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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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
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 December 22, 2024.

Round-trip from

$151
(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 December 22, 2024.

This FlightHub deal was found by Cheapflights users on 12/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/279:00 pmSJU - ORD
1 stop14h 54mFrontier
Sat 1/410:49 amORD - SJU
1 stop14h 00mFrontier
Deal found 12/20$244
This Booking.com deal was found by Cheapflights users on 12/21. 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.
Mon 12/307:13 pmSJU - ORD
1 stop19h 33mMultiple Airlines
Sun 1/51:00 pmORD - SJU
Nonstop4h 36mMultiple Airlines
Deal found 12/21$265
This eDestinos deal was found by Cheapflights users on 12/21. 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.
Sat 12/285:10 pmSJU - ORD
Nonstop5h 30mSpirit Airlines
Tue 1/71:00 pmORD - SJU
Nonstop4h 36mSpirit Airlines
Deal found 12/21$268
This Frontier deal was found by Cheapflights users on 12/21. 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 12/318:10 pmSJU - MDW
1 stop14h 11mFrontier
Sat 1/47:35 amMDW - SJU
1 stop11h 35mFrontier
Deal found 12/21$279
This Booking.com deal was found by Cheapflights users on 12/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2711:04 amSDQ - ORD
1 stop7h 02mMultiple Airlines
Thu 1/210:15 pmORD - SDQ
1 stop11h 28mMultiple Airlines
Deal found 12/20$314
This Priceline deal was found by Cheapflights users on 12/20. 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.
Fri 12/2711:04 amSDQ - ORD
1 stop10h 47mSpirit Airlines
Wed 1/15:00 amORD - SDQ
1 stop10h 51mSpirit Airlines
Deal found 12/20$353
This Trip.com deal was found by Cheapflights users on 12/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/312:45 amSJU - MDW
1 stop12h 39mMultiple Airlines
Sat 1/47:35 amMDW - SJU
1 stop11h 35mMultiple Airlines
Deal found 12/20$403
This United Airlines deal was found by Cheapflights users on 12/21. 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.
Sat 12/284:30 pmPUJ - ORD
Nonstop5h 10mUnited Airlines
Mon 1/136:00 amORD - PUJ
1 stop8h 15mUnited Airlines
Deal found 12/21$415
This American Airlines deal was found by Cheapflights users on 12/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/257:05 amSJU - ORD
2 stops11h 04mAmerican Airlines
Wed 1/112:15 pmORD - SJU
1 stop8h 55mAmerican Airlines
Deal found 12/21$424
This Delta deal was found by Cheapflights users on 12/21. 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.
Wed 12/254:59 pmPUJ - ORD
1 stop8h 57mDelta
Wed 1/15:45 amORD - PUJ
1 stop8h 49mDelta
Deal found 12/21$452
This American Airlines deal was found by Cheapflights users on 12/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/243:47 pmPUJ - ORD
Nonstop5h 15mAmerican Airlines
Sat 12/285:27 pmORD - PUJ
1 stop16h 13mAmerican Airlines
Deal found 12/21$471
This American Airlines deal was found by Cheapflights users on 12/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/211:10 pmMBJ - ORD
Nonstop4h 35mAmerican Airlines
Sat 1/49:05 amORD - MBJ
Nonstop4h 15mAmerican Airlines
Deal found 12/21$477

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mon 2/24

10:43 pm-3:12 pm

1 stop18h 29m

Chicago Midway

Fri 2/28

2:41 pm-1:11 am

1 stop8h 30m

$151

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/16

9:26 pm-12:51 am

Nonstop5h 25m

Chicago O'Hare Intl

Tue 1/21

1:44 pm-8:21 pm

Nonstop4h 37m

$151

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sun 2/23

3:54 am-4:03 pm

1 stop14h 09m

Chicago O'Hare Intl

Fri 2/28

7:18 pm-9:35 am

1 stop12h 17m

$152

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

7:08 pm-9:35 am

1 stop12h 27m

$153

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/23

6:55 pm-2:19 pm

1 stop21h 24m

Chicago Midway

Mon 1/27

7:45 am-1:59 am

1 stop16h 14m

$209

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/2

3:05 pm-7:25 pm

Nonstop5h 20m

Chicago O'Hare Intl

Mon 5/5

8:05 am-1:45 pm

Nonstop4h 40m

$230

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Tue 3/4

4:00 pm-4:31 pm

2 stops26h 31m

Chicago O'Hare Intl

Sat 3/8

9:25 am-1:49 pm

1 stop26h 24m

$284

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 1/29

2:55 pm-7:45 pm

1 stop6h 50m

Chicago Midway

Sun 2/2

1:20 pm-12:50 am

2 stops9h 30m

$304

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 2/19

4:48 pm-11:58 pm

1 stop9h 10m

Chicago O'Hare Intl

Tue 2/25

7:10 am-3:43 pm

1 stop6h 33m

$321

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/24

6:15 am-11:59 am

1 stop7h 44m

Chicago Midway

Tue 1/28

12:44 pm-11:46 pm

1 stop9h 02m

$324

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

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 $317). 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 December 22, 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 December 22, 2024.

The most flights from zzEPX to CHI are scheduled on a Saturday (11 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 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 December 22, 2024.
Read reviews from past customers who have flown Spirit Airlines, American Airlines and Air Canada 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
4,804 reviews

Entertainment

7.7

Crew

8.7

Food

7.2

Overall

8.1

Comfort

8.1

Boarding

8.2

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
4,804 reviews
Southwest
8.1
Very good
4,804 reviews

Entertainment

7.7

Crew

8.7

Food

7.2

Overall

8.1

Comfort

8.1

Boarding

8.2

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
8,594 reviews
Southwest
8.1
Very good
4,804 reviews

Entertainment

7.7

Crew

8.7

Food

7.2

Overall

8.1

Comfort

8.1

Boarding

8.2

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.

Alaska Airlines
8.0
Very good
9,537 reviews
Southwest
8.1
Very good
4,804 reviews

Entertainment

7.7

Crew

8.7

Food

7.2

Overall

8.1

Comfort

8.1

Boarding

8.2

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.

KLM
7.8
Good
1,342 reviews
Southwest
8.1
Very good
4,804 reviews

Entertainment

7.7

Crew

8.7

Food

7.2

Overall

8.1

Comfort

8.1

Boarding

8.2

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
1,713 reviews
Southwest
8.1
Very good
4,804 reviews

Entertainment

7.7

Crew

8.7

Food

7.2

Overall

8.1

Comfort

8.1

Boarding

8.2

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 $117 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 American Airlines (90%), Alaska Airlines (90%) and Spirit Airlines (88%).

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

    While on average a flight from Caribbean Islands to Chicago is generally $416, our data shows the cheapest flight currently is $65. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $126 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 $317). 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

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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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$120Average$289FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$148Average$344FlexibilityNo cancel feeOn-time65%
DeltaCheapest$187Average$564FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$196Average$548FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$220Average$386FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$306Average$570FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$400Average$521FlexibilityNo cancel feeOn-time70%
JetBlueCheapest$467Average$619FlexibilityNo cancel feeOn-time62%
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