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$79+ Cheap flights from Chicago (CHI) to Caribbean

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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Jan 21 — Jan 281
Tue 1/21
Tue 1/28
1 adult, Economy
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Cheap flight deals from Chicago to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Caribbean (0CB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 16, 2025.

Round-trip from

$159
(Mytrip)

One-way from

$79
(eDestinos)
From Chicago (CHI) to Caribbean
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One-way flight from Chicago (CHI) to Caribbean
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Find flight deals from Chicago to Caribbean

Cheapest flights from Chicago to Caribbean
Explore the most affordable flight options available from Chicago to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 16, 2025.

This Mytrip deal was found by Cheapflights users on 1/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/3010:33 amORD - SJU
1 stop13h 46mFrontier
Mon 3/33:49 amSJU - ORD
1 stop20h 49mFrontier
Deal found 1/16$159
This Trip.com deal was found by Cheapflights users on 1/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/258:47 amMDW - SJU
1 stop7h 02mFrontier
Mon 3/109:35 pmSJU - MDW
1 stop18h 38mFrontier
Deal found 1/16$159
This Kiwi.com deal was found by Cheapflights users on 1/16. 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.
Tue 3/412:21 pmORD - SJU
Nonstop4h 31mSpirit Airlines
Fri 3/77:00 amSJU - ORD
Nonstop5h 36mSpirit Airlines
Deal found 1/16$161
This FlightHub deal was found by Cheapflights users on 1/16. 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.
Tue 3/118:39 amORD - SJU
Nonstop4h 36mMultiple Airlines
Tue 3/185:35 amSJU - ORD
1 stop27h 32mMultiple Airlines
Deal found 1/16$163
This American Airlines deal was found by Cheapflights users on 1/16. 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.
Mon 1/278:10 amORD - SJU
Nonstop4h 35mAmerican Airlines
Fri 1/313:36 pmSJU - ORD
Nonstop5h 30mAmerican Airlines
Deal found 1/16$226
This United Airlines deal was found by Cheapflights users on 1/16. 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.
Tue 1/281:15 pmORD - SJU
1 stop7h 07mUnited Airlines
Thu 1/302:05 amSJU - ORD
1 stop9h 35mUnited Airlines
Deal found 1/16$245
This Kiwi.com deal was found by Cheapflights users on 1/16. 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 2/78:12 pmORD - PUJ
1 stop12h 58mMultiple Airlines
Sat 2/154:48 pmPUJ - ORD
1 stop9h 10mMultiple Airlines
Deal found 1/16$293
This JetBlue deal was found by Cheapflights users on 1/16. 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.
Tue 2/2511:44 amORD - SJU
1 stop10h 06mJetBlue
Thu 2/275:10 amSJU - ORD
1 stop7h 49mJetBlue
Deal found 1/16$293
This Booking.com deal was found by Cheapflights users on 1/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/316:40 amMDW - PUJ
1 stop26h 30mFrontier
Sat 2/812:20 pmPUJ - MDW
1 stop13h 09mFrontier
Deal found 1/14$294
This CheapOair deal was found by Cheapflights users on 1/16. 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.
Sat 2/83:56 pmORD - PUJ
1 stop21h 49mSpirit Airlines
Sat 2/154:48 pmPUJ - ORD
1 stop9h 10mSpirit Airlines
Deal found 1/16$295
This Frontier deal was found by Cheapflights users on 1/15. 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.
Wed 1/296:10 amORD - PUJ
Nonstop4h 50mFrontier
Sat 2/16:10 pmPUJ - ORD
Nonstop5h 17mFrontier
Deal found 1/15$303
This CheapOair deal was found by Cheapflights users on 1/16. 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.
Mon 2/1712:02 pmORD - STT
2 stops20h 44mSpirit Airlines
Mon 2/2411:41 amSTT - ORD
1 stop24h 59mSpirit Airlines
Deal found 1/16$319

Find flights from Chicago to Caribbean within your budget

Customize your flight search to find flights from Chicago to Caribbean 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 January 16, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 2/25

7:10 am-4:27 pm

1 stop7h 17m

San Juan Luis Munoz Marin Intl

Fri 2/28

8:31 pm-11:55 pm

Nonstop5h 24m

$157

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 2/6

6:50 am-12:36 am

1 stop15h 46m

San Juan Luis Munoz Marin Intl

Tue 2/11

8:40 pm-10:40 am

1 stop16h 00m

$159

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 2/25

8:47 am-5:49 pm

1 stop7h 02m

San Juan Luis Munoz Marin Intl

Mon 3/10

9:35 pm-3:13 pm

1 stop18h 38m

$159

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 2/26

7:25 am-12:27 am

1 stop15h 02m

San Juan Luis Munoz Marin Intl

Fri 2/28

3:54 am-7:09 am

1 stop29h 15m

$160

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 4/25

8:52 am-2:44 pm

Nonstop4h 52m

San Juan Luis Munoz Marin Intl

Tue 4/29

1:05 am-10:48 am

1 stop10h 43m

$266

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 2/25

11:44 am-11:50 pm

1 stop10h 06m

San Juan Luis Munoz Marin Intl

Thu 2/27

5:10 am-10:59 am

1 stop7h 49m

$293

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 2/7

8:12 pm-11:10 am

1 stop12h 58m

Punta Cana

Fri 2/14

4:48 pm-10:40 am

1 stop19h 52m

$293

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 2/9

6:10 am-1:00 pm

Nonstop4h 50m

Punta Cana

Wed 2/26

6:10 pm-9:27 pm

Nonstop5h 17m

$294

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 2/8

3:56 pm-3:45 pm

1 stop21h 49m

Punta Cana

Sat 2/15

1:39 pm-11:58 pm

2 stops12h 19m

$309

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 2/22

7:10 pm-1:14 pm

2 stops16h 04m

Punta Cana

Sat 3/1

12:00 pm-5:31 am

2 stops19h 31m

$314

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/15

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

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

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

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

Currently, September is the cheapest month in which you can book a flight from Chicago to Caribbean (average of $254). Flying from Chicago to Caribbean in March is currently the most expensive (average of $378). 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 CHI to CB?

Find hourly flight availability from Chicago to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 16, 2025.

When flying from Chicago to Caribbean, 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 Chicago to Caribbean

Explore weekly flight availability from Chicago to Caribbean. 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 January 16, 2025.

The most flights from CHI to 0CB 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 Caribbean by month

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

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated January 16, 2025.
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,681 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

KLM
7.8
Good
1,339 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Copa Airlines
7.7
Good
1,658 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Caribbean. 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 Chicago to Caribbean one-way?

    $79 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and JetBlue, with prices starting from $80 and $157, respectively.

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

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

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

    The top 3 most reliable airlines when flying from Chicago to Caribbean are American Airlines (83%), Alaska Airlines (83%) and Spirit Airlines (80%).

  • What are the cheapest flights from Chicago to Caribbean?

    Looking for the cheapest flight from Chicago to Caribbean? While on average our users pay $1,242, our data indicates the cheapest price to be $104. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $124.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Caribbean 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 Chicago to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Caribbean (average of $254). Flying from Chicago to Caribbean in March is currently the most expensive (average of $378). 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

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Alternative routes for Chicago to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 10 airlines flying from Chicago to Caribbean

Discover the top 10 airlines that operate flights from Chicago to Caribbean. 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 January 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$366FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$156Average$355FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$173Average$507FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$226Average$518FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$256Average$640FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$317Average$641FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$322Average$625FlexibilityNo cancel feeOn-time71%
DeltaCheapest$324Average$678FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$335Average$761FlexibilityNo cancel feeOn-time67%
AviancaCheapest$1,422Average$1,422FlexibilityNo cancel feeOn-time71%
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