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$86+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
nov. 9 — nov. 161
sáb. 11/9
sáb. 11/16
1 adult, Economy
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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 noviembre 4, 2024.

This Booking.com deal was found by Cheapflights users on 11/3. 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.
mié. 11/2011:18 amSJU - ORD
1 stop28h 09mMultiple Airlines
lun. 11/256:10 pmORD - SJU
Nonstop4h 32mMultiple Airlines
Deal found 11/3$165
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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.
vie. 12/62:17 pmSJU - ORD
Nonstop5h 30mSpirit Airlines
mié. 12/111:13 pmORD - SJU
1 stop10h 27mSpirit Airlines
Deal found 11/4$166
This Frontier deal was found by Cheapflights users on 11/4. 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.
dom. 12/223:54 amSJU - ORD
1 stop8h 00mFrontier
jue. 1/22:19 pmORD - SJU
1 stop8h 22mFrontier
Deal found 11/4$168
This Mytrip deal was found by Cheapflights users on 11/3. 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.
sáb. 12/218:10 pmSJU - MDW
1 stop25h 32mFrontier
lun. 12/306:00 amMDW - SJU
1 stop18h 35mFrontier
Deal found 11/3$171
This eDestinos deal was found by Cheapflights users on 11/3. 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. 12/46:40 pmSJU - MDW
2 stops25h 32mMultiple Airlines
lun. 12/97:25 amMDW - SJU
1 stop16h 32mMultiple Airlines
Deal found 11/3$185
This Priceline deal was found by Cheapflights users on 11/4. 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.
mié. 12/410:14 amKIN - ORD
1 stop11h 53mSpirit Airlines
mar. 12/105:11 pmORD - KIN
1 stop14h 58mSpirit Airlines
Deal found 11/4$274
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
mié. 12/255:10 pmSDQ - ORD
1 stop8h 48mMultiple Airlines
mar. 2/255:56 pmORD - SDQ
2 stops13h 16mMultiple Airlines
Deal found 11/2$343
This United Airlines deal was found by Cheapflights users on 11/3. 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.
vie. 12/202:50 pmPUJ - ORD
Nonstop5h 10mUnited Airlines
lun. 12/309:29 pmORD - PUJ
1 stop16h 46mUnited Airlines
Deal found 11/3$348
This Delta deal was found by Cheapflights users on 11/3. 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.
mié. 12/253:50 pmPUJ - ORD
1 stop10h 06mDelta
mié. 1/15:45 amORD - PUJ
1 stop7h 49mDelta
Deal found 11/3$351
This Mytrip deal was found by Cheapflights users on 11/2. 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.
sáb. 11/2312:05 pmPUJ - ORD
1 stop10h 18mFrontier
sáb. 11/306:00 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 11/2$359
This FlightHub deal was found by Cheapflights users on 11/3. 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. 12/186:00 amSDQ - MDW
2 stops26h 39mFrontier
lun. 12/306:49 pmMDW - SDQ
1 stop13h 52mFrontier
Deal found 11/3$368
This Booking.com deal was found by Cheapflights users on 11/2. 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.
sáb. 11/2312:05 pmPUJ - ORD
1 stop10h 18mMultiple Airlines
sáb. 11/305:00 amORD - PUJ
1 stop8h 55mMultiple Airlines
Deal found 11/2$376

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 2,455,398 searches. Data last updated noviembre 4, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

dom. 12/8

9:49 pm-10:21 am

1 stop14h 32m

$86

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 12/20

8:31 pm-11:58 pm

Nonstop5h 27m

$94

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mar. 12/3

5:25 pm-7:07 pm

1 stop27h 42m

$111

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

lun. 2/3

6:45 am-3:28 pm

1 stop10h 43m

$146

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

lun. 12/16

7:16 pm-10:28 am

1 stop17h 12m

$86

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

sáb. 1/18

2:55 pm-6:10 pm

Nonstop5h 15m

$183

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

jue. 12/19

3:47 pm-7:02 pm

Nonstop5h 15m

$187

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 2/27

2:05 am-9:46 am

1 stop9h 41m

$187

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

jue. 12/19

2:05 pm-10:06 pm

1 stop10h 01m

$193

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

mié. 11/27

2:39 pm-11:21 pm

1 stop10h 42m

$207

Flights are sorted by cheapest first

Deals found on 11/3

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 noviembre 4, 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 noviembre 4, 2024.

The most flights from 0CB to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Tuesday, 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 noviembre 4, 2024.
Southwest
8.1
Very good
5,089 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

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

Southwest
8.1
Very good
5,089 reviews
Southwest
8.1
Very good
5,089 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

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

Delta
8.0
Very good
8,829 reviews
Southwest
8.1
Very good
5,089 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

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

Alaska Airlines
8.0
Very good
9,423 reviews
Southwest
8.1
Very good
5,089 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

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

Copa Airlines
7.8
Good
1,869 reviews
Southwest
8.1
Very good
5,089 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

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

Aeromexico
7.5
Good
2,027 reviews
Southwest
8.1
Very good
5,089 reviews

Overall

8.1

Boarding

8.3

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

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 to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find flights from Caribbean to Chicago for under $200 on Cheapflights?

    Yes, there are multiple flights from Caribbean to Chicago for under $200. The cheapest flight booked recently is on Multiple Airlines for just $165, but on average you can expect to pay $325.

  • Are there nonstop flights from Caribbean to Chicago for under $200 on Cheapflights?

    Cheapflights has at least 10 direct flights from Caribbean to Chicago under $200. A good price for a nonstop flight from Caribbean to Chicago is less than $631.

  • Are there last-minute flights available from Caribbean to Chicago for under $200?

    There are currently 13+ open flights from Caribbean to Chicago within the next 7 days for less than $200.

  • 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 $86. Users have also found prices from $94 and $175 on Spirit Airlines and JetBlue, 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 Spirit Airlines (86%), Air Canada (85%) and United Airlines (85%).

  • What are the cheapest flights from Caribbean to Chicago?

    While on average a flight from Caribbean to Chicago is generally $614, 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 $126 for that flight.

  • What does SJU to ORD mean?

    Great question - SJU to ORD just means San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport. Now you’ll know what these unique codes when you look for flights! Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

  • Can I find deals for flights from Caribbean to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Caribbean to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Caribbean to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Caribbean to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Caribbean to Chicago that allow pets onboard?

    Many airlines flying from Caribbean to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Caribbean to Chicago?

    Yes, you can often find last-minute deals on Caribbean to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Caribbean to Chicago flight deals updated?

    The Caribbean to Chicago flight deals you see on this page were last updated on 11/4.

  • 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.

See more FAQs

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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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Dulles Intl to Midway flights
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LaGuardia to St. Louis flights

Top 7 airlines flying from Caribbean to Chicago

Discover the top 7 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 2,455,398 searches. Data last updated noviembre 4, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$114Average$267FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$142Average$337FlexibilityNo cancel feeOn-time65%
DeltaCheapest$182Average$584FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$195Average$512FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$274Average$351FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$298Average$571FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$400Average$521FlexibilityNo cancel feeOn-time70%
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