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$68+ 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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
dic. 23 — dic. 301
lun. 12/23
lun. 12/30
1 adult, Economy
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Cheap flight deals from Caribbean to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Caribbean (0CB) 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 diciembre 18, 2024.

Round-trip from

$150
(eDestinos)

One-way from

$68
(Trip.com)
From Caribbean to Chicago (CHI)
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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 diciembre 18, 2024.

This eDestinos deal was found by Cheapflights users on 12/16. 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.
dom. 12/223:54 amSJU - ORD
1 stop8h 00mFrontier
jue. 1/210:15 pmORD - SJU
1 stop23h 39mFrontier
Deal found 12/16$206
This Trip.com deal was found by Cheapflights users on 12/16. 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.
mar. 12/2410:28 amSJU - MDW
1 stop14h 05mFrontier
jue. 1/27:34 amMDW - SJU
1 stop14h 20mFrontier
Deal found 12/16$215
This eDestinos deal was found by Cheapflights users on 12/17. 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.
sáb. 12/218:31 pmSJU - ORD
Nonstop5h 27mSpirit Airlines
lun. 1/61:00 pmORD - SJU
Nonstop4h 36mSpirit Airlines
Deal found 12/17$221
This Cheapflightsfares deal was found by Cheapflights users on 12/17. 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. 12/193:59 amSJU - ORD
1 stop7h 55mMultiple Airlines
mar. 1/71:00 pmORD - SJU
Nonstop4h 36mMultiple Airlines
Deal found 12/17$251
This eDestinos deal was found by Cheapflights users on 12/17. 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.
mié. 12/2511:04 amSDQ - ORD
1 stop10h 47mSpirit Airlines
mié. 1/15:00 amORD - SDQ
1 stop10h 51mSpirit Airlines
Deal found 12/17$258
This Booking.com deal was found by Cheapflights users on 12/16. 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. 12/2612:02 pmSDQ - ORD
1 stop23h 52mMultiple Airlines
mié. 1/155:11 amORD - SDQ
1 stop8h 43mMultiple Airlines
Deal found 12/16$301
This FlightHub deal was found by Cheapflights users on 12/17. 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.
vie. 12/276:02 pmPUJ - ORD
1 stop17h 52mFrontier
jue. 1/27:29 pmORD - PUJ
1 stop19h 18mFrontier
Deal found 12/17$348
This eDestinos deal was found by Cheapflights users on 12/18. 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.
mar. 12/312:45 amSJU - MDW
1 stop20h 32mMultiple Airlines
vie. 1/32:35 pmMDW - SJU
1 stop9h 00mMultiple Airlines
Deal found 12/18$395
This Delta deal was found by Cheapflights users on 12/17. 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.
sáb. 12/284:59 pmPUJ - ORD
1 stop8h 54mDelta
lun. 1/135:45 amORD - PUJ
1 stop6h 38mDelta
Deal found 12/17$416
This FlightHub deal was found by Cheapflights users on 12/17. 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.
vie. 12/271:59 pmPUJ - MDW
1 stop11h 15mFrontier
jue. 1/212:58 pmMDW - PUJ
1 stop25h 49mFrontier
Deal found 12/17$424
This American Airlines deal was found by Cheapflights users on 12/18. 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.
mar. 12/245:18 amSJU - ORD
2 stops10h 54mAmerican Airlines
jue. 1/29:55 amORD - SJU
1 stop12h 00mAmerican Airlines
Deal found 12/18$424
This United Airlines deal was found by Cheapflights users on 12/17. 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.
mié. 12/251:00 pmPUJ - ORD
1 stop12h 25mUnited Airlines
mié. 1/110:43 amORD - PUJ
Nonstop4h 28mUnited Airlines
Deal found 12/17$428

Find flights from Caribbean to Chicago within your budget

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 diciembre 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 1/17

9:26 pm-12:51 am

Nonstop5h 25m

Chicago O'Hare Intl

mié. 1/22

3:56 pm-9:21 am

1 stop15h 25m

$150

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 1/16

2:51 pm-9:52 am

1 stop21h 01m

Chicago O'Hare Intl

jue. 1/23

10:33 am-1:58 pm

1 stop25h 25m

$152

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

vie. 1/24

6:00 am-5:53 pm

1 stop13h 53m

Chicago Midway

lun. 1/27

11:33 am-2:19 am

1 stop12h 46m

$153

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 1/16

9:49 pm-9:52 am

1 stop14h 03m

Chicago O'Hare Intl

lun. 1/20

1:44 pm-8:21 pm

Nonstop4h 37m

$160

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

mié. 1/15

6:10 pm-9:24 pm

Nonstop5h 14m

Chicago O'Hare Intl

mar. 1/28

6:10 am-1:00 pm

Nonstop4h 50m

$212

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

vie. 1/17

10:09 pm-11:29 pm

2 stops27h 20m

Chicago Midway

lun. 1/20

7:45 am-1:59 am

1 stop16h 14m

$214

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mié. 1/22

2:05 am-9:40 am

1 stop9h 35m

Chicago O'Hare Intl

mar. 1/28

9:00 am-3:38 pm

Nonstop4h 38m

$230

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 3/13

5:00 am-12:02 pm

1 stop8h 02m

Chicago O'Hare Intl

lun. 3/17

10:05 am-11:35 pm

1 stop12h 30m

$239

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

vie. 1/17

6:10 pm-9:27 pm

Nonstop5h 17m

Chicago O'Hare Intl

sáb. 1/25

5:11 am-3:45 pm

1 stop8h 34m

$247

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

vie. 1/17

4:50 pm-11:32 pm

1 stop8h 42m

Chicago O'Hare Intl

sáb. 1/25

5:11 am-3:45 pm

1 stop8h 34m

$263

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

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.

Travel insights for flights from Caribbean to Chicago

Get recent, data-driven insights about flights from Caribbean to Chicago including ideal travel times, pricing trends, and more.

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

Currently, September is the cheapest month in which you can book a flight from Caribbean to Chicago (average of $232). Flying from Caribbean 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 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 diciembre 18, 2024.

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 diciembre 18, 2024.

The most flights from 0CB to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (6 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 diciembre 18, 2024.
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

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
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

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
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

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
9,552 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

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
1,723 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

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
1,930 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

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 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 $68. Users have also found prices from $68 and $113 on Spirit Airlines and United Airlines, 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 Punta Cana - 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 American Airlines (90%), Alaska Airlines (90%) and Spirit Airlines (88%).

  • What are the cheapest flights from Caribbean to Chicago?

    While on average a flight from Caribbean 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 $124 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, September is the cheapest month in which you can book a flight from Caribbean to Chicago (average of $232). Flying from Caribbean 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.

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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 8 airlines flying from Caribbean to Chicago

Discover the top 8 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 diciembre 18, 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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