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$77+ 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 3/19. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Feb 27 — Mrz 61
Do 2/27
Do 3/6
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 Februar 22, 2025.

Round-trip from

$139
(Cheapflightsfares)

One-way from

$77
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$302

Good round-trip deal

$257 or less

Good one-way deal

$171 or less
From Caribbean to Chicago (CHI)
Search Deals
One-way flight from Caribbean to Chicago (CHI)
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High demand for flights, 2% potential price rise
Search Deals
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 February 2025
Search Deals
Price to beat on a round-trip flight from Caribbean to Chicago (CHI).
Search Deals
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 Februar 22, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/22. 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.
Di 5/66:15 pmSJU - ORD
1 stop15h 36mSpirit Airlines
Mo 5/126:00 amORD - SJU
1 stop17h 12mSpirit Airlines
Deal found 2/22$139
This Booking.com deal was found by Cheapflights users on 2/21. 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.
Do 5/19:58 pmSJU - ORD
1 stop9h 44mMultiple Airlines
Di 5/68:04 amORD - SJU
Nonstop4h 41mMultiple Airlines
Deal found 2/21$141
This Frontier deal was found by Cheapflights users on 2/22. 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.
Mo 5/510:46 amSJU - MDW
1 stop14h 01mFrontier
Mo 5/1212:15 pmMDW - SJU
1 stop12h 35mFrontier
Deal found 2/22$150
This Frontier deal was found by Cheapflights users on 2/22. 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.
Fr 5/26:00 amSJU - ORD
1 stop14h 18mFrontier
Mo 5/54:15 pmORD - SJU
1 stop9h 36mFrontier
Deal found 2/22$150
This Kiwi.com deal was found by Cheapflights users on 2/21. 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.
Do 5/15:54 pmPUJ - ORD
Nonstop5h 06mFrontier
Mo 5/56:10 amORD - PUJ
Nonstop4h 35mFrontier
Deal found 2/21$216
This Kiwi.com deal was found by Cheapflights users on 2/21. 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.
Do 5/13:07 pmPUJ - ORD
2 stops17h 57mMultiple Airlines
Mo 5/56:10 amORD - PUJ
Nonstop4h 35mMultiple Airlines
Deal found 2/21$267
This Delta deal was found by Cheapflights users on 2/22. 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.
Fr 5/212:50 pmSJU - MDW
1 stop10h 36mDelta
So 5/46:04 amMDW - SJU
1 stop8h 57mDelta
Deal found 2/22$271
This FlightHub deal was found by Cheapflights users on 2/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 3/64:47 pmPUJ - ORD
1 stop9h 12mSpirit Airlines
Mi 3/125:10 amORD - PUJ
1 stop8h 32mSpirit Airlines
Deal found 2/22$285
This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 5/1412:21 pmKIN - ORD
2 stops10h 07mSpirit Airlines
Mo 5/195:05 amORD - KIN
1 stop6h 11mSpirit Airlines
Deal found 2/20$289
This Frontier deal was found by Cheapflights users on 2/22. 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.
Do 5/13:07 pmPUJ - MDW
1 stop9h 32mFrontier
Mo 5/56:15 amMDW - PUJ
2 stops10h 23mFrontier
Deal found 2/22$299
This Cheapflightsfares deal was found by Cheapflights users on 2/21. 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.
Do 5/112:00 pmMBJ - ORD
1 stop12h 41mSpirit Airlines
Do 5/86:34 pmORD - MBJ
1 stop14h 40mSpirit Airlines
Deal found 2/21$305
This Booking.com deal was found by Cheapflights users on 2/21. 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.
Fr 5/233:12 pmSDQ - ORD
1 stop17h 44mMultiple Airlines
Sa 5/318:00 amORD - SDQ
1 stop16h 41mMultiple Airlines
Deal found 2/21$324

Find flights from Caribbean to Chicago within your budget

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 Februar 22, 2025.

Fly from

Caribbean

Fly to

Chicago

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Di 5/6

6:15 pm-8:51 am

1 stop15h 36m

Chicago O'Hare Intl

Mo 5/12

6:00 am-12:12 am

1 stop17h 12m

$139

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Do 5/1

9:58 pm-6:42 am

1 stop9h 44m

Chicago O'Hare Intl

Di 5/6

8:04 am-1:45 pm

Nonstop4h 41m

$141

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mo 5/5

10:46 am-11:47 pm

1 stop14h 01m

Chicago Midway

Mo 5/12

12:15 pm-1:50 am

1 stop12h 35m

$150

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fr 5/2

6:00 am-7:18 pm

1 stop14h 18m

Chicago O'Hare Intl

Mo 5/5

4:15 pm-2:51 am

1 stop9h 36m

$150

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Do 5/1

5:54 pm-10:00 pm

Nonstop5h 06m

Chicago O'Hare Intl

Mo 5/5

6:10 am-11:45 am

Nonstop4h 35m

$216

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Do 5/1

3:07 pm-8:04 am

2 stops17h 57m

Chicago O'Hare Intl

Mo 5/5

6:10 am-11:45 am

Nonstop4h 35m

$267

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fr 5/2

12:50 pm-10:26 pm

1 stop10h 36m

Chicago Midway

So 5/4

6:04 am-4:01 pm

1 stop8h 57m

$271

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Do 3/6

4:47 pm-11:59 pm

1 stop9h 12m

Chicago O'Hare Intl

Mi 3/12

5:10 am-2:42 pm

1 stop8h 32m

$285

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Mi 5/14

12:21 pm-10:28 pm

2 stops10h 07m

Chicago O'Hare Intl

Mo 5/19

5:05 am-11:16 am

1 stop6h 11m

$289

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Do 5/1

3:07 pm-11:39 pm

1 stop9h 32m

Chicago Midway

Mo 5/5

6:15 am-5:38 pm

2 stops10h 23m

$299

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 60 results
1
2
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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.

Travel insights for flights from Caribbean to Chicago

Get recent, data-driven insights about flights from Caribbean to Chicago including ideal travel times, pricing trends, and more.

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 Februar 22, 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 Februar 22, 2025.

The most flights from 0CB to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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 Februar 22, 2025.
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,395 reviews
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Air Transat
7.8
Good
382 reviews
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Copa Airlines
7.6
Good
1,502 reviews
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

LATAM Airlines
7.5
Good
1,789 reviews
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Frontier. According to our data, you can fly for as low as $77. Users have also found prices from $82 and $136 on Spirit Airlines and Delta, 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 Air Canada (84%), United Airlines (84%) and Air New Zealand (84%).

  • What are the cheapest flights from Caribbean to Chicago?

    While on average a flight from Caribbean to Chicago is generally $498, our data shows the cheapest flight currently is $87. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $132 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
New Buffalo
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.
John F Kennedy Intl to O'Hare Intl flights
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Reagan-National to O'Hare Intl flights
Denver to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Newark to Midway flights
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Raleigh to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Los Angeles to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Hobby to O'Hare Intl flights
Burbank to O'Hare Intl flights
LaGuardia to Midway flights
Austin to O'Hare Intl flights
San Diego to O'Hare Intl flights
Dulles Intl to Midway flights
Orlando to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Seattle to Midway flights
Charlotte to O'Hare Intl flights
Atlanta to Midway flights
Dallas/Fort Worth to Midway flights
Hobby to Midway flights
Mexico City to O'Hare Intl flights
Tampa to O'Hare Intl flights
San Francisco to Midway flights
Newark to St. Louis flights
Miami to O'Hare Intl flights
Love Field to O'Hare Intl flights
Hartford to O'Hare Intl flights
Portland to O'Hare Intl flights
Minneapolis to Midway flights
LaGuardia to St. Louis flights
Baltimore to Midway flights
Boston to Midway flights
Cleveland to O'Hare Intl flights
Detroit to O'Hare Intl flights

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 Februar 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$137Average$304FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$312FlexibilityNo cancel feeOn-time65%
DeltaCheapest$182Average$445FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$213Average$568FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$220Average$386FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$314Average$565FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$400Average$568FlexibilityNo cancel feeOn-time70%
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