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St Kitts

$480+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SKB
Sep 10 — Sep 171
Wed 9/10
Wed 9/17
1 adult, Economy
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Cheap 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 September 5, 2025.

Round-trip from

$480
(American Airlines)

Popular in

August

Cheapest in

July

Average price

$652
From Chicago (CHI) to St Kitts
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($251 potential increase over avg. RT price).
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Cheapest flight prices on average. 14% potential price decrease ($117 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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Find 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 September 5, 2025.

This American Airlines deal was found by Cheapflights users on 9/2. 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 11/157:07 pmORD - SKB
1 stop18h 11mAmerican Airlines
Wed 11/194:28 pmSKB - ORD
1 stop8h 31mAmerican Airlines
Deal found 9/2$480
This American Airlines deal was found by Cheapflights users on 9/2. 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 11/146:35 pmORD - SKB
1 stop17h 36mAmerican Airlines
Tue 11/184:28 pmSKB - ORD
1 stop8h 31mAmerican Airlines
Deal found 9/2$505
This Priceline deal was found by Cheapflights users on 9/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/151:35 pmORD - SKB
1 stop23h 43mJetBlue
Sun 10/193:23 pmSKB - ORD
1 stop22h 00mJetBlue
Deal found 9/3$525
This American Airlines deal was found by Cheapflights users on 9/2. 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 12/47:07 pmORD - SKB
1 stop17h 13mAmerican Airlines
Mon 12/83:21 pmSKB - ORD
1 stop11h 16mAmerican Airlines
Deal found 9/2$530
This American Airlines deal was found by Cheapflights users on 9/1. 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 12/135:00 amORD - SKB
1 stop7h 07mAmerican Airlines
Thu 12/185:29 pmSKB - ORD
1 stop17h 18mAmerican Airlines
Deal found 9/1$548
This American Airlines deal was found by Cheapflights users on 9/2. 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 12/135:00 amORD - SKB
1 stop7h 07mAmerican Airlines
Sat 12/203:27 pmSKB - ORD
1 stop9h 32mAmerican Airlines
Deal found 9/2$573
This American Airlines deal was found by Cheapflights users on 9/3. 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 10/105:00 amORD - SKB
1 stop7h 35mAmerican Airlines
Wed 10/152:35 pmSKB - ORD
1 stop10h 23mAmerican Airlines
Deal found 9/3$591

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 September 5, 2025.
Use the filters below to find and compare flights from Chicago to St Kitts that are best for you.

Fly from

Chicago

Fly to

St Kitts

Route

Depart

Return

Price

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 11/15

7:07 pm-3:18 pm

1 stop18h 11m

Basseterre Robert Bradshaw Intl

Wed 11/19

4:28 pm-10:59 pm

1 stop8h 31m

$480

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Mon 12/1

7:17 pm-3:18 pm

1 stop18h 01m

Basseterre Robert Bradshaw Intl

Sat 12/6

3:12 pm-12:01 am

1 stop10h 49m

$505

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Fri 11/14

6:35 pm-2:11 pm

1 stop17h 36m

Basseterre Robert Bradshaw Intl

Tue 11/18

4:28 pm-10:59 pm

1 stop8h 31m

$505

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Wed 10/15

1:35 pm-2:18 pm

1 stop23h 43m

Basseterre Robert Bradshaw Intl

Sun 10/19

3:23 pm-12:23 pm

1 stop22h 00m

$525

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Thu 12/4

7:07 pm-2:20 pm

1 stop17h 13m

Basseterre Robert Bradshaw Intl

Mon 12/8

3:21 pm-12:37 am

1 stop11h 16m

$530

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/2

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, May is the cheapest month in which you can book a flight from Chicago to St Kitts (average of $559). Flying from Chicago to St Kitts in December is currently the most expensive (average of $677). 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 September 5, 2025.
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
7.2
Good
10,000 reviews

Entertainment

6.9

Boarding

7.5

Food

6.5

Crew

8.0

Overall

7.2

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Boarding

7.5

Food

6.5

Crew

8.0

Overall

7.2

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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 18h 11m. American Airlines provides one of the quickest options available for as low as $480. Airlines will cover a distance of 2260 mi.

  • 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, May is the cheapest month in which you can book a flight from Chicago to St Kitts (average of $559). Flying from Chicago to St Kitts in December is currently the most expensive (average of $677). 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 Chicago to St Kitts

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Basseterre flights
St. Louis to Basseterre flights

Top 2 airlines flying from Chicago to St Kitts

Discover the top 2 airlines 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 September 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$488Average$769FlexibilityNo cancel feeOn-time71%
DeltaCheapest$614Average$615FlexibilityNo cancel feeOn-timeN/A

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