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$88+ 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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
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 November 21, 2024.

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 November 21, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/71:00 pmORD - SJU
Nonstop4h 36mSpirit Airlines
Thu 12/122:17 pmSJU - ORD
Nonstop5h 30mSpirit Airlines
Deal found 11/20$170
This Trip.com deal was found by Cheapflights users on 11/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/167:25 amMDW - SJU
1 stop16h 32mFrontier
Thu 12/193:59 amSJU - MDW
1 stop7h 32mFrontier
Deal found 11/20$174
This FlightHub deal was found by Cheapflights users on 11/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/89:35 amORD - SJU
1 stop26h 19mFrontier
Thu 12/125:05 pmSJU - ORD
1 stop18h 49mFrontier
Deal found 11/21$175
This Justfly.com deal was found by Cheapflights users on 11/20. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/89:35 amORD - SJU
1 stop26h 19mMultiple Airlines
Thu 12/122:17 pmSJU - ORD
Nonstop5h 30mMultiple Airlines
Deal found 11/20$177
This eDestinos deal was found by Cheapflights users on 11/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/98:15 amMDW - SJU
2 stops31h 28mMultiple Airlines
Sat 12/143:20 amSJU - MDW
2 stops45h 25mMultiple Airlines
Deal found 11/20$254
This FlightHub deal was found by Cheapflights users on 11/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/46:00 amORD - PUJ
Nonstop4h 29mFrontier
Wed 12/115:00 pmPUJ - ORD
Nonstop5h 31mFrontier
Deal found 11/21$269
This Kiwi.com deal was found by Cheapflights users on 11/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/136:07 pmORD - PUJ
1 stop15h 24mMultiple Airlines
Wed 12/182:35 pmPUJ - ORD
1 stop7h 38mMultiple Airlines
Deal found 11/20$281
This FlightHub deal was found by Cheapflights users on 11/20. 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.
Fri 12/136:48 pmMDW - PUJ
1 stop14h 43mFrontier
Fri 12/201:59 pmPUJ - MDW
1 stop11h 15mFrontier
Deal found 11/20$301
This Southwest deal was found by Cheapflights users on 11/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/712:25 pmMDW - SJU
2 stops10h 05mSouthwest
Tue 12/106:10 amSJU - MDW
2 stops10h 00mSouthwest
Deal found 11/20$312
This United Airlines deal was found by Cheapflights users on 11/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/92:20 pmORD - SJU
Nonstop4h 35mUnited Airlines
Mon 12/162:05 amSJU - ORD
1 stop8h 54mUnited Airlines
Deal found 11/21$316
This FlightHub deal was found by Cheapflights users on 11/20. 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.
Fri 12/137:45 pmORD - STT
1 stop15h 38mSpirit Airlines
Fri 1/1711:46 amSTT - ORD
1 stop13h 16mSpirit Airlines
Deal found 11/20$324
This Mytrip deal was found by Cheapflights users on 11/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/239:25 pmORD - STT
3 stops35h 14mMultiple Airlines
Tue 12/3111:44 amSTT - ORD
1 stop10h 07mMultiple Airlines
Deal found 11/20$337

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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 12/7

1:00 pm-7:36 pm

Nonstop4h 36m

San Juan Luis Munoz Marin Intl

Thu 12/12

2:17 pm-5:47 pm

Nonstop5h 30m

$170

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/8

8:14 pm-11:18 am

1 stop13h 04m

San Juan Luis Munoz Marin Intl

Wed 1/15

4:49 pm-1:50 pm

1 stop23h 01m

$174

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 12/16

7:25 am-1:57 am

1 stop16h 32m

San Juan Luis Munoz Marin Intl

Fri 12/20

6:00 am-1:06 pm

1 stop9h 06m

$174

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 12/8

9:35 am-1:54 pm

1 stop26h 19m

San Juan Luis Munoz Marin Intl

Thu 12/12

5:05 pm-9:54 am

1 stop18h 49m

$175

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 2/2

1:20 pm-12:50 am

2 stops9h 30m

San Juan Luis Munoz Marin Intl

Wed 2/5

2:55 pm-7:45 pm

1 stop6h 50m

$210

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/9

3:04 pm-6:02 pm

1 stop24h 58m

San Juan Luis Munoz Marin Intl

Sat 1/25

8:00 am-11:29 pm

2 stops17h 29m

$239

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 1/25

5:10 am-3:49 pm

1 stop8h 39m

Punta Cana

Wed 1/29

6:10 pm-9:27 pm

Nonstop5h 17m

$268

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 12/4

6:00 am-12:29 pm

Nonstop4h 29m

Punta Cana

Wed 12/11

5:00 pm-8:31 pm

Nonstop5h 31m

$269

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 2/14

6:38 pm-10:40 am

1 stop14h 02m

Punta Cana

Mon 2/17

3:15 pm-7:02 am

1 stop17h 47m

$294

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 1/24

8:50 am-10:22 pm

1 stop11h 32m

San Juan Luis Munoz Marin Intl

Mon 1/27

2:05 am-10:44 am

1 stop10h 39m

$300

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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 $335). 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 November 21, 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 November 21, 2024.

The most flights from CHI to 0CB are scheduled on a Wednesday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 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 November 21, 2024.
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,015 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,758 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,458 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

KLM
7.8
Good
1,350 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,172 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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?

    $88 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 $91 and $105, 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 Air Canada (90%), United Airlines (90%) and Air New Zealand (90%).

  • What are the cheapest flights from Chicago to Caribbean?

    Looking for the cheapest flight from Chicago to Caribbean? While on average our users pay $741, our data indicates the cheapest price to be $90. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $117.

  • 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 $335). 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 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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$352FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$137Average$521FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$166Average$354FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$267Average$618FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$275Average$660FlexibilityNo cancel feeOn-time63%
DeltaCheapest$324Average$607FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$324Average$618FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$379Average$518FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$514Average$872FlexibilityNo cancel feeOn-time67%
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