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$87+ 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 4/17. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
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 March 31, 2025.

Round-trip from

$175
(Cheapflightsfares)

One-way from

$87
(FlightHub)

Popular in

March

Cheapest in

January

Average price

$354

Good round-trip deal

$323 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. 8% potential increase in price ($29 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 March 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 March 31, 2025.

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.
Fri 4/256:35 amSJU - ORD
Nonstop5h 23mSpirit Airlines
Tue 4/297:00 pmORD - SJU
1 stop12h 26mSpirit Airlines
Deal found 3/31$175
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/11:50 pmPUJ - ORD
Nonstop5h 05mUnited Airlines
Mon 5/59:23 amORD - PUJ
Nonstop4h 42mUnited Airlines
Deal found 3/31$253
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/243:56 amSJU - ORD
1 stop20h 40mMultiple Airlines
Tue 4/297:00 pmORD - SJU
1 stop12h 26mMultiple Airlines
Deal found 3/31$255
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/13:21 pmPUJ - ORD
Nonstop5h 15mAmerican Airlines
Mon 5/51:35 pmORD - PUJ
1 stop20h 00mAmerican Airlines
Deal found 3/30$291
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/172:56 amSJU - MDW
1 stop17h 59mFrontier
Sun 4/278:00 amMDW - SJU
1 stop13h 02mFrontier
Deal found 3/30$293
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/77:01 amSJU - ORD
1 stop9h 03mJetBlue
Tue 5/136:15 amORD - SJU
1 stop9h 00mJetBlue
Deal found 3/31$295
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/312:00 pmMBJ - ORD
1 stop12h 58mSpirit Airlines
Sun 5/47:33 pmORD - MBJ
1 stop15h 22mSpirit Airlines
Deal found 3/31$298
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/109:58 pmSJU - ORD
1 stop11h 45mFrontier
Sat 5/174:15 pmORD - SJU
1 stop9h 36mFrontier
Deal found 3/29$306
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/21:39 pmKIN - ORD
1 stop11h 19mSpirit Airlines
Wed 5/75:05 amORD - KIN
1 stop7h 24mSpirit Airlines
Deal found 3/30$324
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.
Thu 5/812:42 pmPUJ - ORD
1 stop8h 21mSpirit Airlines
Sun 5/115:05 amORD - PUJ
1 stop8h 12mSpirit Airlines
Deal found 3/31$333
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1212:55 pmPUJ - MDW
1 stop10h 26mDelta
Sat 4/196:04 amMDW - PUJ
1 stop7h 26mDelta
Deal found 3/30$341
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/212:50 pmPUJ - ORD
1 stop9h 08mDelta
Fri 4/46:15 amORD - PUJ
1 stop8h 51mDelta
Deal found 3/30$365

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 March 31, 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 4/25

6:35 am-10:58 am

Nonstop5h 23m

Chicago O'Hare Intl

Tue 4/29

7:00 pm-8:26 am

1 stop12h 26m

$175

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 5/1

1:50 pm-5:55 pm

Nonstop5h 05m

Chicago O'Hare Intl

Mon 5/5

9:23 am-3:05 pm

Nonstop4h 42m

$253

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 4/16

6:21 am-1:02 pm

1 stop7h 41m

Chicago O'Hare Intl

Tue 4/22

8:04 am-1:45 pm

Nonstop4h 41m

$261

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 5/1

3:21 pm-7:36 pm

Nonstop5h 15m

Chicago O'Hare Intl

Mon 5/5

1:35 pm-10:35 am

1 stop20h 00m

$291

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 4/17

2:56 am-7:55 pm

1 stop17h 59m

Chicago Midway

Sun 4/27

8:00 am-10:02 pm

1 stop13h 02m

$293

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 5/7

7:01 am-3:04 pm

1 stop9h 03m

Chicago O'Hare Intl

Tue 5/13

6:15 am-4:15 pm

1 stop9h 00m

$295

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/3

12:00 pm-12:58 am

1 stop12h 58m

Chicago O'Hare Intl

Sun 5/4

7:33 pm-10:55 am

1 stop15h 22m

$298

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sat 5/10

9:58 pm-8:43 am

1 stop11h 45m

Chicago O'Hare Intl

Fri 5/16

4:15 pm-2:51 am

1 stop9h 36m

$306

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 5/2

1:39 pm-12:58 am

1 stop11h 19m

Chicago O'Hare Intl

Wed 5/7

5:05 am-12:29 pm

1 stop7h 24m

$324

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 5/8

12:42 pm-8:03 pm

1 stop8h 21m

Chicago O'Hare Intl

Sun 5/11

5:05 am-2:17 pm

1 stop8h 12m

$333

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

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 $323). 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 March 31, 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 March 31, 2025.

The most flights from 0CB to CHI are scheduled on a Monday (11 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (9 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 March 31, 2025.
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

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
7,899 reviews
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

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
4,276 reviews
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

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
7.6
Good
1,400 reviews
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

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
1,700 reviews
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

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
LATAM Airlines
7.5
Good
1,754 reviews
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

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 $87. Users have also found prices from $140 and $148 on Frontier and JetBlue, 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 Punta Cana - 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 (95%), Air Canada (94%) and United Airlines (94%).

  • What are the cheapest flights from Caribbean to Chicago?

    While on average a flight from Caribbean to Chicago is generally $480, our data shows the cheapest flight currently is $99. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $180 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 $323). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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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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LaGuardia to Midway flights
Atlanta to Midway flights
Newark to St. Louis flights
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Top 7 airlines flying from Caribbean to Chicago

Discover the top 7 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 March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$137Average$277FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$283FlexibilityNo cancel feeOn-time65%
DeltaCheapest$172Average$492FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$214Average$553FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$420FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$308Average$562FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$400Average$483FlexibilityNo cancel feeOn-time70%
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