ORD - SKB

$643 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 6/19. 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.
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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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Cheap Flights from Chicago to Basseterre

 
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.

Recent round-trip flight deals from Chicago to Basseterre

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Basseterre.
Discover the best prices for you by selecting your travel dates on KAYAK.
American Airlines Logo
5:00 am - 1:30 pmORD-SKB
7h 30m1 stop
American Airlines Logo
2:30 pm - 11:51 pmSKB-ORD
10h 21m1 stop
$643American Airlines
Find Deal
Thu, Jun 19 - Wed, Jun 25
American Airlines Logo
8:50 pm - 1:30 pmORD-SKB
15h 40m2 stops
American Airlines Logo
2:30 pm - 12:59 amSKB-ORD
11h 29m2 stops
$647American Airlines
Find Deal
Thu, Jun 19 - Wed, Jun 25
American Airlines Logo
8:50 pm - 1:30 pmORD-SKB
15h 40m2 stops
American Airlines Logo
2:05 pm - 9:25 pmSKB-ORD
8h 20m1 stop
$677American Airlines
Find Deal
Sat, Jun 14 - Sat, Jun 21
American Airlines Logo
8:50 pm - 1:30 pmORD-SKB
15h 40m2 stops
American Airlines Logo
2:30 pm - 12:59 amSKB-ORD
11h 29m2 stops
$682American Airlines
Find Deal
Sat, Jun 14 - Wed, Jun 18
American Airlines Logo
5:00 am - 3:25 pmORD-SKB
9h 25m1 stop
American Airlines Logo
4:25 pm - 9:05 amSKB-ORD
17h 40m1 stop
$698American Airlines
Find Deal
Sat, Jun 14 - Sat, Jun 21
American Airlines Logo
6:00 am - 3:25 pmORD-SKB
8h 25m1 stop
American Airlines Logo
2:30 pm - 11:51 pmSKB-ORD
10h 21m1 stop
$703American Airlines
Find Deal
Sat, Jun 14 - Wed, Jun 18
Delta Logo
5:30 am - 2:22 pmORD-SKB
7h 52m1 stop
Delta Logo
3:59 pm - 11:58 pmSKB-ORD
8h 59m1 stop
$728Delta
Find Deal
Sat, Jun 7 - Sat, Jun 14
American Airlines Logo
5:29 am - 3:25 pmORD-SKB
8h 56m2 stops
American Airlines Logo
2:05 pm - 11:57 pmSKB-ORD
10h 52m1 stop
$733American Airlines
Find Deal
Sat, Jun 7 - Sat, Jun 14
American Airlines Logo
6:55 pm - 1:30 pmORD-SKB
17h 35m1 stop
American Airlines Logo
2:30 pm - 9:05 amSKB-ORD
19h 35m1 stop
$749American Airlines
Find Deal
Wed, Jun 18 - Sun, Jun 22
 Logo
9:55 am - 10:55 amORD-SKB
24h 00m3 stops
 Logo
12:45 pm - 12:55 pmSKB-ORD
25h 10m2 stops
$1,220
Find Deal
Thu, May 22 - Sun, May 25
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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 May, where tickets cost $655 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $1,200 and $1,029 respectively.

Good to know

Low seasonJuly
High seasonFebruary
Cheapest flight$643
Best time to beat the crowds but there is an average 23% increase in price.
Most popular time to fly and prices are also 18% 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 $643 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?

    oneworld, and SkyTeam 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 $660 and an overall rating of 8.0, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $771 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.

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.
8.0
DeltaOverall score based on 7934 reviews
8.2Boarding
7.3Food
7.9Entertainment
8.5Crew
7.9Comfort
Airline reviews

Flight was delayed due to weather. Crew did a nice job of making us comfortable. No complain complaints.

6.0 GoodTina, Apr 2025MSP - CLT
Read more Delta reviews

Flight was delayed due to weather. Crew did a nice job of making us comfortable. No complain complaints.

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

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

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

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

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