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$111+ Cheap flights from Caribbean 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Caribbean to Chicago

Keep the following information in mind while searching for Caribbean to Chicago flight deals. Data was last updated September 15, 2025.

Round-trip from

$181
(Cheapflightsfares)

One-way from

$111
(Travelocity)

Popular in

August

Cheapest in

January

Average price

$297

Good round-trip deal

$171 or less

Good one-way deal

$174 or less
From Caribbean to Chicago (CHI)
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One-way flight from Caribbean to Chicago (CHI)
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Highest demand for flights based on searches. 3% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Caribbean to Chicago (CHI).
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Price to beat on a one-way flight from Caribbean to Chicago (CHI).
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Find flight deals from Caribbean to Chicago

Cheapest flights from Caribbean to Chicago
Explore the most affordable flight options available from Caribbean to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 10/119:48 amSJU - ORD
Nonstop5h 08mSpirit Airlines
Fri 10/177:51 pmORD - SJU
1 stop17h 21mSpirit Airlines
Deal found 9/13$181
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 10/211:59 amSJU - ORD
1 stop6h 40mSpirit Airlines
Mon 10/69:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/14$186
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Mon 10/279:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/13$187
This eDestinos deal was found by Cheapflights users on 9/12. 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 9/263:19 pmSJU - ORD
1 stop7h 39mSpirit Airlines
Tue 9/306:30 amORD - SJU
1 stop6h 41mSpirit Airlines
Deal found 9/12$190
This Expedia deal was found by Cheapflights users on 9/13. 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.
Sat 11/155:47 amPUJ - ORD
Nonstop5h 10mArajet
Sun 11/163:30 amORD - PUJ
Nonstop4h 45mArajet
Deal found 9/13$193
This eDestinos deal was found by Cheapflights users on 9/13. 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.
Sat 9/276:44 amSJU - ORD
1 stop10h 28mSpirit Airlines
Sun 9/2812:55 pmORD - SJU
Nonstop4h 39mSpirit Airlines
Deal found 9/13$195
This Cheapflightsfares deal was found by Cheapflights users on 9/12. 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.
Mon 10/277:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Sat 11/12:03 pmORD - SJU
Nonstop4h 39mSpirit Airlines
Deal found 9/12$196
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 10/16:44 amSJU - ORD
1 stop10h 28mSpirit Airlines
Wed 10/86:00 amORD - SJU
1 stop7h 12mSpirit Airlines
Deal found 9/13$201
This eDestinos deal was found by Cheapflights users on 9/13. 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 9/253:19 pmSJU - ORD
1 stop7h 39mSpirit Airlines
Wed 10/16:30 amORD - SJU
1 stop13h 26mSpirit Airlines
Deal found 9/13$203
This Frontier deal was found by Cheapflights users on 9/13. 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 10/315:51 pmSJU - ORD
2 stops18h 39mFrontier
Sun 11/25:40 amORD - SJU
1 stop9h 14mFrontier
Deal found 9/13$207
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Sun 10/266:00 amORD - SJU
1 stop7h 12mSpirit Airlines
Deal found 9/13$208
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/235:50 amSJU - MDW
1 stop9h 30mSouthwest
Wed 10/299:15 amMDW - SJU
1 stop10h 30mSouthwest
Deal found 9/13$227

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean 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 September 15, 2025.
Use the filters below to find and compare flights from Caribbean to Chicago that are best for you.

Fly from

Caribbean

Fly to

Chicago

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 10/24

3:19 pm-9:33 pm

1 stop7h 14m

Chicago O'Hare Intl

Mon 10/27

9:06 pm-2:51 am

Nonstop4h 45m

$208

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 12/3

2:38 pm-6:00 pm

Nonstop5h 22m

Chicago O'Hare Intl

Mon 12/8

6:55 am-1:33 pm

Nonstop4h 38m

$215

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 10/23

3:56 pm-8:03 pm

Nonstop5h 07m

Chicago O'Hare Intl

Mon 10/27

2:20 pm-8:00 pm

Nonstop4h 40m

$218

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 10/23

4:55 pm-11:15 pm

1 stop7h 20m

Chicago O'Hare Intl

Sun 10/26

2:20 pm-8:00 pm

Nonstop4h 40m

$223

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 11/4

3:46 pm-11:10 pm

1 stop9h 24m

Chicago O'Hare Intl

Sun 11/9

2:20 pm-9:00 pm

Nonstop4h 40m

$223

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 10/22

1:05 am-8:38 am

1 stop8h 33m

Chicago O'Hare Intl

Wed 10/29

2:20 pm-8:00 pm

Nonstop4h 40m

$223

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 10/22

1:59 am-11:39 pm

2 stops22h 40m

Chicago O'Hare Intl

Mon 10/27

6:40 am-3:24 pm

1 stop7h 44m

$226

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/9

1:05 pm-9:55 pm

1 stop9h 50m

Chicago Midway

Fri 10/17

4:35 pm-11:50 pm

1 stop6h 15m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 10/24

5:43 pm-11:58 pm

1 stop7h 15m

Chicago O'Hare Intl

Mon 10/27

7:00 am-4:25 pm

1 stop8h 25m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/30

5:50 am-2:10 pm

1 stop9h 20m

Chicago Midway

Sun 11/2

1:40 pm-9:45 pm

1 stop6h 05m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 60 results
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Best time to book a flight from Caribbean to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Caribbean 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 to Chicago

What is the cheapest month to book a flight from Caribbean to Chicago?

Currently, August is the cheapest month in which you can book a flight from Caribbean to Chicago (average of $245). Flying from Caribbean 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 CB to CHI?

Find hourly flight availability from Caribbean 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 September 15, 2025.

When flying from Caribbean 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 to Chicago

Explore weekly flight availability from Caribbean 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 September 15, 2025.

The most flights from 0CB to CHI are scheduled on a Friday (4 on average). You will have fewer flight options on Monday, 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 September 15, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Caribbean to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,956 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,956 reviews
Delta
8.0
Very good
7,956 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
United Airlines
7.4
Good
8,931 reviews
Delta
8.0
Very good
7,956 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,956 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Spirit Airlines
6.3
Okay
8,016 reviews
Delta
8.0
Very good
7,956 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Frontier
5.8
Fair
3,173 reviews
Delta
8.0
Very good
7,956 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

Related info for your journey

Find useful and relevant information for your journey from Caribbean 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 to Chicago?

    A quick flight from Caribbean to Chicago can take about 5h 07m. Spirit Airlines provides one of the quickest options available for as low as $218. Caribbean and Chicago are separated by a distance of 2073 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Caribbean to Chicago one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $133. Users have also found prices from $138 and $160 on United Airlines and Spirit Airlines, respectively.

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

    The most popular flight routes from Caribbean to Chicago are San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl, San Juan Luis Munoz Marin Intl - Chicago Midway and Santo Domingo Las Americas - Chicago O'Hare Intl.

  • What are the most reliable airlines from Caribbean to Chicago?

    The top 3 most reliable airlines when flying from Caribbean to Chicago are Air Canada (86%), United Airlines (86%) and Air New Zealand (86%).

  • What are the cheapest flights from Caribbean to Chicago?

    While on average a flight from Caribbean to Chicago is generally $623, our data shows the cheapest flight currently is $106. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $177 for that flight.

  • Can I find deals for flights from Caribbean to Chicago that include hotel bookings?

    Yes. In addition to deals on Caribbean to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean to Chicago.

  • Can I find deals for business class flights from Caribbean to Chicago?

    Yes. Cheapflights offers flight deals from Caribbean 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 to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Caribbean to Chicago (average of $245). Flying from Caribbean 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 Chicago?

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

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Alternative routes for Caribbean 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 to Chicago

Discover the top 6 airlines that operate flights from Caribbean 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$135Average$309FlexibilityNo cancel feeOn-time65%
FrontierCheapest$137Average$310FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$421FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$238Average$548FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$505FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$333Average$518FlexibilityNo cancel feeOn-time71%

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