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Cheap flights from Caribbean to Chicago from $107

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 1/17. 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

Spirit Airlines Logo
3:19 pm - 9:33 pmSJU-ORD
7h 14m1 stop
Spirit Airlines Logo
9:06 pm - 2:51 amORD-SJU
4h 45mnonstop
$177Spirit Airlines
Find Deal
Sat, Oct 25 - Fri, Oct 31
Spirit Airlines Logo
3:19 pm - 9:33 pmSJU-ORD
7h 14m1 stop
Spirit Airlines Logo
9:06 pm - 2:51 amORD-SJU
4h 45mnonstop
$179Spirit Airlines
Find Deal
Sat, Oct 25 - Fri, Oct 31
United Airlines Logo
7:10 am - 11:32 amSJU-ORD
5h 22mnonstop
United Airlines Logo
8:55 am - 3:40 pmORD-SJU
4h 45mnonstop
$218United Airlines
Find Deal
Tue, Oct 28 - Mon, Nov 3
United Airlines Logo
4:55 pm - 11:15 pmSJU-ORD
7h 20m1 stop
United Airlines Logo
2:20 pm - 8:00 pmORD-SJU
4h 40mnonstop
$223United Airlines
Find Deal
Thu, Oct 23 - Thu, Oct 30
Delta Logo
5:43 pm - 11:58 pmSJU-ORD
7h 15m1 stop
Delta Logo
1:08 pm - 11:56 pmORD-SJU
9h 48m1 stop
$227Delta
Find Deal
Fri, Oct 24 - Mon, Oct 27
American Airlines Logo
4:44 pm - 11:40 pmSJU-ORD
8h 56m1 stop
American Airlines Logo
6:50 am - 3:53 pmORD-SJU
7h 03m1 stop
$232American Airlines
Find Deal
Thu, Nov 13 - Sun, Nov 16
Frontier Logo
2:59 am - 5:13 pmBQN-ORD
15h 14m1 stop
Frontier Logo
8:15 am - 2:04 amORD-BQN
16h 49m1 stop
$272Frontier
Find Deal
Sun, Oct 19 - Mon, Oct 27
Frontier Logo
2:59 am - 5:40 pmBQN-ORD
15h 41m2 stops
Frontier Logo
6:23 pm - 2:04 amORD-BQN
6h 41m1 stop
$312Frontier
Find Deal
Sun, Oct 19 - Mon, Oct 27
Delta Logo
3:10 pm - 8:45 amAUA-ORD
19h 35m2 stops
Delta Logo
6:30 pm - 1:55 pmORD-AUA
17h 25m1 stop
$333Delta
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Wed, Dec 3 - Tue, Dec 9
American Airlines Logo
5:24 pm - 11:37 pmPUJ-ORD
8h 13m1 stop
American Airlines Logo
9:50 am - 4:27 pmORD-PUJ
4h 37mnonstop
$335American Airlines
Find Deal
Wed, Nov 12 - Sun, Nov 16

Air Canada flights from Caribbean to Chicago O'Hare Intl Airport

Our best Air Canada deals on Caribbean to Chicago O'Hare Intl Airport flight tickets
Air Canada
Dec 3
AUA4:05 pmOranjestad Reina Beatrix
25h 05m
1 stop
ORD3:10 pmChicago O'Hare Intl
Dec 9
ORD3:55 pmChicago O'Hare Intl
21h 05m
1 stop
AUA3:00 pmOranjestad Reina Beatrix
$329
Find similar
Air Canada
Oct 27
MBJ1:40 pmMontego Bay Sangster Intl
29h 50m
1 stop
ORD7:30 pmChicago O'Hare Intl
Nov 2
ORD12:50 pmChicago O'Hare Intl
26h 45m
2 stops
MBJ4:35 pmMontego Bay Sangster Intl
$342
Find similar
Air Canada
Oct 27
MBJ4:45 pmMontego Bay Sangster Intl
16h 30m
1 stop
ORD9:15 amChicago O'Hare Intl
Nov 2
ORD7:15 amChicago O'Hare Intl
9h 50m
1 stop
MBJ6:05 pmMontego Bay Sangster Intl
$348
Find similar

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
Oct 25
SJU3:19 pmSan Juan Luis Munoz Marin Intl
7h 14m
1 stop
ORD9:33 pmChicago O'Hare Intl
Oct 31
ORD9:06 pmChicago O'Hare Intl
4h 45m
SJU2:51 amSan Juan Luis Munoz Marin Intl
$177
Find similar
Spirit Airlines
Oct 25
SJU3:19 pmSan Juan Luis Munoz Marin Intl
7h 14m
1 stop
ORD9:33 pmChicago O'Hare Intl
Oct 31
ORD9:06 pmChicago O'Hare Intl
4h 45m
SJU2:51 amSan Juan Luis Munoz Marin Intl
$179
Find similar
Spirit Airlines
Oct 25
SJU9:48 amSan Juan Luis Munoz Marin Intl
5h 08m
ORD1:56 pmChicago O'Hare Intl
Nov 3
ORD9:16 pmChicago O'Hare Intl
4h 45m
SJU4:01 amSan Juan Luis Munoz Marin Intl
$187
Find similar

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 September 24, 2025.
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

Sat 10/25

3:19 pm-9:33 pm

1 stop7h 14m

Chicago O'Hare Intl

Fri 10/31

9:06 pm-2:51 am

Nonstop4h 45m

$177

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sat 10/25

3:19 pm-9:33 pm

1 stop7h 14m

Chicago O'Hare Intl

Fri 10/31

9:06 pm-2:51 am

Nonstop4h 45m

$179

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 10/28

7:10 am-11:32 am

Nonstop5h 22m

Chicago O'Hare Intl

Mon 11/3

8:55 am-3:40 pm

Nonstop4h 45m

$218

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 10/23

4:55 pm-11:15 pm

1 stop7h 20m

Chicago O'Hare Intl

Thu 10/30

2:20 pm-8:00 pm

Nonstop4h 40m

$223

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 10/24

5:43 pm-11:58 pm

1 stop7h 15m

Chicago O'Hare Intl

Mon 10/27

1:08 pm-11:56 pm

1 stop9h 48m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 11/13

4:44 pm-11:40 pm

1 stop8h 56m

Chicago O'Hare Intl

Sun 11/16

6:50 am-3:53 pm

1 stop7h 03m

$232

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Sun 10/19

2:59 am-5:13 pm

1 stop15h 14m

Chicago O'Hare Intl

Mon 10/27

8:15 am-2:04 am

1 stop16h 49m

$272

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Sun 10/19

2:59 am-5:40 pm

2 stops15h 41m

Chicago O'Hare Intl

Mon 10/27

6:23 pm-2:04 am

1 stop6h 41m

$312

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Wed 12/3

3:10 pm-8:45 am

2 stops19h 35m

Chicago O'Hare Intl

Tue 12/9

6:30 pm-1:55 pm

1 stop17h 25m

$333

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 11/12

5:24 pm-11:37 pm

1 stop8h 13m

Chicago O'Hare Intl

Sun 11/16

9:50 am-4:27 pm

Nonstop4h 37m

$335

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 December is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Caribbean averaging around $290.

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 $371. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday 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 $506.

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 $249 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $477. 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 $328 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 $268 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

$173

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 $173. The best round-trip flight deal from Caribbean to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $171.
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

  • 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
Spirit AirlinesPriceFrom $136Free CancellationRating
6.3
8,042 reviews
Search Spirit Airlines flights
FrontierPriceFrom $137Free CancellationRating
5.8
3,163 reviews
Search Frontier flights
DeltaPriceFrom $162Free CancellationRating
7.9
7,973 reviews
Search Delta flights
United AirlinesPriceFrom $255Free CancellationRating
7.4
8,928 reviews
Search United Airlines flights
SouthwestPriceFrom $257Free CancellationRating
8.0
4,244 reviews
Search Southwest flights
American AirlinesPriceFrom $336Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Traveling to a place near Chicago?

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

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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