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$115+ 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 6/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
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 June 18, 2025.

Round-trip from

$185
(Priceline)

One-way from

$115
(Frontier)
From Caribbean Islands to Chicago (CHI)
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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 June 18, 2025.

This Priceline deal was found by Cheapflights users on 6/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/28:15 amSJU - MDW
1 stop12h 15mFrontier
Sat 7/129:12 pmMDW - SJU
1 stop28h 27mFrontier
Deal found 6/17$185
This Priceline deal was found by Cheapflights users on 6/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/113:13 pmSJU - ORD
1 stop10h 09mFrontier
Tue 7/1511:28 amORD - SJU
1 stop14h 11mFrontier
Deal found 6/16$194
This Priceline deal was found by Cheapflights users on 6/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/154:43 pmSJU - ORD
1 stop15h 21mMultiple Airlines
Wed 7/1611:28 amORD - SJU
1 stop14h 11mMultiple Airlines
Deal found 6/17$197
This SmartFares deal was found by Cheapflights users on 6/17. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/113:50 pmSJU - ORD
1 stop16h 14mSpirit Airlines
Mon 7/145:05 amORD - SJU
1 stop15h 04mSpirit Airlines
Deal found 6/17$207
This American Airlines deal was found by Cheapflights users on 6/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/93:31 pmPUJ - ORD
Nonstop5h 05mAmerican Airlines
Wed 8/135:54 pmORD - PUJ
1 stop16h 11mAmerican Airlines
Deal found 6/18$284
This Cheapflightsfares deal was found by Cheapflights users on 6/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2512:07 pmMBJ - ORD
1 stop11h 38mSpirit Airlines
Mon 6/307:39 pmORD - MBJ
1 stop15h 23mSpirit Airlines
Deal found 6/16$300
This CheapOair deal was found by Cheapflights users on 6/16. 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 8/25:00 pmPUJ - ORD
1 stop7h 53mSpirit Airlines
Wed 8/65:05 amORD - PUJ
1 stop8h 25mSpirit Airlines
Deal found 6/16$301
This United Airlines deal was found by Cheapflights users on 6/16. 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.
Thu 7/34:35 pmPUJ - ORD
1 stop25h 17mUnited Airlines
Wed 7/169:23 amORD - PUJ
Nonstop4h 42mUnited Airlines
Deal found 6/16$302
This Cheapflightsfares deal was found by Cheapflights users on 6/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1410:55 amSDQ - ORD
1 stop13h 58mSpirit Airlines
Sat 7/195:38 pmORD - SDQ
1 stop15h 12mSpirit Airlines
Deal found 6/16$317
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1111:25 amSJU - MDW
1 stop9h 20mSouthwest
Tue 7/1511:15 amMDW - SJU
1 stop9h 00mSouthwest
Deal found 6/16$327
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/251:51 pmMBJ - ORD
Nonstop4h 29mUnited Airlines
Sun 8/178:42 amORD - MBJ
Nonstop4h 07mUnited Airlines
Deal found 6/17$334
This American Airlines deal was found by Cheapflights users on 6/16. 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.
Wed 9/104:42 pmSJU - ORD
1 stop7h 30mAmerican Airlines
Sun 9/147:00 amORD - SJU
2 stops10h 15mAmerican Airlines
Deal found 6/16$339

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 June 18, 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 - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 7/2

8:15 am-7:30 pm

1 stop12h 15m

Chicago Midway

Sat 7/12

9:12 pm-2:39 am

1 stop28h 27m

$185

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 7/11

3:13 pm-12:22 am

1 stop10h 09m

Chicago O'Hare Intl

Tue 7/15

11:28 am-2:39 am

1 stop14h 11m

$194

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 7/15

4:43 pm-7:04 am

1 stop15h 21m

Chicago O'Hare Intl

Wed 7/16

11:28 am-2:39 am

1 stop14h 11m

$197

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 7/11

3:50 pm-7:04 am

1 stop16h 14m

Chicago O'Hare Intl

Mon 7/14

5:05 am-9:09 pm

1 stop15h 04m

$207

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 7/9

3:31 pm-7:36 pm

Nonstop5h 05m

Chicago O'Hare Intl

Wed 8/13

5:54 pm-11:05 am

1 stop16h 11m

$284

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 8/2

5:00 pm-11:53 pm

1 stop7h 53m

Chicago O'Hare Intl

Wed 8/6

5:05 am-2:30 pm

1 stop8h 25m

$301

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 7/3

4:35 pm-4:52 pm

1 stop25h 17m

Chicago O'Hare Intl

Wed 7/16

9:23 am-3:05 pm

Nonstop4h 42m

$302

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Sat 7/19

12:10 pm-11:53 pm

1 stop11h 43m

Chicago O'Hare Intl

Sat 7/26

5:05 am-11:05 am

1 stop6h 00m

$305

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Mon 7/14

10:55 am-11:53 pm

1 stop13h 58m

Chicago O'Hare Intl

Sat 7/19

5:38 pm-9:50 am

1 stop15h 12m

$317

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 7/11

11:25 am-7:45 pm

1 stop9h 20m

Chicago Midway

Tue 7/15

11:15 am-9:15 pm

1 stop9h 00m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

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 June 18, 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 June 18, 2025.

The most flights from zzEPX to CHI are scheduled on a Tuesday (10 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (9 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 June 18, 2025.
Read reviews from past customers who have flown Delta, Southwest 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.
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Southwest
8.0
Very good
4,280 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Copa Airlines
7.5
Good
1,455 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Aeromexico
7.5
Good
1,714 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,810 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 $115 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $123 and American Airlines from $146 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 (96%), Air Canada (91%) and United Airlines (91%).

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

    While on average a flight from Caribbean Islands to Chicago is generally $675, our data shows the cheapest flight currently is $116. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $187 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
Lansing
Benton Harbor
Porter
Hammond
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 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 June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$135Average$328FlexibilityNo cancel feeOn-time65%
FrontierCheapest$137Average$293FlexibilityNo cancel feeOn-time62%
DeltaCheapest$172Average$438FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$217Average$526FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$495FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$329Average$560FlexibilityNo cancel feeOn-time71%

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