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$107+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 November 6, 2025.

Round-trip from

$182
(Priceline)

One-way from

$107
(Super.com)
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 November 6, 2025.

This Priceline deal was found by Cheapflights users on 11/4. 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.
Sat 12/66:50 pmPUJ - ORD
Nonstop5h 10mFrontier
Sat 12/137:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 11/4$182
This CheapOair deal was found by Cheapflights users on 11/5. 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.
Sun 11/237:20 amSJU - ORD
1 stop11h 51mSpirit Airlines
Tue 11/254:58 pmORD - SJU
1 stop15h 51mSpirit Airlines
Deal found 11/5$187
This Priceline deal was found by Cheapflights users on 11/5. 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.
Fri 12/56:50 pmPUJ - ORD
Nonstop5h 10mFrontier
Fri 12/127:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 11/5$189
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:05 amSJU - ORD
1 stop11h 18mMultiple Airlines
Mon 11/2411:40 amORD - SJU
1 stop8h 10mMultiple Airlines
Deal found 11/5$189
This eDestinos deal was found by Cheapflights users on 11/6. 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 12/44:31 pmSJU - ORD
1 stop7h 53mFrontier
Mon 12/86:11 amORD - SJU
1 stop7h 00mFrontier
Deal found 11/6$196
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2311:55 amSJU - ORD
1 stop13h 18mMultiple Airlines
Mon 11/2411:48 amORD - SJU
1 stop26h 07mMultiple Airlines
Deal found 11/6$197
This Priceline deal was found by Cheapflights users on 11/5. 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.
Thu 12/46:50 pmPUJ - ORD
Nonstop5h 10mFrontier
Thu 12/117:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 11/5$201
This eDestinos deal was found by Cheapflights users on 11/4. 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.
Wed 12/247:30 amSJU - MDW
1 stop16h 42mFrontier
Sat 1/32:24 pmMDW - SJU
1 stop10h 15mFrontier
Deal found 11/4$203
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/44:31 pmSJU - ORD
1 stop7h 53mMultiple Airlines
Mon 12/89:14 pmORD - SJU
1 stop24h 11mMultiple Airlines
Deal found 11/5$203
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/53:06 pmSJU - ORD
1 stop7h 36mMultiple Airlines
Sun 12/145:40 amORD - SJU
Nonstop4h 41mMultiple Airlines
Deal found 11/4$205
This Cheapflightsfares deal was found by Cheapflights users on 11/6. 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.
Wed 12/107:31 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Fri 12/125:40 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 11/6$206
This Mytrip deal was found by Cheapflights users on 11/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/124:31 pmSJU - ORD
1 stop7h 53mMultiple Airlines
Mon 12/155:40 amORD - SJU
Nonstop4h 41mMultiple Airlines
Deal found 11/6$208

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 November 6, 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

Thu 2/26

8:35 am-11:57 am

Nonstop5h 22m

Chicago O'Hare Intl

Mon 3/2

2:20 pm-9:00 pm

Nonstop4h 40m

$218

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/23

7:30 am-12:01 pm

1 stop6h 31m

Chicago Midway

Tue 2/3

12:48 pm-8:57 pm

1 stop6h 09m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 11/20

4:12 pm-7:23 pm

Nonstop5h 11m

Chicago O'Hare Intl

Sun 11/23

10:12 am-8:27 pm

1 stop8h 15m

$241

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 12/24

4:16 pm-5:38 pm

1 stop27h 22m

Chicago Midway

Sat 1/3

2:24 pm-2:39 am

1 stop10h 15m

$245

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Mon 1/26

2:38 pm-6:00 pm

Nonstop5h 22m

Chicago O'Hare Intl

Sun 2/1

4:35 pm-11:18 pm

Nonstop4h 43m

$247

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 12/4

8:45 pm-11:59 pm

Nonstop5h 14m

Chicago O'Hare Intl

Sun 12/7

1:52 pm-11:25 pm

1 stop7h 33m

$250

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sun 1/25

3:55 am-9:58 pm

2 stops20h 03m

Chicago O'Hare Intl

Sun 2/1

5:20 am-3:06 pm

1 stop7h 46m

$262

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 12/25

3:54 am-5:00 pm

1 stop15h 06m

Chicago O'Hare Intl

Sat 1/3

6:05 pm-2:39 am

1 stop30h 34m

$277

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 12/23

4:10 am-11:14 am

1 stop9h 04m

Chicago O'Hare Intl

Sat 1/3

5:45 am-12:26 pm

Nonstop4h 41m

$280

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Wed 11/26

4:35 pm-11:13 pm

1 stop8h 38m

Chicago O'Hare Intl

Sat 12/6

7:10 am-3:23 pm

1 stop6h 13m

$282

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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, January is the cheapest month in which you can book a flight from Caribbean Islands to Chicago (average of $116). Flying from Caribbean Islands to Chicago in June is currently the most expensive (average of $193). 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 November 6, 2025.

It’s typically best to fly out from Caribbean Islands to Chicago in the morning. Doing so could potentially save you 27% on the flight price compared to flying in the afternoon, which is usually more expensive.

What is the cheapest day to fly from Caribbean Islands to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Caribbean Islands to Chicago. Price data was last updated on December 1, 2024.

Travelers seeking maximum savings on their Caribbean Islands to Chicago flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 6, 2025.

The most flights from zzEPX to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).

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 November 6, 2025.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Caribbean Islands to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,001 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,001 reviews
Delta
7.9
Good
8,001 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,007 reviews
Delta
7.9
Good
8,001 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,040 reviews
Delta
7.9
Good
8,001 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Frontier
5.8
Fair
3,115 reviews
Delta
7.9
Good
8,001 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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.

  • How long is the flight from Caribbean Islands to Chicago?

    United Airlines, Delta, and Spirit Airlines can get you from Caribbean Islands to Chicago in just under 5h 11m. Your travel time can differ by up to 1h 20m. There are 2073 mi between Caribbean Islands and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $108 on United Airlines. Other airlines that offer cheap prices include Spirit Airlines from $108 and Southwest from $114 one-way.

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

    The most popular route from Caribbean Islands to Chicago is Punta Cana - Chicago O'Hare Intl. You may also consider Punta Cana - Chicago Midway or San Juan Luis Munoz Marin Intl - 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 (100%), Air Canada (78%) and United Airlines (78%).

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

    While on average a flight from Caribbean Islands to Chicago is generally $625, our data shows the cheapest flight currently is $108. When looking at the most popular route, (Punta Cana - Chicago O'Hare Intl), you can expect to pay $219 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, January is the cheapest month in which you can book a flight from Caribbean Islands to Chicago (average of $116). Flying from Caribbean Islands to Chicago in June is currently the most expensive (average of $193). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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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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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$137Average$335FlexibilityNo cancel feeOn-time65%
FrontierCheapest$139Average$312FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$562FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$269Average$520FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$334Average$576FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$384Average$523FlexibilityNo cancel feeOn-time63%

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