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$77+ Cheap flights from Caribbean Islands 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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
feb. 28 — mar. 71
vie. 2/28
vie. 3/7
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Chicago

Keep the following information in mind while searching for Caribbean Islands to Chicago flight deals. Data was last updated febrero 23, 2025.

Round-trip from

$138
(Cheapflightsfares)

One-way from

$77
(Kiwi.com)
From Caribbean Islands to Chicago (CHI)
Search Deals
One-way flight from Caribbean Islands to Chicago (CHI)
Search Deals

Find flight deals from Caribbean Islands to Chicago

Cheapest flights from Caribbean Islands to Chicago
Explore the most affordable flight options available from Caribbean Islands to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on febrero 23, 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.
mar. 5/66:15 pmSJU - ORD
1 stop15h 36mSpirit Airlines
lun. 5/126:00 amORD - SJU
1 stop17h 12mSpirit Airlines
Deal found 2/22$138
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/16:35 amSJU - ORD
Nonstop5h 23mMultiple Airlines
mar. 5/64:15 pmORD - SJU
1 stop9h 36mMultiple Airlines
Deal found 2/22$141
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/116:00 amSJU - MDW
1 stop10h 32mFrontier
mié. 3/193:14 pmMDW - SJU
1 stop8h 45mFrontier
Deal found 2/21$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.
vie. 5/26:00 amSJU - ORD
1 stop14h 18mFrontier
lun. 5/54:15 pmORD - SJU
1 stop9h 36mFrontier
Deal found 2/22$150
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.
jue. 3/66:15 amSJU - MDW
1 stop7h 44mDelta
mar. 3/1112:51 pmMDW - SJU
1 stop9h 16mDelta
Deal found 2/22$271
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.
jue. 3/67:30 amSJU - ORD
1 stop8h 19mDelta
mié. 3/122:55 pmORD - SJU
1 stop7h 12mDelta
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.
jue. 3/64:47 pmPUJ - ORD
1 stop9h 12mSpirit Airlines
mié. 3/125:10 amORD - PUJ
1 stop8h 32mSpirit Airlines
Deal found 2/22$285
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.
jue. 5/13:07 pmPUJ - MDW
1 stop9h 32mFrontier
lun. 5/56:15 amMDW - PUJ
2 stops10h 23mFrontier
Deal found 2/22$299
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.
jue. 5/11:39 pmKIN - ORD
1 stop11h 02mSpirit Airlines
jue. 5/85:05 amORD - KIN
1 stop6h 11mSpirit Airlines
Deal found 2/22$304
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.
jue. 5/112:00 pmMBJ - ORD
1 stop12h 41mSpirit Airlines
jue. 5/86:34 pmORD - MBJ
1 stop14h 40mSpirit Airlines
Deal found 2/21$305
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/2411:38 amPUJ - ORD
2 stops22h 06mMultiple Airlines
lun. 3/318:42 pmORD - PUJ
1 stop14h 35mMultiple Airlines
Deal found 2/22$323
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.
vie. 5/233:12 pmSDQ - ORD
1 stop17h 44mMultiple Airlines
sáb. 5/318:00 amORD - SDQ
1 stop16h 41mMultiple Airlines
Deal found 2/21$324

Find flights from Caribbean Islands to Chicago within your budget

Customize your flight search to find flights from Caribbean Islands 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 febrero 23, 2025.

Fly from

Caribbean Islands

Fly to

Chicago

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mar. 5/6

6:15 pm-8:51 am

1 stop15h 36m

Chicago O'Hare Intl

lun. 5/12

6:00 am-12:12 am

1 stop17h 12m

$138

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 5/1

6:35 am-10:58 am

Nonstop5h 23m

Chicago O'Hare Intl

mar. 5/6

4:15 pm-2:51 am

1 stop9h 36m

$141

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

mar. 3/11

6:00 am-3:32 pm

1 stop10h 32m

Chicago Midway

mié. 3/19

3:14 pm-12:59 am

1 stop8h 45m

$150

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 5/2

6:00 am-7:18 pm

1 stop14h 18m

Chicago O'Hare Intl

lun. 5/5

4:15 pm-2:51 am

1 stop9h 36m

$150

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 3/6

6:15 am-11:59 am

1 stop7h 44m

Chicago Midway

mar. 3/11

12:51 pm-11:07 pm

1 stop9h 16m

$271

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 3/6

7:30 am-3:45 pm

1 stop10h 15m

Chicago O'Hare Intl

lun. 3/10

7:35 am-4:43 pm

1 stop8h 08m

$271

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

jue. 3/6

4:47 pm-11:59 pm

1 stop9h 12m

Chicago O'Hare Intl

mié. 3/12

5:10 am-2:42 pm

1 stop8h 32m

$285

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

jue. 5/1

3:07 pm-11:39 pm

1 stop9h 32m

Chicago Midway

lun. 5/5

6:15 am-5:38 pm

2 stops10h 23m

$299

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

jue. 5/1

1:39 pm-12:41 am

1 stop11h 02m

Chicago O'Hare Intl

jue. 5/8

5:05 am-11:16 am

1 stop6h 11m

$304

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

jue. 5/1

12:00 pm-12:41 am

1 stop12h 41m

Chicago O'Hare Intl

jue. 5/8

6:34 pm-9:14 am

1 stop14h 40m

$305

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

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

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

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

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

Currently, August is the cheapest month in which you can book a flight from Caribbean Islands to Chicago (average of $245). Flying from Caribbean Islands 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 EPX to CHI?

Find hourly flight availability from Caribbean Islands 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 febrero 23, 2025.

When flying from Caribbean Islands 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 Islands to Chicago

Explore weekly flight availability from Caribbean Islands 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 febrero 23, 2025.

The most flights from zzEPX 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 febrero 23, 2025.
Read reviews from past customers who have flown Southwest, Delta and Copa Airlines from Caribbean Islands to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Entertainment

7.6

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

Overall

8.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Entertainment

7.6

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

Overall

8.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Entertainment

7.6

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
1,500 reviews
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Entertainment

7.6

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

Overall

8.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Entertainment

7.6

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.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Entertainment

7.6

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 Islands 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 Islands to Chicago one-way?

    One-way options have recently been found by users for as low as $77 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $86 and Delta from $136 one-way.

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

    The most popular route from Caribbean Islands to Chicago is San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl. You may also consider San Juan Luis Munoz Marin Intl - Chicago Midway or Punta Cana - Chicago O'Hare Intl.

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

    The top 3 most reliable airlines when flying from Caribbean Islands to Chicago are Air Canada (84%), United Airlines (84%) and Air New Zealand (84%).

  • What are the cheapest flights from Caribbean Islands to Chicago?

    While on average a flight from Caribbean Islands 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 Islands to Chicago that include hotel bookings?

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Caribbean Islands to Chicago (average of $245). Flying from Caribbean Islands 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 Islands?

Book flights to Caribbean Islands 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 Islands to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Caribbean Islands to Chicago

Discover the top 7 airlines that operate flights from Caribbean Islands 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 febrero 23, 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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