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St Kitts

$544+ Cheap flights from Chicago (CHI) to St Kitts

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SKB
Jul 9 — Jul 161
Thu 7/9
Thu 7/16
1 adult, Economy
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Cheap flight deals from Chicago to St Kitts

Cheapest flights from Chicago to St Kitts
Explore the most affordable flight options available from Chicago to St Kitts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 9, 2026.

This Travelocity deal was found by Cheapflights users on 6/5. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/231:00 pm
ORD
-
SKB
1 stop23h 03m
JetBlue
Sun 9/272:10 pm
SKB
-
ORD
1 stop22h 37m
JetBlue
Deal found 6/5$544
This Travelocity deal was found by Cheapflights users on 6/7. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:30 pm
ORD
-
SKB
1 stop19h 03m
JetBlue
Sun 7/263:38 pm
SKB
-
ORD
1 stop18h 12m
JetBlue
Deal found 6/7$624
This Justfly.com deal was found by Cheapflights users on 6/5. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:00 am
ORD
-
SKB
1 stop7h 49m
JetBlue
Thu 7/23:55 pm
SKB
-
ORD
1 stop30h 35m
JetBlue
Deal found 6/5$631
This American Airlines deal was found by Cheapflights users on 6/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/315:59 pm
ORD
-
SKB
1 stop18h 44m
American Airlines
Fri 8/72:44 pm
SKB
-
ORD
1 stop9h 46m
American Airlines
Deal found 6/4$637
This American Airlines deal was found by Cheapflights users on 6/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:00 pm
ORD
-
SKB
1 stop17h 35m
American Airlines
Sun 9/272:40 pm
SKB
-
ORD
1 stop9h 52m
American Airlines
Deal found 6/5$642
This Delta deal was found by Cheapflights users on 6/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:30 am
ORD
-
SKB
1 stop7h 20m
Delta
Sat 8/223:15 pm
SKB
-
ORD
1 stop9h 42m
Delta
Deal found 6/8$647
This Delta deal was found by Cheapflights users on 6/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:00 am
MDW
-
SKB
1 stop7h 03m
Delta
Sat 8/13:18 pm
SKB
-
MDW
1 stop7h 57m
Delta
Deal found 6/6$647
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/68:54 pm
ORD
-
SKB
2 stops15h 49m
American Airlines
Mon 7/132:43 pm
SKB
-
ORD
2 stops16h 55m
American Airlines
Deal found 6/7$652
This American Airlines deal was found by Cheapflights users on 6/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:00 am
ORD
-
SKB
1 stop7h 15m
American Airlines
Sun 11/13:39 pm
SKB
-
ORD
2 stops17h 37m
American Airlines
Deal found 6/6$657
This American Airlines deal was found by Cheapflights users on 6/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:59 pm
ORD
-
SKB
1 stop17h 45m
American Airlines
Fri 9/112:40 pm
SKB
-
ORD
1 stop10h 52m
American Airlines
Deal found 6/4$659
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/165:00 am
ORD
-
SKB
1 stop7h 43m
American Airlines
Mon 7/202:43 pm
SKB
-
ORD
1 stop19h 25m
American Airlines
Deal found 6/7$662

Find flight deals from Chicago to St Kitts

Keep the following information in mind while searching for Chicago to St Kitts flight deals. Data was last updated June 9, 2026.

Round-trip from

$544
(Travelocity)

Popular in

March

Cheapest in

February

Average price

$692
From Chicago (CHI) to St Kitts
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($83 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($72 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to St Kitts 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 June 9, 2026.
Use the filters below to find and compare flights from Chicago to St Kitts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Wed 7/22

6:30 pm-2:33 pm

1 stop19h 03m

Basseterre Robert Bradshaw Intl

Sun 7/26

3:38 pm-8:50 am

1 stop18h 12m

$624

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 8/15

5:00 am-1:44 pm

1 stop7h 44m

Basseterre Robert Bradshaw Intl

Sat 8/22

2:44 pm-11:30 pm

1 stop9h 46m

$647

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 8/15

5:30 am-1:50 pm

1 stop7h 20m

Basseterre Robert Bradshaw Intl

Sat 8/22

3:15 pm-11:57 pm

1 stop9h 42m

$647

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Mon 7/6

5:00 am-1:43 pm

1 stop7h 43m

Basseterre Robert Bradshaw Intl

Mon 7/13

2:43 pm-11:30 pm

1 stop9h 47m

$647

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 7/25

5:30 am-2:03 pm

1 stop7h 33m

Basseterre Robert Bradshaw Intl

Sat 8/1

3:18 pm-11:53 pm

1 stop9h 35m

$647

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 8/1

5:59 pm-1:43 pm

1 stop18h 44m

Basseterre Robert Bradshaw Intl

Sat 8/8

3:30 pm-9:05 am

1 stop18h 35m

$647
Quickest round-trip

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Sat 7/25

6:00 am-2:03 pm

1 stop7h 03m

Basseterre Robert Bradshaw Intl

Sat 8/1

3:18 pm-10:15 pm

1 stop7h 57m

$647

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Thu 7/23

5:00 am-1:43 pm

1 stop7h 43m

Basseterre Robert Bradshaw Intl

Thu 7/30

2:43 pm-12:26 am

1 stop10h 43m

$647

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sun 10/25

7:05 pm-1:15 pm

1 stop17h 10m

Basseterre Robert Bradshaw Intl

Sun 11/1

3:39 pm-11:08 pm

1 stop9h 29m

$652

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Thu 7/16

5:00 am-1:43 pm

1 stop7h 43m

Basseterre Robert Bradshaw Intl

Mon 7/20

2:43 pm-6:38 am

2 stops16h 55m

$652

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/7

Sorted by cheapest first

Best time to book a flight from Chicago to St Kitts

Have a flexible travel schedule? Discover the best time to fly to St Kitts 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 St Kitts

What is the cheapest month to book a flight from Chicago to St Kitts?

Currently, February is the cheapest month in which you can book a flight from Chicago to St Kitts (average of $471). Flying from Chicago to St Kitts in March is currently the most expensive (average of $779). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing St Kitts

Get insights into the airlines that provide service to St Kitts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to St Kitts. Reviews last updated June 9, 2026.
See what other customers who have flown with American Airlines from Chicago to St Kitts have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,640 reviews

Entertainment

6.9

Comfort

7.2

Overall

7.1

Food

6.4

Boarding

7.5

Crew

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!
American Airlines
7.1
Good
11,640 reviews
American Airlines
7.1
Good
11,640 reviews

Entertainment

6.9

Comfort

7.2

Overall

7.1

Food

6.4

Boarding

7.5

Crew

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!

Related info for your journey

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

  • How long is the flight from Chicago to St Kitts?

    A quick flight from Chicago to St Kitts can take about 7h 03m. JetBlue provides one of the quickest options available for as low as $647. Airlines will cover a distance of 2245 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

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

  • How can I find direct flights from Chicago to St Kitts?

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

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

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

  • What is the cheapest month to book a flight from Chicago to St Kitts?

    Currently, February is the cheapest month in which you can book a flight from Chicago to St Kitts (average of $471). Flying from Chicago to St Kitts in March is currently the most expensive (average of $779). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Complete your trip

Complete your trip to St Kitts by adding a car rental and/or hotel reservation to your travel itinerary.
Basseterre Robert Bradshaw Intl Airport car rentals
Basseterre car rentals

Top airline flying from Chicago to St Kitts

Discover the top airline that operate flights from Chicago to St Kitts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$488Average$779FlexibilityNo cancel feeOn-time71%

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