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$85+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
nov. 25 — dic. 21
lun. 11/25
lun. 12/2
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 noviembre 20, 2024.

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 20, 2024.

This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/131:55 pmSJU - MDW
1 stop12h 25mFrontier
lun. 12/167:25 amMDW - SJU
1 stop16h 32mFrontier
Deal found 11/20$158
This Cheapflightsfares deal was found by Cheapflights users on 11/19. 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.
mié. 12/188:31 pmSJU - ORD
Nonstop5h 27mSpirit Airlines
jue. 1/21:00 pmORD - SJU
Nonstop4h 36mSpirit Airlines
Deal found 11/19$158
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/62:17 pmSJU - ORD
Nonstop5h 30mMultiple Airlines
lun. 12/94:58 pmORD - SJU
1 stop7h 04mMultiple Airlines
Deal found 11/20$161
This Gotogate deal was found by Cheapflights users on 11/19. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/203:54 amSJU - ORD
1 stop8h 00mFrontier
mar. 12/3111:24 amORD - SJU
1 stop7h 32mFrontier
Deal found 11/19$163
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.
sáb. 12/76:20 amSJU - MDW
2 stops37h 52mMultiple Airlines
mar. 12/1012:57 pmMDW - SJU
2 stops34h 43mMultiple Airlines
Deal found 11/20$241
This Cheapflightsfares deal was found by Cheapflights users on 11/19. 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.
sáb. 12/215:00 pmPUJ - ORD
Nonstop5h 31mFrontier
mar. 1/146:10 amORD - PUJ
Nonstop4h 29mFrontier
Deal found 11/19$252
This United Airlines deal was found by Cheapflights users on 11/19. 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. 12/62:05 amSJU - ORD
1 stop9h 38mUnited Airlines
mar. 12/1012:53 pmORD - SJU
1 stop9h 43mUnited Airlines
Deal found 11/19$290
This Kiwi.com deal was found by Cheapflights users on 11/19. 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.
sáb. 12/212:33 pmPUJ - ORD
1 stop7h 40mMultiple Airlines
mar. 1/146:10 amORD - PUJ
Nonstop4h 29mMultiple Airlines
Deal found 11/19$292
This Cheapflightsfares deal was found by Cheapflights users on 11/19. 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.
mar. 12/101:12 pmKIN - ORD
1 stop8h 55mSpirit Airlines
sáb. 12/145:11 pmORD - KIN
1 stop14h 58mSpirit Airlines
Deal found 11/19$311
This Southwest deal was found by Cheapflights users on 11/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/126:10 amSJU - MDW
2 stops12h 55mSouthwest
lun. 12/169:45 amMDW - SJU
2 stops13h 00mSouthwest
Deal found 11/18$325
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/254:50 pmPUJ - ORD
1 stop25h 16mSpirit Airlines
mié. 1/15:00 amORD - PUJ
1 stop8h 55mSpirit Airlines
Deal found 11/20$353
This United Airlines deal was found by Cheapflights users on 11/19. 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. 1/16:00 amORD - PUJ
1 stop8h 15mUnited Airlines
Deal found 11/19$354

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 2,629,791 searches. Data last updated noviembre 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

vie. 12/13

1:55 pm-12:20 am

1 stop12h 25m

Chicago Midway

lun. 12/16

7:25 am-1:57 am

1 stop16h 32m

$158

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

lun. 2/3

6:00 am-10:16 pm

1 stop18h 16m

Chicago O'Hare Intl

lun. 2/10

3:16 pm-12:39 am

1 stop7h 23m

$158

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 12/20

4:43 pm-8:13 pm

Nonstop5h 30m

Chicago O'Hare Intl

mar. 1/7

9:32 am-4:15 pm

Nonstop4h 43m

$159

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 12/6

2:17 pm-5:47 pm

Nonstop5h 30m

Chicago O'Hare Intl

lun. 12/9

4:58 pm-2:02 am

1 stop7h 04m

$161

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 1/23

4:50 pm-6:01 pm

1 stop27h 11m

Chicago Midway

lun. 1/27

6:15 am-12:39 am

2 stops16h 24m

$194

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

vie. 1/31

6:10 pm-9:27 pm

Nonstop5h 17m

Chicago O'Hare Intl

mié. 2/5

6:10 am-1:00 pm

Nonstop4h 50m

$200

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 1/23

2:55 pm-7:45 pm

1 stop6h 50m

Chicago Midway

lun. 1/27

10:05 am-12:25 am

2 stops12h 20m

$210

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 12/6

8:35 am-11:54 am

Nonstop5h 19m

Chicago O'Hare Intl

lun. 12/9

2:20 pm-8:55 pm

Nonstop4h 35m

$221

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

sáb. 12/21

2:33 pm-8:13 pm

1 stop7h 40m

Chicago O'Hare Intl

mar. 1/14

6:10 am-12:39 pm

Nonstop4h 29m

$292

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

mié. 1/22

1:15 pm-8:13 pm

1 stop7h 58m

Chicago O'Hare Intl

mié. 1/29

5:10 am-12:10 pm

1 stop6h 00m

$303

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

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 20, 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 20, 2024.

The most flights from 0CB to CHI are scheduled on a Wednesday (7 on average). You will have fewer flight options on Monday, 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 20, 2024.
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

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

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

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

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

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

Alaska Airlines
8.0
Very good
9,461 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

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

Copa Airlines
7.8
Good
1,785 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

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

LATAM Airlines
7.5
Good
1,934 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

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.

  • 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 $85. Users have also found prices from $85 and $100 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 Air Canada (84%), United Airlines (84%) and Air New Zealand (84%).

  • What are the cheapest flights from Caribbean to Chicago?

    While on average a flight from Caribbean 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 $122 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.

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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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 2,629,791 searches. Data last updated noviembre 20, 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%
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