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Cheap flights from Chicago to Saint Kitts and Nevis from $251

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Saint Kitts and Nevis departing on 12/30. 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 to Saint Kitts and Nevis

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
9:40 am - 2:13 pm
ORD
-
SKB
26h 33m1 stop
JetBlue Logo
3:20 pm - 7:36 pm
SKB
-
ORD
30h 16m1 stop
$463JetBlue
Sat, Jan 24 - Tue, Jan 27
American Airlines Logo
5:00 am - 2:47 pm
ORD
-
SKB
7h 47m1 stop
American Airlines Logo
3:47 pm - 11:08 pm
SKB
-
ORD
9h 21m1 stop
$524American Airlines
Wed, Jan 14 - Wed, Jan 21
American Airlines Logo
9:10 pm - 2:47 pm
ORD
-
SKB
15h 37m2 stops
American Airlines Logo
3:47 pm - 9:05 am
SKB
-
ORD
19h 18m2 stops
$529American Airlines
Sat, Jan 24 - Tue, Jan 27
American Airlines Logo
11:44 am - 1:11 pm
ORD
-
SKB
23h 27m1 stop
American Airlines Logo
3:47 pm - 12:30 am
SKB
-
ORD
10h 43m1 stop
$534American Airlines
Fri, Jan 9 - Wed, Jan 14
American Airlines Logo
5:00 am - 2:17 pm
ORD
-
SKB
7h 17m1 stop
American Airlines Logo
2:23 pm - 10:55 am
SKB
-
ORD
21h 32m1 stop
$536American Airlines
Tue, Mar 3 - Mon, Mar 9
American Airlines Logo
11:44 am - 1:11 pm
ORD
-
SKB
23h 27m1 stop
American Airlines Logo
3:47 pm - 8:31 am
SKB
-
ORD
18h 44m2 stops
$538American Airlines
Fri, Jan 9 - Wed, Jan 14
American Airlines Logo
7:58 pm - 2:17 pm
ORD
-
SKB
16h 19m2 stops
American Airlines Logo
2:23 pm - 12:05 pm
SKB
-
ORD
22h 42m1 stop
$541American Airlines
Tue, Mar 3 - Mon, Mar 9
American Airlines Logo
7:17 pm - 1:10 pm
ORD
-
SKB
16h 53m1 stop
American Airlines Logo
4:06 pm - 7:10 am
SKB
-
ORD
16h 04m2 stops
$565American Airlines
Sat, Apr 18 - Sat, Apr 25
Delta Logo
6:00 am - 2:08 pm
ORD
-
SKB
7h 08m1 stop
Delta Logo
1:53 pm - 11:55 pm
SKB
-
ORD
11h 02m1 stop
$590Delta
Sat, Apr 18 - Sat, Apr 25
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

American Airlines flights from Chicago to Saint Kitts and Nevis

Our best American Airlines deals on Chicago to Saint Kitts and Nevis flight tickets
American Airlines
Jan 14
ORD5:00 amChicago O'Hare Intl
7h 47m
1 stop
SKB2:47 pmBasseterre Robert Bradshaw Intl
Jan 21
SKB3:47 pmBasseterre Robert Bradshaw Intl
9h 21m
1 stop
ORD11:08 pmChicago O'Hare Intl
$524
Find similar
American Airlines
Jan 24
ORD7:48 pmChicago O'Hare Intl
16h 59m
2 stops
SKB2:47 pmBasseterre Robert Bradshaw Intl
Jan 27
SKB3:47 pmBasseterre Robert Bradshaw Intl
10h 43m
1 stop
ORD12:30 amChicago O'Hare Intl
$529
Find similar
American Airlines
Jan 9
ORD11:44 amChicago O'Hare Intl
23h 27m
1 stop
SKB1:11 pmBasseterre Robert Bradshaw Intl
Jan 14
SKB3:47 pmBasseterre Robert Bradshaw Intl
10h 43m
1 stop
ORD12:30 amChicago O'Hare Intl
$534
Find similar

Delta flights from Chicago to Saint Kitts and Nevis

Our best Delta deals on Chicago to Saint Kitts and Nevis flight tickets
Delta
Apr 18
ORD6:00 amChicago O'Hare Intl
7h 08m
1 stop
SKB2:08 pmBasseterre Robert Bradshaw Intl
Apr 25
SKB1:53 pmBasseterre Robert Bradshaw Intl
11h 02m
1 stop
ORD11:55 pmChicago O'Hare Intl
$590
Find similar
Delta
Dec 20
MDW6:00 amChicago Midway
7h 13m
1 stop
SKB3:13 pmBasseterre Robert Bradshaw Intl
Jan 3
SKB2:53 pmBasseterre Robert Bradshaw Intl
9h 29m
1 stop
MDW10:22 pmChicago Midway
$3,403
Find similar
Delta
Dec 20
MDW6:00 amChicago Midway
7h 13m
1 stop
SKB3:13 pmBasseterre Robert Bradshaw Intl
Jan 3
SKB2:53 pmBasseterre Robert Bradshaw Intl
9h 29m
1 stop
MDW10:22 pmChicago Midway
$3,829
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated December 18, 2025.
Use the filters below to find and compare flights from Chicago to Saint Kitts and Nevis that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 1/24

9:40 am-2:13 pm

1 stop26h 33m

Basseterre Robert Bradshaw Intl

Tue 1/27

3:20 pm-7:36 pm

1 stop30h 16m

$463

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Wed 1/14

5:00 am-2:47 pm

1 stop7h 47m

Basseterre Robert Bradshaw Intl

Wed 1/21

3:47 pm-11:08 pm

1 stop9h 21m

$524

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 1/24

9:10 pm-2:47 pm

2 stops15h 37m

Basseterre Robert Bradshaw Intl

Tue 1/27

3:47 pm-9:05 am

2 stops19h 18m

$529

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Fri 1/9

11:44 am-1:11 pm

1 stop23h 27m

Basseterre Robert Bradshaw Intl

Wed 1/14

3:47 pm-12:30 am

1 stop10h 43m

$534

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Tue 3/3

5:00 am-2:17 pm

1 stop7h 17m

Basseterre Robert Bradshaw Intl

Mon 3/9

2:23 pm-10:55 am

1 stop21h 32m

$536

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Fri 1/9

11:44 am-1:11 pm

1 stop23h 27m

Basseterre Robert Bradshaw Intl

Wed 1/14

3:47 pm-8:31 am

2 stops18h 44m

$538

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Tue 3/3

7:58 pm-2:17 pm

2 stops16h 19m

Basseterre Robert Bradshaw Intl

Mon 3/9

2:23 pm-12:05 pm

1 stop22h 42m

$541

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 4/18

7:17 pm-1:10 pm

1 stop16h 53m

Basseterre Robert Bradshaw Intl

Sat 4/25

4:06 pm-7:10 am

2 stops16h 04m

$565

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 4/18

6:00 am-2:08 pm

1 stop7h 08m

Basseterre Robert Bradshaw Intl

Sat 4/25

1:53 pm-11:55 pm

1 stop11h 02m

$590

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

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Saint Kitts and Nevis from

How to get the cheapest flight ticket from Chicago to Saint Kitts and Nevis

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Saint Kitts and Nevis?

According to our data, Wednesday is the cheapest day to fly to Saint Kitts and Nevis from Chicago. The lowest ticket price found for a Wednesday departure recently was $674. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $891. These prices are subject to change though, so be sure to set up a Price Alert for flights to Saint Kitts and Nevis.

What is the cheapest time of day to depart on your flight to Saint Kitts and Nevis?

In the afternoon is the cheapest time of day to fly from Chicago to Saint Kitts and Nevis when you can find flight prices for as low as $611. Flying to Saint Kitts and Nevis in the afternoon is an ideal time because this is during off-peak travel hours. In contrast, the most expensive time of day to depart to Saint Kitts and Nevis is in the evening when prices are around $826.

Cheap Chicago to Saint Kitts and Nevis flight deals and tips

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

Fastest flight time

7h 08m

Direct flights

None
The fastest flight from Chicago to Saint Kitts and Nevis takes 7h 08m
There are no direct flights from Chicago to Saint Kitts and Nevis. There are no popular flight routes from Chicago to Saint Kitts and Nevis.
Search flight deals

  • When did momondo last update prices for flights from Chicago to Saint Kitts and Nevis?

    Prices for flights from Chicago to Saint Kitts and Nevis are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago to Saint Kitts and Nevis?

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Saint Kitts and Nevis.

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

    The travel and health documents you'll need for your trip to Saint Kitts and Nevis may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Saint Kitts and Nevis. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Chicago to Saint Kitts and Nevis

Compare and see reviews for airlines that fly from Chicago to Saint Kitts and Nevis with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $488Free CancellationRating
7.2
11,055 reviews
Search American Airlines flights

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Saint Kitts and Nevis. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. All flights to Saint Kitts and Nevis from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Saint Kitts and Nevis from Chicago.

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

If you are not ready to book a flight from Chicago to Saint Kitts and Nevis now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Saint Kitts and Nevis and let you know when they change.

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Find better results for your trip to Saint Kitts and Nevis

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