HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
St Kitts

$369+ Cheap flights from Chicago (CHI) to St Kitts

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 11/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SKB
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to St Kitts with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 23, 2025.

Round-trip from

$452
(Expedia)

One-way from

$369
(Trip.com)

Popular in

August

Cheapest in

July
From Chicago (CHI) to St Kitts
Search Deals
One-way flight from Chicago (CHI) to St Kitts
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($200 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 14% potential price decrease ($124 potential savings vs. average RT price).
Search Deals

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 October 23, 2025.

This Expedia deal was found by Cheapflights users on 10/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/87:00 amORD - SKB
1 stop29h 51mJetBlue
Tue 12/164:00 pmSKB - ORD
2 stops20h 35mJetBlue
Deal found 10/21$452
This American Airlines deal was found by Cheapflights users on 10/22. 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 12/183:27 pmSKB - ORD
1 stop11h 16mAmerican Airlines
Deal found 10/22$524
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/295:00 amORD - SKB
1 stop8h 40mAmerican Airlines
Tue 12/24:28 pmSKB - ORD
1 stop8h 31mAmerican Airlines
Deal found 10/21$574
This American Airlines deal was found by Cheapflights users on 10/23. 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 12/83:27 pmSKB - ORD
1 stop19h 22mAmerican Airlines
Deal found 10/23$576
This American Airlines deal was found by Cheapflights users on 10/22. 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 12/203:27 pmSKB - ORD
1 stop11h 16mAmerican Airlines
Deal found 10/22$636
This American Airlines deal was found by Cheapflights users on 10/22. 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 12/65:00 amORD - SKB
1 stop7h 07mAmerican Airlines
Sat 12/134:29 pmSKB - ORD
1 stop20h 20mAmerican Airlines
Deal found 10/22$674
This American Airlines deal was found by Cheapflights users on 10/22. 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 12/185:00 amORD - SKB
1 stop9h 29mAmerican Airlines
Tue 12/233:27 pmSKB - ORD
1 stop11h 16mAmerican Airlines
Deal found 10/22$676
This Delta deal was found by Cheapflights users on 10/22. 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 10/22$1,909

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 October 23, 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 12/13

7:00 am-4:19 pm

1 stop7h 19m

Basseterre Robert Bradshaw Intl

Thu 12/18

3:27 pm-12:43 am

1 stop11h 16m

$524

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 11/29

5:00 am-3:40 pm

1 stop8h 40m

Basseterre Robert Bradshaw Intl

Tue 12/2

4:28 pm-10:59 pm

1 stop8h 31m

$574

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

3:27 pm-11:07 am

1 stop21h 40m

$576

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Sat 12/20

6:00 am-3:13 pm

1 stop7h 13m

Basseterre Robert Bradshaw Intl

Sat 1/3

2:53 pm-10:22 pm

1 stop9h 29m

$1,909

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 11/29

5:00 am-5:45 pm

2 stops10h 45m

$369

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Fri 11/28

5:00 am-5:55 pm

2 stops10h 55m

$392

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Wed 12/17

5:00 am-2:20 pm

1 stop7h 20m

$404

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 11/29

7:30 pm-3:18 pm

1 stop17h 48m

$404

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Wed 12/17

7:05 am-5:55 pm

2 stops32h 50m

$413

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Fri 11/28

5:00 am-3:18 pm

1 stop8h 18m

$429

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

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 $465). Flying from Chicago to St Kitts in July is currently the most expensive (average of $993). 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 October 23, 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
11,033 reviews

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Crew

8.0

Food

6.4

Overall

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
11,033 reviews
American Airlines
7.2
Good
11,033 reviews

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Crew

8.0

Food

6.4

Overall

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 7h 13m. American Airlines provides one of the quickest options available for as low as $1,909. 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, May is the cheapest month in which you can book a flight from Chicago to St Kitts (average of $465). Flying from Chicago to St Kitts in July is currently the most expensive (average of $993). 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.

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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$488Average$767FlexibilityNo cancel feeOn-time71%
DeltaCheapest$614Average$615FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.