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$118+ 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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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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 April 24, 2025.

Round-trip from

$188
(eDestinos)

One-way from

$119
(eDestinos)
From Caribbean Islands to Chicago (CHI)
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One-way flight from Caribbean Islands to Chicago (CHI)
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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 April 24, 2025.

This eDestinos deal was found by Cheapflights users on 4/23. 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.
Fri 5/96:09 amSJU - ORD
Nonstop5h 16mSpirit Airlines
Fri 5/94:35 pmORD - SJU
1 stop17h 10mSpirit Airlines
Deal found 4/23$188
This CheapOair deal was found by Cheapflights users on 4/23. 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.
Thu 5/85:54 pmPUJ - ORD
Nonstop5h 06mFrontier
Sun 5/116:10 amORD - PUJ
Nonstop4h 41mFrontier
Deal found 4/23$226
This CheapOair deal was found by Cheapflights users on 4/23. 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.
Fri 5/210:46 amSJU - ORD
1 stop13h 25mMultiple Airlines
Sat 5/104:35 pmORD - SJU
1 stop17h 10mMultiple Airlines
Deal found 4/23$238
This Booking.com deal was found by Cheapflights users on 4/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/85:54 pmPUJ - ORD
Nonstop5h 06mMultiple Airlines
Sun 5/115:05 amORD - PUJ
1 stop8h 12mMultiple Airlines
Deal found 4/22$270
This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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.
Thu 5/86:00 amSJU - MDW
1 stop7h 24mFrontier
Mon 5/126:15 amMDW - SJU
1 stop7h 32mFrontier
Deal found 4/23$292
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Wed 7/94:55 pmPUJ - ORD
1 stop8h 02mAmerican Airlines
Wed 8/67:00 amORD - PUJ
1 stop6h 45mAmerican Airlines
Deal found 4/23$296
This Frontier deal was found by Cheapflights users on 4/23. 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.
Fri 5/210:46 amSJU - ORD
1 stop13h 25mFrontier
Mon 5/56:55 amORD - SJU
1 stop10h 52mFrontier
Deal found 4/23$296
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/307:30 amSJU - ORD
1 stop10h 16mDelta
Wed 9/31:31 pmORD - SJU
1 stop9h 15mDelta
Deal found 4/23$307
This United Airlines deal was found by Cheapflights users on 4/22. 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.
Thu 5/11:50 pmPUJ - ORD
Nonstop5h 05mUnited Airlines
Mon 5/59:23 amORD - PUJ
Nonstop4h 42mUnited Airlines
Deal found 4/22$310
This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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.
Sat 5/3112:07 pmMBJ - ORD
1 stop11h 58mSpirit Airlines
Sun 6/85:05 amORD - MBJ
1 stop5h 57mSpirit Airlines
Deal found 4/23$312
This eDestinos deal was found by Cheapflights users on 4/23. 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.
Thu 5/83:22 pmPUJ - ORD
1 stop9h 43mSpirit Airlines
Sun 5/115:05 amORD - PUJ
1 stop8h 12mSpirit Airlines
Deal found 4/23$313
This FlightHub deal was found by Cheapflights users on 4/23. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/151:34 pmKIN - ORD
2 stops19h 21mSpirit Airlines
Mon 5/197:35 pmORD - KIN
1 stop16h 54mSpirit Airlines
Deal found 4/23$332

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 April 24, 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

Fri 5/9

8:12 pm-8:50 am

1 stop13h 38m

Chicago O'Hare Intl

Sun 5/11

11:30 am-5:16 pm

Nonstop4h 46m

$188

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 5/14

5:54 pm-10:00 pm

Nonstop5h 06m

Chicago O'Hare Intl

Wed 5/21

7:25 am-1:15 pm

Nonstop4h 50m

$226

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/2

10:46 am-11:11 pm

1 stop13h 25m

Chicago O'Hare Intl

Sat 5/10

4:35 pm-10:45 am

1 stop17h 10m

$243

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 5/8

5:54 pm-10:00 pm

Nonstop5h 06m

Chicago O'Hare Intl

Sun 5/11

5:05 am-2:17 pm

1 stop8h 12m

$291

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/8

6:00 am-12:24 pm

1 stop7h 24m

Chicago Midway

Mon 5/12

6:15 am-2:47 pm

1 stop7h 32m

$292

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 7/9

4:55 pm-11:57 pm

1 stop8h 02m

Chicago O'Hare Intl

Wed 8/6

7:00 am-2:45 pm

1 stop6h 45m

$296

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/2

10:46 am-11:11 pm

1 stop13h 25m

Chicago O'Hare Intl

Mon 5/5

4:15 pm-12:05 am

1 stop6h 50m

$298

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/31

12:07 pm-12:05 am

1 stop11h 58m

Chicago O'Hare Intl

Sun 6/8

5:05 am-11:02 am

1 stop5h 57m

$312

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 5/8

3:22 pm-12:05 am

1 stop9h 43m

Chicago O'Hare Intl

Sun 5/11

5:05 am-2:17 pm

1 stop8h 12m

$313

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Thu 5/15

1:34 pm-8:55 am

2 stops19h 21m

Chicago O'Hare Intl

Mon 5/19

7:35 pm-12:29 pm

1 stop16h 54m

$332

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 60 results
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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 April 24, 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 April 24, 2025.

The most flights from zzEPX to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (9 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 April 24, 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
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

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
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

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
4,287 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

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
1,411 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

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
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

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
Avelo Airlines
7.5
Good
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

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 $119 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $135 and United Airlines from $148 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 (81%), American Airlines (78%) and Alaska Airlines (76%).

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

    While on average a flight from Caribbean Islands to Chicago is generally $500, our data shows the cheapest flight currently is $138. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $189 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Caribbean Islands to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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San Francisco to Midway flights
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LaGuardia to Midway flights
Dulles Intl to Midway flights
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Atlanta to Midway flights
Portland to O'Hare Intl flights
Burbank to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
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Minneapolis to O'Hare Intl flights
Miami to O'Hare Intl flights
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Los Angeles to Midway flights
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Newark to St. Louis flights
Mexico City to O'Hare Intl flights
Philadelphia to Midway flights
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Minneapolis to Midway flights
Baltimore to Midway flights
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John F Kennedy Intl to St. Louis flights

Top 6 airlines flying from Caribbean Islands to Chicago

Discover the top 6 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$137Average$278FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$322FlexibilityNo cancel feeOn-time65%
DeltaCheapest$172Average$438FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$555FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$498FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$309Average$561FlexibilityNo cancel feeOn-time71%

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