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Saint Kitts and Nevis

$1,022+ Cheap flights from Midway (MDW) 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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SKB
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Find flight deals from Midway to Saint Kitts and Nevis

Cheapest flights from Midway to Saint Kitts and Nevis
Explore the most affordable flight options available from Midway to Saint Kitts and Nevis. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2025.

This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/276:00 amMDW - SKB
1 stop7h 13mDelta
Sat 1/102:50 pmSKB - MDW
1 stop9h 19mDelta
Deal found 10/26$1,371
This Mytrip deal was found by Cheapflights users on 10/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/284:15 pmMDW - SKB
3 stops23h 30mMultiple Airlines
Thu 12/48:35 amSKB - MDW
3 stops27h 30mMultiple Airlines
Deal found 10/28$1,406
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/265:05 pmMDW - SKB
1 stop20h 08mDelta
Sat 1/102:50 pmSKB - MDW
1 stop9h 19mDelta
Deal found 10/26$1,567
This Delta deal was found by Cheapflights users on 10/28. 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 12/206:00 amMDW - SKB
1 stop7h 13mDelta
Sat 1/32:53 pmSKB - MDW
1 stop9h 29mDelta
Deal found 10/28$1,909

Cheap flight deals from Midway to Saint Kitts and Nevis

Keep the following information in mind while searching for Midway to Saint Kitts and Nevis flight deals. Data was last updated October 29, 2025.

Round-trip from

$678
(Delta)

Popular in

August

Cheapest in

July
From Chicago Midway 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 Midway 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 29, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Saint Kitts and Nevis that are best for you.

Fly from

Midway

Fly to

Saint Kitts and Nevis

Route

Depart

Return

Price

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Thu 1/1

5:59 pm-1:38 pm

2 stops41h 39m

Basseterre Robert Bradshaw Intl

Sat 1/10

2:50 pm-10:09 pm

1 stop9h 19m

$1,022

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Sat 12/27

6:00 am-3:13 pm

1 stop7h 13m

Basseterre Robert Bradshaw Intl

Sat 1/10

2:50 pm-10:09 pm

1 stop9h 19m

$1,371

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Fri 11/28

4:15 pm-5:45 pm

3 stops23h 30m

Basseterre Robert Bradshaw Intl

Thu 12/4

8:35 am-10:05 am

3 stops27h 30m

$1,406

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Fri 12/26

5:05 pm-3:13 pm

1 stop20h 08m

Basseterre Robert Bradshaw Intl

Sat 1/10

2:50 pm-10:09 pm

1 stop9h 19m

$1,567

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

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Best time to book a flight from Midway to Saint Kitts and Nevis

Have a flexible travel schedule? Discover the best time to fly to Saint Kitts and Nevis 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 Saint Kitts and Nevis
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 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 Midway Airport to Saint Kitts and Nevis?

    There are many flights that can get you from Chicago Midway Airport to Saint Kitts and Nevis in 41h 39m. Fly via Delta to get the fastest option. There are 2245 mi between Chicago Midway Airport and Saint Kitts and Nevis.

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

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

  • How can I find direct flights from Midway 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 Midway to Saint Kitts and Nevis.

  • Can I find deals for business class flights from Midway to Saint Kitts and Nevis?

    Yes. Cheapflights offers flight deals from Midway 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.

See more FAQs

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