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St Kitts

$370+ 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 3/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SKB
Mar 31 — Apr 71
Tue 3/31
Tue 4/7
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 March 1, 2026.

This Air Canada deal was found by Cheapflights users on 2/26. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/278:40 pm
ORD
-
SKB
1 stop16h 45m
Air Canada
Sat 4/43:20 pm
SKB
-
ORD
1 stop19h 30m
Air Canada
Deal found 2/26$579
This Orbitz deal was found by Cheapflights users on 2/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/177:55 am
ORD
-
SKB
1 stop29h 20m
Multiple Airlines
Thu 4/232:14 pm
SKB
-
ORD
1 stop18h 27m
Multiple Airlines
Deal found 2/28$591
This Kiwi.com deal was found by Cheapflights users on 2/28. 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.
Sat 4/251:27 pm
ORD
-
SKB
2 stops28h 03m
Multiple Airlines
Fri 5/18:30 am
SKB
-
ORD
1 stop13h 19m
Multiple Airlines
Deal found 2/28$601
This Orbitz deal was found by Cheapflights users on 2/26. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:31 am
ORD
-
SKB
1 stop27h 48m
Multiple Airlines
Sat 4/253:20 pm
SKB
-
ORD
1 stop24h 55m
Multiple Airlines
Deal found 2/26$609
This American Airlines deal was found by Cheapflights users on 2/26. 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 4/207:00 pm
ORD
-
SKB
1 stop17h 26m
American Airlines
Fri 4/242:35 pm
SKB
-
ORD
1 stop9h 22m
American Airlines
Deal found 2/26$679
This Delta deal was found by Cheapflights users on 2/28. 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 4/256:00 am
MDW
-
SKB
1 stop7h 10m
Delta
Sat 5/21:55 pm
SKB
-
MDW
1 stop9h 33m
Delta
Deal found 2/28$729
This Delta deal was found by Cheapflights users on 2/27. 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 4/186:00 am
MDW
-
SKB
1 stop7h 10m
Delta
Sat 4/251:55 pm
SKB
-
MDW
1 stop9h 33m
Delta
Deal found 2/27$839
This Delta deal was found by Cheapflights users on 2/26. 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 3/286:00 am
MDW
-
SKB
1 stop7h 10m
Delta
Sat 4/41:50 pm
SKB
-
MDW
1 stop9h 41m
Delta
Deal found 2/26$1,149
This Delta deal was found by Cheapflights users on 3/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:00 am
MDW
-
SKB
1 stop7h 10m
Delta
Sat 4/111:50 pm
SKB
-
MDW
1 stop9h 41m
Delta
Deal found 3/1$1,356
This Mytrip deal was found by Cheapflights users on 2/26. 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.
Sat 3/286:34 pm
MDW
-
SKB
3 stops22h 21m
Multiple Airlines
Sat 4/43:20 pm
SKB
-
MDW
2 stops18h 33m
Multiple Airlines
Deal found 2/26$1,554

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 March 1, 2026.

Round-trip from

$579
(Air Canada)

Popular in

August

Cheapest in

February

Average price

$1,462
From Chicago (CHI) to St Kitts
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($214 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 15% potential price decrease ($125 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 1, 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

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Fri 3/27

8:40 pm-2:25 pm

1 stop16h 45m

Basseterre Robert Bradshaw Intl

Sat 4/4

3:20 pm-9:50 am

1 stop19h 30m

$579

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 4/18

12:53 pm-6:25 pm

3 stops28h 32m

Basseterre Robert Bradshaw Intl

Sat 4/25

3:20 pm-5:50 pm

1 stop27h 30m

$687

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Wed 4/22

5:00 am-1:31 pm

1 stop7h 31m

Basseterre Robert Bradshaw Intl

Sun 4/26

2:35 pm-12:25 am

1 stop10h 50m

$709

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Wed 4/15

5:00 am-1:35 pm

1 stop7h 35m

Basseterre Robert Bradshaw Intl

Wed 4/22

2:35 pm-7:24 am

2 stops17h 49m

$714

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Sat 4/25

6:00 am-2:10 pm

1 stop7h 10m

Basseterre Robert Bradshaw Intl

Sat 5/2

1:55 pm-10:28 pm

1 stop9h 33m

$729

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Thu 4/30

8:46 pm-1:26 pm

2 stops15h 40m

Basseterre Robert Bradshaw Intl

Mon 5/4

2:35 pm-7:29 am

2 stops17h 54m

$734

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 4/18

9:01 pm-1:26 pm

2 stops15h 25m

Basseterre Robert Bradshaw Intl

Sat 4/25

2:35 pm-10:57 pm

1 stop9h 22m

$739

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Wed 4/15

5:00 am-1:35 pm

1 stop7h 35m

Basseterre Robert Bradshaw Intl

Sun 4/19

2:35 pm-11:04 am

1 stop21h 29m

$755

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 4/11

6:50 am-3:15 pm

1 stop7h 25m

Basseterre Robert Bradshaw Intl

Sat 4/18

4:50 pm-12:25 am

1 stop8h 35m

$759

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 8/8

7:05 pm-1:20 pm

1 stop17h 15m

Basseterre Robert Bradshaw Intl

Sat 8/15

2:20 pm-10:31 pm

1 stop9h 11m

$814

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/1

Showing 1-10 of 16 resultsSorted by cheapest first
1
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 $465). Flying from Chicago to St Kitts in March is currently the most expensive (average of $781). 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 March 1, 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
11,369 reviews

Boarding

7.5

Overall

7.1

Comfort

7.2

Entertainment

6.9

Food

6.4

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.1
Good
11,369 reviews
American Airlines
7.1
Good
11,369 reviews

Boarding

7.5

Overall

7.1

Comfort

7.2

Entertainment

6.9

Food

6.4

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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 10m. Air Canada provides one of the quickest options available for as low as $729. 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 March is currently the most expensive (average of $781). 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 March 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$485Average$677FlexibilityNo cancel feeOn-time71%

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