Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Basseterre from $263

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Basseterre departing on 10/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Basseterre

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
5:07 am - 1:12 pm
ORD
-
SKB
7h 05m
1 stop
American Airlines Logo
2:43 pm - 7:34 am
SKB
-
ORD
17h 51m
1 stop
$637American Airlines
Sat, Aug 1 - Tue, Aug 4
American Airlines Logo
8:54 pm - 1:43 pm
ORD
-
SKB
15h 49m
2 stops
American Airlines Logo
2:43 pm - 12:26 am
SKB
-
ORD
10h 43m
1 stop
$642American Airlines
Sat, Aug 1 - Tue, Aug 4
American Airlines Logo
8:58 pm - 1:36 pm
ORD
-
SKB
15h 38m
2 stops
American Airlines Logo
2:44 pm - 7:30 am
SKB
-
ORD
17h 46m
2 stops
$647American Airlines
Tue, Aug 18 - Sun, Aug 23
American Airlines Logo
5:00 am - 1:35 pm
ORD
-
SKB
7h 35m
1 stop
American Airlines Logo
2:40 pm - 11:32 pm
SKB
-
ORD
9h 52m
1 stop
$679American Airlines
Mon, Sep 21 - Sat, Sep 26
American Airlines Logo
5:00 am - 1:43 pm
ORD
-
SKB
7h 43m
1 stop
American Airlines Logo
2:12 pm - 10:00 pm
SKB
-
ORD
8h 48m
1 stop
$682American Airlines
Sat, Jul 18 - Sat, Jul 25
American Airlines Logo
7:00 pm - 1:35 pm
ORD
-
SKB
17h 35m
1 stop
American Airlines Logo
2:40 pm - 7:58 am
SKB
-
ORD
18h 18m
2 stops
$684American Airlines
Mon, Sep 21 - Sat, Sep 26
American Airlines Logo
8:59 pm - 1:43 pm
ORD
-
SKB
15h 44m
2 stops
American Airlines Logo
2:43 pm - 6:38 am
SKB
-
ORD
16h 55m
2 stops
$687American Airlines
Sat, Jul 18 - Sat, Jul 25
Multiple Airlines Logo
1:00 pm - 1:03 pm
ORD
-
SKB
23h 03m
1 stop
Multiple Airlines Logo
8:35 am - 11:44 pm
SKB
-
ORD
16h 09m
2 stops
$695Multiple Airlines
Wed, Oct 7 - Wed, Oct 14
American Airlines Logo
5:07 am - 1:12 pm
ORD
-
SKB
7h 05m
1 stop
American Airlines Logo
2:43 pm - 9:08 am
SKB
-
ORD
19h 25m
1 stop
$702American Airlines
Sat, Jul 18 - Sun, Jul 26
American Airlines Logo
8:54 pm - 1:43 pm
ORD
-
SKB
15h 49m
2 stops
American Airlines Logo
2:43 pm - 9:08 am
SKB
-
ORD
19h 25m
1 stop
$706American Airlines
Sat, Jul 18 - Sun, Jul 26

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

American Airlines flights from Chicago to Basseterre

Our best American Airlines deals on Chicago to Basseterre flight tickets
American Airlines
Aug 1
ORD5:07 amChicago O'Hare Intl
7h 05m
1 stop
SKB1:12 pmBasseterre Robert Bradshaw Intl
Aug 4
SKB2:43 pmBasseterre Robert Bradshaw Intl
17h 51m
1 stop
ORD7:34 amChicago O'Hare Intl
$637
American Airlines
Aug 1
ORD9:29 pmChicago O'Hare Intl
15h 14m
2 stops
SKB1:43 pmBasseterre Robert Bradshaw Intl
Aug 4
SKB2:43 pmBasseterre Robert Bradshaw Intl
17h 47m
2 stops
ORD7:30 amChicago O'Hare Intl
$642
American Airlines
Aug 18
ORD8:58 pmChicago O'Hare Intl
15h 38m
2 stops
SKB1:36 pmBasseterre Robert Bradshaw Intl
Aug 23
SKB2:44 pmBasseterre Robert Bradshaw Intl
17h 46m
2 stops
ORD7:30 amChicago O'Hare Intl
$647

British Airways flights from Chicago to Basseterre

Our best British Airways deals on Chicago to Basseterre flight tickets
British Airways
Sep 21
ORD5:00 pmChicago O'Hare Intl
21h 30m
2 stops
SKB3:30 pmBasseterre Robert Bradshaw Intl
Sep 26
SKB5:10 pmBasseterre Robert Bradshaw Intl
51h 05m
3 stops
ORD7:15 pmChicago O'Hare Intl
$5,969
British Airways
Sep 21
ORD7:47 amChicago O'Hare Intl
30h 43m
3 stops
SKB3:30 pmBasseterre Robert Bradshaw Intl
Sep 26
SKB5:10 pmBasseterre Robert Bradshaw Intl
27h 05m
3 stops
ORD7:15 pmChicago O'Hare Intl
$5,974

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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, momondo users made 832,500 searches. Data last updated June 29, 2026.
Use the filters below to find and compare flights from Chicago to Basseterre that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 8/1

5:07 am-1:12 pm

1 stop7h 05m

Basseterre Robert Bradshaw Intl

Tue 8/4

2:43 pm-7:34 am

1 stop17h 51m

$637

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 8/1

8:54 pm-1:43 pm

2 stops15h 49m

Basseterre Robert Bradshaw Intl

Tue 8/4

2:43 pm-12:26 am

1 stop10h 43m

$642

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Tue 8/18

8:58 pm-1:36 pm

2 stops15h 38m

Basseterre Robert Bradshaw Intl

Sun 8/23

2:44 pm-7:30 am

2 stops17h 46m

$647

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Mon 9/21

5:00 am-1:35 pm

1 stop7h 35m

Basseterre Robert Bradshaw Intl

Sat 9/26

2:40 pm-11:32 pm

1 stop9h 52m

$679
Quickest round-trip

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 7/18

5:00 am-1:43 pm

1 stop7h 43m

Basseterre Robert Bradshaw Intl

Sat 7/25

2:12 pm-10:00 pm

1 stop8h 48m

$682

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Mon 9/21

7:00 pm-1:35 pm

1 stop17h 35m

Basseterre Robert Bradshaw Intl

Sat 9/26

2:40 pm-7:58 am

2 stops18h 18m

$684

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 7/18

8:59 pm-1:43 pm

2 stops15h 44m

Basseterre Robert Bradshaw Intl

Sat 7/25

2:43 pm-6:38 am

2 stops16h 55m

$687

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Wed 10/7

1:00 pm-1:03 pm

1 stop23h 03m

Basseterre Robert Bradshaw Intl

Wed 10/14

8:35 am-11:44 pm

2 stops16h 09m

$695

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 7/18

5:07 am-1:12 pm

1 stop7h 05m

Basseterre Robert Bradshaw Intl

Sun 7/26

2:43 pm-9:08 am

1 stop19h 25m

$702

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 7/18

8:54 pm-1:43 pm

2 stops15h 49m

Basseterre Robert Bradshaw Intl

Sun 7/26

2:43 pm-9:08 am

1 stop19h 25m

$706

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Basseterre from

How to get the cheapest flight ticket from Chicago to Basseterre

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Basseterre?

If you don’t want to visit Basseterre in February, then you should wait until October to fly from Chicago, when ticket prices are also cheap, with an average price of $485.

When to book flights from Chicago to Basseterre

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Basseterre according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Basseterre (CHI to SKB) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Basseterre

Fastest flight time

7h 44m

Direct flights

None
The fastest flight from Chicago to Basseterre takes 7h 44m
There are no direct flights from Chicago to Basseterre. There are no popular flight routes from Chicago to Basseterre.
Search flight deals

Frequently asked questions about flying from Chicago to Basseterre

  • How far is Chicago to Basseterre Robert Bradshaw Intl by plane?

    The distance between Chicago and Basseterre Robert Bradshaw Intl is about 2244.7 mi. In terms of flight time, this usually takes a little over 7h 44m.

  • When did momondo last update prices for flights from Chicago to Basseterre Robert Bradshaw Intl Airport?

    Prices for flights from Chicago to Basseterre Robert Bradshaw Intl Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to Basseterre Robert Bradshaw Intl Airport?

  • How old do you have to be to fly from Chicago to Basseterre Robert Bradshaw Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Basseterre Robert Bradshaw Intl Airport.

  • What documentation or ID do you need to fly to Basseterre Robert Bradshaw Intl Airport?

    The travel and health documents required for your trip to Basseterre Robert Bradshaw Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Basseterre Robert Bradshaw Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Chicago to Basseterre?

Best airlines flying from Chicago to Basseterre

Compare and see reviews for airlines that fly from Chicago to Basseterre with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $488Free CancellationRating
7.1
11,768 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Basseterre?

It is quick and easy to find Chicago to Basseterre flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Basseterre that suits you.

Can I find flights from Chicago to Basseterre with flexible booking policies on momondo?

Flights from Chicago to Basseterre with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Basseterre?

Once you have performed a search for Chicago to Basseterre flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Basseterre right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Basseterre now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Basseterre and let you know when they change.

An easier way to manage your Basseterre trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 7/29
Wed 8/5
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Saint Kitts and Nevis

Airports servicing Saint Kitts and Nevis

Newcastle Airport
St Kitts Airport
Nevis Island Airport