HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$85+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Caribbean Islands to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 November 21, 2024.

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 November 21, 2024.

This FlightHub deal was found by Cheapflights users on 11/21. 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.
Fri 12/65:03 pmSJU - MDW
1 stop9h 17mFrontier
Mon 12/97:25 amMDW - SJU
1 stop16h 32mFrontier
Deal found 11/21$158
This Cheapflightsfares deal was found by Cheapflights users on 11/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/188:31 pmSJU - ORD
Nonstop5h 27mSpirit Airlines
Thu 1/29:32 amORD - SJU
Nonstop4h 43mSpirit Airlines
Deal found 11/20$158
This Mytrip deal was found by Cheapflights users on 11/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/248:31 pmSJU - ORD
Nonstop5h 27mMultiple Airlines
Fri 1/36:40 amORD - SJU
1 stop24h 43mMultiple Airlines
Deal found 11/21$160
This Frontier deal was found by Cheapflights users on 11/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2410:01 pmSJU - ORD
1 stop13h 23mFrontier
Thu 1/29:45 pmORD - SJU
1 stop10h 50mFrontier
Deal found 11/21$168
This United Airlines deal was found by Cheapflights users on 11/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/52:05 amSJU - ORD
1 stop8h 54mUnited Airlines
Mon 12/92:20 pmORD - SJU
Nonstop4h 35mUnited Airlines
Deal found 11/20$226
This eDestinos deal was found by Cheapflights users on 11/20. 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.
Fri 12/65:25 amSJU - MDW
2 stops17h 37mMultiple Airlines
Mon 12/98:15 amMDW - SJU
2 stops31h 28mMultiple Airlines
Deal found 11/20$238
This Kiwi.com deal was found by Cheapflights users on 11/21. 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 12/65:00 pmPUJ - ORD
Nonstop5h 31mFrontier
Mon 12/96:00 amORD - PUJ
Nonstop4h 29mFrontier
Deal found 11/21$284
This Booking.com deal was found by Cheapflights users on 11/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/215:00 pmPUJ - ORD
Nonstop5h 31mMultiple Airlines
Sat 1/45:00 amORD - PUJ
1 stop8h 55mMultiple Airlines
Deal found 11/21$308
This Southwest deal was found by Cheapflights users on 11/20. 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 12/126:10 amSJU - MDW
2 stops12h 55mSouthwest
Mon 12/1611:55 amMDW - SJU
2 stops10h 50mSouthwest
Deal found 11/20$312
This Cheapflightsfares deal was found by Cheapflights users on 11/21. 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.
Wed 12/42:38 pmMBJ - ORD
1 stop7h 29mSpirit Airlines
Fri 12/67:45 pmORD - MBJ
1 stop17h 00mSpirit Airlines
Deal found 11/21$318
This Cheapflightsfares deal was found by Cheapflights users on 11/21. 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.
Tue 12/1010:14 amKIN - ORD
1 stop6h 52mSpirit Airlines
Sat 12/145:11 pmORD - KIN
1 stop14h 58mSpirit Airlines
Deal found 11/21$321
This FlightHub deal was found by Cheapflights users on 11/21. 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.
Wed 12/254:50 pmPUJ - ORD
1 stop25h 16mSpirit Airlines
Wed 1/15:00 amORD - PUJ
1 stop8h 55mSpirit Airlines
Deal found 11/21$353

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 2,612,795 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/6

5:03 pm-12:20 am

1 stop9h 17m

Chicago Midway

Mon 12/9

7:25 am-1:57 am

1 stop16h 32m

$158

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 12/17

3:54 am-9:24 am

1 stop7h 30m

Chicago O'Hare Intl

Thu 1/2

2:19 pm-12:41 am

1 stop8h 22m

$158

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 12/20

4:43 pm-8:13 pm

Nonstop5h 30m

Chicago O'Hare Intl

Wed 1/8

1:00 pm-7:36 pm

Nonstop4h 36m

$159

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 12/24

8:31 pm-11:58 pm

Nonstop5h 27m

Chicago O'Hare Intl

Fri 1/3

6:40 am-9:23 am

1 stop24h 43m

$160

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 1/14

6:45 pm-9:59 pm

Nonstop5h 14m

Chicago O'Hare Intl

Tue 1/21

6:10 am-1:00 pm

Nonstop4h 50m

$196

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/23

4:50 pm-6:01 pm

1 stop27h 11m

Chicago Midway

Mon 1/27

6:15 am-3:19 pm

2 stops31h 04m

$200

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 1/25

4:54 pm-11:02 pm

1 stop8h 08m

Chicago O'Hare Intl

Tue 1/28

6:10 am-1:00 pm

Nonstop4h 50m

$281

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 2/20

4:00 pm-7:15 pm

1 stop29h 15m

Chicago Midway

Mon 3/3

12:29 pm-2:40 pm

1 stop24h 11m

$289

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 2/12

6:00 am-2:00 pm

1 stop10h 00m

Chicago O'Hare Intl

Mon 2/24

11:25 am-12:35 am

2 stops11h 10m

$297

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 1/15

2:05 am-10:44 am

1 stop10h 39m

Chicago O'Hare Intl

Tue 1/21

7:35 am-9:28 pm

1 stop11h 53m

$300

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

Showing 1-10 of 60 results
1
2
3
...
6

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, September is the cheapest month in which you can book a flight from Caribbean Islands to Chicago (average of $232). Flying from Caribbean Islands to Chicago in June is currently the most expensive (average of $308). 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 November 21, 2024.

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 November 21, 2024.

The most flights from zzEPX to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 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 November 21, 2024.
Read reviews from past customers who have flown Spirit Airlines, United Airlines and Frontier 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
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,464 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Copa Airlines
7.8
Good
1,779 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Aeromexico
7.5
Good
2,004 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $85 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $91 and Southwest from $105 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 Punta Cana - 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 Air Canada (84%), United Airlines (84%) and Air New Zealand (84%).

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

    While on average a flight from Caribbean Islands to Chicago is generally $736, our data shows the cheapest flight currently is $95. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $129 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, September is the cheapest month in which you can book a flight from Caribbean Islands to Chicago (average of $232). Flying from Caribbean Islands to Chicago in June is currently the most expensive (average of $308). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Caribbean Islands to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Newark to O'Hare Intl flights
Boston to O'Hare Intl flights
Seattle to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Newark to Midway flights
Orlando to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Atlanta to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Baltimore to O'Hare Intl flights
Atlanta to Midway flights
Dulles Intl to O'Hare Intl flights
Denver to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Miami to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Hobby to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Mexico City to O'Hare Intl flights
Los Angeles to Midway flights
Minneapolis to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Baltimore to Midway flights
Hobby to Midway flights
Burbank to O'Hare Intl flights
LaGuardia to Midway flights
Tampa to O'Hare Intl flights
Ontario to O'Hare Intl flights
San Francisco to Midway flights
Seattle to Midway flights
Portland to O'Hare Intl flights
Minneapolis to Midway flights
San Diego to O'Hare Intl flights
Orlando to Midway flights
Santa Ana to O'Hare Intl flights
Dulles Intl to Midway flights
Raleigh to O'Hare Intl flights
San Jose to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Austin to O'Hare Intl flights
Love Field to O'Hare Intl flights
Reagan-National to Midway flights
Nashville to O'Hare Intl flights
Oakland to O'Hare Intl flights
Boston to Midway flights

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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$120Average$300FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$148Average$347FlexibilityNo cancel feeOn-time65%
DeltaCheapest$182Average$472FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$195Average$509FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$220Average$379FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$303Average$557FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$400Average$521FlexibilityNo cancel feeOn-time70%
JetBlueCheapest$467Average$619FlexibilityNo cancel feeOn-time62%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines