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Cheap flights from Chicago to Basseterre from $446

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 6/15. 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

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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.
JetBlue Logo
1:56 pm - 2:35 pm
ORD
-
SKB
23h 39m
2 stops
JetBlue Logo
3:47 pm - 9:54 am
SKB
-
ORD
19h 07m
1 stop
$658JetBlue
Sat, May 30 - Thu, Jun 4
Multiple Airlines Logo
8:31 am - 1:19 pm
ORD
-
SKB
27h 48m
1 stop
Multiple Airlines Logo
3:20 pm - 9:10 am
SKB
-
ORD
18h 50m
1 stop
$664Multiple Airlines
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
8:00 am - 6:30 pm
ORD
-
SKB
9h 30m
1 stop
Multiple Airlines Logo
8:30 am - 11:26 pm
SKB
-
ORD
15h 56m
1 stop
$668Multiple Airlines
Sun, May 31 - Fri, Jun 5
JetBlue Logo
10:45 am - 2:35 pm
ORD
-
SKB
26h 50m
1 stop
JetBlue Logo
3:47 pm - 9:54 am
SKB
-
ORD
19h 07m
1 stop
$669JetBlue
Sat, May 30 - Thu, Jun 4
Multiple Airlines Logo
8:31 am - 1:19 pm
ORD
-
SKB
27h 48m
1 stop
Multiple Airlines Logo
3:20 pm - 8:00 am
SKB
-
ORD
17h 40m
2 stops
$673Multiple Airlines
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
7:52 pm - 6:30 pm
ORD
-
SKB
21h 38m
2 stops
Multiple Airlines Logo
8:30 am - 11:26 pm
SKB
-
ORD
15h 56m
1 stop
$705Multiple Airlines
Sat, May 30 - Fri, Jun 5
Multiple Airlines Logo
5:30 pm - 6:30 pm
ORD
-
SKB
24h 00m
2 stops
Multiple Airlines Logo
8:30 am - 11:26 pm
SKB
-
ORD
15h 56m
1 stop
$706Multiple Airlines
Wed, Jun 3 - Mon, Jun 8
Multiple Airlines Logo
12:45 pm - 6:30 pm
ORD
-
SKB
28h 45m
2 stops
Multiple Airlines Logo
8:30 am - 3:41 pm
SKB
-
ORD
8h 11m
1 stop
$707Multiple Airlines
Sat, Apr 4 - Fri, Apr 10
Multiple Airlines Logo
8:00 am - 6:30 pm
ORD
-
SKB
9h 30m
1 stop
Multiple Airlines Logo
8:30 am - 4:16 pm
SKB
-
ORD
32h 46m
2 stops
$708Multiple Airlines
Sun, May 31 - Fri, Jun 5
Delta Logo
1:16 pm - 2:03 pm
MDW
-
SKB
23h 47m
2 stops
Delta Logo
3:18 pm - 10:17 pm
SKB
-
MDW
7h 59m
1 stop
$854Delta
Fri, Jun 19 - Sat, Jun 27

American Airlines flights from Chicago to Basseterre

Our best American Airlines deals on Chicago to Basseterre flight tickets
American Airlines
Jun 1
ORD5:00 amChicago O'Hare Intl
7h 40m
1 stop
SKB1:40 pmBasseterre Robert Bradshaw Intl
Jun 9
SKB2:40 pmBasseterre Robert Bradshaw Intl
10h 44m
1 stop
ORD12:24 amChicago O'Hare Intl
$719
American Airlines
Jun 1
ORD8:57 pmChicago O'Hare Intl
15h 43m
2 stops
SKB1:40 pmBasseterre Robert Bradshaw Intl
Jun 9
SKB2:40 pmBasseterre Robert Bradshaw Intl
8h 53m
1 stop
ORD10:33 pmChicago O'Hare Intl
$724
American Airlines
May 6
ORD5:00 amChicago O'Hare Intl
7h 35m
1 stop
SKB1:35 pmBasseterre Robert Bradshaw Intl
May 13
SKB2:35 pmBasseterre Robert Bradshaw Intl
17h 49m
2 stops
ORD7:24 amChicago O'Hare Intl
$759

JetBlue flights from Chicago to Basseterre

Our best JetBlue deals on Chicago to Basseterre flight tickets
JetBlue
May 30
ORD1:56 pmChicago O'Hare Intl
23h 39m
2 stops
SKB2:35 pmBasseterre Robert Bradshaw Intl
Jun 4
SKB3:47 pmBasseterre Robert Bradshaw Intl
19h 07m
1 stop
ORD9:54 amChicago O'Hare Intl
$658
JetBlue
May 30
ORD10:45 amChicago O'Hare Intl
26h 50m
1 stop
SKB2:35 pmBasseterre Robert Bradshaw Intl
Jun 4
SKB3:47 pmBasseterre Robert Bradshaw Intl
19h 07m
1 stop
ORD9:54 amChicago O'Hare Intl
$669

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 March 25, 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 5/30

1:56 pm-2:35 pm

2 stops23h 39m

Basseterre Robert Bradshaw Intl

Thu 6/4

3:47 pm-9:54 am

1 stop19h 07m

$658

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 4/18

8:31 am-1:19 pm

1 stop27h 48m

Basseterre Robert Bradshaw Intl

Sat 4/25

3:20 pm-9:10 am

1 stop18h 50m

$664
Quickest round-trip

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sun 5/31

8:00 am-6:30 pm

1 stop9h 30m

Basseterre Robert Bradshaw Intl

Fri 6/5

8:30 am-11:26 pm

1 stop15h 56m

$668

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 5/30

10:45 am-2:35 pm

1 stop26h 50m

Basseterre Robert Bradshaw Intl

Thu 6/4

3:47 pm-9:54 am

1 stop19h 07m

$669

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 4/18

8:31 am-1:19 pm

1 stop27h 48m

Basseterre Robert Bradshaw Intl

Sat 4/25

3:20 pm-8:00 am

2 stops17h 40m

$673

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 5/30

7:52 pm-6:30 pm

2 stops21h 38m

Basseterre Robert Bradshaw Intl

Fri 6/5

8:30 am-11:26 pm

1 stop15h 56m

$705

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Wed 6/3

5:30 pm-6:30 pm

2 stops24h 00m

Basseterre Robert Bradshaw Intl

Mon 6/8

8:30 am-11:26 pm

1 stop15h 56m

$706

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 4/4

12:45 pm-6:30 pm

2 stops28h 45m

Basseterre Robert Bradshaw Intl

Fri 4/10

8:30 am-3:41 pm

1 stop8h 11m

$707

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sun 5/31

8:00 am-6:30 pm

1 stop9h 30m

Basseterre Robert Bradshaw Intl

Fri 6/5

8:30 am-4:16 pm

2 stops32h 46m

$708

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Fri 6/19

1:16 pm-2:03 pm

2 stops23h 47m

Basseterre Robert Bradshaw Intl

Sat 6/27

3:18 pm-10:17 pm

1 stop7h 59m

$854

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 resultsSorted by cheapest first
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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?

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

11h 30m

Direct flights

None
The fastest flight from Chicago to Basseterre takes 11h 30m
There are no direct flights from Chicago to Basseterre. There are no popular flight routes from Chicago to Basseterre.
Search flight deals

  • 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 11h 30m.

  • 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
11,494 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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