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$113+ 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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$221
(FlightHub)

One-way from

$113
(Cheapflightsfares)
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 July 31, 2025.

This FlightHub deal was found by Cheapflights users on 7/31. 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 8/1510:16 pmSJU - ORD
1 stop12h 06mSpirit Airlines
Mon 8/1812:55 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 7/31$221
This KAYAK deal was found by Cheapflights users on 7/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/73:00 pmSJU - ORD
Nonstop5h 20mAmerican Airlines
Wed 10/87:11 amORD - SJU
2 stops15h 48mAmerican Airlines
Deal found 7/29$230
This SmartFares deal was found by Cheapflights users on 7/29. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/13:21 pmSJU - MDW
1 stop8h 48mFrontier
Sat 11/156:10 amMDW - SJU
1 stop7h 05mFrontier
Deal found 7/29$234
This Expedia deal was found by Cheapflights users on 7/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/133:29 amSJU - ORD
1 stop12h 58mMultiple Airlines
Sun 8/176:56 amORD - SJU
1 stop7h 14mMultiple Airlines
Deal found 7/30$242
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/123:40 amSJU - ORD
1 stop7h 34mFrontier
Sat 9/138:00 amORD - SJU
1 stop14h 59mFrontier
Deal found 7/30$248
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/193:32 amBQN - ORD
1 stop12h 45mFrontier
Fri 10/38:49 pmORD - BQN
1 stop13h 07mFrontier
Deal found 7/30$258
This Priceline deal was found by Cheapflights users on 7/31. 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 9/35:05 pmSDQ - ORD
1 stop7h 54mSpirit Airlines
Sat 9/205:05 amORD - SDQ
1 stop8h 37mSpirit Airlines
Deal found 7/31$262
This CheapOair deal was found by Cheapflights users on 7/28. 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.
Wed 8/274:05 pmPUJ - ORD
1 stop8h 54mSpirit Airlines
Wed 9/35:05 amORD - PUJ
1 stop8h 55mSpirit Airlines
Deal found 7/28$276
This Trip.com deal was found by Cheapflights users on 7/31. 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 8/112:59 amBQN - ORD
1 stop8h 15mMultiple Airlines
Thu 8/215:16 pmORD - BQN
1 stop8h 32mMultiple Airlines
Deal found 7/31$284
This FlightHub deal was found by Cheapflights users on 7/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1312:19 pmMBJ - ORD
1 stop6h 48mSpirit Airlines
Wed 10/155:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
Deal found 7/29$294
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/145:45 pmPUJ - ORD
Nonstop5h 08mFrontier
Mon 8/186:45 amORD - PUJ
Nonstop4h 40mFrontier
Deal found 7/29$294
This Gotogate deal was found by Cheapflights users on 7/31. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/121:48 amSDQ - ORD
1 stop9h 37mMultiple Airlines
Wed 9/35:05 amORD - SDQ
1 stop9h 55mMultiple Airlines
Deal found 7/31$321

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 July 31, 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 8/15

10:16 pm-9:22 am

1 stop12h 06m

Chicago O'Hare Intl

Mon 8/18

12:55 pm-6:40 pm

Nonstop4h 45m

$221

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 10/7

3:00 pm-7:20 pm

Nonstop5h 20m

Chicago O'Hare Intl

Wed 10/8

7:11 am-11:59 pm

2 stops15h 48m

$230

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 11/1

3:21 pm-11:09 pm

1 stop8h 48m

Chicago Midway

Sat 11/15

6:10 am-3:15 pm

1 stop7h 05m

$234

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 8/13

3:29 am-3:27 pm

1 stop12h 58m

Chicago O'Hare Intl

Sun 8/17

6:56 am-3:10 pm

1 stop7h 14m

$242

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 8/12

3:40 am-10:14 am

1 stop7h 34m

Chicago O'Hare Intl

Sat 9/13

8:00 am-8:02 am

1 stop23h 02m

$248

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Fri 9/19

3:32 am-3:17 pm

1 stop12h 45m

Chicago O'Hare Intl

Fri 10/3

8:49 pm-10:56 am

1 stop13h 07m

$258

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Wed 9/3

5:05 pm-11:59 pm

1 stop7h 54m

Chicago O'Hare Intl

Sat 9/20

5:05 am-2:42 pm

1 stop8h 37m

$262

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 8/27

4:05 pm-11:59 pm

1 stop8h 54m

Chicago O'Hare Intl

Wed 9/3

5:05 am-3:00 pm

1 stop8h 55m

$276

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Mon 8/11

2:59 am-10:14 am

1 stop8h 15m

Chicago O'Hare Intl

Thu 8/21

5:16 pm-2:48 am

1 stop8h 32m

$284

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 8/13

12:19 pm-7:07 pm

1 stop6h 48m

Chicago O'Hare Intl

Wed 10/15

5:05 am-11:05 am

1 stop6h 00m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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 July 31, 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 July 31, 2025.

The most flights from zzEPX to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (8 on average).

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 July 31, 2025.
See what other customers who have flown with Southwest, Delta, and Copa Airlines from Caribbean Islands to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Copa Airlines
7.5
Good
1,493 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $113 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $113 and Southwest from $171 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 Aguadilla Borinquen - 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 (99%), Air Canada (92%) and United Airlines (92%).

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

    While on average a flight from Caribbean Islands to Chicago is generally $1,810, our data shows the cheapest flight currently is $127. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $190 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$130Average$305FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$137Average$293FlexibilityNo cancel feeOn-time65%
DeltaCheapest$162Average$440FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$219Average$575FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$480FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$329Average$530FlexibilityNo cancel feeOn-time71%

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