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Cheap flights from Caribbean to Chicago from $113

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Caribbean to Chicago departing on 5/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
12:57 pm - 12:24 am
SJU
-
ORD
12h 27m
1 stop
Spirit Airlines Logo
4:44 pm - 10:21 pm
ORD
-
SJU
4h 37mnonstop
$147Spirit Airlines
Fri, May 1 - Mon, May 4
Spirit Airlines Logo
4:34 pm - 8:49 pm
SJU
-
ORD
5h 15mnonstop
Spirit Airlines Logo
4:44 pm - 10:21 pm
ORD
-
SJU
4h 37mnonstop
$150Spirit Airlines
Thu, Apr 30 - Mon, May 4
Frontier Logo
11:00 am - 11:59 pm
SJU
-
ORD
13h 59m
1 stop
Frontier Logo
12:33 am - 6:24 am
ORD
-
SJU
4h 51mnonstop
$152Frontier
Fri, May 15 - Sat, May 30
Frontier Logo
6:09 pm - 11:13 pm
SJU
-
ORD
30h 04m
1 stop
Frontier Logo
7:30 am - 11:28 pm
ORD
-
SJU
14h 58m
1 stop
$159Frontier
Thu, May 7 - Sun, May 10
American Airlines Logo
2:23 pm - 7:16 pm
MBJ
-
ORD
4h 53mnonstop
American Airlines Logo
9:13 am - 1:23 pm
ORD
-
MBJ
4h 10mnonstop
$281American Airlines
Thu, Jul 16 - Sun, Jul 19
United Airlines Logo
1:52 pm - 6:15 pm
MBJ
-
ORD
4h 23mnonstop
United Airlines Logo
11:00 pm - 1:30 pm
ORD
-
MBJ
14h 30m
1 stop
$286United Airlines
Sat, May 16 - Mon, May 18
American Airlines Logo
2:00 pm - 6:30 pm
MBJ
-
ORD
4h 30mnonstop
American Airlines Logo
7:30 am - 1:28 pm
ORD
-
MBJ
5h 58m
1 stop
$291American Airlines
Fri, Aug 21 - Wed, Aug 26
United Airlines Logo
4:12 pm - 4:30 pm
MBJ
-
ORD
24h 18m
1 stop
United Airlines Logo
10:30 am - 1:30 pm
ORD
-
MBJ
27h 00m
1 stop
$292United Airlines
Fri, May 8 - Tue, May 12
Air Canada Logo
6:00 pm - 9:00 am
SXM
-
ORD
16h 00m
1 stop
Air Canada Logo
5:53 pm - 5:00 pm
ORD
-
SXM
22h 07m
1 stop
$403Air Canada
Thu, Aug 13 - Fri, Aug 28
Air Canada Logo
6:00 pm - 7:45 am
SXM
-
ORD
14h 45m
2 stops
Air Canada Logo
7:09 am - 5:00 pm
ORD
-
SXM
8h 51m
1 stop
$407Air Canada
Thu, Jun 25 - Thu, Jul 2

Spirit Airlines flights from Caribbean to Chicago O'Hare Intl Airport

Our best Spirit Airlines deals on Caribbean to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
May 1
SJU12:57 pmSan Juan Luis Munoz Marin Intl
12h 27m
1 stop
ORD12:24 amChicago O'Hare Intl
May 4
ORD4:44 pmChicago O'Hare Intl
4h 37m
SJU10:21 pmSan Juan Luis Munoz Marin Intl
$147
Spirit Airlines
Apr 23
SJU4:34 pmSan Juan Luis Munoz Marin Intl
5h 15m
ORD8:49 pmChicago O'Hare Intl
Apr 27
ORD5:05 amChicago O'Hare Intl
13h 17m
1 stop
SJU7:22 pmSan Juan Luis Munoz Marin Intl
$149
Spirit Airlines
Apr 30
SJU4:34 pmSan Juan Luis Munoz Marin Intl
5h 15m
ORD8:49 pmChicago O'Hare Intl
May 4
ORD4:44 pmChicago O'Hare Intl
4h 37m
SJU10:21 pmSan Juan Luis Munoz Marin Intl
$150

Frontier flights from Caribbean to Chicago O'Hare Intl Airport

Our best Frontier deals on Caribbean to Chicago O'Hare Intl Airport flight tickets
Frontier
May 7
SJU6:46 pmSan Juan Luis Munoz Marin Intl
24h 58m
1 stop
ORD6:44 pmChicago O'Hare Intl
May 10
ORD7:30 amChicago O'Hare Intl
14h 58m
1 stop
SJU11:28 pmSan Juan Luis Munoz Marin Intl
$168
Frontier
May 6
SJU6:41 pmSan Juan Luis Munoz Marin Intl
23h 09m
1 stop
ORD4:50 pmChicago O'Hare Intl
May 10
ORD7:30 amChicago O'Hare Intl
14h 58m
1 stop
SJU11:28 pmSan Juan Luis Munoz Marin Intl
$176
Frontier
May 2
SJU11:30 amSan Juan Luis Munoz Marin Intl
13h 29m
1 stop
ORD11:59 pmChicago O'Hare Intl
May 4
ORD2:10 pmChicago O'Hare Intl
8h 33m
1 stop
SJU11:43 pmSan Juan Luis Munoz Marin Intl
$186

momondo Fare Finder

 
Customize your flight search to find flights from Caribbean to Chicago O'Hare Intl Airport 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 15, 2026.
Use the filters below to find and compare flights from Caribbean to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/1

12:57 pm-12:24 am

1 stop12h 27m

Chicago O'Hare Intl

Mon 5/4

4:44 pm-10:21 pm

Nonstop4h 37m

$147

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 4/30

4:34 pm-8:49 pm

Nonstop5h 15m

Chicago O'Hare Intl

Mon 5/4

4:44 pm-10:21 pm

Nonstop4h 37m

$150

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/15

11:00 am-11:59 pm

1 stop13h 59m

Chicago O'Hare Intl

Sat 5/30

12:33 am-6:24 am

Nonstop4h 51m

$152

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 5/7

6:09 pm-11:13 pm

1 stop30h 04m

Chicago O'Hare Intl

Sun 5/10

7:30 am-11:28 pm

1 stop14h 58m

$159
Quickest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 7/16

2:23 pm-7:16 pm

Nonstop4h 53m

Chicago O'Hare Intl

Sun 7/19

9:13 am-1:23 pm

Nonstop4h 10m

$281

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/16

1:52 pm-6:15 pm

Nonstop4h 23m

Chicago O'Hare Intl

Mon 5/18

11:00 pm-1:30 pm

1 stop14h 30m

$286

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 8/21

2:00 pm-6:30 pm

Nonstop4h 30m

Chicago O'Hare Intl

Wed 8/26

7:30 am-1:28 pm

1 stop5h 58m

$291

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 5/8

4:12 pm-4:30 pm

1 stop24h 18m

Chicago O'Hare Intl

Tue 5/12

10:30 am-1:30 pm

1 stop27h 00m

$292

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 8/13

6:00 pm-9:00 am

1 stop16h 00m

Chicago O'Hare Intl

Fri 8/28

5:53 pm-5:00 pm

1 stop22h 07m

$403

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 6/25

6:00 pm-7:45 am

2 stops14h 45m

Chicago O'Hare Intl

Thu 7/2

7:09 am-5:00 pm

1 stop8h 51m

$407

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 Chicago from

How to get the cheapest flight ticket from Caribbean to Chicago O'Hare Intl Airport

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 Chicago O'Hare Intl Airport?

The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Caribbean averaging around $257.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $388. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Caribbean because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $567.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Caribbean in the evening is the least expensive time of day to depart. momondo users have found prices as low as $298 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $483. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Caribbean to Chicago O'Hare Intl flight route?

Fly from San Juan Luis Munoz Marin Intl to Chicago O'Hare Intl for the best Caribbean - Chicago O'Hare Intl flight prices

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Caribbean when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $324 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Caribbean for as low as $272 on momondo.

What cabin class options are available on Caribbean to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Caribbean to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Caribbean to Chicago O'Hare Intl Airport flights?

You could potentially save up to 4% on your flight if you consider stops on a Caribbean to Chicago O'Hare Intl Airport flight.

Cheap Caribbean to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Caribbean to Chicago O'Hare Intl Airport

Best Price Found

$204

Fastest flight time

3h 56m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Caribbean in the past 72 hours is $204. The best round-trip flight deal from Caribbean to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $308.
The fastest flight from Caribbean to Chicago O'Hare Intl Airport takes 3h 56m
Direct flights go from Caribbean to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from Caribbean to Chicago O'Hare Intl Airport

  • When did momondo last update prices for flights from Caribbean to Chicago O'Hare Intl Airport?

    Prices for flights from Caribbean to Chicago O'Hare Intl Airport were last updated today.

  • How many operators does momondo search for flights from Caribbean to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Caribbean to Chicago O'Hare Intl Airport?

    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 Caribbean to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport 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 Caribbean to Chicago O'Hare Intl Airport?

Best airlines flying from Caribbean to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Caribbean to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $111Free CancellationRating
5.7
2,988 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $124Free CancellationRating
6.3
8,616 reviews
Search Spirit Airlines flights
JetBluePriceFrom $131Free CancellationRating
7.2
2,938 reviews
Search JetBlue flights
DeltaPriceFrom $191Free CancellationRating
7.9
8,409 reviews
Search Delta flights
ArajetPriceFrom $195Free CancellationRating
6.5
47 reviews
Search Arajet flights
United AirlinesPriceFrom $256Free CancellationRating
7.4
9,594 reviews
Search United Airlines flights
American AirlinesPriceFrom $257Free CancellationRating
7.1
11,584 reviews
Search American Airlines flights
SouthwestPriceFrom $292Free CancellationRating
8.0
4,328 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Oak Brook
Kenosha
Joliet
Aurora
Janesville
Racine
Hammond
Elgin
Tinley Park
Evanston

Why use momondo?

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

It is quick and easy to find Caribbean to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

All flight searches from Caribbean to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Caribbean to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Caribbean to Chicago.

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

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

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