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St Kitts

$628+ Cheap flights from Chicago (CHI) to St Kitts

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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SKB
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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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 June 12, 2025.

Round-trip from

$628
(American Airlines)

Popular in

December

Cheapest in

July

Average price

$672
From Chicago (CHI) to St Kitts
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($238 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($74 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/11. 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 8/177:05 pmORD - SKB
1 stop17h 17mAmerican Airlines
Thu 8/212:30 pmSKB - ORD
1 stop9h 11mAmerican Airlines
Deal found 6/11$628
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/78:52 amORD - SKB
1 stop25h 28mUnited Airlines
Fri 9/122:35 pmSKB - ORD
2 stops18h 03mUnited Airlines
Deal found 6/10$714
This Mytrip deal was found by Cheapflights users on 6/11. 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 7/265:05 amORD - SKB
2 stops11h 40mMultiple Airlines
Sat 8/21:00 pmSKB - ORD
2 stops11h 53mMultiple Airlines
Deal found 6/11$819

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 June 12, 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

Sun 8/17

7:05 pm-1:22 pm

1 stop17h 17m

Basseterre Robert Bradshaw Intl

Thu 8/21

2:30 pm-10:41 pm

1 stop9h 11m

$628

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sun 9/7

8:52 am-11:20 am

1 stop25h 28m

Basseterre Robert Bradshaw Intl

Fri 9/12

2:35 pm-7:38 am

2 stops18h 03m

$714

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 7/26

5:05 am-5:45 pm

2 stops11h 40m

Basseterre Robert Bradshaw Intl

Sat 8/2

1:00 pm-11:53 pm

2 stops11h 53m

$819

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 $559). Flying from Chicago to St Kitts in December is currently the most expensive (average of $677). 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.

Rainfall in St Kitts by month

Plan your trip to St Kitts by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in St Kitts ranges from 1.9 - 5.6 inches per month. September is typically the wettest month, when rainfall can reach 5.6 in. February is typically the driest time to visit St Kitts when rainfall is around 1.9 in.

Temperature in St Kitts by month

Plan your trip to St Kitts by taking into account the average temperature totals by month.

If weather is an important factor for your trip to St Kitts, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 June 12, 2025.
United Airlines
7.4
Good
8,790 reviews

Entertainment

7.0

Overall

7.4

Boarding

7.7

Food

6.6

Crew

8.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
United Airlines
7.4
Good
8,790 reviews
United Airlines
7.4
Good
8,790 reviews

Entertainment

7.0

Overall

7.4

Boarding

7.7

Food

6.6

Crew

8.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,790 reviews

Entertainment

7.0

Overall

7.4

Boarding

7.7

Food

6.6

Crew

8.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

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.

  • 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 $559). Flying from Chicago to St Kitts in December is currently the most expensive (average of $677). 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

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Alternative routes for Chicago to St Kitts

See prices for flight routes from nearby airports that may be better suited for you.
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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$606Average$773FlexibilityNo cancel feeOn-time71%
DeltaCheapest$614Average$660FlexibilityNo cancel feeOn-timeN/A

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