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Cheap flights from Chicago to Basseterre from $327

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 8/8. 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
0 bags

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Find the cheapest flights from Chicago to Basseterre

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
2:00 pm - 4:00 pm
ORD
-
SKB
24h 00m
1 stop
Air Canada Logo
5:00 pm - 12:56 pm
SKB
-
ORD
21h 56m
1 stop
$658Air Canada
Fri, Nov 6 - Sat, Nov 14
American Airlines Logo
7:16 pm - 1:20 pm
ORD
-
SKB
17h 04m
1 stop
American Airlines Logo
2:50 pm - 10:31 pm
SKB
-
ORD
8h 41m
1 stop
$659American Airlines
Sat, Oct 3 - Wed, Oct 7
Air Canada Logo
6:30 pm - 4:00 pm
ORD
-
SKB
19h 30m
1 stop
Air Canada Logo
5:00 pm - 11:10 am
SKB
-
ORD
20h 10m
2 stops
$662Air Canada
Fri, Nov 6 - Sat, Nov 14
Multiple Airlines Logo
12:50 pm - 12:15 pm
ORD
-
SKB
46h 25m
2 stops
Multiple Airlines Logo
5:00 pm - 1:56 pm
SKB
-
ORD
21h 56m
1 stop
$663Multiple Airlines
Sun, Oct 25 - Sat, Oct 31
American Airlines Logo
8:00 pm - 1:20 pm
ORD
-
SKB
16h 20m
2 stops
American Airlines Logo
2:50 pm - 11:42 pm
SKB
-
ORD
9h 52m
1 stop
$664American Airlines
Sat, Oct 3 - Wed, Oct 7
Air Canada Logo
3:55 pm - 4:00 pm
ORD
-
SKB
22h 05m
2 stops
Air Canada Logo
5:00 pm - 11:10 am
SKB
-
ORD
20h 10m
2 stops
$665Air Canada
Fri, Nov 6 - Sat, Nov 14
Multiple Airlines Logo
7:15 am - 12:15 pm
ORD
-
SKB
52h 00m
2 stops
Multiple Airlines Logo
5:00 pm - 8:50 am
SKB
-
ORD
16h 50m
2 stops
$694Multiple Airlines
Sun, Oct 25 - Sat, Oct 31
American Airlines Logo
8:53 pm - 1:38 pm
ORD
-
SKB
15h 45m
2 stops
American Airlines Logo
2:40 pm - 7:28 am
SKB
-
ORD
17h 48m
2 stops
$699American Airlines
Sat, Aug 22 - Mon, Aug 24
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
$729American Airlines
Fri, Oct 9 - Mon, Oct 12
Delta Logo
6:00 am - 2:03 pm
MDW
-
SKB
7h 03m
1 stop
Delta Logo
3:18 pm - 10:17 pm
SKB
-
MDW
7h 59m
1 stop
$789Delta
Sat, Jun 27 - Sat, Jul 4

JetBlue flights from Chicago to Basseterre

Our best JetBlue deals on Chicago to Basseterre flight tickets
JetBlue
Jun 5
ORD8:30 pmChicago O'Hare Intl
41h 05m
2 stops
SKB2:35 pmBasseterre Robert Bradshaw Intl
Jun 14
SKB3:55 pmBasseterre Robert Bradshaw Intl
17h 50m
1 stop
ORD8:45 amChicago O'Hare Intl
$782
JetBlue
Jun 29
ORD5:22 pmChicago O'Hare Intl
20h 27m
1 stop
SKB2:49 pmBasseterre Robert Bradshaw Intl
Jul 7
SKB3:38 pmBasseterre Robert Bradshaw Intl
26h 42m
1 stop
ORD5:20 pmChicago O'Hare Intl
$783

Delta flights from Chicago to Basseterre

Our best Delta deals on Chicago to Basseterre flight tickets
Delta
Jun 27
MDW6:00 amChicago Midway
7h 03m
1 stop
SKB2:03 pmBasseterre Robert Bradshaw Intl
Jul 4
SKB3:18 pmBasseterre Robert Bradshaw Intl
7h 59m
1 stop
MDW10:17 pmChicago Midway
$789
Delta
May 23
ORD5:30 amChicago O'Hare Intl
7h 30m
1 stop
SKB2:00 pmBasseterre Robert Bradshaw Intl
May 30
SKB3:15 pmBasseterre Robert Bradshaw Intl
9h 48m
1 stop
ORD12:03 amChicago O'Hare Intl
$1,009

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 May 14, 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

Fri 11/6

2:00 pm-4:00 pm

1 stop24h 00m

Basseterre Robert Bradshaw Intl

Sat 11/14

5:00 pm-12:56 pm

1 stop21h 56m

$658

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 10/3

7:16 pm-1:20 pm

1 stop17h 04m

Basseterre Robert Bradshaw Intl

Wed 10/7

2:50 pm-10:31 pm

1 stop8h 41m

$659

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Fri 11/6

6:30 pm-4:00 pm

1 stop19h 30m

Basseterre Robert Bradshaw Intl

Sat 11/14

5:00 pm-11:10 am

2 stops20h 10m

$662

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sun 10/25

12:50 pm-12:15 pm

2 stops46h 25m

Basseterre Robert Bradshaw Intl

Sat 10/31

5:00 pm-1:56 pm

1 stop21h 56m

$663

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 10/3

8:00 pm-1:20 pm

2 stops16h 20m

Basseterre Robert Bradshaw Intl

Wed 10/7

2:50 pm-11:42 pm

1 stop9h 52m

$664

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Fri 11/6

3:55 pm-4:00 pm

2 stops22h 05m

Basseterre Robert Bradshaw Intl

Sat 11/14

5:00 pm-11:10 am

2 stops20h 10m

$665

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sun 10/25

7:15 am-12:15 pm

2 stops52h 00m

Basseterre Robert Bradshaw Intl

Sat 10/31

5:00 pm-8:50 am

2 stops16h 50m

$694

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 8/22

8:53 pm-1:38 pm

2 stops15h 45m

Basseterre Robert Bradshaw Intl

Mon 8/24

2:40 pm-7:28 am

2 stops17h 48m

$699

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Fri 10/9

7:05 pm-1:15 pm

1 stop17h 10m

Basseterre Robert Bradshaw Intl

Mon 10/12

2:50 pm-10:31 pm

1 stop8h 41m

$729
Quickest round-trip

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Sat 6/27

6:00 am-2:03 pm

1 stop7h 03m

Basseterre Robert Bradshaw Intl

Sat 7/4

3:18 pm-10:17 pm

1 stop7h 59m

$789

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 typical price of a round-trip flight between Chicago and Basseterre?

What is the cheapest month to fly to Basseterre?

If you don’t want to visit Basseterre in August, then you should wait until February to fly from Chicago, when ticket prices are also cheap, with an average price of $471.

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 03m

Direct flights

None
The fastest flight from Chicago to Basseterre takes 7h 03m
There are no direct flights from Chicago to Basseterre. There are no popular flight routes from Chicago to Basseterre.
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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 03m.

  • 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
11,662 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.

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