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Cheap flights from Chicago to St Kitts from $579

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 to St Kitts departing on 3/27. 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 St Kitts

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
8:40 pm - 2:25 pm
ORD
-
SKB
16h 45m
1 stop
Air Canada Logo
3:20 pm - 9:50 am
SKB
-
ORD
19h 30m
1 stop
$579Air Canada
Fri, Mar 27 - Sat, Apr 4
Multiple Airlines Logo
7:55 am - 2:15 pm
ORD
-
SKB
29h 20m
1 stop
Multiple Airlines Logo
2:14 pm - 7:41 am
SKB
-
ORD
18h 27m
1 stop
$591Multiple Airlines
Fri, Apr 17 - Thu, Apr 23
Multiple Airlines Logo
1:27 pm - 6:30 pm
ORD
-
SKB
28h 03m
2 stops
Multiple Airlines Logo
8:30 am - 8:49 pm
SKB
-
ORD
13h 19m
1 stop
$601Multiple Airlines
Sat, Apr 25 - Fri, May 1
Multiple Airlines Logo
8:31 am - 1:19 pm
ORD
-
SKB
27h 48m
1 stop
Multiple Airlines Logo
3:20 pm - 3:15 pm
SKB
-
ORD
24h 55m
1 stop
$609Multiple Airlines
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
8:31 am - 1:19 pm
ORD
-
SKB
27h 48m
1 stop
Multiple Airlines Logo
3:20 pm - 7:25 pm
SKB
-
ORD
29h 05m
1 stop
$610Multiple Airlines
Sat, Apr 18 - Sat, Apr 25
American Airlines Logo
5:00 am - 1:31 pm
ORD
-
SKB
7h 31m
1 stop
American Airlines Logo
2:35 pm - 10:57 pm
SKB
-
ORD
9h 22m
1 stop
$679American Airlines
Mon, Apr 20 - Fri, Apr 24
American Airlines Logo
7:00 pm - 1:26 pm
ORD
-
SKB
17h 26m
1 stop
American Airlines Logo
2:35 pm - 7:29 am
SKB
-
ORD
17h 54m
2 stops
$684American Airlines
Mon, Apr 20 - Fri, Apr 24
Delta Logo
6:00 am - 2:10 pm
MDW
-
SKB
7h 10m
1 stop
Delta Logo
1:55 pm - 10:28 pm
SKB
-
MDW
9h 33m
1 stop
$729Delta
Sat, Apr 18 - Sat, Apr 25
Delta Logo
6:00 am - 2:10 pm
MDW
-
SKB
7h 10m
1 stop
Delta Logo
1:55 pm - 10:28 pm
SKB
-
MDW
9h 33m
1 stop
$789Delta
Sat, Apr 11 - Sat, Apr 18
Delta Logo
6:00 am - 2:10 pm
MDW
-
SKB
7h 10m
1 stop
Delta Logo
1:55 pm - 10:28 pm
SKB
-
MDW
9h 33m
1 stop
$839Delta
Sat, Apr 18 - Sat, Apr 25

American Airlines flights from Chicago to St Kitts

Our best American Airlines deals on Chicago to St Kitts flight tickets
American Airlines
Apr 20
ORD5:00 amChicago O'Hare Intl
7h 31m
1 stop
SKB1:31 pmBasseterre Robert Bradshaw Intl
Apr 24
SKB2:35 pmBasseterre Robert Bradshaw Intl
9h 22m
1 stop
ORD10:57 pmChicago O'Hare Intl
$679
American Airlines
Apr 20
ORD7:00 pmChicago O'Hare Intl
17h 26m
1 stop
SKB1:26 pmBasseterre Robert Bradshaw Intl
Apr 24
SKB2:35 pmBasseterre Robert Bradshaw Intl
17h 54m
2 stops
ORD7:29 amChicago O'Hare Intl
$684
American Airlines
Jun 29
ORD5:00 amChicago O'Hare Intl
7h 38m
1 stop
SKB1:38 pmBasseterre Robert Bradshaw Intl
Jul 3
SKB2:40 pmBasseterre Robert Bradshaw Intl
21h 07m
1 stop
ORD10:47 amChicago O'Hare Intl
$694

Delta flights from Chicago to St Kitts

Our best Delta deals on Chicago to St Kitts flight tickets
Delta
Apr 18
MDW6:00 amChicago Midway
7h 10m
1 stop
SKB2:10 pmBasseterre Robert Bradshaw Intl
Apr 25
SKB1:55 pmBasseterre Robert Bradshaw Intl
9h 33m
1 stop
MDW10:28 pmChicago Midway
$729
Delta
Apr 11
MDW6:00 amChicago Midway
7h 10m
1 stop
SKB2:10 pmBasseterre Robert Bradshaw Intl
Apr 18
SKB1:55 pmBasseterre Robert Bradshaw Intl
9h 33m
1 stop
MDW10:28 pmChicago Midway
$789
Delta
Apr 18
MDW6:00 amChicago Midway
7h 10m
1 stop
SKB2:10 pmBasseterre Robert Bradshaw Intl
Apr 25
SKB1:55 pmBasseterre Robert Bradshaw Intl
9h 33m
1 stop
MDW10:28 pmChicago Midway
$839

momondo 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, momondo users made 832,500 searches. Data last updated March 1, 2026.
Use the filters below to find and compare flights from Chicago to St Kitts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Fri 3/27

8:40 pm-2:25 pm

1 stop16h 45m

Basseterre Robert Bradshaw Intl

Sat 4/4

3:20 pm-9:50 am

1 stop19h 30m

$579

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Fri 4/17

7:55 am-2:15 pm

1 stop29h 20m

Basseterre Robert Bradshaw Intl

Thu 4/23

2:14 pm-7:41 am

1 stop18h 27m

$591

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 4/25

1:27 pm-6:30 pm

2 stops28h 03m

Basseterre Robert Bradshaw Intl

Fri 5/1

8:30 am-8:49 pm

1 stop13h 19m

$601

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 4/18

8:31 am-1:19 pm

1 stop27h 48m

Basseterre Robert Bradshaw Intl

Sat 4/25

3:20 pm-3:15 pm

1 stop24h 55m

$609

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 4/18

8:31 am-1:19 pm

1 stop27h 48m

Basseterre Robert Bradshaw Intl

Sat 4/25

3:20 pm-7:25 pm

1 stop29h 05m

$610

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Mon 4/20

5:00 am-1:31 pm

1 stop7h 31m

Basseterre Robert Bradshaw Intl

Fri 4/24

2:35 pm-10:57 pm

1 stop9h 22m

$679

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Mon 4/20

7:00 pm-1:26 pm

1 stop17h 26m

Basseterre Robert Bradshaw Intl

Fri 4/24

2:35 pm-7:29 am

2 stops17h 54m

$684

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

$729

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Sat 4/11

6:00 am-2:10 pm

1 stop7h 10m

Basseterre Robert Bradshaw Intl

Sat 4/18

1:55 pm-10:28 pm

1 stop9h 33m

$789

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

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to St Kitts from

How to get the cheapest flight ticket from Chicago to St Kitts

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

Can stopping save me money on Chicago to St Kitts flights?

No. A direct flight is the cheapest option for a flight between Chicago to St Kitts.

Cheap Chicago to St Kitts flight deals and tips

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

Fastest flight time

7h 04m

Direct flights

None
The fastest flight from Chicago to St Kitts takes 7h 04m
There are no direct flights from Chicago to St Kitts. There are no popular flight routes from Chicago to St Kitts.
Search flight deals

  • When did momondo last update prices for flights from Chicago to St Kitts?

    Prices for flights from Chicago to St Kitts are updated daily.

  • How many operators does momondo search for flights from Chicago to St Kitts?

  • How old do you have to be to fly from Chicago to St Kitts?

    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 St Kitts.

  • What documentation or ID do you need to fly to St Kitts?

    The necessary travel and health documents for your St Kitts trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to St Kitts?

Best airlines flying from Chicago to St Kitts

Compare and see reviews for airlines that fly from Chicago to St Kitts with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $485Free CancellationRating
7.1
11,370 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to St Kitts?

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

Can I find flights from Chicago to St Kitts with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to St Kitts from Chicago with this policy.

How can momondo help me find flights from Chicago to St Kitts?

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 St Kitts from Chicago.

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

If you are simply researching potential flights to St Kitts, momondo offers a useful price alert feature which will track prices for flights to St Kitts from Chicago and alert you when they change.

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