HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$96+ Cheap flights from Caribbean Islands to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
abr. 7 — abr. 141
lun. 4/7
lun. 4/14
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Caribbean Islands to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Caribbean Islands to Chicago

Keep the following information in mind while searching for Caribbean Islands to Chicago flight deals. Data was last updated abril 2, 2025.

Round-trip from

$192
(eDestinos)

One-way from

$96
(Mytrip)
From Caribbean Islands to Chicago (CHI)
Search Deals
One-way flight from Caribbean Islands to Chicago (CHI)
Search Deals

Find flight deals from Caribbean Islands to Chicago

Cheapest flights from Caribbean Islands to Chicago
Explore the most affordable flight options available from Caribbean Islands to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on abril 2, 2025.

This eDestinos deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/246:38 pmSJU - ORD
1 stop7h 20mSpirit Airlines
mar. 4/295:36 amORD - SJU
1 stop8h 59mSpirit Airlines
Deal found 4/1$192
This CheapOair deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/165:03 pmPUJ - ORD
Nonstop5h 13mFrontier
dom. 4/206:00 amORD - PUJ
Nonstop4h 36mFrontier
Deal found 4/1$225
This CheapOair deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/119:37 pmSJU - ORD
1 stop18h 21mMultiple Airlines
mar. 4/157:00 pmORD - SJU
1 stop12h 26mMultiple Airlines
Deal found 4/1$246
This Priceline deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/612:00 pmMBJ - ORD
1 stop12h 20mSpirit Airlines
mar. 5/205:05 amORD - MBJ
1 stop5h 57mSpirit Airlines
Deal found 4/1$250
This United Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/11:50 pmPUJ - ORD
Nonstop5h 05mUnited Airlines
lun. 5/59:23 amORD - PUJ
Nonstop4h 42mUnited Airlines
Deal found 3/31$253
This eDestinos deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/19:58 pmSJU - ORD
1 stop22h 20mFrontier
jue. 5/86:00 amORD - SJU
1 stop12h 44mFrontier
Deal found 4/1$270
This CheapOair deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/812:42 pmPUJ - ORD
1 stop11h 47mMultiple Airlines
dom. 5/116:10 amORD - PUJ
Nonstop4h 41mMultiple Airlines
Deal found 4/1$281
This American Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/13:21 pmPUJ - ORD
Nonstop5h 15mAmerican Airlines
lun. 5/53:01 pmORD - PUJ
1 stop21h 09mAmerican Airlines
Deal found 4/1$291
This Frontier deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/96:00 amSJU - MDW
1 stop7h 24mFrontier
dom. 5/118:30 amMDW - SJU
1 stop10h 14mFrontier
Deal found 4/1$296
This American Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/198:30 amSJU - ORD
1 stop16h 27mAmerican Airlines
lun. 9/226:00 amORD - SJU
1 stop7h 47mAmerican Airlines
Deal found 4/1$307
This JetBlue deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/293:28 amSJU - ORD
1 stop9h 45mJetBlue
mié. 5/74:03 pmORD - SJU
1 stop8h 46mJetBlue
Deal found 3/31$314
This Cheapflightsfares deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/231:39 pmKIN - ORD
1 stop10h 41mSpirit Airlines
dom. 4/277:33 pmORD - KIN
1 stop16h 58mSpirit Airlines
Deal found 4/1$322

Cheapflights Fare Finder

Customize your flight search to find flights from Caribbean Islands to Chicago 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, Cheapflights users made 2,558,603 searches. Data last updated abril 2, 2025.
Use the filters below to find and compare flights from Caribbean Islands to Chicago that are best for you.

Fly from

Caribbean Islands

Fly to

Chicago

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 4/24

6:38 pm-12:58 am

1 stop7h 20m

Chicago O'Hare Intl

mar. 4/29

5:36 am-3:35 pm

1 stop8h 59m

$192

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

mié. 4/16

5:03 pm-9:16 pm

Nonstop5h 13m

Chicago O'Hare Intl

dom. 4/20

6:00 am-11:36 am

Nonstop4h 36m

$225

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mar. 5/6

12:00 pm-12:20 am

1 stop12h 20m

Chicago O'Hare Intl

mar. 5/20

5:05 am-11:02 am

1 stop5h 57m

$250

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

jue. 5/1

1:50 pm-5:55 pm

Nonstop5h 05m

Chicago O'Hare Intl

lun. 5/5

9:23 am-3:05 pm

Nonstop4h 42m

$256

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mié. 4/23

5:59 pm-12:20 am

1 stop7h 21m

Chicago O'Hare Intl

lun. 4/28

4:30 pm-2:49 am

1 stop9h 19m

$265

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 5/1

9:58 pm-7:18 pm

1 stop22h 20m

Chicago O'Hare Intl

jue. 5/8

6:00 am-7:44 pm

1 stop12h 44m

$270

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

jue. 5/8

12:42 pm-11:29 pm

1 stop11h 47m

Chicago O'Hare Intl

dom. 5/11

6:10 am-11:51 am

Nonstop4h 41m

$281

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

jue. 5/1

3:21 pm-7:36 pm

Nonstop5h 15m

Chicago O'Hare Intl

lun. 5/5

3:01 pm-1:10 pm

1 stop21h 09m

$291

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

vie. 5/9

6:00 am-12:24 pm

1 stop7h 24m

Chicago Midway

dom. 5/11

8:30 am-7:44 pm

1 stop10h 14m

$296

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 9/19

11:55 am-9:25 pm

2 stops10h 30m

Chicago O'Hare Intl

lun. 9/22

5:15 am-4:20 pm

2 stops10h 05m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Caribbean Islands to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Caribbean Islands with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Caribbean Islands to Chicago

What is the cheapest month to book a flight from Caribbean Islands to Chicago?

Currently, August is the cheapest month in which you can book a flight from Caribbean Islands to Chicago (average of $245). Flying from Caribbean Islands to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from EPX to CHI?

Find hourly flight availability from Caribbean Islands to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated abril 2, 2025.

When flying from Caribbean Islands to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Caribbean Islands to Chicago

Explore weekly flight availability from Caribbean Islands to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated abril 2, 2025.

The most flights from zzEPX to CHI are scheduled on a Monday (11 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (8 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated abril 2, 2025.
Read reviews from past customers who have flown Delta, Southwest and Copa Airlines from Caribbean Islands to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,897 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,897 reviews
Delta
8.0
Very good
7,897 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Southwest
8.0
Very good
4,275 reviews
Delta
8.0
Very good
7,897 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Copa Airlines
7.6
Good
1,400 reviews
Delta
8.0
Very good
7,897 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Aeromexico
7.5
Good
1,700 reviews
Delta
8.0
Very good
7,897 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
LATAM Airlines
7.5
Good
1,754 reviews
Delta
8.0
Very good
7,897 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Caribbean Islands to Chicago one-way?

    One-way options have recently been found by users for as low as $96 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $135 and Avelo Airlines from $172 one-way.

  • What are the most popular routes from Caribbean Islands to Chicago?

    The most popular route from Caribbean Islands to Chicago is San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl. You may also consider San Juan Luis Munoz Marin Intl - Chicago Midway or Santo Domingo Las Americas - Chicago O'Hare Intl.

  • What are the most reliable airlines from Caribbean Islands to Chicago?

    The top 3 most reliable airlines when flying from Caribbean Islands to Chicago are Spirit Airlines (95%), Air Canada (94%) and United Airlines (94%).

  • What are the cheapest flights from Caribbean Islands to Chicago?

    While on average a flight from Caribbean Islands to Chicago is generally $481, our data shows the cheapest flight currently is $135. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $199 for that flight.

  • Can I find deals for flights from Caribbean Islands to Chicago that include hotel bookings?

    Yes. In addition to deals on Caribbean Islands to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean Islands to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean Islands to Chicago.

  • Can I find deals for business class flights from Caribbean Islands to Chicago?

    Yes. Cheapflights offers flight deals from Caribbean Islands to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Caribbean Islands to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Caribbean Islands to Chicago (average of $245). Flying from Caribbean Islands to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Caribbean Islands?

Book flights to Caribbean Islands if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Caribbean Islands to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Newark to O'Hare Intl flights
Boston to O'Hare Intl flights
Newark to Midway flights
John F Kennedy Intl to Midway flights
Philadelphia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Seattle to O'Hare Intl flights
Denver to O'Hare Intl flights
Baltimore to O'Hare Intl flights
San Francisco to Midway flights
Ontario to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Mexico City to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Dulles Intl to Midway flights
Orlando to O'Hare Intl flights
San Diego to O'Hare Intl flights
Burbank to O'Hare Intl flights
Boston to Midway flights
Austin to O'Hare Intl flights
Charlotte to O'Hare Intl flights
LaGuardia to Midway flights
Philadelphia to Midway flights
Fort Lauderdale to O'Hare Intl flights
Hartford to O'Hare Intl flights
Atlanta to Midway flights
Hobby to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Newark to St. Louis flights
Portland to O'Hare Intl flights
LaGuardia to St. Louis flights
Minneapolis to Midway flights
San Jose to O'Hare Intl flights
Baltimore to Midway flights
Hobby to Midway flights
Cleveland to O'Hare Intl flights
Detroit to O'Hare Intl flights
Seattle to Midway flights
John F Kennedy Intl to St. Louis flights
Miami to O'Hare Intl flights
Tampa to O'Hare Intl flights

Top 7 airlines flying from Caribbean Islands to Chicago

Discover the top 7 airlines that operate flights from Caribbean Islands to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated abril 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$137Average$275FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$283FlexibilityNo cancel feeOn-time65%
DeltaCheapest$172Average$492FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$214Average$552FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$420FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$307Average$558FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$400Average$483FlexibilityNo cancel feeOn-time70%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.