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$90+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
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 December 18, 2024.

Round-trip from

$161
(Kiwi.com)

One-way from

$90
(Trip.com)
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 December 18, 2024.

This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/311:47 pmORD - SJU
1 stop8h 54mMultiple Airlines
Tue 1/149:26 pmSJU - ORD
Nonstop5h 25mMultiple Airlines
Deal found 12/17$191
This Cheapflightsfares deal was found by Cheapflights users on 12/17. 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.
Tue 12/311:00 pmORD - SJU
Nonstop4h 36mSpirit Airlines
Tue 1/149:26 pmSJU - ORD
Nonstop5h 25mSpirit Airlines
Deal found 12/17$209
This Frontier deal was found by Cheapflights users on 12/18. 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.
Mon 12/304:41 pmORD - SJU
1 stop11h 49mFrontier
Sat 1/189:15 pmSJU - ORD
1 stop14h 37mFrontier
Deal found 12/18$278
This FlightHub deal was found by Cheapflights users on 12/17. 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.
Mon 12/309:16 amMDW - SJU
1 stop9h 54mFrontier
Sat 1/189:15 pmSJU - MDW
1 stop14h 47mFrontier
Deal found 12/17$288
This Kiwi.com deal was found by Cheapflights users on 12/18. 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 12/316:10 amORD - PUJ
Nonstop4h 29mFrontier
Tue 12/316:45 pmPUJ - ORD
Nonstop5h 14mFrontier
Deal found 12/18$315
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/315:11 pmORD - STT
1 stop15h 28mSpirit Airlines
Thu 1/911:51 amSTT - ORD
1 stop10h 22mSpirit Airlines
Deal found 12/16$379
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/316:39 pmORD - PUJ
1 stop17h 31mAmerican Airlines
Thu 1/95:40 pmPUJ - ORD
1 stop17h 05mAmerican Airlines
Deal found 12/17$383
This CheapOair deal was found by Cheapflights users on 12/17. 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.
Tue 12/316:10 amORD - PUJ
Nonstop4h 29mMultiple Airlines
Sun 1/124:50 pmPUJ - ORD
1 stop8h 42mMultiple Airlines
Deal found 12/17$408
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/316:39 pmORD - SJU
1 stop16h 55mAmerican Airlines
Sun 7/273:15 pmSJU - ORD
Nonstop5h 10mAmerican Airlines
Deal found 12/17$420
This Southwest deal was found by Cheapflights users on 12/17. 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.
Tue 12/3111:55 amMDW - SJU
2 stops10h 50mSouthwest
Tue 1/146:00 amSJU - MDW
2 stops12h 50mSouthwest
Deal found 12/17$434
This Booking.com deal was found by Cheapflights users on 12/17. 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 12/278:25 amMDW - PUJ
1 stop26h 24mFrontier
Mon 12/301:59 pmPUJ - MDW
1 stop27h 12mFrontier
Deal found 12/17$447
This CheapOair deal was found by Cheapflights users on 12/17. 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.
Tue 12/313:31 pmORD - MBJ
1 stop21h 14mSpirit Airlines
Wed 1/221:16 pmMBJ - ORD
1 stop7h 57mSpirit Airlines
Deal found 12/17$451

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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/8

3:31 pm-1:25 am

1 stop7h 54m

San Juan Luis Munoz Marin Intl

Fri 1/17

9:26 pm-12:51 am

Nonstop5h 25m

$161

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 1/23

6:50 am-12:36 am

1 stop15h 46m

San Juan Luis Munoz Marin Intl

Sun 1/26

6:55 pm-4:23 pm

1 stop23h 28m

$162

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 1/17

6:45 am-1:59 am

1 stop17h 14m

San Juan Luis Munoz Marin Intl

Thu 1/23

9:49 pm-2:42 pm

1 stop18h 53m

$162

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/27

1:44 pm-8:21 pm

Nonstop4h 37m

San Juan Luis Munoz Marin Intl

Mon 2/3

6:00 am-10:16 pm

1 stop18h 16m

$163

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/12

11:15 am-10:22 pm

1 stop9h 07m

San Juan Luis Munoz Marin Intl

Wed 1/22

2:05 am-9:40 am

1 stop9h 35m

$234

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 1/25

5:11 am-3:45 pm

1 stop8h 34m

Punta Cana

Fri 1/31

6:10 pm-9:27 pm

Nonstop5h 17m

$249

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/28

5:31 pm-9:41 pm

2 stops26h 10m

San Juan Luis Munoz Marin Intl

Sun 2/2

10:09 pm-3:43 pm

2 stops19h 34m

$249

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 1/29

6:10 am-1:00 pm

Nonstop4h 50m

Punta Cana

Fri 1/31

6:10 pm-9:27 pm

Nonstop5h 17m

$255

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Thu 2/27

4:13 pm-2:00 pm

1 stop19h 47m

Punta Cana

Mon 3/3

3:10 pm-7:32 am

1 stop18h 22m

$257

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/27

12:25 pm-9:38 pm

1 stop7h 13m

San Juan Luis Munoz Marin Intl

Sat 2/1

6:00 am-12:14 pm

1 stop8h 14m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

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 $334). 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 December 18, 2024.

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 December 18, 2024.

The most flights from CHI to 0CB are scheduled on a Monday (10 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (8 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 December 18, 2024.
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

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
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

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
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

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
9,552 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

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
1,723 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

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.

United Airlines
7.4
Good
9,059 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

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?

    $90 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 United Airlines, with prices starting from $93 and $113, 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 (100%), Alaska Airlines (100%) and Air Canada (85%).

  • What are the cheapest flights from Chicago to Caribbean?

    Looking for the cheapest flight from Chicago to Caribbean? While on average our users pay $687, our data indicates the cheapest price to be $64. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $126.

  • 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 $334). 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.

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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 9 airlines flying from Chicago to Caribbean

Discover the top 9 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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$361FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$137Average$489FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$159Average$351FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$254Average$641FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$304Average$632FlexibilityNo cancel feeOn-time63%
DeltaCheapest$307Average$658FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$324Average$620FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$379Average$496FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$514Average$753FlexibilityNo cancel feeOn-time67%
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