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St Kitts

$446+ Cheap flights from Illinois 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SKB
Jan 19 — Jan 261
Mon 1/19
Mon 1/26
1 adult, Economy
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Cheap flight deals from Illinois to St Kitts

Cheapest flights from Illinois to St Kitts
Explore the most affordable flight options available from Illinois to St Kitts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 20, 2025.

This American Airlines deal was found by Cheapflights users on 12/19. 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 12/297:26 pmORD - SKB
1 stop17h 01mAmerican Airlines
Mon 1/55:29 pmSKB - ORD
1 stop17h 36mAmerican Airlines
Deal found 12/19$1,213
This Mytrip deal was found by Cheapflights users on 12/19. 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.
Mon 12/295:00 amORD - SKB
2 stops10h 45mMultiple Airlines
Mon 1/54:20 pmSKB - ORD
3 stops31h 47mMultiple Airlines
Deal found 12/19$1,487
This American Airlines deal was found by Cheapflights users on 12/19. 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.
Tue 12/308:45 pmORD - SKB
2 stops15h 42mAmerican Airlines
Sat 1/34:24 pmSKB - ORD
1 stop23h 55mAmerican Airlines
Deal found 12/19$1,559
This American Airlines deal was found by Cheapflights users on 12/19. 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 12/1912:02 amORD - SKB
1 stop11h 57mAmerican Airlines
Sat 1/34:24 pmSKB - ORD
1 stop23h 55mAmerican Airlines
Deal found 12/19$1,920
This Mytrip deal was found by Cheapflights users on 12/20. 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.
Sun 12/286:05 pmORD - SKB
3 stops17h 05mMultiple Airlines
Sun 1/48:35 amSKB - ORD
3 stops16h 50mMultiple Airlines
Deal found 12/20$1,999
This American Airlines deal was found by Cheapflights users on 12/20. 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 12/287:12 pmORD - SKB
1 stop17h 15mAmerican Airlines
Sun 1/45:29 pmSKB - ORD
1 stop17h 18mAmerican Airlines
Deal found 12/20$2,081
This Delta deal was found by Cheapflights users on 12/19. 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 12/206:00 amMDW - SKB
1 stop7h 13mDelta
Sat 1/32:53 pmSKB - MDW
1 stop9h 29mDelta
Deal found 12/19$3,403

Find flight deals from Illinois to St Kitts

Keep the following information in mind while searching for Illinois to St Kitts flight deals. Data was last updated December 20, 2025.

Round-trip from

$446
(American Airlines)

Popular in

August

Cheapest in

July

Average price

$1,645
From Illinois to St Kitts
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($148 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 13% potential price decrease ($118 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois 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 December 20, 2025.
Use the filters below to find and compare flights from Illinois to St Kitts that are best for you.

Fly from

Illinois

Fly to

St Kitts

Route

Depart

Return

Price

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 1/24

7:30 pm-2:47 pm

1 stop17h 17m

Basseterre Robert Bradshaw Intl

Tue 1/27

3:47 pm-12:30 am

1 stop10h 43m

$446

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Tue 1/20

7:30 pm-2:47 pm

1 stop17h 17m

Basseterre Robert Bradshaw Intl

Tue 1/27

3:47 pm-11:08 pm

1 stop9h 21m

$446

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Tue 2/3

5:00 am-2:47 pm

1 stop7h 47m

Basseterre Robert Bradshaw Intl

Tue 2/10

3:47 pm-7:22 am

2 stops17h 35m

$451

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 1/24

9:40 am-2:13 pm

1 stop26h 33m

Basseterre Robert Bradshaw Intl

Tue 1/27

3:20 pm-7:36 pm

1 stop30h 16m

$468

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 4/18

7:17 pm-1:10 pm

1 stop16h 53m

Basseterre Robert Bradshaw Intl

Sat 4/25

4:06 pm-7:10 am

2 stops16h 04m

$565

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 4/18

6:00 am-2:08 pm

1 stop7h 08m

Basseterre Robert Bradshaw Intl

Sat 4/25

1:53 pm-11:55 pm

1 stop11h 02m

$590

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Sat 4/18

6:00 am-2:08 pm

1 stop7h 08m

Basseterre Robert Bradshaw Intl

Sat 4/25

1:53 pm-9:45 pm

1 stop8h 52m

$590

St. LouisBasseterre

STL - SKB

STLSKB

Lambert-St Louis

Wed 2/4

5:04 pm-2:47 pm

2 stops19h 43m

Basseterre Robert Bradshaw Intl

Wed 2/11

3:47 pm-8:32 am

2 stops18h 45m

$688

St. LouisBasseterre

STL - SKB

STLSKB

Lambert-St Louis

Sun 1/25

5:05 am-2:47 pm

1 stop7h 42m

Basseterre Robert Bradshaw Intl

Sat 1/31

5:35 pm-11:59 pm

1 stop8h 24m

$713

St. LouisBasseterre

STL - SKB

STLSKB

Lambert-St Louis

Sat 5/2

4:44 pm-4:13 pm

2 stops46h 29m

Basseterre Robert Bradshaw Intl

Wed 5/6

9:50 am-11:56 pm

2 stops15h 06m

$1,368

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

Best time to book a flight from Illinois to St Kitts

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

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

Currently, May is the cheapest month in which you can book a flight from Illinois to St Kitts (average of $465). Flying from Illinois to St Kitts in August is currently the most expensive (average of $737). 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.

Related info for your journey

Find useful and relevant information for your journey from Illinois 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 Illinois to St Kitts?

    For as low as $590, American Airlines can have you in St Kitts from Illinois in 7h 08m. The distance from Illinois to St Kitts is about 2245 mi. This flight may include one or multiple stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Illinois 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 Illinois to St Kitts?

    Currently, May is the cheapest month in which you can book a flight from Illinois to St Kitts (average of $465). Flying from Illinois to St Kitts in August is currently the most expensive (average of $737). 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

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Alternative routes for Illinois to St Kitts

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Top airline flying from Illinois to St Kitts

Discover the top airline that operate flights from Illinois 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 December 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$488Average$737FlexibilityNo cancel feeOn-time71%

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