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Cheap flights from Chicago to Basseterre from $397

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 9/13. 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.
Air Canada Logo
8:50 pm - 4:25 pmORD  Chicago O'Hare Intl-SKB Basseterre Robert Bradshaw Intl
17h 35m1 stop Toronto Pearson Intl
Air Canada Logo
5:25 pm - 9:08 amSKB  Basseterre Robert Bradshaw Intl-ORD Chicago O'Hare Intl
17h 43m1 stop Toronto Pearson Intl
$586Air Canada
Fri, Feb 5 - Sat, Feb 13
Air Canada Logo
3:45 pm - 4:25 pmORD  Chicago O'Hare Intl-SKB Basseterre Robert Bradshaw Intl
22h 40m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
5:25 pm - 9:08 amSKB  Basseterre Robert Bradshaw Intl-ORD Chicago O'Hare Intl
17h 43m1 stop Toronto Pearson Intl
$589Air Canada
Fri, Feb 5 - Sat, Feb 13
Air Canada Logo
3:45 pm - 4:25 pmORD  Chicago O'Hare Intl-SKB Basseterre Robert Bradshaw Intl
22h 40m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
5:25 pm - 11:07 amSKB  Basseterre Robert Bradshaw Intl-ORD Chicago O'Hare Intl
19h 42m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
$592Air Canada
Fri, Feb 5 - Sat, Feb 13
Multiple Airlines Logo
8:50 pm - 4:25 pmORD  Chicago O'Hare Intl-SKB Basseterre Robert Bradshaw Intl
17h 35m1 stop Toronto Pearson Intl
Multiple Airlines Logo
12:45 pm - 9:08 amSKB  Basseterre Robert Bradshaw Intl-ORD Chicago O'Hare Intl
22h 23m2 stops Bridgetown Grantley Adams Intl Toronto Pearson Intl
$625Multiple Airlines
Fri, Jan 15 - Tue, Jan 19
Multiple Airlines Logo
8:50 pm - 4:25 pmORD  Chicago O'Hare Intl-SKB Basseterre Robert Bradshaw Intl
17h 35m1 stop Toronto Pearson Intl
Multiple Airlines Logo
12:45 pm - 9:08 amSKB  Basseterre Robert Bradshaw Intl-ORD Chicago O'Hare Intl
22h 23m2 stops Bridgetown Grantley Adams Intl Toronto Pearson Intl
$626Multiple Airlines
Fri, Jan 15 - Tue, Jan 19
Multiple Airlines Logo
3:45 pm - 4:25 pmORD  Chicago O'Hare Intl-SKB Basseterre Robert Bradshaw Intl
22h 40m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Multiple Airlines Logo
12:45 pm - 9:08 amSKB  Basseterre Robert Bradshaw Intl-ORD Chicago O'Hare Intl
22h 23m2 stops Bridgetown Grantley Adams Intl Toronto Pearson Intl
$629Multiple Airlines
Fri, Jan 15 - Tue, Jan 19
Multiple Airlines Logo
8:50 pm - 4:25 pmORD  Chicago O'Hare Intl-SKB Basseterre Robert Bradshaw Intl
17h 35m1 stop Toronto Pearson Intl
Multiple Airlines Logo
12:45 pm - 9:08 amSKB  Basseterre Robert Bradshaw Intl-ORD Chicago O'Hare Intl
22h 23m2 stops Bridgetown Grantley Adams Intl Toronto Pearson Intl
$634Multiple Airlines
Fri, Jan 15 - Tue, Jan 19
Multiple Airlines Logo
6:04 pm - 4:25 pmORD  Chicago O'Hare Intl-SKB Basseterre Robert Bradshaw Intl
44h 21m2 stops Ottawa Toronto Pearson Intl
Multiple Airlines Logo
12:45 pm - 7:52 pmSKB  Basseterre Robert Bradshaw Intl-ORD Chicago O'Hare Intl
33h 07m2 stops Bridgetown Grantley Adams Intl Montreal Pierre Elliott Trudeau Intl
$647Multiple Airlines
Thu, Jan 21 - Thu, Jan 28
American Airlines Logo
6:05 pm - 2:33 pmORD  Chicago O'Hare Intl-SKB Basseterre Robert Bradshaw Intl
18h 28m1 stop Miami
American Airlines Logo
3:33 pm - 8:00 amSKB  Basseterre Robert Bradshaw Intl-ORD Chicago O'Hare Intl
18h 27m1 stop Miami
$739American Airlines
Tue, Nov 3 - Thu, Nov 5
American Airlines Logo
9:06 pm - 2:33 pmORD  Chicago O'Hare Intl-SKB Basseterre Robert Bradshaw Intl
15h 27m2 stops Charlotte Douglas Miami
American Airlines Logo
3:33 pm - 7:23 amSKB  Basseterre Robert Bradshaw Intl-ORD Chicago O'Hare Intl
17h 50m2 stops Miami Washington, D.C. Reagan-National
$744American Airlines
Tue, Nov 3 - Thu, Nov 5

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Air Canada flights from Chicago to Basseterre

Our best Air Canada deals on Chicago to Basseterre flight tickets
Air Canada
Feb 5
ORD8:50 pmChicago O'Hare Intl
17h 35m
1 stop
SKB4:25 pmBasseterre Robert Bradshaw Intl
Feb 13
SKB5:25 pmBasseterre Robert Bradshaw Intl
17h 43m
1 stop
ORD9:08 amChicago O'Hare Intl
$586
Air Canada
Feb 5
ORD3:45 pmChicago O'Hare Intl
22h 40m
2 stops
SKB4:25 pmBasseterre Robert Bradshaw Intl
Feb 13
SKB5:25 pmBasseterre Robert Bradshaw Intl
17h 43m
1 stop
ORD9:08 amChicago O'Hare Intl
$589
Air Canada
Feb 5
ORD3:45 pmChicago O'Hare Intl
22h 40m
2 stops
SKB4:25 pmBasseterre Robert Bradshaw Intl
Feb 13
SKB5:25 pmBasseterre Robert Bradshaw Intl
19h 42m
2 stops
ORD11:07 amChicago O'Hare Intl
$592

Delta flights from Chicago to Basseterre

Our best Delta deals on Chicago to Basseterre flight tickets
Delta
Jan 23
ORD5:30 amChicago O'Hare Intl
7h 30m
1 stop
SKB3:00 pmBasseterre Robert Bradshaw Intl
Jan 30
SKB2:50 pmBasseterre Robert Bradshaw Intl
11h 00m
1 stop
ORD11:50 pmChicago O'Hare Intl
$717
Delta
Jan 23
MDW6:00 amChicago Midway
7h 00m
1 stop
SKB3:00 pmBasseterre Robert Bradshaw Intl
Jan 30
SKB2:50 pmBasseterre Robert Bradshaw Intl
9h 20m
1 stop
MDW10:10 pmChicago Midway
$792

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 August 12, 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 Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl

ORDSKB

Chicago O'Hare Intl

Fri 2/5

8:50 pm-4:25 pm

1 stop17h 35m

Basseterre Robert Bradshaw Intl

Sat 2/13

5:25 pm-9:08 am

1 stop17h 43m

$586

ChicagoBasseterre

ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl

ORDSKB

Chicago O'Hare Intl

Fri 2/5

3:45 pm-4:25 pm

2 stops22h 40m

Basseterre Robert Bradshaw Intl

Sat 2/13

5:25 pm-9:08 am

1 stop17h 43m

$589

ChicagoBasseterre

ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl

ORDSKB

Chicago O'Hare Intl

Fri 2/5

3:45 pm-4:25 pm

2 stops22h 40m

Basseterre Robert Bradshaw Intl

Sat 2/13

5:25 pm-11:07 am

2 stops19h 42m

$592

ChicagoBasseterre

ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl

ORDSKB

Chicago O'Hare Intl

Fri 1/15

8:50 pm-4:25 pm

1 stop17h 35m

Basseterre Robert Bradshaw Intl

Tue 1/19

12:45 pm-9:08 am

2 stops22h 23m

$625

ChicagoBasseterre

ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl

ORDSKB

Chicago O'Hare Intl

Fri 1/15

8:50 pm-4:25 pm

1 stop17h 35m

Basseterre Robert Bradshaw Intl

Tue 1/19

12:45 pm-9:08 am

2 stops22h 23m

$626

ChicagoBasseterre

ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl

ORDSKB

Chicago O'Hare Intl

Fri 1/15

3:45 pm-4:25 pm

2 stops22h 40m

Basseterre Robert Bradshaw Intl

Tue 1/19

12:45 pm-9:08 am

2 stops22h 23m

$629

ChicagoBasseterre

ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl

ORDSKB

Chicago O'Hare Intl

Fri 1/15

8:50 pm-4:25 pm

1 stop17h 35m

Basseterre Robert Bradshaw Intl

Tue 1/19

12:45 pm-9:08 am

2 stops22h 23m

$634

ChicagoBasseterre

ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl

ORDSKB

Chicago O'Hare Intl

Thu 1/21

6:04 pm-4:25 pm

2 stops44h 21m

Basseterre Robert Bradshaw Intl

Thu 1/28

12:45 pm-7:52 pm

2 stops33h 07m

$647

ChicagoBasseterre

ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl

ORDSKB

Chicago O'Hare Intl

Tue 11/3

6:05 pm-2:33 pm

1 stop18h 28m

Basseterre Robert Bradshaw Intl

Thu 11/5

3:33 pm-8:00 am

1 stop18h 27m

$739
Quickest round-trip

ChicagoBasseterre

ORD Chicago O'Hare Intl - SKB Basseterre Robert Bradshaw Intl

ORDSKB

Chicago O'Hare Intl

Tue 11/3

9:06 pm-2:33 pm

2 stops15h 27m

Basseterre Robert Bradshaw Intl

Thu 11/5

3:33 pm-7:23 am

2 stops17h 50m

$744

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 cheapest month to fly to Basseterre?

If you don’t want to visit Basseterre in October, then you should wait until September to fly from Chicago, when ticket prices are also cheap, with an average price of $647.

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 00m

Direct flights

None
The fastest flight from Chicago to Basseterre takes 7h 00m
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 00m.

  • 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 $590Free CancellationRating
7.1
11,904 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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