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Cheap flights from Chicago to St Kitts from $311

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 St Kitts departing on 5/18. 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 to St Kitts

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:00 pm - 1:43 pm
ORD
-
SKB
18h 43m
1 stop
American Airlines Logo
2:43 pm - 12:24 am
SKB
-
ORD
10h 41m
1 stop
$719American Airlines
Sat, Jul 11 - Thu, Jul 16
American Airlines Logo
6:00 pm - 1:43 pm
ORD
-
SKB
18h 43m
1 stop
American Airlines Logo
2:43 pm - 7:30 am
SKB
-
ORD
17h 47m
2 stops
$724American Airlines
Sat, Jul 11 - Thu, Jul 16
American Airlines Logo
5:00 am - 1:40 pm
ORD
-
SKB
7h 40m
1 stop
American Airlines Logo
2:40 pm - 10:26 pm
SKB
-
ORD
8h 46m
1 stop
$749American Airlines
Wed, Jun 3 - Wed, Jun 10
American Airlines Logo
5:00 am - 1:40 pm
ORD
-
SKB
7h 40m
1 stop
American Airlines Logo
2:40 pm - 7:28 am
SKB
-
ORD
17h 48m
2 stops
$754American Airlines
Wed, Jun 3 - Wed, Jun 10
American Airlines Logo
8:54 pm - 1:43 pm
ORD
-
SKB
15h 49m
2 stops
American Airlines Logo
4:11 pm - 9:11 am
SKB
-
ORD
18h 00m
1 stop
$759American Airlines
Sat, Aug 1 - Sat, Aug 8
Delta Logo
6:05 am - 2:03 pm
MDW
-
SKB
6h 58m
1 stop
Delta Logo
3:18 pm - 10:15 pm
SKB
-
MDW
7h 57m
1 stop
$789Delta
Sat, Aug 1 - Sat, Aug 8
American Airlines Logo
9:08 pm - 1:40 pm
ORD
-
SKB
15h 32m
2 stops
American Airlines Logo
2:40 pm - 7:00 am
SKB
-
ORD
17h 20m
2 stops
$789American Airlines
Wed, Jun 3 - Wed, Jun 10
Multiple Airlines Logo
12:59 pm - 6:30 pm
ORD
-
SKB
28h 31m
1 stop
Multiple Airlines Logo
3:35 pm - 8:22 am
SKB
-
ORD
41h 47m
2 stops
$794Multiple Airlines
Sat, May 23 - Sat, May 30
American Airlines Logo
6:47 pm - 1:07 pm
ORD
-
SKB
17h 20m
1 stop
American Airlines Logo
2:40 pm - 12:19 am
SKB
-
ORD
10h 39m
1 stop
$819American Airlines
Fri, Jun 5 - Sun, Jun 7
American Airlines Logo
8:52 pm - 1:07 pm
ORD
-
SKB
15h 15m
1 stop
American Airlines Logo
2:40 pm - 7:00 am
SKB
-
ORD
17h 20m
2 stops
$824American Airlines
Fri, Jun 5 - Sun, Jun 7

American Airlines flights from Chicago to St Kitts

Our best American Airlines deals on Chicago to St Kitts flight tickets
American Airlines
Jul 11
ORD6:00 pmChicago O'Hare Intl
18h 43m
1 stop
SKB1:43 pmBasseterre Robert Bradshaw Intl
Jul 16
SKB2:43 pmBasseterre Robert Bradshaw Intl
10h 41m
1 stop
ORD12:24 amChicago O'Hare Intl
$719
American Airlines
Jul 11
ORD6:00 pmChicago O'Hare Intl
18h 43m
1 stop
SKB1:43 pmBasseterre Robert Bradshaw Intl
Jul 16
SKB2:43 pmBasseterre Robert Bradshaw Intl
17h 47m
2 stops
ORD7:30 amChicago O'Hare Intl
$724
American Airlines
Jun 3
ORD5:00 amChicago O'Hare Intl
7h 40m
1 stop
SKB1:40 pmBasseterre Robert Bradshaw Intl
Jun 10
SKB2:40 pmBasseterre Robert Bradshaw Intl
8h 46m
1 stop
ORD10:26 pmChicago O'Hare Intl
$749

JetBlue flights from Chicago to St Kitts

Our best JetBlue deals on Chicago to St Kitts flight tickets
JetBlue
Jul 1
ORD8:20 pmChicago O'Hare Intl
17h 29m
2 stops
SKB2:49 pmBasseterre Robert Bradshaw Intl
Jul 5
SKB3:55 pmBasseterre Robert Bradshaw Intl
30h 32m
1 stop
ORD9:27 pmChicago O'Hare Intl
$1,193
JetBlue
Jul 1
ORD8:20 pmChicago O'Hare Intl
17h 29m
2 stops
SKB2:49 pmBasseterre Robert Bradshaw Intl
Jul 5
SKB3:55 pmBasseterre Robert Bradshaw Intl
19h 11m
2 stops
ORD10:06 amChicago O'Hare Intl
$1,203

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 April 20, 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

Cheapest round-trip

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 7/11

6:00 pm-1:43 pm

1 stop18h 43m

Basseterre Robert Bradshaw Intl

Thu 7/16

2:43 pm-12:24 am

1 stop10h 41m

$719

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 7/11

6:00 pm-1:43 pm

1 stop18h 43m

Basseterre Robert Bradshaw Intl

Thu 7/16

2:43 pm-7:30 am

2 stops17h 47m

$724

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Wed 6/3

5:00 am-1:40 pm

1 stop7h 40m

Basseterre Robert Bradshaw Intl

Wed 6/10

2:40 pm-10:26 pm

1 stop8h 46m

$749

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Wed 6/3

5:00 am-1:40 pm

1 stop7h 40m

Basseterre Robert Bradshaw Intl

Wed 6/10

2:40 pm-7:28 am

2 stops17h 48m

$754

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 8/1

8:54 pm-1:43 pm

2 stops15h 49m

Basseterre Robert Bradshaw Intl

Sat 8/8

4:11 pm-9:11 am

1 stop18h 00m

$759
Quickest round-trip

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Sat 8/1

6:05 am-2:03 pm

1 stop6h 58m

Basseterre Robert Bradshaw Intl

Sat 8/8

3:18 pm-10:15 pm

1 stop7h 57m

$789

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Wed 6/3

9:08 pm-1:40 pm

2 stops15h 32m

Basseterre Robert Bradshaw Intl

Wed 6/10

2:40 pm-7:00 am

2 stops17h 20m

$789

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 5/23

12:59 pm-6:30 pm

1 stop28h 31m

Basseterre Robert Bradshaw Intl

Sat 5/30

3:35 pm-8:22 am

2 stops41h 47m

$794

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Fri 6/5

6:47 pm-1:07 pm

1 stop17h 20m

Basseterre Robert Bradshaw Intl

Sun 6/7

2:40 pm-12:19 am

1 stop10h 39m

$819

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Fri 6/5

8:52 pm-1:07 pm

1 stop15h 15m

Basseterre Robert Bradshaw Intl

Sun 6/7

2:40 pm-7:00 am

2 stops17h 20m

$824

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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

6h 58m

Direct flights

None
The fastest flight from Chicago to St Kitts takes 6h 58m
There are no direct flights from Chicago to St Kitts. There are no popular flight routes from Chicago to St Kitts.
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Frequently asked questions about flying from Chicago to St Kitts

  • 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
7.1
11,629 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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