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$121+ 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 6/19. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Round-trip from

$187
(Cheapflightsfares)

One-way from

$121
(Mytrip)
From Caribbean Islands to Chicago (CHI)
Search Deals
One-way flight from Caribbean Islands to Chicago (CHI)
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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 May 1, 2025.

This eDestinos deal was found by Cheapflights users on 4/30. 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.
Fri 5/98:12 pmSJU - ORD
1 stop13h 38mSpirit Airlines
Sat 5/177:47 amORD - SJU
1 stop16h 07mSpirit Airlines
Deal found 4/30$190
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 5/205:54 pmPUJ - ORD
Nonstop5h 06mFrontier
Sun 5/256:45 amORD - PUJ
Nonstop4h 41mFrontier
Deal found 5/1$232
This Booking.com deal was found by Cheapflights users on 4/30. 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.
Thu 5/83:56 amSJU - ORD
1 stop20h 36mMultiple Airlines
Sat 5/177:47 amORD - SJU
1 stop16h 07mMultiple Airlines
Deal found 4/30$244
This Priceline deal was found by Cheapflights users on 5/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2312:42 pmPUJ - ORD
1 stop8h 21mMultiple Airlines
Sun 5/256:45 amORD - PUJ
Nonstop4h 41mMultiple Airlines
Deal found 5/1$267
This eDestinos deal was found by Cheapflights users on 4/29. 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.
Wed 5/73:56 amSJU - ORD
1 stop20h 36mFrontier
Sun 5/114:15 pmORD - SJU
1 stop6h 50mFrontier
Deal found 4/29$270
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
Thu 5/86:00 amSJU - MDW
1 stop7h 24mFrontier
Mon 5/126:15 amMDW - SJU
1 stop7h 32mFrontier
Deal found 4/30$292
This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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.
Sat 5/3112:07 pmMBJ - ORD
2 stops11h 22mSpirit Airlines
Sun 6/84:35 pmORD - MBJ
2 stops18h 27mSpirit Airlines
Deal found 5/1$293
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 7/161:50 pmPUJ - ORD
Nonstop5h 05mUnited Airlines
Wed 8/69:23 amORD - PUJ
Nonstop4h 42mUnited Airlines
Deal found 4/30$313
This eDestinos deal was found by Cheapflights users on 5/1. 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.
Thu 5/812:42 pmPUJ - ORD
1 stop11h 47mSpirit Airlines
Tue 5/135:05 amORD - PUJ
1 stop8h 12mSpirit Airlines
Deal found 5/1$316
This Priceline deal was found by Cheapflights users on 4/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/141:34 pmKIN - ORD
1 stop9h 30mSpirit Airlines
Sat 5/175:05 amORD - KIN
1 stop7h 24mSpirit Airlines
Deal found 4/30$320
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Thu 5/83:16 pmPUJ - ORD
Nonstop5h 20mAmerican Airlines
Sun 5/115:00 amORD - PUJ
1 stop9h 49mAmerican Airlines
Deal found 5/1$320
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 5/82:47 pmPUJ - MDW
1 stop7h 41mDelta
Sun 5/116:00 amMDW - PUJ
1 stop6h 22mDelta
Deal found 4/30$341

Cheapflights Fare Finder

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 May 1, 2025.
Use the filters below to find and compare flights from Caribbean Islands to Chicago that are best for you.

Fly from

Caribbean Islands

Fly to

Chicago

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/30

8:12 pm-8:50 am

1 stop13h 38m

Chicago O'Hare Intl

Fri 6/20

5:05 am-7:19 pm

1 stop13h 14m

$190

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 5/20

5:54 pm-10:00 pm

Nonstop5h 06m

Chicago O'Hare Intl

Sun 5/25

6:45 am-12:26 pm

Nonstop4h 41m

$232

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sun 5/11

3:56 am-11:32 pm

1 stop20h 36m

Chicago O'Hare Intl

Sat 5/17

7:47 am-12:54 am

1 stop16h 07m

$244

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 5/23

12:42 pm-8:03 pm

1 stop8h 21m

Chicago O'Hare Intl

Sun 5/25

6:45 am-12:26 pm

Nonstop4h 41m

$267

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 5/31

12:07 pm-11:29 pm

2 stops11h 22m

Chicago O'Hare Intl

Sun 6/8

4:35 pm-11:02 am

2 stops18h 27m

$293

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sun 5/11

10:46 am-11:54 pm

1 stop14h 08m

Chicago Midway

Fri 5/16

1:19 pm-10:01 pm

1 stop7h 42m

$298

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 5/15

10:46 am-11:11 pm

1 stop13h 25m

Chicago O'Hare Intl

Sat 6/7

5:01 am-2:20 pm

1 stop8h 19m

$308

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 7/16

1:50 pm-5:55 pm

Nonstop5h 05m

Chicago O'Hare Intl

Wed 8/6

9:23 am-3:05 pm

Nonstop4h 42m

$313

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 5/28

3:22 pm-11:04 pm

1 stop8h 42m

Chicago O'Hare Intl

Wed 6/25

5:05 am-2:10 pm

1 stop8h 05m

$318

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Wed 5/14

1:34 pm-11:04 pm

1 stop9h 30m

Chicago O'Hare Intl

Sat 5/17

5:05 am-12:29 pm

1 stop7h 24m

$320

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

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.

Cheapflights Insights

Everything you need to know about your flight from Caribbean Islands to Chicago

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 May 1, 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 May 1, 2025.

The most flights from zzEPX to CHI are scheduled on a Thursday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 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 May 1, 2025.
Read reviews from past customers who have flown Delta, Alaska Airlines and Southwest from Caribbean Islands to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,934 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Alaska Airlines
8.0
Very good
9,972 reviews
Delta
8.0
Very good
7,934 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Southwest
8.0
Very good
4,293 reviews
Delta
8.0
Very good
7,934 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Copa Airlines
7.5
Good
1,415 reviews
Delta
8.0
Very good
7,934 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Aeromexico
7.5
Good
1,698 reviews
Delta
8.0
Very good
7,934 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 $121 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $140 and United Airlines from $149 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 Santo Domingo Las Americas - 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 Spirit Airlines (81%), American Airlines (78%) and Alaska Airlines (76%).

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

    While on average a flight from Caribbean Islands to Chicago is generally $487, our data shows the cheapest flight currently is $134. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $167 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 6 airlines flying from Caribbean Islands to Chicago

Discover the top 6 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$137Average$292FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$324FlexibilityNo cancel feeOn-time65%
DeltaCheapest$172Average$438FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$556FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$504FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$326Average$561FlexibilityNo cancel feeOn-time71%

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