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Cheap flights from Chicago (CHI) to Caribbean from $61

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 9/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
CHI — SJU
Jun 11 — Jun 181
From?
To?
Tue 6/11
Tue 6/18
1 adult, Economy
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How far in advance should I book a flight from Chicago to Caribbean?

Travelers have found it’s best to book a flight 57 days in advance to save up to 25% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 57 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to Caribbean 1-2 weeks in advance for as low as $258, or $283 for flights within the next 24 hours.

What is the cheapest month to fly from Chicago to Caribbean?

October is one of the best times of the year to fly to Caribbean from Chicago. Prices for October average $319 per person but you can even find prices for as low as $90. The most expensive prices can be found in the month of March. Opting for a October flight can save you 60% on your journey compared to booking in March

What is the cheapest time of day to fly from CHI to CB?

When flying from Chicago to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap Chicago to Caribbean flights in June & July 2024

Find cheap flight options from Chicago to Caribbean specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,009,960 searches. Prices were last updated on June 6, 2024.
Tue 6/1810:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Tue 6/2512:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Deal found 6/5$156
Tue 6/1810:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Tue 6/2512:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Deal found 6/5$157
Wed 6/266:15 pmORD - SJU
1 stop25h 10mSpirit Airlines
Tue 7/212:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Deal found 6/6$158
Tue 7/98:50 pmORD - SJU
1 stop14h 41mSpirit Airlines
Tue 7/168:15 pmSJU - ORD
1 stop13h 59mSpirit Airlines
Deal found 6/5$159
Tue 7/98:50 pmORD - SJU
1 stop14h 41mSpirit Airlines
Tue 7/166:40 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 6/5$164
Wed 6/266:40 pmORD - SJU
2 stops30h 53mSpirit Airlines
Tue 7/212:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Deal found 6/5$174
Tue 6/185:05 amORD - SJU
1 stop13h 10mSpirit Airlines
Tue 6/2512:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Deal found 6/5$176
Tue 7/29:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Thu 7/119:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 6/4$178
Tue 6/185:05 amORD - SJU
1 stop13h 10mSpirit Airlines
Tue 6/2512:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Deal found 6/5$179

Chicago to Caribbean 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Caribbean in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,009,960 searches. Data last updated June 6, 2024.
Tue 9/105:36 pmORD - SJU
1 stop20h 09mSpirit Airlines
Wed 9/117:39 pmSJU - ORD
1 stop22h 07mSpirit Airlines
Deal found 6/5$106
Tue 9/105:05 amORD - SJU
1 stop12h 49mSpirit Airlines
Wed 9/118:59 pmSJU - ORD
Nonstop4h 59mSpirit Airlines
Deal found 6/5$114
Tue 9/105:05 amORD - SJU
1 stop12h 49mSpirit Airlines
Wed 9/117:39 pmSJU - ORD
1 stop15h 16mSpirit Airlines
Deal found 6/5$122
Tue 9/105:05 amORD - SJU
1 stop12h 49mSpirit Airlines
Wed 9/118:59 pmSJU - ORD
Nonstop4h 59mSpirit Airlines
Deal found 6/5$125
Tue 9/105:36 pmORD - SJU
1 stop20h 09mSpirit Airlines
Wed 9/117:39 pmSJU - ORD
2 stops25h 20mSpirit Airlines
Deal found 6/5$127
Tue 9/105:05 amORD - SJU
1 stop12h 49mSpirit Airlines
Tue 9/103:50 amSJU - ORD
2 stops17h 50mSpirit Airlines
Deal found 6/5$133
Tue 9/102:10 pmORD - SJU
Nonstop4h 47mSpirit Airlines
Wed 9/118:59 pmSJU - ORD
Nonstop4h 59mSpirit Airlines
Deal found 6/5$135
Tue 9/105:05 amORD - SJU
2 stops18h 34mSpirit Airlines
Tue 9/103:50 amSJU - ORD
2 stops17h 50mSpirit Airlines
Deal found 6/5$141
Tue 9/105:05 amORD - SJU
2 stops18h 07mSpirit Airlines
Wed 9/117:39 pmSJU - ORD
1 stop15h 16mSpirit Airlines
Deal found 6/5$143

Chicago to Caribbean flights leaving soon

Find last-minute flight options from Chicago to Caribbean for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,009,960 searches. Data last updated June 6, 2024.
Tue 6/119:19 amORD - SJU
2 stops16h 51mSpirit Airlines
Wed 6/192:00 pmSJU - ORD
1 stop20h 04mSpirit Airlines
Deal found 6/3$200
Tue 6/118:50 pmORD - SJU
1 stop21h 15mSpirit Airlines
Sun 6/1612:30 pmSJU - ORD
1 stop29h 14mSpirit Airlines
Deal found 6/4$205
Mon 6/104:09 pmORD - SJU
1 stop8h 36mSpirit Airlines
Wed 6/123:49 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 6/5$207
Tue 6/118:50 pmORD - SJU
1 stop21h 15mSpirit Airlines
Sun 6/1611:08 pmSJU - ORD
3 stops22h 39mSpirit Airlines
Deal found 6/4$208
Tue 6/118:50 pmORD - SJU
1 stop21h 15mSpirit Airlines
Tue 6/186:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 6/4$211
Fri 6/146:20 pmORD - SJU
1 stop23h 45mSpirit Airlines
Tue 6/182:59 pmSJU - ORD
1 stop18h 22mSpirit Airlines
Deal found 6/4$212
Wed 6/125:05 amORD - SJU
2 stops35h 00mSpirit Airlines
Tue 6/189:06 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Deal found 6/4$215
Tue 6/118:50 pmORD - SJU
1 stop21h 15mSpirit Airlines
Mon 6/178:06 pmSJU - ORD
1 stop14h 55mSpirit Airlines
Deal found 6/4$216
Wed 6/1211:01 amORD - SJU
2 stops34h 17mSpirit Airlines
Mon 6/178:06 pmSJU - ORD
1 stop26h 52mSpirit Airlines
Deal found 6/5$217

One-way flights to Caribbean from Chicago

Search for one-way flight options from Chicago to Caribbean. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,009,960 searches. Data last updated June 6, 2024.
Wed 9/117:00 amORD - SJU
1 stop6h 45mSpirit Airlines
Deal found 6/5$61
Sat 9/218:30 amORD - SJU
1 stop9h 24mSpirit Airlines
Deal found 6/5$68
Mon 9/165:35 pmORD - SJU
1 stop16h 53mSpirit Airlines
Deal found 6/4$69
Tue 7/98:50 pmORD - SJU
1 stop14h 41mSpirit Airlines
Deal found 6/5$70
Mon 9/96:32 pmORD - SJU
1 stop15h 56mSpirit Airlines
Deal found 6/5$71
Wed 9/112:10 pmORD - SJU
Nonstop4h 47mSpirit Airlines
Deal found 6/5$74
Wed 9/1110:33 amORD - SJU
2 stops14h 18mSpirit Airlines
Deal found 6/5$76
Tue 8/206:50 amORD - SJU
1 stop6h 48mSpirit Airlines
Deal found 6/5$77
Tue 7/28:50 pmORD - SJU
1 stop15h 12mSpirit Airlines
Deal found 6/4$80

Find flights from Chicago to Caribbean within your budget

Customize your flight search to find flights from Chicago to Caribbean 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 3,009,960 searches. Data last updated June 6, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$184 - $439

Route

Depart

Return

Price

Chicago O'Hare IntlSaint Thomas Island Cyril E King

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 9/10

1 stop16h 25m

Saint Thomas Island Cyril E King

Tue 9/17

1 stop11h 05m

$184

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 8/22

Nonstop4h 49m

San Juan Luis Munoz Marin Intl

Mon 8/26

2 stops31h 05m

$195

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Tue 7/9

1 stop6h 35m

San Juan Luis Munoz Marin Intl

Tue 7/16

1 stop12h 55m

$196

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 8/22

Nonstop4h 49m

San Juan Luis Munoz Marin Intl

Wed 8/28

Nonstop4h 59m

$196

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 6/11

1 stop21h 15m

San Juan Luis Munoz Marin Intl

Thu 6/13

1 stop23h 09m

$223

Chicago O'Hare IntlPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 9/21

1 stop19h 12m

Punta Cana

Fri 9/27

1 stop10h 13m

$303

Chicago O'Hare IntlPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 10/21

1 stop14h 05m

Punta Cana

Wed 10/30

1 stop12h 12m

$385

Chicago O'Hare IntlNassau Intl

ORD - NAS

ORDNAS

Chicago O'Hare Intl

Thu 8/8

1 stop6h 14m

Nassau Intl

Mon 8/12

1 stop7h 18m

$438

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Thu 10/31

1 stop6h 27m

San Juan Luis Munoz Marin Intl

Mon 11/4

1 stop10h 50m

$439

Flights are sorted by cheapest first

Deals found on 6/5

No data available for this route at this time. Please check back soon.

Best time to book a flight from Chicago to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Chicago 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.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated June 6, 2024.
Southwest
8.2
Very good
5,917 reviews

Entertainment

7.8

Boarding

8.3

Food

7.3

Crew

8.7

Comfort

8.1

Overall

8.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Southwest
8.2
Very good
5,917 reviews
Southwest
8.2
Very good
5,917 reviews

Entertainment

7.8

Boarding

8.3

Food

7.3

Crew

8.7

Comfort

8.1

Overall

8.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Alaska Airlines
8.1
Very good
9,216 reviews
Southwest
8.2
Very good
5,917 reviews

Entertainment

7.8

Boarding

8.3

Food

7.3

Crew

8.7

Comfort

8.1

Overall

8.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Delta
8.0
Very good
10,371 reviews
Southwest
8.2
Very good
5,917 reviews

Entertainment

7.8

Boarding

8.3

Food

7.3

Crew

8.7

Comfort

8.1

Overall

8.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Copa Airlines
8.0
Very good
2,563 reviews
Southwest
8.2
Very good
5,917 reviews

Entertainment

7.8

Boarding

8.3

Food

7.3

Crew

8.7

Comfort

8.1

Overall

8.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

JetBlue
7.6
Good
4,313 reviews
Southwest
8.2
Very good
5,917 reviews

Entertainment

7.8

Boarding

8.3

Food

7.3

Crew

8.7

Comfort

8.1

Overall

8.2

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Caribbean. 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 Chicago to Caribbean for under $200 on Cheapflights?

    Yes, there are multiple flights from Chicago to Caribbean for under $200. The cheapest flight booked recently is on Spirit Airlines for just $184, but on average you can expect to pay $201.

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

    Cheapflights has at least 20 direct flights from Chicago to Caribbean under $200. A good price for a nonstop flight from Chicago to Caribbean is less than $195.

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

    There are currently 20+ open flights from Chicago to Caribbean within the next 7 days for less than $200.

  • What are the most popular routes from Chicago to Caribbean?

    The most popular flight routes from Chicago to Caribbean are Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago O'Hare Intl - Punta Cana and Chicago Midway - San Juan Luis Munoz Marin Intl.

  • What are the most reliable airlines from Chicago to Caribbean?

    The top 3 most reliable airlines when flying from Chicago to Caribbean are Air Canada (92%), United Airlines (92%) and Air New Zealand (92%).

  • What are the cheapest flights from Chicago to Caribbean?

    Looking for the cheapest flight from Chicago to Caribbean? While on average our users pay $808, our data indicates the cheapest price to be $108. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $122.

  • What does ORD to SJU mean?

    Great question - ORD to SJU just means Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport. Now you’ll know what these unique codes when you look for flights! Santo Domingo Las Americas Airport (SDQ), Punta Cana Airport (PUJ), Montego Bay Sangster Intl Airport (MBJ), Oranjestad Reina Beatrix Airport (AUA), Santiago de los Caballeros Airport (STI) are other airports near this flight route and their unique identifiers/IATA codes.

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

    The amount of baggage you can bring on your Chicago to Caribbean 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 Chicago to Caribbean with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Caribbean 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 Chicago to Caribbean that include hotel bookings?

    Yes. In addition to deals on Chicago to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Caribbean.

  • Can I find deals for business class flights from Chicago to Caribbean?

    Yes. Cheapflights offers flight deals from Chicago to Caribbean 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 Chicago to Caribbean that allow pets onboard?

    Many airlines flying from Chicago to Caribbean 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 Chicago to Caribbean?

    Yes, you can often find last-minute deals on Chicago to Caribbean 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 Chicago to Caribbean flight deals updated?

    The Chicago to Caribbean flight deals you see on this page were last updated on 6/5.

  • What are the most popular airlines that fly from Chicago to Caribbean?

    Consider American Airlines, Alaska Airlines or JetBlue when booking your flight. These represent the most popular airlines when flying from Chicago to Caribbean.

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

    Currently, September is the cheapest month in which you can book a flight from Chicago to Caribbean (average of $245). Flying from Chicago to Caribbean in March is currently the most expensive (average of $338). 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 Chicago to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.

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Top 10 airlines flying from Chicago to Caribbean

Discover the top 10 airlines that operate flights from Chicago to Caribbean. 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 3,009,960 searches. Data last updated June 6, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$328FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$129Average$382FlexibilityNo cancel feeOn-time65%
DeltaCheapest$135Average$618FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$152Average$608FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$172Average$545FlexibilityNo cancel feeOn-time62%
AeromexicoCheapest$262Average$548FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$283Average$846FlexibilityNo cancel feeOn-time67%
Alaska AirlinesCheapest$288Average$620FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$293Average$610FlexibilityNo cancel feeOn-time71%
LufthansaCheapest$403Average$446FlexibilityNo cancel feeOn-time76%
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Search flights from Chicago to Caribbean by cabin class

Find flights from Chicago to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Hourly flight availability from Chicago to Caribbean

Find hourly flight availability from Chicago to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 6, 2024.
3%of flight departuresEarly morningMidnight to 6 am
94%of flight departuresMorning6 am to noon
3%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Chicago to Caribbean?

Cheapflights makes it easy to find Chicago to Caribbean flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Chicago to Caribbean?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Caribbean from Chicago.

Can Cheapflights find flights from Chicago to Caribbean with no change fees?

Yes, we can. To see specific flights from Chicago to Caribbean with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Chicago to Caribbean become cheaper?

Of course! You can now track prices for flights from Chicago to Caribbean and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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