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$95+ 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 1/16. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Jan 29 — Feb 51
Thu 1/29
Thu 2/5
1 adult, Economy
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Cheap 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 December 30, 2025.

This JetBlue deal was found by Cheapflights users on 12/29. 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.
Wed 12/312:21 pmSJU - ORD
1 stop9h 43mJetBlue
Mon 1/56:45 amORD - SJU
1 stop7h 41mJetBlue
Deal found 12/29$260
This CheapOair deal was found by Cheapflights users on 12/29. 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.
Wed 12/312:21 pmSJU - ORD
1 stop9h 43mJetBlue
Tue 1/610:55 amORD - SJU
1 stop11h 19mJetBlue
Deal found 12/29$261
This CheapOair deal was found by Cheapflights users on 12/29. 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.
Wed 12/312:21 pmSJU - ORD
1 stop9h 43mJetBlue
Sun 1/46:45 amORD - SJU
1 stop10h 04mJetBlue
Deal found 12/29$275
This Expedia deal was found by Cheapflights users on 12/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:21 pmSJU - ORD
1 stop9h 43mMultiple Airlines
Tue 1/65:45 amORD - SJU
Nonstop4h 41mMultiple Airlines
Deal found 12/29$284
This eDestinos deal was found by Cheapflights users on 12/28. 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 12/318:08 pmSJU - ORD
Nonstop5h 17mSpirit Airlines
Sun 1/45:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 12/28$292
This Expedia deal was found by Cheapflights users on 12/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:21 pmSJU - ORD
1 stop9h 43mMultiple Airlines
Sun 1/45:45 amORD - SJU
Nonstop4h 41mMultiple Airlines
Deal found 12/28$301
This eDestinos deal was found by Cheapflights users on 12/29. 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 12/318:08 pmSJU - ORD
Nonstop5h 17mSpirit Airlines
Mon 1/55:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 12/29$310
This Expedia deal was found by Cheapflights users on 12/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:21 pmSJU - ORD
1 stop9h 43mJetBlue
Fri 1/26:45 amORD - SJU
1 stop10h 04mJetBlue
Deal found 12/30$312
This Expedia deal was found by Cheapflights users on 12/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:49 pmPUJ - ORD
Nonstop5h 10mMultiple Airlines
Wed 1/75:45 amORD - PUJ
Nonstop4h 45mMultiple Airlines
Deal found 12/28$323
This Expedia deal was found by Cheapflights users on 12/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:49 pmPUJ - ORD
Nonstop5h 10mMultiple Airlines
Mon 1/55:45 amORD - PUJ
Nonstop4h 45mMultiple Airlines
Deal found 12/28$334
This eDestinos deal was found by Cheapflights users on 12/29. 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.
Tue 12/307:30 pmPUJ - ORD
Nonstop5h 10mArajet
Mon 1/55:45 amORD - PUJ
Nonstop4h 45mArajet
Deal found 12/29$363
This Expedia deal was found by Cheapflights users on 12/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:30 pmPUJ - ORD
Nonstop5h 10mMultiple Airlines
Tue 1/67:30 amORD - PUJ
1 stop7h 20mMultiple Airlines
Deal found 12/29$372

Find 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 December 30, 2025.

Round-trip from

$162
(SmartFares)

One-way from

$95
(JetBlue)
From Caribbean Islands to Chicago (CHI)
Search Deals
One-way flight from Caribbean Islands to Chicago (CHI)
Search Deals

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 December 30, 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 1/15

11:06 am-7:36 pm

1 stop10h 30m

Chicago O'Hare Intl

Mon 1/19

7:45 am-6:05 pm

1 stop8h 20m

$179

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 2/7

4:36 pm-7:52 pm

1 stop29h 16m

Chicago Midway

Thu 2/12

7:30 am-2:53 am

1 stop17h 23m

$180

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/29

7:10 am-6:29 pm

1 stop13h 19m

Chicago O'Hare Intl

Sun 2/1

4:43 pm-11:36 pm

1 stop28h 53m

$181

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/29

4:22 pm-10:46 pm

1 stop8h 24m

Chicago O'Hare Intl

Sun 2/1

12:17 pm-6:49 pm

Nonstop4h 32m

$184

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/29

1:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

Sun 2/1

12:17 pm-6:49 pm

Nonstop4h 32m

$187

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 2/25

5:25 pm-2:26 pm

1 stop23h 01m

Chicago Midway

Mon 3/9

6:15 am-10:45 pm

1 stop15h 30m

$196

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 1/14

11:06 am-7:36 pm

1 stop10h 30m

Chicago O'Hare Intl

Sun 1/18

9:15 am-7:26 pm

1 stop8h 11m

$202

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 1/13

9:00 am-4:52 pm

1 stop9h 52m

Chicago O'Hare Intl

Fri 1/16

10:00 am-11:35 pm

1 stop11h 35m

$215

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/26

4:52 pm-8:20 pm

Nonstop5h 28m

Chicago O'Hare Intl

Mon 3/2

8:55 am-3:40 pm

Nonstop4h 45m

$216

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 2/25

8:30 am-11:52 am

Nonstop5h 22m

Chicago O'Hare Intl

Mon 3/9

2:20 pm-8:00 pm

Nonstop4h 40m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/30

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 $121). Flying from Caribbean Islands to Chicago in June is currently the most expensive (average of $175). 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 December 30, 2025.

It’s typically best to fly out from Caribbean Islands to Chicago in the evening. Doing so could potentially save you 51% 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 27, 2025.

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. Monday at noon 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 December 30, 2025.

The most flights from zzEPX to CHI are scheduled on a Saturday (13 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (12 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 December 30, 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
8,013 reviews

Overall

7.9

Crew

8.5

Comfort

7.9

Food

7.2

Entertainment

7.8

Boarding

8.1

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
8,013 reviews
Delta
7.9
Good
8,013 reviews

Overall

7.9

Crew

8.5

Comfort

7.9

Food

7.2

Entertainment

7.8

Boarding

8.1

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
9,124 reviews
Delta
7.9
Good
8,013 reviews

Overall

7.9

Crew

8.5

Comfort

7.9

Food

7.2

Entertainment

7.8

Boarding

8.1

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
11,074 reviews
Delta
7.9
Good
8,013 reviews

Overall

7.9

Crew

8.5

Comfort

7.9

Food

7.2

Entertainment

7.8

Boarding

8.1

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
5.7
Fair
3,068 reviews
Delta
7.9
Good
8,013 reviews

Overall

7.9

Crew

8.5

Comfort

7.9

Food

7.2

Entertainment

7.8

Boarding

8.1

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?

    Frontier, JetBlue, and Spirit Airlines can get you from Caribbean Islands to Chicago in just under 5h 15m. Your travel time can differ by up to 5h 15m. 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 $71 on JetBlue. Other airlines that offer cheap prices include Frontier from $90 and Spirit Airlines from $94 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 (87%), Air Canada (82%) and United Airlines (82%).

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

    While on average a flight from Caribbean Islands to Chicago is generally $416, 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 $207 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 $121). Flying from Caribbean Islands to Chicago in June is currently the most expensive (average of $175). 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
Merrillville
Hammond
Porter
Benton Harbor

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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 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 December 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$120Average$228FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$137Average$329FlexibilityNo cancel feeOn-time65%
FrontierCheapest$138Average$349FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$626FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$254Average$556FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$277Average$542FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$392Average$551FlexibilityNo cancel feeOn-time63%

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