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Cheap flights from Chicago Midway Airport to Saint Kitts and Nevis from $590

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Saint Kitts and Nevis departing on 4/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago Midway Airport to Saint Kitts and Nevis

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 2:08 pm
MDW
-
SKB
7h 08m1 stop
Delta Logo
1:53 pm - 9:45 pm
SKB
-
MDW
8h 52m1 stop
$590Delta
Sat, Apr 18 - Sat, Apr 25
Delta Logo
6:14 pm - 1:33 pm
MDW
-
SKB
17h 19m2 stops
Delta Logo
4:07 pm - 12:46 pm
SKB
-
MDW
22h 39m2 stops
$595Delta
Fri, Jan 30 - Sat, Feb 7
Delta Logo
10:48 am - 2:46 pm
MDW
-
SKB
25h 58m1 stop
Delta Logo
2:50 pm - 10:22 pm
SKB
-
MDW
9h 32m1 stop
$804Delta
Fri, Jan 30 - Sat, Feb 7
Delta Logo
11:48 am - 1:38 pm
MDW
-
SKB
23h 50m2 stops
Delta Logo
2:50 pm - 10:07 pm
SKB
-
MDW
9h 17m1 stop
$1,003Delta
Fri, Jan 2 - Sat, Jan 10

Delta flights from Chicago Midway Airport to Saint Kitts and Nevis

Our best Delta deals on Chicago Midway Airport to Saint Kitts and Nevis flight tickets
Delta
Apr 18
MDW6:00 amChicago Midway
7h 08m
1 stop
SKB2:08 pmBasseterre Robert Bradshaw Intl
Apr 25
SKB1:53 pmBasseterre Robert Bradshaw Intl
8h 52m
1 stop
MDW9:45 pmChicago Midway
$590
Find similar
Delta
Jan 30
MDW6:14 pmChicago Midway
17h 19m
2 stops
SKB1:33 pmBasseterre Robert Bradshaw Intl
Feb 7
SKB4:07 pmBasseterre Robert Bradshaw Intl
22h 39m
2 stops
MDW12:46 pmChicago Midway
$595
Find similar
Delta
Jan 30
MDW10:48 amChicago Midway
25h 58m
1 stop
SKB2:46 pmBasseterre Robert Bradshaw Intl
Feb 7
SKB2:50 pmBasseterre Robert Bradshaw Intl
9h 32m
1 stop
MDW10:22 pmChicago Midway
$804
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated December 11, 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

Fly to

Route

Depart

Return

Price

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Sat 4/18

6:00 am-2:08 pm

1 stop7h 08m

Basseterre Robert Bradshaw Intl

Sat 4/25

1:53 pm-9:45 pm

1 stop8h 52m

$590

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Fri 1/30

6:14 pm-1:33 pm

2 stops17h 19m

Basseterre Robert Bradshaw Intl

Sat 2/7

4:07 pm-12:46 pm

2 stops22h 39m

$595

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Fri 1/30

10:48 am-2:46 pm

1 stop25h 58m

Basseterre Robert Bradshaw Intl

Sat 2/7

2:50 pm-10:22 pm

1 stop9h 32m

$804

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Fri 1/2

11:48 am-1:38 pm

2 stops23h 50m

Basseterre Robert Bradshaw Intl

Sat 1/10

2:50 pm-10:07 pm

1 stop9h 17m

$1,003

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Tue 12/30

3:10 pm-3:30 pm

3 stops22h 20m

$644

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Mon 12/29

6:15 am-12:45 pm

3 stops28h 30m

$689

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

Cheap Chicago Midway Airport to Saint Kitts and Nevis flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Saint Kitts and Nevis

Fastest flight time

7h 08m

Direct flights

None
The fastest flight from Chicago Midway Airport to Saint Kitts and Nevis takes 7h 08m
There are no direct flights from Chicago Midway Airport to Saint Kitts and Nevis. There are no popular flight routes from Chicago Midway Airport to Saint Kitts and Nevis.
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  • When did momondo last update prices for flights from Chicago Midway Airport to Saint Kitts and Nevis?

    Prices for flights from Chicago Midway Airport to Saint Kitts and Nevis are updated daily.

  • How old do you have to be to fly from Chicago Midway Airport to Saint Kitts and Nevis?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Saint Kitts and Nevis.

  • What documentation or ID do you need to fly to Saint Kitts and Nevis?

    The travel and health documents required for your trip to Saint Kitts and Nevis can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Saint Kitts and Nevis. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • How do I get Price Alerts for flights from Chicago Midway Airport to Saint Kitts and Nevis?

    Confirm your travel details to search for the latest offers for flights from Chicago Midway Airport to Saint Kitts and Nevis. While browsing offers there will be the option to toggle “Price Alerts”. You’ll then receive updates when prices for the flight route increase or decrease.

  • How can I save money on flights from Chicago Midway Airport to Saint Kitts and Nevis with momondo?

    With “Price Forecast”, learn how soon you should book your flight in advance. Down to the day of week and time of day, our information can inform you on the ideal time to book to save on your travel. Our “Price Calendar” shows you at a quick glance when to book your travel for lower rates. By setting “Price Alerts” you can monitor changes in price and target the ideal time to book. Search for your trip destination by budget amount via our “Explore” feature. Whether you’re looking for ideas for your next travel adventure or cost-cutting tips, our “Discover” content is a great place to start.

  • How does momondo find its flight prices?

    We compare prices from 700+ competitors to help you find the price that works best for you. momondo operates in over 30 international markets, bringing you access to a wide range of fares and deals. Search for your travel using momondo for a diverse range of options from airlines and OTAs.

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Saint Kitts and Nevis?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Saint Kitts and Nevis for you.

Can I find flights from Chicago to Saint Kitts and Nevis with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Saint Kitts and Nevis flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Saint Kitts and Nevis?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Saint Kitts and Nevis.

I’m not ready to book a flight from Chicago to Saint Kitts and Nevis right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Saint Kitts and Nevis flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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