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Cheap flights from Caribbean to Chicago from $118

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 8/26. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Caribbean to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:00 am - 12:15 pm
SJU
-
ORD
31h 15m
1 stop
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
$225Frontier
Fri, Aug 7 - Sat, Aug 15
Frontier Logo
6:11 pm - 10:26 pm
SJU
-
ORD
5h 15mnonstop
Frontier Logo
12:29 am - 6:26 am
ORD
-
SJU
4h 57mnonstop
$227Frontier
Thu, Sep 3 - Sun, Sep 6
United Airlines Logo
2:20 pm - 11:26 pm
SJU
-
ORD
10h 06m
1 stop
United Airlines Logo
8:55 am - 2:44 pm
ORD
-
SJU
4h 49mnonstop
$232United Airlines
Wed, Aug 19 - Sat, Aug 22
American Airlines Logo
5:10 pm - 12:35 am
SJU
-
ORD
8h 25m
1 stop
American Airlines Logo
6:59 pm - 9:43 am
ORD
-
SJU
13h 44m
1 stop
$236American Airlines
Thu, Aug 27 - Sat, Aug 29
Arajet Logo
7:02 am - 11:12 am
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
12:12 pm - 5:57 pm
ORD
-
PUJ
4h 45mnonstop
$280Arajet
Sat, Sep 12 - Sat, Sep 19
Arajet Logo
7:02 am - 11:12 am
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
12:12 pm - 5:57 pm
ORD
-
PUJ
4h 45mnonstop
$290Arajet
Sat, Oct 17 - Sat, Oct 24
United Airlines Logo
2:48 pm - 6:16 pm
MBJ
-
ORD
4h 28mnonstop
United Airlines Logo
8:42 am - 1:46 pm
ORD
-
MBJ
4h 04mnonstop
$311United Airlines
Sun, Nov 1 - Thu, Nov 12
JetBlue Logo
12:20 pm - 11:44 pm
NAS
-
ORD
12h 24m
1 stop
JetBlue Logo
7:00 am - 5:22 pm
ORD
-
NAS
9h 22m
1 stop
$325JetBlue
Thu, Jul 16 - Tue, Jul 21
American Airlines Logo
2:12 pm - 6:55 pm
MBJ
-
ORD
4h 43mnonstop
American Airlines Logo
5:00 am - 4:08 pm
ORD
-
MBJ
11h 08m
1 stop
$326American Airlines
Sat, Aug 29 - Sat, Sep 5
JetBlue Logo
6:27 pm - 11:44 pm
NAS
-
ORD
6h 17m
1 stop
JetBlue Logo
7:00 am - 5:22 pm
ORD
-
NAS
9h 22m
1 stop
$334JetBlue
Wed, Jul 15 - Thu, Jul 16

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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
Aug 7
SJU6:00 amSan Juan Luis Munoz Marin Intl
31h 15m
1 stop
ORD12:15 pmChicago O'Hare Intl
Aug 16
ORD12:44 amChicago O'Hare Intl
5h 00m
SJU6:44 amSan Juan Luis Munoz Marin Intl
$225
Frontier
Sep 3
SJU6:11 pmSan Juan Luis Munoz Marin Intl
5h 15m
ORD10:26 pmChicago O'Hare Intl
Sep 6
ORD12:29 amChicago O'Hare Intl
4h 57m
SJU6:26 amSan Juan Luis Munoz Marin Intl
$227
Frontier
Aug 26
SJU6:11 pmSan Juan Luis Munoz Marin Intl
5h 15m
ORD10:26 pmChicago O'Hare Intl
Sep 1
ORD12:29 amChicago O'Hare Intl
4h 57m
SJU6:26 amSan Juan Luis Munoz Marin Intl
$228

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

Our best United Airlines deals on Caribbean to Chicago O'Hare Intl Airport flight tickets
United Airlines
Aug 19
SJU2:20 pmSan Juan Luis Munoz Marin Intl
10h 06m
1 stop
ORD11:26 pmChicago O'Hare Intl
Aug 22
ORD8:55 amChicago O'Hare Intl
4h 49m
SJU2:44 pmSan Juan Luis Munoz Marin Intl
$232
United Airlines
Aug 23
SJU1:00 amSan Juan Luis Munoz Marin Intl
9h 13m
1 stop
ORD9:13 amChicago O'Hare Intl
Aug 31
ORD5:30 amChicago O'Hare Intl
9h 12m
1 stop
SJU3:42 pmSan Juan Luis Munoz Marin Intl
$272
United Airlines
Sep 5
SJU2:55 pmSan Juan Luis Munoz Marin Intl
9h 31m
1 stop
ORD11:26 pmChicago O'Hare Intl
Sep 8
ORD5:00 amChicago O'Hare Intl
7h 53m
1 stop
SJU1:53 pmSan Juan Luis Munoz Marin Intl
$275

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 June 20, 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 8/7

6:00 am-12:15 pm

1 stop31h 15m

Chicago O'Hare Intl

Sat 8/15

12:44 am-6:44 am

Nonstop5h 00m

$225

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 9/3

6:11 pm-10:26 pm

Nonstop5h 15m

Chicago O'Hare Intl

Sun 9/6

12:29 am-6:26 am

Nonstop4h 57m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 8/19

2:20 pm-11:26 pm

1 stop10h 06m

Chicago O'Hare Intl

Sat 8/22

8:55 am-2:44 pm

Nonstop4h 49m

$232

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 8/27

5:10 pm-12:35 am

1 stop8h 25m

Chicago O'Hare Intl

Sat 8/29

6:59 pm-9:43 am

1 stop13h 44m

$236

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 9/12

7:02 am-11:12 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 9/19

12:12 pm-5:57 pm

Nonstop4h 45m

$280

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 10/17

7:02 am-11:12 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 10/24

12:12 pm-5:57 pm

Nonstop4h 45m

$290
Quickest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sun 11/1

2:48 pm-6:16 pm

Nonstop4h 28m

Chicago O'Hare Intl

Thu 11/12

8:42 am-1:46 pm

Nonstop4h 04m

$311

NassauChicago

NAS - ORD

NASORD

Nassau Intl

Thu 7/16

12:20 pm-11:44 pm

1 stop12h 24m

Chicago O'Hare Intl

Tue 7/21

7:00 am-5:22 pm

1 stop9h 22m

$325

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 8/29

2:12 pm-6:55 pm

Nonstop4h 43m

Chicago O'Hare Intl

Sat 9/5

5:00 am-4:08 pm

1 stop11h 08m

$326

NassauChicago

NAS - ORD

NASORD

Nassau Intl

Wed 7/15

6:27 pm-11:44 pm

1 stop6h 17m

Chicago O'Hare Intl

Thu 7/16

7:00 am-5:22 pm

1 stop9h 22m

$334

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 June is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Caribbean averaging around $75.

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 Thursday when prices can be found for as low as $453. 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 $629.

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 $447 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $517. 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 Punta Cana to Chicago O'Hare Intl for the best Caribbean - Chicago O'Hare Intl flight prices

How far in advance should I book a flight from Caribbean 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 $339 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 $287 on momondo.

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

There are 4 cabin classes available to choose from on Caribbean to Chicago O'Hare Intl Airport 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

$194

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 $194. The best round-trip flight deal from Caribbean to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $213.
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
DeltaPriceFrom $112Free CancellationRating
7.8
8,420 reviews
Search Delta flights
FrontierPriceFrom $119Free CancellationRating
5.6
2,877 reviews
Search Frontier flights
JetBluePriceFrom $131Free CancellationRating
7.1
2,987 reviews
Search JetBlue flights
ArajetPriceFrom $195Free CancellationRating
6.5
49 reviews
Search Arajet flights
American AirlinesPriceFrom $227Free CancellationRating
7.1
11,715 reviews
Search American Airlines flights
United AirlinesPriceFrom $263Free CancellationRating
7.4
9,865 reviews
Search United Airlines flights
SouthwestPriceFrom $292Free CancellationRating
7.9
4,241 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
Orland Park
Oak Brook
New Buffalo
Joliet
Kenosha
Aurora
Hammond
Racine
Janesville
Evanston
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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