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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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Mar 13 — Mar 201
Fri 3/13
Fri 3/20
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 February 11, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 2/11. 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 2/2612:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Mon 3/212:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/11$146
This Cheapflightsfares deal was found by Cheapflights users on 2/11. 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.
Fri 2/2712:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Mon 3/212:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/11$162
This Cheapflightsfares deal was found by Cheapflights users on 2/10. 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 3/121:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Mon 3/1610:55 am
ORD
-
SJU
1 stop12h 03m
Spirit Airlines
Deal found 2/10$177
This Cheapflightsfares deal was found by Cheapflights users on 2/10. 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.
Tue 3/171:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Tue 3/248:56 pm
ORD
-
SJU
Nonstop4h 33m
Spirit Airlines
Deal found 2/10$178
This Orbitz deal was found by Cheapflights users on 2/10. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:22 pm
SJU
-
ORD
Nonstop5h 15m
Spirit Airlines
Tue 9/112:22 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/10$179
This CheapOair deal was found by Cheapflights users on 2/11. 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 2/2612:32 pm
SJU
-
ORD
Nonstop5h 16m
Multiple Airlines
Tue 3/38:30 am
ORD
-
SJU
1 stop14h 13m
Multiple Airlines
Deal found 2/11$180
This Expedia deal was found by Cheapflights users on 2/10. 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 2/2512:32 pm
SJU
-
ORD
Nonstop5h 16m
Multiple Airlines
Sun 3/12:13 pm
ORD
-
SJU
1 stop10h 12m
Multiple Airlines
Deal found 2/10$182
This eDestinos deal was found by Cheapflights users on 2/9. 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 2/267:09 pm
SJU
-
ORD
1 stop28h 31m
Frontier
Mon 3/23:50 pm
ORD
-
SJU
1 stop16h 04m
Frontier
Deal found 2/9$183
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Wed 2/254:31 pm
SJU
-
MDW
2 stops25h 45m
Multiple Airlines
Sun 3/16:15 am
MDW
-
SJU
1 stop17h 54m
Multiple Airlines
Deal found 2/10$198
This Frontier deal was found by Cheapflights users on 2/10. 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.
Thu 5/73:18 pm
SJU
-
MDW
1 stop8h 01m
Frontier
Sun 5/106:00 am
MDW
-
SJU
1 stop7h 08m
Frontier
Deal found 2/10$202
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/56:00 am
SJU
-
MDW
1 stop9h 56m
Multiple Airlines
Mon 3/96:00 am
MDW
-
SJU
1 stop10h 58m
Multiple Airlines
Deal found 2/10$206
This Kiwi.com deal was found by Cheapflights users on 2/7. 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 2/274:16 pm
SJU
-
MDW
1 stop8h 21m
Multiple Airlines
Mon 3/22:19 pm
MDW
-
SJU
2 stops26h 39m
Multiple Airlines
Deal found 2/7$208

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 February 11, 2026.

Round-trip from

$146
(Cheapflightsfares)

One-way from

$95
(Trip.com)
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 February 11, 2026.
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

12:32 pm-3:48 pm

Nonstop5h 16m

Chicago O'Hare Intl

Mon 3/2

12:17 pm-6:49 pm

Nonstop4h 32m

$146

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 3/12

1:29 am-5:45 am

Nonstop5h 16m

Chicago O'Hare Intl

Mon 3/16

10:55 am-11:58 pm

1 stop12h 03m

$188

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 3/5

12:32 pm-3:48 pm

Nonstop5h 16m

Chicago O'Hare Intl

Mon 3/9

9:18 am-5:58 pm

1 stop7h 40m

$190

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 4/22

11:07 am-6:15 pm

1 stop8h 08m

Chicago O'Hare Intl

Sat 4/25

12:22 pm-5:54 pm

Nonstop4h 32m

$192

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/7

3:18 pm-10:19 pm

1 stop8h 01m

Chicago Midway

Sun 5/10

6:00 am-2:08 pm

1 stop7h 08m

$202

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/1

3:18 pm-10:19 pm

1 stop8h 01m

Chicago Midway

Mon 5/4

9:14 am-10:48 pm

1 stop12h 34m

$202

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/26

6:00 am-1:56 pm

1 stop9h 56m

Chicago Midway

Mon 3/2

9:22 pm-9:54 am

1 stop10h 32m

$202

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 3/17

11:03 am-6:31 pm

1 stop8h 28m

Chicago O'Hare Intl

Mon 3/23

4:30 pm-11:10 am

1 stop17h 40m

$208

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/8

12:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

Mon 5/11

5:15 am-2:31 pm

1 stop8h 16m

$211

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 3/18

4:35 pm-11:17 pm

1 stop7h 42m

Chicago O'Hare Intl

Tue 3/24

5:05 am-3:28 pm

1 stop9h 23m

$225

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

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, February is the cheapest month in which you can book a flight from Caribbean Islands to Chicago (average of $101). Flying from Caribbean Islands to Chicago in December is currently the most expensive (average of $157). 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 February 11, 2026.

It’s typically best to fly out from Caribbean Islands to Chicago in the evening. Doing so could potentially save you 52% 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 February 7, 2026.

Travelers seeking maximum savings on their Caribbean Islands to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Monday 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 February 11, 2026.

The most flights from zzEPX to CHI are scheduled on a Wednesday (12 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (3 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 February 11, 2026.
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
8,180 reviews

Crew

8.5

Entertainment

7.8

Food

7.2

Comfort

7.9

Overall

7.9

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
8,180 reviews
Delta
7.9
Good
8,180 reviews

Crew

8.5

Entertainment

7.8

Food

7.2

Comfort

7.9

Overall

7.9

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
9,279 reviews
Delta
7.9
Good
8,180 reviews

Crew

8.5

Entertainment

7.8

Food

7.2

Comfort

7.9

Overall

7.9

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
11,271 reviews
Delta
7.9
Good
8,180 reviews

Crew

8.5

Entertainment

7.8

Food

7.2

Comfort

7.9

Overall

7.9

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
3,052 reviews
Delta
7.9
Good
8,180 reviews

Crew

8.5

Entertainment

7.8

Food

7.2

Comfort

7.9

Overall

7.9

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?

    Spirit Airlines, Frontier, and Delta can get you from Caribbean Islands to Chicago in just under 5h 16m. Your travel time can differ by up to 4h 39m. 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 $74 on JetBlue. Other airlines that offer cheap prices include Frontier from $92 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 San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl. You may also consider San Juan Luis Munoz Marin Intl - Chicago Midway or Punta Cana - 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 Air Canada (83%), United Airlines (83%) and Air New Zealand (83%).

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

    While on average a flight from Caribbean Islands to Chicago is generally $458, our data shows the cheapest flight currently is $122. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $147 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, February is the cheapest month in which you can book a flight from Caribbean Islands to Chicago (average of $101). Flying from Caribbean Islands to Chicago in December is currently the most expensive (average of $157). 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 February 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$626FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$122Average$334FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$131Average$201FlexibilityNo cancel feeOn-time62%
FrontierCheapest$137Average$335FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$256Average$520FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$258Average$544FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$392Average$545FlexibilityNo cancel feeOn-time63%

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