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$121+ 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 6/19. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
mai 6 — mai 131
mar. 5/6
mar. 5/13
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 mai 1, 2025.

Round-trip from

$188
(eDestinos)

One-way from

$121
(Priceline)

Popular in

March

Cheapest in

January

Average price

$262

Good round-trip deal

$212 or less

Good one-way deal

$186 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. 9% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in May 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 mai 1, 2025.

This eDestinos deal was found by Cheapflights users on 4/29. 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.
jeu. 5/298:12 pmSJU - ORD
1 stop13h 38mSpirit Airlines
jeu. 6/511:30 amORD - SJU
Nonstop4h 46mSpirit Airlines
Deal found 4/29$188
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/65:54 pmPUJ - ORD
Nonstop5h 06mFrontier
dim. 5/116:10 amORD - PUJ
Nonstop4h 41mFrontier
Deal found 4/29$234
This Booking.com deal was found by Cheapflights users on 4/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/83:56 amSJU - ORD
1 stop20h 36mMultiple Airlines
sam. 5/177:47 amORD - SJU
1 stop16h 07mMultiple Airlines
Deal found 4/30$244
This eDestinos deal was found by Cheapflights users on 4/29. 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.
mer. 5/73:56 amSJU - ORD
1 stop20h 36mFrontier
dim. 5/114:15 pmORD - SJU
1 stop6h 50mFrontier
Deal found 4/29$270
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/86:00 amSJU - MDW
1 stop7h 24mFrontier
lun. 5/126:15 amMDW - SJU
1 stop7h 32mFrontier
Deal found 4/29$292
This Booking.com deal was found by Cheapflights users on 5/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/85:54 pmPUJ - ORD
Nonstop5h 06mMultiple Airlines
mar. 5/135:05 amORD - PUJ
1 stop8h 12mMultiple Airlines
Deal found 5/1$293
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 5/2412:07 pmMBJ - ORD
1 stop11h 58mSpirit Airlines
jeu. 5/297:35 pmORD - MBJ
1 stop15h 27mSpirit Airlines
Deal found 4/30$300
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 7/161:50 pmPUJ - ORD
Nonstop5h 05mUnited Airlines
mer. 8/69:23 amORD - PUJ
Nonstop4h 42mUnited Airlines
Deal found 4/30$313
This eDestinos deal was found by Cheapflights users on 5/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/812:42 pmPUJ - ORD
1 stop11h 47mSpirit Airlines
mar. 5/135:05 amORD - PUJ
1 stop8h 12mSpirit Airlines
Deal found 5/1$316
This Priceline deal was found by Cheapflights users on 4/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 5/141:34 pmKIN - ORD
1 stop9h 30mSpirit Airlines
sam. 5/175:05 amORD - KIN
1 stop7h 24mSpirit Airlines
Deal found 4/30$320
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/611:46 amPUJ - ORD
1 stop9h 38mAmerican Airlines
dim. 5/116:00 amORD - PUJ
1 stop8h 49mAmerican Airlines
Deal found 4/29$325
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/82:47 pmPUJ - MDW
1 stop7h 41mDelta
dim. 5/116:00 amMDW - PUJ
1 stop7h 45mDelta
Deal found 4/29$341

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 mai 1, 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

jeu. 5/29

8:12 pm-8:50 am

1 stop13h 38m

Chicago O'Hare Intl

jeu. 6/5

11:30 am-5:16 pm

Nonstop4h 46m

$188

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

mer. 7/16

5:08 pm-9:16 pm

Nonstop5h 08m

Chicago O'Hare Intl

mer. 8/13

6:45 am-12:25 pm

Nonstop4h 40m

$234

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jeu. 5/8

3:56 am-11:32 pm

1 stop20h 36m

Chicago O'Hare Intl

sam. 5/17

7:47 am-12:54 am

1 stop16h 07m

$244

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mer. 5/7

3:56 am-11:32 pm

1 stop20h 36m

Chicago O'Hare Intl

dim. 5/11

4:15 pm-12:05 am

1 stop6h 50m

$270

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jeu. 5/8

6:00 am-12:24 pm

1 stop7h 24m

Chicago Midway

lun. 5/12

6:15 am-2:47 pm

1 stop7h 32m

$292

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

sam. 5/24

12:07 pm-12:05 am

1 stop11h 58m

Chicago O'Hare Intl

jeu. 5/29

7:35 pm-11:02 am

1 stop15h 27m

$300

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

mer. 7/16

5:08 pm-9:16 pm

Nonstop5h 08m

Chicago O'Hare Intl

mer. 8/6

8:00 am-3:08 pm

1 stop6h 08m

$303

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

mer. 5/28

3:22 pm-11:04 pm

1 stop8h 42m

Chicago O'Hare Intl

mer. 6/25

5:05 am-2:10 pm

1 stop8h 05m

$309

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

mer. 7/16

1:50 pm-5:55 pm

Nonstop5h 05m

Chicago O'Hare Intl

mer. 8/6

9:23 am-3:05 pm

Nonstop4h 42m

$313

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

mer. 5/14

1:34 pm-11:04 pm

1 stop9h 30m

Chicago O'Hare Intl

sam. 5/17

5:05 am-12:29 pm

1 stop7h 24m

$320

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 mai 1, 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 mai 1, 2025.

The most flights from 0CB to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (4 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 mai 1, 2025.
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Alaska Airlines
8.0
Very good
9,968 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Southwest
8.0
Very good
4,294 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Copa Airlines
7.5
Good
1,414 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Aeromexico
7.5
Good
1,698 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $121. Users have also found prices from $140 and $149 on Frontier and United 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 Spirit Airlines (81%), American Airlines (78%) and Alaska Airlines (76%).

  • What are the cheapest flights from Caribbean to Chicago?

    While on average a flight from Caribbean to Chicago is generally $487, our data shows the cheapest flight currently is $134. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $167 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 Caribbean?

Book flights to Caribbean if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 mai 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$137Average$292FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$324FlexibilityNo cancel feeOn-time65%
DeltaCheapest$172Average$438FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$556FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$504FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$326Average$561FlexibilityNo cancel feeOn-time71%

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