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Cheap flights from Chicago to St Kitts from $446

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 1/20. 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.
American Airlines Logo
7:30 pm - 2:47 pm
ORD
-
SKB
17h 17m1 stop
American Airlines Logo
3:47 pm - 11:08 pm
SKB
-
ORD
9h 21m1 stop
$446American Airlines
Tue, Jan 20 - Tue, Jan 27
American Airlines Logo
9:10 pm - 2:47 pm
ORD
-
SKB
15h 37m2 stops
American Airlines Logo
3:47 pm - 8:31 am
SKB
-
ORD
18h 44m2 stops
$451American Airlines
Tue, Jan 20 - Tue, Jan 27
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
$468JetBlue
Sat, Jan 24 - Tue, Jan 27
American Airlines Logo
8:56 pm - 2:47 pm
ORD
-
SKB
15h 51m2 stops
American Airlines Logo
3:47 pm - 7:51 am
SKB
-
ORD
18h 04m2 stops
$491American Airlines
Tue, Feb 3 - Tue, Feb 10
American Airlines Logo
5:00 am - 2:26 pm
ORD
-
SKB
7h 26m1 stop
American Airlines Logo
5:30 pm - 12:33 am
SKB
-
ORD
9h 03m1 stop
$506American Airlines
Sat, Feb 21 - Sat, Feb 28
American Airlines Logo
7:00 am - 4:30 pm
ORD
-
SKB
7h 30m1 stop
American Airlines Logo
5:30 pm - 7:20 am
SKB
-
ORD
15h 50m2 stops
$511American Airlines
Sat, Feb 21 - Sat, Feb 28
American Airlines Logo
8:55 pm - 2:47 pm
ORD
-
SKB
15h 52m2 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
5:00 am - 4:30 pm
ORD
-
SKB
9h 30m1 stop
American Airlines Logo
3:17 pm - 11:06 pm
SKB
-
ORD
9h 49m1 stop
$536American Airlines
Sat, Feb 21 - Tue, Feb 24
American Airlines Logo
7:00 am - 4:30 pm
ORD
-
SKB
7h 30m1 stop
American Airlines Logo
3:17 pm - 7:20 am
SKB
-
ORD
18h 03m2 stops
$541American Airlines
Sat, Feb 21 - Tue, Feb 24
American Airlines Logo
5:00 am - 4:30 pm
ORD
-
SKB
9h 30m2 stops
American Airlines Logo
5:30 pm - 7:20 am
SKB
-
ORD
15h 50m2 stops
$551American Airlines
Sat, Feb 21 - Sat, Feb 28

American Airlines flights from Chicago to St Kitts

Our best American Airlines deals on Chicago to St Kitts flight tickets
American Airlines
Jan 20
ORD7:30 pmChicago O'Hare Intl
17h 17m
1 stop
SKB2:47 pmBasseterre Robert Bradshaw Intl
Jan 27
SKB3:47 pmBasseterre Robert Bradshaw Intl
9h 21m
1 stop
ORD11:08 pmChicago O'Hare Intl
$446
Find similar
American Airlines
Jan 20
ORD8:55 pmChicago O'Hare Intl
15h 52m
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
$451
Find similar
American Airlines
Feb 4
ORD7:30 pmChicago O'Hare Intl
17h 17m
1 stop
SKB2:47 pmBasseterre Robert Bradshaw Intl
Feb 11
SKB3:47 pmBasseterre Robert Bradshaw Intl
10h 43m
1 stop
ORD12:30 amChicago O'Hare Intl
$476
Find similar

United Airlines flights from Chicago to St Kitts

Our best United Airlines deals on Chicago to St Kitts flight tickets
United Airlines
Feb 23
ORD2:20 pmChicago O'Hare Intl
47h 53m
2 stops
SKB4:13 pmBasseterre Robert Bradshaw Intl
Feb 26
SKB9:50 amBasseterre Robert Bradshaw Intl
10h 55m
1 stop
ORD6:45 pmChicago O'Hare Intl
$2,944
Find similar
United Airlines
Feb 23
ORD2:20 pmChicago O'Hare Intl
47h 53m
2 stops
SKB4:13 pmBasseterre Robert Bradshaw Intl
Feb 26
SKB9:50 amBasseterre Robert Bradshaw Intl
10h 51m
2 stops
ORD6:41 pmChicago O'Hare Intl
$3,937
Find similar

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 December 21, 2025.
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

Tue 1/20

7:30 pm-2:47 pm

1 stop17h 17m

Basseterre Robert Bradshaw Intl

Tue 1/27

3:47 pm-11:08 pm

1 stop9h 21m

$446

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Tue 1/20

9:10 pm-2:47 pm

2 stops15h 37m

Basseterre Robert Bradshaw Intl

Tue 1/27

3:47 pm-8:31 am

2 stops18h 44m

$451

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

$468

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Tue 2/3

8:56 pm-2:47 pm

2 stops15h 51m

Basseterre Robert Bradshaw Intl

Tue 2/10

3:47 pm-7:51 am

2 stops18h 04m

$491

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 2/21

5:00 am-2:26 pm

1 stop7h 26m

Basseterre Robert Bradshaw Intl

Sat 2/28

5:30 pm-12:33 am

1 stop9h 03m

$506

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 2/21

7:00 am-4:30 pm

1 stop7h 30m

Basseterre Robert Bradshaw Intl

Sat 2/28

5:30 pm-7:20 am

2 stops15h 50m

$511

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 1/24

8:55 pm-2:47 pm

2 stops15h 52m

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

Sat 2/21

5:00 am-4:30 pm

1 stop9h 30m

Basseterre Robert Bradshaw Intl

Tue 2/24

3:17 pm-11:06 pm

1 stop9h 49m

$536

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 2/21

7:00 am-4:30 pm

1 stop7h 30m

Basseterre Robert Bradshaw Intl

Tue 2/24

3:17 pm-7:20 am

2 stops18h 03m

$541

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 2/21

5:00 am-4:30 pm

2 stops9h 30m

Basseterre Robert Bradshaw Intl

Sat 2/28

5:30 pm-7:20 am

2 stops15h 50m

$551

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

What is the cheapest day to depart on your flight to St Kitts?

Our data shows that Wednesday is the least expensive day to fly to St Kitts. Tickets to fly out on this day can be as low as $674. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to St Kitts for around $891.

What is the cheapest time of day to depart on your flight to St Kitts?

The cheapest time of day to fly to St Kitts is in the afternoon when flights can be purchased for as low as $611. If you have a flexible travel schedule, then try to avoid flying in the evening when prices are $826 on average. Flights to St Kitts from Chicago in the evening are generally more expensive because this time of day is more convenient for travelers’ schedules.

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

6h 53m

Direct flights

None
The fastest flight from Chicago to St Kitts takes 6h 53m
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 $488Free CancellationRating
7.2
11,052 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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Tue 1/20
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