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$115+ 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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
maj 3 — maj 101
ndz. 5/3
ndz. 5/10
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 Kwiecień 3, 2026.

This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
czw. 4/233:03 pm
SJU
-
ORD
1 stop8h 36m
Frontier
pon. 4/275:50 am
ORD
-
SJU
1 stop7h 18m
Frontier
Deal found 3/31$159
This CheapOair deal was found by Cheapflights users on 3/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
pon. 4/131:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
sob. 4/186:40 am
ORD
-
SJU
1 stop17h 18m
Spirit Airlines
Deal found 3/30$163
This eDestinos deal was found by Cheapflights users on 3/29. 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.
czw. 5/76:46 pm
SJU
-
ORD
1 stop24h 58m
Frontier
pon. 5/115:30 pm
ORD
-
SJU
1 stop7h 38m
Frontier
Deal found 3/29$168
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
czw. 4/1611:30 am
SJU
-
ORD
1 stop13h 29m
Frontier
sob. 4/251:27 pm
ORD
-
SJU
1 stop21h 56m
Frontier
Deal found 3/30$170
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
czw. 4/911:03 am
SJU
-
ORD
1 stop8h 28m
Spirit Airlines
sob. 4/186:40 am
ORD
-
SJU
1 stop17h 18m
Spirit Airlines
Deal found 3/31$172
This Expedia deal was found by Cheapflights users on 4/2. 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.
śr. 4/221:59 am
SJU
-
ORD
1 stop10h 04m
Multiple Airlines
pon. 4/277:50 am
ORD
-
SJU
1 stop16h 08m
Multiple Airlines
Deal found 4/2$173
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
pt. 4/174:34 pm
SJU
-
ORD
Nonstop5h 15m
Spirit Airlines
pon. 4/207:50 am
ORD
-
SJU
1 stop16h 08m
Spirit Airlines
Deal found 3/31$174
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
czw. 4/1611:30 am
SJU
-
ORD
1 stop13h 29m
Multiple Airlines
pon. 4/277:50 am
ORD
-
SJU
1 stop16h 08m
Multiple Airlines
Deal found 3/30$175
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
pt. 5/13:23 pm
SJU
-
MDW
1 stop8h 03m
Frontier
pt. 5/84:52 pm
MDW
-
SJU
1 stop8h 16m
Frontier
Deal found 4/1$176
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
pt. 4/243:23 pm
SJU
-
ORD
1 stop8h 16m
Frontier
ndz. 4/265:50 am
ORD
-
SJU
1 stop7h 18m
Frontier
Deal found 3/31$176
This Cheapflightsfares deal was found by Cheapflights users on 4/3. 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.
czw. 4/234:34 pm
SJU
-
ORD
Nonstop5h 15m
Spirit Airlines
ndz. 4/2610:00 am
ORD
-
SJU
Nonstop4h 39m
Spirit Airlines
Deal found 4/3$177
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
pt. 5/13:23 pm
SJU
-
MDW
1 stop8h 03m
Frontier
pon. 5/46:00 am
MDW
-
SJU
1 stop7h 13m
Frontier
Deal found 3/31$186

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 Kwiecień 3, 2026.

Round-trip from

$159
(eDestinos)

One-way from

$115
(Kiwi.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 Kwiecień 3, 2026.
Use the filters below to find and compare flights from Caribbean Islands to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

sob. 4/25

1:15 pm-5:55 pm

Nonstop4h 40m

Chicago O'Hare Intl

ndz. 8/23

8:30 am-12:31 pm

Nonstop4h 01m

$281

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

sob. 5/16

1:52 pm-6:15 pm

Nonstop4h 23m

Chicago O'Hare Intl

pon. 5/18

11:00 pm-1:30 pm

1 stop14h 30m

$286

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

sob. 5/16

2:40 pm-9:00 am

1 stop18h 20m

Chicago O'Hare Intl

sob. 5/23

3:53 pm-3:10 pm

1 stop23h 17m

$291

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

wt. 5/12

4:37 pm-12:25 am

1 stop7h 48m

Chicago O'Hare Intl

ndz. 8/30

8:30 am-12:31 pm

Nonstop4h 01m

$292

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

pt. 4/17

4:12 pm-2:27 pm

1 stop22h 15m

Chicago O'Hare Intl

pon. 4/20

9:35 pm-3:10 pm

1 stop17h 35m

$292

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

pt. 5/8

2:40 pm-1:27 am

1 stop10h 47m

Chicago O'Hare Intl

pt. 5/15

11:00 pm-1:30 pm

1 stop14h 30m

$296

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

śr. 4/22

9:13 pm-8:49 pm

1 stop24h 36m

Chicago O'Hare Intl

pt. 5/15

5:30 pm-9:18 am

1 stop14h 48m

$312

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

czw. 5/7

6:15 am-4:12 pm

1 stop10h 57m

Chicago Midway

ndz. 5/10

6:23 am-4:33 pm

1 stop9h 10m

$316

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

czw. 6/11

5:56 pm-11:59 pm

1 stop7h 03m

Chicago O'Hare Intl

pon. 6/15

5:30 am-4:46 pm

1 stop10h 16m

$316

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

pt. 5/1

3:54 pm-12:24 am

1 stop9h 30m

Chicago O'Hare Intl

wt. 5/5

1:59 pm-2:24 pm

1 stop23h 25m

$320

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 60 resultsSorted by cheapest first
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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 $114). 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 Kwiecień 3, 2026.

It’s typically best to fly out from Caribbean Islands to Chicago in the evening. Doing so could potentially save you 54% 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 March 28, 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 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 Kwiecień 3, 2026.

The most flights from zzEPX to CHI are scheduled on a Monday (12 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 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 Kwiecień 3, 2026.
See what other customers who have flown with Delta,United Airlines, andAmerican 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
8,374 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

Overall

7.9

Crew

8.5

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
8,374 reviews
Delta
7.9
Good
8,374 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

Overall

7.9

Crew

8.5

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
9,538 reviews
Delta
7.9
Good
8,374 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

Overall

7.9

Crew

8.5

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
7.1
Good
11,551 reviews
Delta
7.9
Good
8,374 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

Overall

7.9

Crew

8.5

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?

    American Airlines, United Airlines, and Spirit Airlines can get you from Caribbean Islands to Chicago in just under 4h 23m. Your travel time can differ by up to 5h 20m. There are 1724 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 Spirit Airlines from $94 and Frontier from $104 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 (89%), United Airlines (89%) and Air New Zealand (89%).

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

    While on average a flight from Caribbean Islands to Chicago is generally $505, 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 $176 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 $114). 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 8 airlines flying from Caribbean Islands to Chicago

Discover the top 8 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 Kwiecień 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$64Average$335FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$121Average$315FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$131Average$201FlexibilityNo cancel feeOn-time62%
DeltaCheapest$191Average$714FlexibilityNo cancel feeOn-timeN/A
ArajetCheapest$195Average$359FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$256Average$492FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$257Average$529FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$292Average$511FlexibilityNo cancel feeOn-time63%

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