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Saint Kitts and Nevis

$245+ Cheap flights from Chicago (CHI) to Saint Kitts and Nevis

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 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SKB
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Chicago to Saint Kitts and Nevis

Cheapest flights from Chicago to Saint Kitts and Nevis
Explore the most affordable flight options available from Chicago to Saint Kitts and Nevis. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This American Airlines deal was found by Cheapflights users on 12/11. 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.
Sat 12/137:07 pmORD - SKB
1 stop17h 20mAmerican Airlines
Thu 12/185:29 pmSKB - ORD
1 stop17h 18mAmerican Airlines
Deal found 12/11$530
This American Airlines deal was found by Cheapflights users on 12/11. 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.
Sat 12/137:07 pmORD - SKB
1 stop17h 20mAmerican Airlines
Sat 12/203:27 pmSKB - ORD
1 stop9h 32mAmerican Airlines
Deal found 12/11$560
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/157:07 pmORD - SKB
1 stop17h 20mAmerican Airlines
Sat 12/205:29 pmSKB - ORD
1 stop17h 18mAmerican Airlines
Deal found 12/11$600
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/157:07 pmORD - SKB
1 stop17h 20mAmerican Airlines
Thu 12/185:29 pmSKB - ORD
1 stop17h 18mAmerican Airlines
Deal found 12/10$643
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Wed 12/2411:23 amORD - SKB
2 stops29h 07mMultiple Airlines
Fri 12/268:30 amSKB - ORD
1 stop16h 55mMultiple Airlines
Deal found 12/10$751
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/298:03 amORD - SKB
2 stops28h 24mAmerican Airlines
Wed 12/313:27 pmSKB - ORD
1 stop11h 16mAmerican Airlines
Deal found 12/10$773
This Delta deal was found by Cheapflights users on 12/10. 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 12/10$3,403

Find flight deals from Chicago to Saint Kitts and Nevis

Keep the following information in mind while searching for Chicago to Saint Kitts and Nevis flight deals. Data was last updated December 12, 2025.

Round-trip from

$524
(American Airlines)

One-way from

$245
(American Airlines)

Popular in

August

Cheapest in

July

Average price

$1,645
From Chicago (CHI) to Saint Kitts and Nevis
Search Deals
One-way flight from Chicago (CHI) to Saint Kitts and Nevis
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).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Saint Kitts and Nevis 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 12, 2025.
Use the filters below to find and compare flights from Chicago to Saint Kitts and Nevis that are best for you.

Fly from

Chicago

Fly to

Saint Kitts and Nevis

Route

Depart

Return

Price

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Tue 1/20

5:00 am-2:47 pm

1 stop7h 47m

Basseterre Robert Bradshaw Intl

Tue 1/27

3:47 pm-12:30 am

1 stop10h 43m

$524

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 1/31

7:30 pm-2:47 pm

1 stop17h 17m

Basseterre Robert Bradshaw Intl

Sat 2/7

5:35 pm-9:05 am

1 stop17h 30m

$560

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Tue 2/24

5:00 am-2:17 pm

1 stop7h 17m

Basseterre Robert Bradshaw Intl

Sat 2/28

5:30 pm-9:02 am

1 stop17h 32m

$560

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Wed 2/25

5:00 am-2:17 pm

1 stop7h 17m

Basseterre Robert Bradshaw Intl

Sat 2/28

5:30 pm-7:20 am

2 stops15h 50m

$565

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

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Fri 1/30

6:14 pm-1:33 pm

2 stops17h 19m

Basseterre Robert Bradshaw Intl

Sat 2/7

4:07 pm-12:46 pm

2 stops22h 39m

$595

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Fri 1/2

11:48 am-1:38 pm

2 stops23h 50m

Basseterre Robert Bradshaw Intl

Sat 1/10

2:50 pm-10:07 pm

1 stop9h 17m

$1,003

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Tue 12/16

8:50 pm-2:20 pm

2 stops15h 30m

$251

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Tue 12/30

7:26 pm-2:27 pm

1 stop17h 01m

$290

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 3/14

12:25 pm-6:30 pm

2 stops29h 05m

$324

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/9

Showing 1-10 of 16 results
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Best time to book a flight from Chicago to Saint Kitts and Nevis

Have a flexible travel schedule? Discover the best time to fly to Saint Kitts and Nevis 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 Saint Kitts and Nevis

What is the cheapest month to book a flight from Chicago to Saint Kitts and Nevis?

Currently, May is the cheapest month in which you can book a flight from Chicago to Saint Kitts and Nevis (average of $465). Flying from Chicago to Saint Kitts and Nevis 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.

Reviews of airlines servicing Saint Kitts and Nevis

Get insights into the airlines that provide service to Saint Kitts and Nevis. 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 Saint Kitts and Nevis. Reviews last updated December 12, 2025.
Read through reviews of airlines operating flights from Chicago to Saint Kitts and Nevis, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,050 reviews

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Crew

8.0

Overall

7.2

Food

6.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,050 reviews
American Airlines
7.2
Good
11,050 reviews

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Crew

8.0

Overall

7.2

Food

6.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

Related info for your journey

Find useful and relevant information for your journey from Chicago to Saint Kitts and Nevis. 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 Saint Kitts and Nevis?

    A quick flight from Chicago to Saint Kitts and Nevis can take about 7h 08m. American Airlines provides one of the quickest options available for as low as $590. Chicago and Saint Kitts and Nevis are separated by a distance of 2245 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

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

  • How can I find direct flights from Chicago to Saint Kitts and Nevis?

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

  • Can I find deals for business class flights from Chicago to Saint Kitts and Nevis?

    Yes. Cheapflights offers flight deals from Chicago to Saint Kitts and Nevis 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 Saint Kitts and Nevis?

    Currently, May is the cheapest month in which you can book a flight from Chicago to Saint Kitts and Nevis (average of $465). Flying from Chicago to Saint Kitts and Nevis 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Saint Kitts and Nevis

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Chicago to Saint Kitts and Nevis

Discover the top airline that operate flights from Chicago to Saint Kitts and Nevis. 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 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$488Average$737FlexibilityNo cancel feeOn-time71%

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