HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Saint Kitts and Nevis

$479+ 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 12/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SKB
Nov 25 — Dec 21
Tue 11/25
Tue 12/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Saint Kitts and Nevis 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.

Find 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 October 26, 2025.

This American Airlines deal was found by Cheapflights users on 10/26. 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.
Sat 12/135:00 amORD - SKB
1 stop7h 07mAmerican Airlines
Sat 12/203:27 pmSKB - ORD
1 stop11h 16mAmerican Airlines
Deal found 10/26$524
This American Airlines deal was found by Cheapflights users on 10/24. 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 12/137:00 amORD - SKB
1 stop7h 19mAmerican Airlines
Thu 12/185:29 pmSKB - ORD
2 stops16h 57mAmerican Airlines
Deal found 10/24$529
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Thu 12/47:07 pmORD - SKB
1 stop17h 13mAmerican Airlines
Mon 12/83:27 pmSKB - ORD
1 stop19h 22mAmerican Airlines
Deal found 10/26$536
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.
Mon 12/157:07 pmORD - SKB
1 stop17h 20mAmerican Airlines
Sat 12/203:27 pmSKB - ORD
1 stop11h 16mAmerican Airlines
Deal found 10/23$564
This American Airlines deal was found by Cheapflights users on 10/25. 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 12/307:26 pmORD - SKB
1 stop19h 03mAmerican Airlines
Tue 1/63:47 pmSKB - ORD
2 stops18h 04mAmerican Airlines
Deal found 10/25$1,129
This Delta deal was found by Cheapflights users on 10/24. 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 10/24$1,909

Cheap 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 October 26, 2025.

Round-trip from

$524
(American Airlines)

One-way from

$479
(Kiwi.com)

Popular in

August

Cheapest in

July
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. 17% potential increase in price ($203 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 14% potential price decrease ($123 potential savings vs. average RT price).
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 October 26, 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

Mon 12/15

7:07 pm-2:27 pm

1 stop17h 20m

Basseterre Robert Bradshaw Intl

Sat 12/20

3:27 pm-12:43 am

1 stop11h 16m

$524

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-10:59 pm

1 stop9h 32m

$524

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 12/13

5:00 am-2:07 pm

1 stop7h 07m

Basseterre Robert Bradshaw Intl

Sat 12/20

5:29 pm-7:29 am

2 stops16h 00m

$529

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-8:49 am

1 stop19h 22m

$536

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

Sun 12/28

6:00 am-5:45 pm

3 stops33h 45m

$479

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sun 12/28

7:12 pm-2:27 pm

1 stop17h 15m

$554

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

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 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 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 October 26, 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
11,030 reviews

Food

6.4

Boarding

7.5

Overall

7.2

Comfort

7.2

Crew

8.0

Entertainment

6.9

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
11,030 reviews
American Airlines
7.2
Good
11,030 reviews

Food

6.4

Boarding

7.5

Overall

7.2

Comfort

7.2

Crew

8.0

Entertainment

6.9

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 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 13m. American Airlines provides one of the quickest options available for as low as $1,909. 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 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 Saint Kitts and Nevis

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
Midway to Punta Cana flights
O'Hare Intl to Montego Bay flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Nassau flights
O'Hare Intl to Providenciales flights
St. Louis to Luis Munoz Marin Intl flights
O'Hare Intl to George Town flights
O'Hare Intl to Simpson Bay flights
Midway to Montego Bay flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Castries flights
Midway to Oranjestad flights
Midway to Saint Thomas Island flights
St. Louis to Punta Cana flights
Midway to Nassau flights
St. Louis to Montego Bay flights
Midway to Simpson Bay flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Christiansted flights
St. Louis to Saint Thomas Island flights
Midway to Providenciales flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to St. John's flights
St. Louis to Oranjestad flights
Midway to George Town flights
St. Louis to Georgetown flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Road Town flights
St. Louis to Simpson Bay flights
O'Hare Intl to Port of Spain flights
O'Hare Intl to Aguadilla flights
Moline to Luis Munoz Marin Intl flights
O'Hare Intl to Kingston flights
St. Louis to Nassau flights
St. Louis to Willemstad flights
Midway to Castries flights
Midway to Santo Domingo flights
St. Louis to Castries flights
Peoria to Luis Munoz Marin Intl flights
O'Hare Intl to Kralendijk flights
St. Louis to Bridgetown flights
O'Hare Intl to Castries flights
O'Hare Intl to Basseterre flights
O'Hare Intl to St. George's flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Ponce flights

Top 2 airlines flying from Chicago to Saint Kitts and Nevis

Discover the top 2 airlines 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 October 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$488Average$764FlexibilityNo 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.