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St Kitts

$729+ Cheap flights from Midway (MDW) 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SKB
Mar 31 — Apr 71
Tue 3/31
Tue 4/7
1 adult, Economy
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Cheap flight deals from Midway to St Kitts

Cheapest flights from Midway to St Kitts
Explore the most affordable flight options available from Midway to St Kitts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 1, 2026.

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 Midway to St Kitts

Keep the following information in mind while searching for Midway to St Kitts flight deals. Data was last updated March 1, 2026.

Round-trip from

$729
(Delta)

Popular in

August

Cheapest in

February

Average price

$1,462
From Chicago Midway 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 Midway 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 Midway Airport to St Kitts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

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

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

$839

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Sat 3/28

6:00 am-2:10 pm

1 stop7h 10m

Basseterre Robert Bradshaw Intl

Sat 4/4

1:50 pm-10:31 pm

1 stop9h 41m

$1,149

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Sat 4/4

6:00 am-2:10 pm

1 stop7h 10m

Basseterre Robert Bradshaw Intl

Sat 4/11

1:50 pm-10:31 pm

1 stop9h 41m

$1,356

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Sat 3/28

6:34 pm-5:55 pm

3 stops22h 21m

Basseterre Robert Bradshaw Intl

Sat 4/4

3:20 pm-8:53 am

2 stops18h 33m

$1,554

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/28

Sorted by cheapest first

Best time to book a flight from Midway to St Kitts

Have a flexible travel schedule? Discover the best time to fly to St Kitts from Midway 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 Midway Airport to St Kitts
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Midway 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 Midway Airport to St Kitts?

    A quick flight from Chicago Midway Airport to St Kitts can take about 7h 10m. Delta provides one of the quickest options available for as low as $729. Airlines will cover a distance of 2245 mi.

  • Can I find deals for flights from Midway to St Kitts that include hotel bookings?

    Yes. In addition to deals on Midway to St Kitts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to St Kitts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to St Kitts.

  • Can I find deals for business class flights from Midway to St Kitts?

    Yes. Cheapflights offers flight deals from Midway 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.

See more FAQs

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