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$68+ 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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Caribbean Islands (zzEPX) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$136
(Mytrip)

One-way from

$68
(Mytrip)
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 January 21, 2025.

This eDestinos deal was found by Cheapflights users on 1/21. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/207:57 pmSJU - ORD
Nonstop5h 23mSpirit Airlines
Mon 2/2412:55 pmORD - SJU
Nonstop4h 31mSpirit Airlines
Deal found 1/21$136
This FlightHub deal was found by Cheapflights users on 1/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/89:15 pmSJU - MDW
1 stop14h 47mFrontier
Mon 2/1011:33 amMDW - SJU
1 stop12h 46mFrontier
Deal found 1/21$140
This Priceline deal was found by Cheapflights users on 1/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/276:35 amSJU - ORD
1 stop8h 45mFrontier
Tue 3/43:14 pmORD - SJU
1 stop16h 35mFrontier
Deal found 1/21$140
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/218:31 pmSJU - ORD
Nonstop5h 24mMultiple Airlines
Mon 2/247:08 pmORD - SJU
1 stop12h 41mMultiple Airlines
Deal found 1/21$142
This United Airlines deal was found by Cheapflights users on 1/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/52:05 amSJU - ORD
1 stop9h 35mUnited Airlines
Sun 2/98:50 amORD - SJU
1 stop10h 38mUnited Airlines
Deal found 1/21$245
This eDestinos deal was found by Cheapflights users on 1/20. 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 1/306:19 pmSDQ - ORD
1 stop7h 13mSpirit Airlines
Thu 2/66:55 amORD - SDQ
1 stop8h 19mSpirit Airlines
Deal found 1/20$246
This Priceline deal was found by Cheapflights users on 1/20. 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 3/42:48 pmMBJ - ORD
1 stop8h 15mSpirit Airlines
Tue 3/115:10 amORD - MBJ
1 stop5h 52mSpirit Airlines
Deal found 1/20$248
This Cheapflightsfares deal was found by Cheapflights users on 1/21. 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.
Thu 1/306:54 pmPUJ - ORD
Nonstop5h 17mFrontier
Tue 2/46:10 amORD - PUJ
Nonstop4h 50mFrontier
Deal found 1/21$251
This Southwest deal was found by Cheapflights users on 1/20. 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.
Thu 2/206:05 amSJU - MDW
1 stop10h 40mSouthwest
Mon 2/241:25 pmMDW - SJU
2 stops9h 25mSouthwest
Deal found 1/20$310
This eDestinos deal was found by Cheapflights users on 1/21. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/134:48 pmPUJ - ORD
1 stop9h 10mSpirit Airlines
Sun 2/167:13 pmORD - PUJ
1 stop15h 29mSpirit Airlines
Deal found 1/21$319
This Delta deal was found by Cheapflights users on 1/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/47:30 amSJU - MDW
1 stop10h 50mDelta
Tue 3/119:54 amMDW - SJU
1 stop9h 16mDelta
Deal found 1/21$325
This Priceline deal was found by Cheapflights users on 1/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/145:08 pmPUJ - ORD
Nonstop5h 06mMultiple Airlines
Wed 5/215:05 amORD - PUJ
1 stop9h 03mMultiple Airlines
Deal found 1/21$328

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/20

7:57 pm-11:20 pm

Nonstop5h 23m

Chicago O'Hare Intl

Mon 2/24

12:55 pm-7:26 pm

Nonstop4h 31m

$136

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/27

6:35 am-1:20 pm

1 stop8h 45m

Chicago O'Hare Intl

Tue 3/4

3:14 pm-9:49 am

1 stop16h 35m

$140

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 2/21

8:31 pm-11:55 pm

Nonstop5h 24m

Chicago O'Hare Intl

Mon 2/24

7:08 pm-9:49 am

1 stop12h 41m

$142

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 3/4

7:59 pm-3:13 pm

1 stop21h 14m

Chicago Midway

Tue 3/11

7:25 am-9:44 am

1 stop25h 19m

$144

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 2/5

2:05 am-9:40 am

1 stop9h 35m

Chicago O'Hare Intl

Sun 2/9

8:50 am-9:28 pm

1 stop10h 38m

$245

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 3/4

2:48 pm-10:03 pm

1 stop8h 15m

Chicago O'Hare Intl

Tue 3/11

5:10 am-11:02 am

1 stop5h 52m

$248

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 5/14

5:08 pm-9:14 pm

Nonstop5h 06m

Chicago O'Hare Intl

Wed 5/21

6:20 am-11:55 am

Nonstop4h 35m

$274

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 2/13

4:48 pm-11:58 pm

1 stop9h 10m

Chicago O'Hare Intl

Wed 2/19

5:00 am-3:43 pm

1 stop8h 43m

$275

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/20

6:05 am-2:45 pm

1 stop10h 40m

Chicago Midway

Mon 2/24

1:25 pm-12:50 am

2 stops9h 25m

$310

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 3/4

7:30 am-4:20 pm

1 stop10h 50m

Chicago Midway

Tue 3/11

12:51 pm-8:10 pm

1 stop6h 19m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

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 $320). 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 January 21, 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 January 21, 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 January 21, 2025.
Read reviews from past customers who have flown United Airlines, Frontier and Avianca 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
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Air Transat
7.8
Good
381 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Copa Airlines
7.7
Good
1,662 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Aeromexico
7.5
Good
1,849 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $68 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $70 and Southwest from $118 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 Nassau Intl - 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 (85%), Air Canada (83%) and United Airlines (83%).

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

    While on average a flight from Caribbean Islands to Chicago is generally $815, our data shows the cheapest flight currently is $109. 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 $320). 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

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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 8 airlines flying from Caribbean Islands to Chicago

Discover the top 8 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$283FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$140Average$344FlexibilityNo cancel feeOn-time65%
DeltaCheapest$187Average$466FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$196Average$556FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$220Average$386FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$274Average$460FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$329Average$578FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$400Average$521FlexibilityNo cancel feeOn-time70%
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