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Cheap flights from Caribbean to Chicago from $109

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 4/20. 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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Frontier Logo
8:10 pm - 12:25 am
SJU
-
ORD
5h 15mnonstop
Frontier Logo
12:59 am - 6:56 am
ORD
-
SJU
4h 57mnonstop
$127Frontier
Thu, Jun 4 - Sat, Jun 6
Frontier Logo
8:10 pm - 12:25 am
SJU
-
ORD
5h 15mnonstop
Frontier Logo
12:59 am - 6:56 am
ORD
-
SJU
4h 57mnonstop
$128Frontier
Thu, May 21 - Sat, May 23
Frontier Logo
4:44 pm - 12:09 pm
SJU
-
ORD
20h 25m
1 stop
Frontier Logo
12:59 am - 6:56 am
ORD
-
SJU
4h 57mnonstop
$165Frontier
Tue, Jun 2 - Sat, Jun 6
Spirit Airlines Logo
11:32 am - 3:48 pm
SJU
-
ORD
5h 16mnonstop
Spirit Airlines Logo
8:56 pm - 2:29 am
ORD
-
SJU
4h 33mnonstop
$198Spirit Airlines
Wed, Mar 11 - Tue, Mar 17
American Airlines Logo
2:23 pm - 7:10 pm
MBJ
-
ORD
4h 47mnonstop
American Airlines Logo
8:05 am - 12:06 pm
ORD
-
MBJ
4h 01mnonstop
$241American Airlines
Thu, Jun 4 - Tue, Oct 6
American Airlines Logo
1:15 pm - 5:55 pm
MBJ
-
ORD
4h 40mnonstop
American Airlines Logo
4:56 pm - 9:25 am
ORD
-
MBJ
16h 29m
1 stop
$246American Airlines
Fri, May 15 - Sat, Sep 5
United Airlines Logo
4:33 pm - 10:20 am
MBJ
-
ORD
17h 47m
1 stop
United Airlines Logo
9:40 pm - 3:10 pm
ORD
-
MBJ
17h 30m
1 stop
$272United Airlines
Sat, Jul 4 - Sat, Aug 1
United Airlines Logo
1:55 pm - 6:08 pm
PUJ
-
ORD
5h 13mnonstop
United Airlines Logo
6:00 am - 4:25 pm
ORD
-
PUJ
9h 25m
1 stop
$275United Airlines
Tue, Mar 17 - Sun, Mar 22
Spirit Airlines Logo
4:35 pm - 11:17 pm
STT
-
ORD
7h 42m
1 stop
Spirit Airlines Logo
4:36 pm - 1:26 pm
ORD
-
STT
19h 50m
2 stops
$292Spirit Airlines
Wed, Mar 25 - Wed, Apr 8
Copa Airlines Logo
12:20 pm - 1:04 am
MBJ
-
ORD
12h 44m
1 stop
Copa Airlines Logo
3:22 pm - 10:11 am
ORD
-
MBJ
18h 49m
1 stop
$338Copa Airlines
Tue, Mar 10 - Fri, Mar 13

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

Our best American Airlines deals on Caribbean to Chicago O'Hare Intl Airport flight tickets
American Airlines
May 20
SJU12:59 amSan Juan Luis Munoz Marin Intl
5h 05m
ORD5:04 amChicago O'Hare Intl
May 26
ORD6:22 pmChicago O'Hare Intl
4h 53m
SJU12:15 amSan Juan Luis Munoz Marin Intl
$237
American Airlines
Jun 4
MBJ2:23 pmMontego Bay Sangster Intl
4h 47m
ORD7:10 pmChicago O'Hare Intl
Oct 6
ORD8:05 amChicago O'Hare Intl
4h 01m
MBJ12:06 pmMontego Bay Sangster Intl
$241
American Airlines
May 7
SJU11:59 pmSan Juan Luis Munoz Marin Intl
8h 32m
1 stop
ORD7:31 amChicago O'Hare Intl
May 10
ORD8:31 amChicago O'Hare Intl
4h 47m
SJU2:18 pmSan Juan Luis Munoz Marin Intl
$242

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
Mar 11
SJU11:32 amSan Juan Luis Munoz Marin Intl
5h 16m
ORD3:48 pmChicago O'Hare Intl
Mar 17
ORD8:56 pmChicago O'Hare Intl
4h 33m
SJU2:29 amSan Juan Luis Munoz Marin Intl
$198
Spirit Airlines
Mar 17
SJU1:29 amSan Juan Luis Munoz Marin Intl
5h 16m
ORD5:45 amChicago O'Hare Intl
Mar 31
ORD10:55 amChicago O'Hare Intl
12h 03m
1 stop
SJU11:58 pmSan Juan Luis Munoz Marin Intl
$212
Spirit Airlines
Mar 5
SJU11:52 amSan Juan Luis Munoz Marin Intl
8h 26m
1 stop
ORD6:18 pmChicago O'Hare Intl
Mar 9
ORD12:44 pmChicago O'Hare Intl
8h 25m
1 stop
SJU10:09 pmSan Juan Luis Munoz Marin Intl
$221

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 February 27, 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

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 6/4

8:10 pm-12:25 am

Nonstop5h 15m

Chicago O'Hare Intl

Sat 6/6

12:59 am-6:56 am

Nonstop4h 57m

$127

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 5/21

8:10 pm-12:25 am

Nonstop5h 15m

Chicago O'Hare Intl

Sat 5/23

12:59 am-6:56 am

Nonstop4h 57m

$128

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 6/2

4:44 pm-12:09 pm

1 stop20h 25m

Chicago O'Hare Intl

Sat 6/6

12:59 am-6:56 am

Nonstop4h 57m

$165

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 3/11

11:32 am-3:48 pm

Nonstop5h 16m

Chicago O'Hare Intl

Tue 3/17

8:56 pm-2:29 am

Nonstop4h 33m

$198

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 6/4

2:23 pm-7:10 pm

Nonstop4h 47m

Chicago O'Hare Intl

Tue 10/6

8:05 am-12:06 pm

Nonstop4h 01m

$241

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Fri 5/15

1:15 pm-5:55 pm

Nonstop4h 40m

Chicago O'Hare Intl

Sat 9/5

4:56 pm-9:25 am

1 stop16h 29m

$246

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 7/4

4:33 pm-10:20 am

1 stop17h 47m

Chicago O'Hare Intl

Sat 8/1

9:40 pm-3:10 pm

1 stop17h 30m

$272

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 3/17

1:55 pm-6:08 pm

Nonstop5h 13m

Chicago O'Hare Intl

Sun 3/22

6:00 am-4:25 pm

1 stop9h 25m

$275

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 3/25

4:35 pm-11:17 pm

1 stop7h 42m

Chicago O'Hare Intl

Wed 4/8

4:36 pm-1:26 pm

2 stops19h 50m

$292

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 3/10

12:20 pm-1:04 am

1 stop12h 44m

Chicago O'Hare Intl

Fri 3/13

3:22 pm-10:11 am

1 stop18h 49m

$338

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 $380. 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 $569.

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 $267 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $487. 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 $325 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 $284 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?

No. A direct flight is the cheapest option for a flight between Caribbean to Chicago O'Hare Intl Airport.

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

$176

Fastest flight time

3h 43m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Caribbean in the past 72 hours is $176. The best round-trip flight deal from Caribbean to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $286.
The fastest flight from Caribbean to Chicago O'Hare Intl Airport takes 3h 43m
Direct flights go from Caribbean to Chicago O'Hare Intl Airport every day.
Search flight deals

  • 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
DeltaPriceFrom $116Free CancellationRating
7.9
8,242 reviews
Search Delta flights
Spirit AirlinesPriceFrom $122Free CancellationRating
6.3
8,493 reviews
Search Spirit Airlines flights
JetBluePriceFrom $131Free CancellationRating
7.2
2,896 reviews
Search JetBlue flights
FrontierPriceFrom $138Free CancellationRating
5.7
3,041 reviews
Search Frontier flights
United AirlinesPriceFrom $256Free CancellationRating
7.4
9,349 reviews
Search United Airlines flights
American AirlinesPriceFrom $258Free CancellationRating
7.2
11,357 reviews
Search American Airlines flights
SouthwestPriceFrom $341Free CancellationRating
8.0
4,301 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
Kenosha
Orland Park
Oak Brook
Joliet
Racine
Janesville
Hammond
Aurora
Tinley Park
Elgin
South Holland

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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