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Cheap flights from Chicago to Saint Kitts and Nevis from $207

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 10/22. 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

American Airlines Logo
5:00 am - 3:18 pmORD-SKB
8h 18m1 stop
American Airlines Logo
4:28 pm - 10:59 pmSKB-ORD
8h 31m1 stop
$480American Airlines
Find Deal
Wed, Nov 5 - Tue, Nov 11
American Airlines Logo
5:00 am - 3:18 pmORD-SKB
8h 18m1 stop
American Airlines Logo
4:28 pm - 7:21 amSKB-ORD
16h 53m2 stops
$484American Airlines
Find Deal
Wed, Nov 5 - Tue, Nov 11
American Airlines Logo
7:30 pm - 3:18 pmORD-SKB
17h 48m1 stop
American Airlines Logo
3:21 pm - 10:57 pmSKB-ORD
9h 36m1 stop
$505American Airlines
Find Deal
Sat, Nov 29 - Sat, Dec 6
American Airlines Logo
8:35 pm - 3:18 pmORD-SKB
17h 43m2 stops
American Airlines Logo
5:23 pm - 7:10 amSKB-ORD
15h 47m2 stops
$509American Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 8
American Airlines Logo
1:51 pm - 3:18 pmORD-SKB
24h 27m1 stop
American Airlines Logo
4:28 pm - 10:59 pmSKB-ORD
8h 31m1 stop
$516American Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 8
American Airlines Logo
7:07 pm - 2:20 pmORD-SKB
17h 13m1 stop
American Airlines Logo
3:21 pm - 12:37 amSKB-ORD
11h 16m1 stop
$530American Airlines
Find Deal
Thu, Dec 4 - Mon, Dec 8
American Airlines Logo
5:00 am - 2:20 pmORD-SKB
7h 20m1 stop
American Airlines Logo
3:21 pm - 7:19 amSKB-ORD
17h 58m2 stops
$534American Airlines
Find Deal
Thu, Dec 4 - Mon, Dec 8
American Airlines Logo
5:00 am - 4:19 pmORD-SKB
9h 19m2 stops
American Airlines Logo
5:29 pm - 8:25 amSKB-ORD
16h 56m2 stops
$552American Airlines
Find Deal
Sat, Dec 13 - Fri, Dec 19
Delta Logo
6:00 am - 3:09 pmMDW-SKB
7h 09m1 stop
Delta Logo
2:53 pm - 9:46 pmSKB-MDW
8h 53m1 stop
$616Delta
Find Deal
Sat, Feb 7 - Sat, Feb 14
Delta Logo
5:25 pm - 1:32 pmMDW-SKB
18h 07m2 stops
Delta Logo
2:52 pm - 12:08 pmSKB-MDW
23h 16m2 stops
$620Delta
Find Deal
Fri, Feb 27 - Sat, Mar 7

Delta flights from Chicago to Saint Kitts and Nevis

Our best Delta deals on Chicago to Saint Kitts and Nevis flight tickets
Delta
Feb 7
MDW6:00 amChicago Midway
7h 09m
1 stop
SKB3:09 pmBasseterre Robert Bradshaw Intl
Feb 14
SKB2:53 pmBasseterre Robert Bradshaw Intl
8h 53m
1 stop
MDW9:46 pmChicago Midway
$616
Find similar
Delta
Feb 27
MDW5:25 pmChicago Midway
18h 07m
2 stops
SKB1:32 pmBasseterre Robert Bradshaw Intl
Mar 7
SKB2:52 pmBasseterre Robert Bradshaw Intl
23h 16m
2 stops
MDW12:08 pmChicago Midway
$620
Find similar
Delta
Feb 27
MDW1:05 pmChicago Midway
24h 04m
1 stop
SKB3:09 pmBasseterre Robert Bradshaw Intl
Mar 7
SKB2:53 pmBasseterre Robert Bradshaw Intl
8h 53m
1 stop
MDW9:46 pmChicago Midway
$829
Find similar

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
Nov 5
ORD5:00 amChicago O'Hare Intl
8h 18m
1 stop
SKB3:18 pmBasseterre Robert Bradshaw Intl
Nov 11
SKB4:28 pmBasseterre Robert Bradshaw Intl
8h 31m
1 stop
ORD10:59 pmChicago O'Hare Intl
$480
Find similar
American Airlines
Nov 5
ORD5:00 amChicago O'Hare Intl
8h 18m
1 stop
SKB3:18 pmBasseterre Robert Bradshaw Intl
Nov 11
SKB4:28 pmBasseterre Robert Bradshaw Intl
16h 53m
2 stops
ORD7:21 amChicago O'Hare Intl
$484
Find similar
American Airlines
Nov 29
ORD7:30 pmChicago O'Hare Intl
17h 48m
1 stop
SKB3:18 pmBasseterre Robert Bradshaw Intl
Dec 6
SKB3:21 pmBasseterre Robert Bradshaw Intl
9h 36m
1 stop
ORD10:57 pmChicago O'Hare Intl
$505
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 September 17, 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

Wed 11/5

5:00 am-3:18 pm

1 stop8h 18m

Basseterre Robert Bradshaw Intl

Tue 11/11

4:28 pm-10:59 pm

1 stop8h 31m

$480

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Wed 11/5

5:00 am-3:18 pm

1 stop8h 18m

Basseterre Robert Bradshaw Intl

Tue 11/11

4:28 pm-7:21 am

2 stops16h 53m

$484

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 11/29

7:30 pm-3:18 pm

1 stop17h 48m

Basseterre Robert Bradshaw Intl

Sat 12/6

3:21 pm-10:57 pm

1 stop9h 36m

$505

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 11/1

8:35 pm-3:18 pm

2 stops17h 43m

Basseterre Robert Bradshaw Intl

Sat 11/8

5:23 pm-7:10 am

2 stops15h 47m

$509

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 11/1

1:51 pm-3:18 pm

1 stop24h 27m

Basseterre Robert Bradshaw Intl

Sat 11/8

4:28 pm-10:59 pm

1 stop8h 31m

$516

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Thu 12/4

7:07 pm-2:20 pm

1 stop17h 13m

Basseterre Robert Bradshaw Intl

Mon 12/8

3:21 pm-12:37 am

1 stop11h 16m

$530

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Thu 12/4

5:00 am-2:20 pm

1 stop7h 20m

Basseterre Robert Bradshaw Intl

Mon 12/8

3:21 pm-7:19 am

2 stops17h 58m

$534

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 12/13

5:00 am-4:19 pm

2 stops9h 19m

Basseterre Robert Bradshaw Intl

Fri 12/19

5:29 pm-8:25 am

2 stops16h 56m

$552

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Sat 2/7

6:00 am-3:09 pm

1 stop7h 09m

Basseterre Robert Bradshaw Intl

Sat 2/14

2:53 pm-9:46 pm

1 stop8h 53m

$616

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Fri 2/27

5:25 pm-1:32 pm

2 stops18h 07m

Basseterre Robert Bradshaw Intl

Sat 3/7

2:52 pm-12:08 pm

2 stops23h 16m

$620

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 month to fly to Saint Kitts and Nevis?

The month of July is, on average, the cheapest month to fly to Saint Kitts and Nevis from Chicago, with most prices found around $642. If you’re not able to fly to Saint Kitts and Nevis in July, then September is your next best option. Flight prices from Chicago to Saint Kitts and Nevis during September average around $652.

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

Direct flights

None
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
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $614Free CancellationRating
7.9
7,961 reviews
Search Delta 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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