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$113+ Cheap flights from Caribbean 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
ago. 4 — ago. 111
lun. 8/4
lun. 8/11
1 adult, Economy
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Cheap flight deals from Caribbean to Chicago

Keep the following information in mind while searching for Caribbean to Chicago flight deals. Data was last updated julio 30, 2025.

Round-trip from

$230
(KAYAK)

One-way from

$113
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$301

Good round-trip deal

$273 or less

Good one-way deal

$164 or less
From Caribbean to Chicago (CHI)
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One-way flight from Caribbean to Chicago (CHI)
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Highest demand for flights based on searches. 1% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Caribbean to Chicago (CHI).
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Price to beat on a one-way flight from Caribbean to Chicago (CHI).
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Find flight deals from Caribbean to Chicago

Cheapest flights from Caribbean to Chicago
Explore the most affordable flight options available from Caribbean to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 30, 2025.

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.
mar. 10/73:00 pmSJU - ORD
Nonstop5h 20mAmerican Airlines
mié. 10/87:11 amORD - SJU
2 stops15h 48mAmerican Airlines
Deal found 7/29$230
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/1811:59 amSJU - ORD
1 stop11h 49mSpirit Airlines
mié. 9/246:44 pmORD - SJU
1 stop15h 20mSpirit Airlines
Deal found 7/29$231
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.
sáb. 11/13:21 pmSJU - MDW
1 stop8h 48mFrontier
sáb. 11/156:10 amMDW - SJU
1 stop7h 05mFrontier
Deal found 7/29$234
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/1510:16 pmSJU - ORD
1 stop12h 06mMultiple Airlines
jue. 8/217:46 pmORD - SJU
1 stop12h 13mMultiple Airlines
Deal found 7/29$234
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/143:40 amSJU - ORD
1 stop29h 27mFrontier
lun. 8/187:45 amORD - SJU
1 stop7h 58mFrontier
Deal found 7/28$252
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.
vie. 9/193:32 amBQN - ORD
1 stop12h 45mFrontier
vie. 10/38:49 pmORD - BQN
1 stop13h 07mFrontier
Deal found 7/30$258
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.
mié. 8/274:05 pmPUJ - ORD
1 stop8h 54mSpirit Airlines
mié. 9/35:05 amORD - PUJ
1 stop8h 55mSpirit Airlines
Deal found 7/28$276
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/145:45 pmPUJ - ORD
Nonstop5h 08mFrontier
lun. 8/186:45 amORD - PUJ
Nonstop4h 40mFrontier
Deal found 7/28$284
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/285:05 pmSDQ - ORD
1 stop7h 54mSpirit Airlines
jue. 9/45:05 amORD - SDQ
1 stop9h 55mSpirit Airlines
Deal found 7/29$292
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.
mié. 8/1312:19 pmMBJ - ORD
1 stop6h 48mSpirit Airlines
mié. 10/155:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
Deal found 7/29$294
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.
jue. 9/113:19 pmSJU - MDW
3 stops26h 24mMultiple Airlines
lun. 9/1512:50 pmMDW - SJU
3 stops31h 06mMultiple Airlines
Deal found 7/30$321
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/144:05 pmPUJ - ORD
1 stop8h 54mMultiple Airlines
lun. 8/186:45 amORD - PUJ
Nonstop4h 40mMultiple Airlines
Deal found 7/29$328

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean 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 julio 30, 2025.
Use the filters below to find and compare flights from Caribbean to Chicago that are best for you.

Fly from

Caribbean

Fly to

Chicago

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mar. 10/7

3:00 pm-7:20 pm

Nonstop5h 20m

Chicago O'Hare Intl

mié. 10/8

7:11 am-11:59 pm

2 stops15h 48m

$230

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 9/18

11:59 am-10:48 pm

1 stop11h 49m

Chicago O'Hare Intl

mié. 9/24

6:44 pm-11:04 am

1 stop15h 20m

$231

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

sáb. 11/1

3:21 pm-11:09 pm

1 stop8h 48m

Chicago Midway

sáb. 11/15

6:10 am-3:15 pm

1 stop7h 05m

$234

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 8/15

10:16 pm-9:22 am

1 stop12h 06m

Chicago O'Hare Intl

jue. 8/21

7:46 pm-8:59 am

1 stop12h 13m

$234

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 8/14

3:40 am-8:07 am

1 stop29h 27m

Chicago O'Hare Intl

lun. 8/18

7:45 am-4:43 pm

1 stop7h 58m

$252

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

vie. 9/19

3:32 am-3:17 pm

1 stop12h 45m

Chicago O'Hare Intl

vie. 10/3

8:49 pm-10:56 am

1 stop13h 07m

$258

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

mié. 8/27

4:05 pm-11:59 pm

1 stop8h 54m

Chicago O'Hare Intl

mié. 9/3

5:05 am-3:00 pm

1 stop8h 55m

$276

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

jue. 8/14

5:45 pm-9:53 pm

Nonstop5h 08m

Chicago O'Hare Intl

lun. 8/18

6:45 am-12:25 pm

Nonstop4h 40m

$284

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

jue. 8/28

5:05 pm-11:59 pm

1 stop7h 54m

Chicago O'Hare Intl

jue. 9/4

5:05 am-4:00 pm

1 stop9h 55m

$292

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mié. 8/13

12:19 pm-7:07 pm

1 stop6h 48m

Chicago O'Hare Intl

mié. 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 to Chicago

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

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

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

Find hourly flight availability from Caribbean 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 julio 30, 2025.

When flying from Caribbean 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 to Chicago

Explore weekly flight availability from Caribbean 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 julio 30, 2025.

The most flights from 0CB to CHI are scheduled on a Tuesday (10 on average). You will have fewer flight options on Thursday, 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 julio 30, 2025.
Read reviews from past customers who have flown Southwest, Delta, and LATAM Airlines from Caribbean to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

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
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

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.
LATAM Airlines
7.5
Good
1,822 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

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
4,241 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

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
8,896 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

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 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 to Chicago one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $113. Users have also found prices from $114 and $176 on Spirit Airlines and Southwest, respectively.

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

    The most popular flight routes from Caribbean to Chicago are San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl, San Juan Luis Munoz Marin Intl - Chicago Midway and Santo Domingo Las Americas - Chicago O'Hare Intl.

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

    The top 3 most reliable airlines when flying from Caribbean to Chicago are Spirit Airlines (99%), Air Canada (92%) and United Airlines (92%).

  • What are the cheapest flights from Caribbean to Chicago?

    While on average a flight from Caribbean 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 $177 for that flight.

  • Can I find deals for flights from Caribbean to Chicago that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean 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 to Chicago?

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

Discover the top 6 airlines that operate flights from Caribbean 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 julio 30, 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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