-SKB
18h 35m2 stops
Multiple Airlines Logo
8:35 am - 11:32 pmSKB-ORD
16h 57m2 stops
$866Multiple Airlines
Find Deal

Everything you should know

Top airlines
American Airlines
Cheapest • from $516 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
October
Cheapest • 39% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$516
Overall average: $846
American Airlines
Fri 11/28Thu 12/4
ORD - SKB • 1 stop
Cheapest one-way
Multiple Airlines
Thu 10/30
ORD - SKB • multi-stop
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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 $488 (return) on average. On the other hand, the most expensive months are March and July, where the average cost of round-trip tickets is $1,284 and $1,038 respectively.

Good to know

Low seasonAugust
Cheapest flight$516
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 24% increase in price.
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 $516 for a round-trip ticket.

  • 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?

    SkyTeam, and oneworld are the airline alliances operating flights between Chicago and Basseterre, with SkyTeam being the most commonly used for this route.

  • 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 $764 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 7992 reviews
8.2Boarding
7.9Comfort
8.5Crew
7.3Food
7.9Entertainment
Airline reviews

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

8.0 ExcellentJulie, Oct 2025LAX - SFO
Read more Delta reviews

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

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!

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

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