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Saint Kitts and Nevis

$596+ Cheap flights from Chicago (CHI) to Saint Kitts and Nevis

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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SKB
Aug 3 — Aug 101
Mon 8/3
Mon 8/10
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 July 4, 2026.

This Travelocity deal was found by Cheapflights users on 7/4. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:00 am
ORD
-
SKB
1 stop29h 45m
Multiple Airlines
Sat 11/75:25 pm
SKB
-
ORD
1 stop17h 58m
Multiple Airlines
Deal found 7/4$596
This American Airlines deal was found by Cheapflights users on 7/3. 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.
Mon 8/175:00 am
ORD
-
SKB
1 stop7h 44m
American Airlines
Mon 8/242:44 pm
SKB
-
ORD
1 stop9h 46m
American Airlines
Deal found 7/3$629
This American Airlines deal was found by Cheapflights users on 7/4. 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 8/165:00 am
ORD
-
SKB
1 stop7h 44m
American Airlines
Sun 8/232:44 pm
SKB
-
ORD
1 stop8h 47m
American Airlines
Deal found 7/4$636
This Delta deal was found by Cheapflights users on 7/1. 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 8/15:30 am
ORD
-
SKB
1 stop7h 33m
Delta
Sat 8/83:15 pm
SKB
-
ORD
1 stop9h 42m
Delta
Deal found 7/1$637
This Delta deal was found by Cheapflights users on 7/4. 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 8/156:11 am
MDW
-
SKB
1 stop6h 39m
Delta
Sat 8/223:15 pm
SKB
-
MDW
1 stop8h 21m
Delta
Deal found 7/4$637
This American Airlines deal was found by Cheapflights users on 7/4. 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 8/184:10 pm
ORD
-
SKB
1 stop20h 26m
American Airlines
Tue 8/252:44 pm
SKB
-
ORD
1 stop25h 21m
American Airlines
Deal found 7/4$638
This Delta deal was found by Cheapflights users on 6/30. 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 12/196:00 am
MDW
-
SKB
1 stop7h 10m
Delta
Sat 12/262:55 pm
SKB
-
MDW
1 stop9h 15m
Delta
Deal found 6/30$1,295

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 July 4, 2026.

Round-trip from

$629
(American Airlines)

One-way from

$533
(American Airlines)

Popular in

December

Cheapest in

February

Average price

$653
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. 18% potential increase in price ($204 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 14% potential price decrease ($112 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

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 July 4, 2026.
Use the filters below to find and compare flights from Chicago to Saint Kitts and Nevis that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Mon 8/17

8:53 pm-1:44 pm

2 stops15h 51m

Basseterre Robert Bradshaw Intl

Mon 8/24

2:44 pm-11:30 pm

1 stop9h 46m

$631

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sun 8/16

5:00 am-1:44 pm

1 stop7h 44m

Basseterre Robert Bradshaw Intl

Sun 8/23

2:44 pm-10:31 pm

1 stop8h 47m

$636

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 8/1

5:30 am-2:03 pm

1 stop7h 33m

Basseterre Robert Bradshaw Intl

Sat 8/8

3:15 pm-11:57 pm

1 stop9h 42m

$637
Quickest round-trip

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Sat 8/15

6:11 am-1:50 pm

1 stop6h 39m

Basseterre Robert Bradshaw Intl

Sat 8/22

3:15 pm-10:36 pm

1 stop8h 21m

$637

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Fri 8/21

6:41 pm-1:49 pm

1 stop18h 08m

Basseterre Robert Bradshaw Intl

Wed 8/26

2:44 pm-7:34 am

1 stop17h 50m

$637

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Fri 7/31

7:05 am-2:03 pm

2 stops29h 58m

Basseterre Robert Bradshaw Intl

Sat 8/8

3:15 pm-8:44 am

1 stop18h 29m

$642

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sun 8/23

6:59 pm-1:44 pm

1 stop17h 45m

Basseterre Robert Bradshaw Intl

Sun 8/30

2:44 pm-7:34 am

1 stop17h 50m

$642

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Mon 8/24

6:59 pm-1:44 pm

1 stop17h 45m

Basseterre Robert Bradshaw Intl

Sun 8/30

2:44 pm-7:34 am

1 stop17h 50m

$642

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Sat 12/19

6:00 am-3:10 pm

1 stop7h 10m

Basseterre Robert Bradshaw Intl

Sat 12/26

2:55 pm-10:10 pm

1 stop9h 15m

$1,295

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Sorted by cheapest first

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, February is the cheapest month in which you can book a flight from Chicago to Saint Kitts and Nevis (average of $471). Flying from Chicago to Saint Kitts and Nevis in March is currently the most expensive (average of $779). 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 July 4, 2026.
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
7.1
Good
11,767 reviews

Overall

7.1

Boarding

7.5

Comfort

7.2

Crew

7.9

Entertainment

6.8

Food

6.4

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.
American Airlines
7.1
Good
11,767 reviews
American Airlines
7.1
Good
11,767 reviews

Overall

7.1

Boarding

7.5

Comfort

7.2

Crew

7.9

Entertainment

6.8

Food

6.4

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.

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 33m. American Airlines provides one of the quickest options available for as low as $637. Chicago and Saint Kitts and Nevis are separated by a distance of 2260 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, February is the cheapest month in which you can book a flight from Chicago to Saint Kitts and Nevis (average of $471). Flying from Chicago to Saint Kitts and Nevis in March is currently the most expensive (average of $779). 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.

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 July 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$488Average$757FlexibilityNo cancel feeOn-time71%

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