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

$573+ 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SKB
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
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.

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 January 28, 2026.

This American Airlines deal was found by Cheapflights users on 1/26. 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 4/186:58 pm
ORD
-
SKB
1 stop17h 32m
American Airlines
Sat 4/254:35 pm
SKB
-
ORD
1 stop8h 52m
American Airlines
Deal found 1/26$573
This American Airlines deal was found by Cheapflights users on 1/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:59 pm
ORD
-
SKB
1 stop17h 22m
American Airlines
Sat 4/114:35 pm
SKB
-
ORD
2 stops15h 45m
American Airlines
Deal found 1/27$578
This American Airlines deal was found by Cheapflights users on 1/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:35 pm
ORD
-
SKB
2 stops15h 40m
American Airlines
Thu 10/222:50 pm
SKB
-
ORD
2 stops17h 40m
American Airlines
Deal found 1/27$592
This Delta deal was found by Cheapflights users on 1/27. 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 4/185:10 am
ORD
-
SKB
1 stop8h 00m
Delta
Sat 4/251:55 pm
SKB
-
ORD
1 stop11h 04m
Delta
Deal found 1/27$603
This Delta deal was found by Cheapflights users on 1/26. 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 4/186:00 am
MDW
-
SKB
1 stop7h 10m
Delta
Sat 4/251:55 pm
SKB
-
MDW
1 stop9h 33m
Delta
Deal found 1/26$603
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Wed 2/258:58 pm
ORD
-
SKB
2 stops15h 24m
American Airlines
Wed 3/43:24 pm
SKB
-
ORD
2 stops18h 01m
American Airlines
Deal found 1/26$617
This American Airlines deal was found by Cheapflights users on 1/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/59:01 pm
ORD
-
SKB
2 stops15h 29m
American Airlines
Sun 5/102:32 pm
SKB
-
ORD
1 stop9h 26m
American Airlines
Deal found 1/27$622
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:23 pm
ORD
-
SKB
2 stops45h 07m
Multiple Airlines
Fri 3/68:30 am
SKB
-
ORD
1 stop9h 18m
Multiple Airlines
Deal found 1/26$624
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/258:30 am
ORD
-
SKB
2 stops32h 00m
Multiple Airlines
Fri 3/68:30 am
SKB
-
ORD
1 stop9h 18m
Multiple Airlines
Deal found 1/26$626
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/225:05 am
ORD
-
SKB
2 stops11h 25m
Multiple Airlines
Fri 3/68:30 am
SKB
-
ORD
1 stop9h 18m
Multiple Airlines
Deal found 1/26$636

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 January 28, 2026.

Round-trip from

$573
(American Airlines)

Popular in

August

Cheapest in

July

Average price

$696
From Chicago (CHI) to Saint Kitts and Nevis
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($206 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
Average for round-trip flights in January 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 January 28, 2026.
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

Sat 4/18

6:58 pm-1:30 pm

1 stop17h 32m

Basseterre Robert Bradshaw Intl

Sat 4/25

4:35 pm-12:27 am

1 stop8h 52m

$573

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 4/4

6:59 pm-1:21 pm

1 stop17h 22m

Basseterre Robert Bradshaw Intl

Sat 4/11

4:35 pm-7:20 am

2 stops15h 45m

$578

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 4/18

5:10 am-2:10 pm

1 stop8h 00m

Basseterre Robert Bradshaw Intl

Sat 4/25

1:55 pm-11:59 pm

1 stop11h 04m

$603

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Sat 4/18

6:00 am-2:10 pm

1 stop7h 10m

Basseterre Robert Bradshaw Intl

Sat 4/25

1:55 pm-10:28 pm

1 stop9h 33m

$603

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Tue 5/5

6:58 pm-1:30 pm

1 stop17h 32m

Basseterre Robert Bradshaw Intl

Sun 5/10

2:32 pm-10:58 pm

1 stop9h 26m

$617

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Wed 2/25

8:58 pm-2:22 pm

2 stops15h 24m

Basseterre Robert Bradshaw Intl

Wed 3/4

3:24 pm-7:25 am

2 stops18h 01m

$617

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

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 March is currently the most expensive (average of $780). 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 January 28, 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
7.2
Good
11,201 reviews

Food

6.4

Entertainment

6.9

Overall

7.2

Crew

8.0

Boarding

7.5

Comfort

7.2

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
7.2
Good
11,201 reviews
American Airlines
7.2
Good
11,201 reviews

Food

6.4

Entertainment

6.9

Overall

7.2

Crew

8.0

Boarding

7.5

Comfort

7.2

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 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 10m. American Airlines provides one of the quickest options available for as low as $603. 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 March is currently the most expensive (average of $780). 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
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
O'Hare Intl to Nassau flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Montego Bay flights
Midway to Punta Cana flights
O'Hare Intl to Providenciales flights
St. Louis to Luis Munoz Marin Intl flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to George Town flights
Midway to Montego Bay flights
St. Louis to Punta Cana flights
Midway to Nassau flights
O'Hare Intl to Santo Domingo flights
Midway to Saint Thomas Island flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Castries flights
Midway to Oranjestad flights
Midway to Providenciales flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to St. John's flights
St. Louis to Oranjestad flights
O'Hare Intl to Christiansted flights
Midway to Simpson Bay flights
Midway to Santo Domingo flights
St. Louis to Nassau flights
St. Louis to Saint Thomas Island flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Puerto Plata flights
St. Louis to Montego Bay flights
St. Louis to Simpson Bay flights
Midway to George Town flights
O'Hare Intl to Road Town flights
O'Hare Intl to Kingston flights
O'Hare Intl to Georgetown flights
St. Louis to George Town flights
O'Hare Intl to Santiago de los Caballeros flights
St. Louis to Providenciales flights
St. Louis to Castries flights
O'Hare Intl to St. George's flights
O'Hare Intl to Port of Spain flights
Peoria to Luis Munoz Marin Intl flights
Moline to Luis Munoz Marin Intl flights
O'Hare Intl to The Valley flights
St. Louis to Willemstad flights
O'Hare Intl to Ponce flights
O'Hare Intl to Marsh Harbour flights

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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$488Average$737FlexibilityNo cancel feeOn-time71%

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.
Site
Cookie settings©2026 Cheapflights