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Gustavia

$324+ Cheap flights from Chicago (CHI) to Gustavia (SBH)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SBH
févr. 28 — mars 71
sam. 2/28
sam. 3/7
1 adult, Economy
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Cheap flight deals from Chicago to Gustavia

Cheapest flights from Chicago to Gustavia
Explore the most affordable flight options available from Chicago to Gustavia. Find the lowest fares from popular airlines and budget airlines, with prices last updated on janvier 29, 2026.

This Mytrip deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 5/155:15 am
ORD
-
SBH
2 stops8h 55m
Multiple Airlines
mar. 5/1911:35 am
SBH
-
ORD
2 stops13h 06m
Multiple Airlines
Deal found 1/27$834
This Mytrip deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/145:15 am
ORD
-
SBH
2 stops10h 00m
Multiple Airlines
lun. 5/1811:35 am
SBH
-
ORD
2 stops13h 06m
Multiple Airlines
Deal found 1/27$908
This Mytrip deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 3/135:05 am
ORD
-
SBH
2 stops11h 10m
Multiple Airlines
ven. 3/2011:30 am
SBH
-
ORD
3 stops25h 17m
Multiple Airlines
Deal found 1/26$997
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 4/225:15 am
ORD
-
SBH
2 stops29h 25m
Multiple Airlines
dim. 4/268:20 am
SBH
-
ORD
1 stop9h 17m
Multiple Airlines
Deal found 1/28$1,141
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 3/157:26 pm
ORD
-
SBH
1 stop12h 56m
Multiple Airlines
dim. 3/225:30 pm
SBH
-
ORD
2 stops42h 06m
Multiple Airlines
Deal found 1/27$1,147
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 2/2012:17 pm
ORD
-
SBH
1 stop17h 35m
Multiple Airlines
lun. 2/235:25 pm
SBH
-
ORD
2 stops32h 22m
Multiple Airlines
Deal found 1/27$1,149
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 2/1912:17 pm
ORD
-
SBH
1 stop17h 35m
Multiple Airlines
lun. 2/235:25 pm
SBH
-
ORD
2 stops32h 22m
Multiple Airlines
Deal found 1/27$1,194

Find flight deals from Chicago to Gustavia

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Gustavia (SBH). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated janvier 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$834
(Mytrip)

One-way from

$324
(Kiwi.com)
Provider with most accurate pricing for Chicago (CHI)-Gustavia St Barthelemy flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Gustavia St Barthelemy flights.
Search Deals
From Chicago (CHI) to Gustavia St Barthelemy
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One-way flight from Chicago (CHI) to Gustavia St Barthelemy
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Gustavia 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, Cheapflights users made 2,558,603 searches. Data last updated janvier 29, 2026.
Use the filters below to find and compare flights from Chicago to Gustavia that are best for you.

Fly from

Chicago

Fly to

Gustavia

Route

Depart

Return

Price

ChicagoGustavia

ORD - SBH

ORDSBH

Chicago O'Hare Intl

ven. 5/15

5:15 am-3:10 pm

2 stops8h 55m

Gustavia St Barthelemy

mar. 5/19

11:35 am-11:41 pm

2 stops13h 06m

$834

ChicagoGustavia

ORD - SBH

ORDSBH

Chicago O'Hare Intl

jeu. 5/14

5:15 am-4:15 pm

2 stops10h 00m

Gustavia St Barthelemy

lun. 5/18

11:35 am-11:41 pm

2 stops13h 06m

$908

ChicagoGustavia

ORD - SBH

ORDSBH

Chicago O'Hare Intl

ven. 3/13

8:55 pm-5:15 pm

3 stops19h 20m

Gustavia St Barthelemy

ven. 3/20

11:35 am-11:47 am

3 stops25h 12m

$1,004

ChicagoGustavia

ORD - SBH

ORDSBH

Chicago O'Hare Intl

dim. 3/15

7:26 pm-9:22 am

1 stop12h 56m

Gustavia St Barthelemy

dim. 3/22

5:30 pm-10:36 am

2 stops42h 06m

$1,147

ChicagoGustavia

ORD - SBH

ORDSBH

Chicago O'Hare Intl

ven. 2/20

12:17 pm-7:52 am

1 stop17h 35m

Gustavia St Barthelemy

lun. 2/23

5:25 pm-11:47 pm

2 stops32h 22m

$1,149

ChicagoGustavia

ORD - SBH

ORDSBH

Chicago O'Hare Intl

jeu. 2/19

12:17 pm-7:52 am

1 stop17h 35m

Gustavia St Barthelemy

lun. 2/23

5:25 pm-11:47 pm

2 stops32h 22m

$1,194

ChicagoGustavia

ORD - SBH

ORDSBH

Chicago O'Hare Intl

lun. 4/6

5:05 am-5:10 pm

2 stops11h 05m

$324

ChicagoGustavia

ORD - SBH

ORDSBH

Chicago O'Hare Intl

sam. 4/11

5:05 am-9:20 am

2 stops27h 15m

$328

ChicagoGustavia

ORD - SBH

ORDSBH

Chicago O'Hare Intl

mar. 4/7

5:05 am-9:20 am

2 stops27h 15m

$328

ChicagoGustavia

ORD - SBH

ORDSBH

Chicago O'Hare Intl

mer. 4/8

5:05 am-9:20 am

2 stops27h 15m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 13 results
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Compare providers for flights from Chicago to Gustavia

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Gustavia in January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Gustavia flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Gustavia flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Gustavia flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Gustavia flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Gustavia flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Gustavia

Have a flexible travel schedule? Discover the best time to fly to Gustavia from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Gustavia
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Gustavia. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Gustavia from Chicago?

    Located just 0.7 mi from the city center, Gustavia St Barthelemy is the airport most travelers will use when flying to Gustavia from Chicago. Booking flights from Chicago to St Barthelemy (SBH) should be relatively easy as there are 0 daily inbound flights from Chicago from 0 different airlines.

  • Can I find deals for flights from Chicago to Gustavia that include hotel bookings?

    Yes. In addition to deals on Chicago to Gustavia flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Gustavia?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Gustavia.

  • Can I find deals for business class flights from Chicago to Gustavia?

    Yes. Cheapflights offers flight deals from Chicago to Gustavia by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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O'Hare Intl to Gustavia flights

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