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Cheap flights from Chicago (CHI) to Caribbean from $63

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
May 19 — May 261
From?
To?
Sun 5/19
Sun 5/26
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 20% 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 $280 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 $318 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

When is the cheapest time to fly from Chicago to Caribbean (CHI - 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 Spirit Airlines flights from Chicago to Caribbean

Explore cheap flight options specifically provided by Spirit Airlines for the route between Chicago and Caribbean. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 14, 2024.
Mon 5/209:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Tue 5/289:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/13$183
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Tue 5/287:57 pmSJU - ORD
1 stop14h 58mSpirit Airlines
Deal found 5/14$184
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Tue 5/287:57 pmSJU - ORD
2 stops25h 38mSpirit Airlines
Deal found 5/14$185
Thu 5/309:03 amORD - SJU
1 stop8h 54mSpirit Airlines
Tue 6/46:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 5/13$186
Sun 6/29:03 amORD - SJU
1 stop8h 54mSpirit Airlines
Sat 6/154:09 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 5/13$189
Tue 6/118:50 pmORD - SJU
1 stop21h 15mSpirit Airlines
Tue 6/182:59 pmSJU - ORD
1 stop18h 22mSpirit Airlines
Deal found 5/13$190
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Mon 6/39:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/13$191
Thu 5/3010:03 amORD - SJU
1 stop7h 54mSpirit Airlines
Tue 6/49:07 pmSJU - ORD
1 stop13h 54mSpirit Airlines
Deal found 5/13$192
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Wed 5/299:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/13$193

Cheap Frontier flights from Chicago to Caribbean

Explore cheap flight options specifically provided by Frontier for the route between Chicago and Caribbean. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 14, 2024.
Tue 6/410:16 amMDW - SJU
1 stop16h 29mFrontier
Tue 6/1111:00 amSJU - MDW
2 stops11h 20mFrontier
Deal found 5/13$212
Tue 5/2810:52 amMDW - SJU
1 stop11h 49mFrontier
Sat 6/110:23 pmSJU - MDW
1 stop9h 31mFrontier
Deal found 5/13$213
Mon 9/1610:00 amMDW - SJU
1 stop10h 47mFrontier
Mon 9/2310:47 pmSJU - MDW
1 stop13h 08mFrontier
Deal found 5/13$214
Thu 6/132:36 pmMDW - SJU
1 stop11h 32mFrontier
Wed 6/199:36 pmSJU - MDW
1 stop9h 24mFrontier
Deal found 5/13$215
Mon 5/205:56 pmORD - SJU
1 stop15h 51mFrontier
Tue 5/283:00 amSJU - ORD
1 stop23h 08mFrontier
Deal found 5/13$216
Sun 6/92:26 pmMDW - SJU
1 stop11h 42mFrontier
Fri 6/148:41 pmSJU - MDW
1 stop12h 53mFrontier
Deal found 5/13$217
Tue 9/1710:00 amMDW - SJU
1 stop10h 47mFrontier
Sat 9/2110:18 pmSJU - MDW
1 stop13h 37mFrontier
Deal found 5/13$218
Tue 5/2110:52 amMDW - SJU
1 stop11h 49mFrontier
Fri 5/319:29 amSJU - MDW
1 stop9h 58mFrontier
Deal found 5/13$223
Mon 5/207:23 pmMDW - SJU
1 stop12h 21mFrontier
Mon 5/272:48 amSJU - MDW
1 stop29h 06mFrontier
Deal found 5/13$224

Cheap Chicago to Caribbean flights in May & June 2024

Find cheap flight options from Chicago to Caribbean specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,632,958 searches. Prices were last updated on May 14, 2024.
Mon 5/209:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Tue 5/289:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/13$183
Wed 5/295:01 amORD - SJU
1 stop11h 50mMultiple Airlines
Wed 6/53:49 pmSJU - ORD
Nonstop5h 11mMultiple Airlines
Deal found 5/14$184
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Tue 5/287:57 pmSJU - ORD
2 stops25h 38mSpirit Airlines
Deal found 5/14$185
Thu 5/309:03 amORD - SJU
1 stop8h 54mSpirit Airlines
Tue 6/46:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 5/13$186
Sun 6/29:03 amORD - SJU
1 stop8h 54mSpirit Airlines
Sat 6/154:09 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 5/13$189
Tue 6/118:50 pmORD - SJU
1 stop21h 15mSpirit Airlines
Tue 6/182:59 pmSJU - ORD
1 stop18h 22mSpirit Airlines
Deal found 5/13$190
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Mon 6/39:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/13$191
Thu 5/3010:03 amORD - SJU
1 stop7h 54mSpirit Airlines
Tue 6/49:07 pmSJU - ORD
1 stop13h 54mSpirit Airlines
Deal found 5/13$192
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Wed 5/299:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/13$193

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 2,632,958 searches. Data last updated May 14, 2024.
Fri 9/279:25 pmORD - SJU
2 stops13h 03mSpirit Airlines
Tue 10/112:28 pmSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 5/13$180
Tue 9/175:00 amORD - SJU
1 stop13h 11mMultiple Airlines
Wed 9/2510:47 pmSJU - ORD
1 stop11h 21mMultiple Airlines
Deal found 5/13$183
Wed 5/295:01 amORD - SJU
1 stop11h 50mMultiple Airlines
Wed 6/53:49 pmSJU - ORD
Nonstop5h 11mMultiple Airlines
Deal found 5/14$184
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Tue 5/287:57 pmSJU - ORD
2 stops25h 38mSpirit Airlines
Deal found 5/14$185
Wed 9/115:00 amORD - STT
1 stop10h 32mSpirit Airlines
Tue 9/175:25 pmSTT - ORD
1 stop7h 35mSpirit Airlines
Deal found 5/13$186
Thu 5/309:03 amORD - SJU
1 stop8h 54mSpirit Airlines
Tue 6/46:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 5/13$186
Fri 8/305:56 pmORD - SJU
1 stop16h 09mMultiple Airlines
Wed 9/48:02 pmSJU - ORD
1 stop14h 31mMultiple Airlines
Deal found 5/13$187
Sun 6/29:03 amORD - SJU
1 stop8h 54mSpirit Airlines
Sat 6/154:09 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 5/13$189
Tue 6/118:50 pmORD - SJU
1 stop21h 15mSpirit Airlines
Tue 6/182:59 pmSJU - ORD
1 stop18h 22mSpirit Airlines
Deal found 5/13$190

Non-stop flights to Caribbean from Chicago

Discover non-stop flight options from Chicago to Caribbean. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 14, 2024.
Wed 6/510:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Wed 6/126:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/13$202
Sat 6/155:11 pmORD - SJU
Nonstop4h 47mSpirit Airlines
Wed 6/196:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/14$204
Sat 5/1811:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Wed 6/53:49 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 5/13$211
Wed 6/59:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Tue 6/116:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/13$216
Sun 6/29:37 amORD - SJU
Nonstop4h 54mSpirit Airlines
Sat 6/156:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/13$217
Wed 6/59:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Tue 6/116:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/13$219
Tue 6/1110:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Sat 6/154:09 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 5/13$225
Tue 6/1810:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Tue 6/256:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/13$226
Tue 6/119:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Tue 6/256:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/14$227

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 2,632,958 searches. Data last updated May 14, 2024.
Mon 5/209:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Tue 5/289:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/13$183
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Tue 5/287:57 pmSJU - ORD
1 stop14h 58mSpirit Airlines
Deal found 5/14$184
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Tue 5/287:57 pmSJU - ORD
2 stops25h 38mSpirit Airlines
Deal found 5/14$185
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Mon 6/39:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/13$191
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Wed 5/299:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/13$193
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Wed 5/291:32 pmSJU - ORD
1 stop8h 03mSpirit Airlines
Deal found 5/13$194
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Sat 6/112:32 pmSJU - ORD
1 stop9h 00mSpirit Airlines
Deal found 5/13$195
Mon 5/209:25 pmORD - SJU
1 stop14h 16mMultiple Airlines
Fri 5/316:08 pmSJU - ORD
1 stop8h 00mMultiple Airlines
Deal found 5/13$197
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Tue 5/289:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/13$198

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 2,632,958 searches. Data last updated May 14, 2024.
Wed 9/115:00 amORD - SJU
1 stop13h 11mSpirit Airlines
Deal found 5/13$63
Tue 8/207:27 amORD - SJU
1 stop10h 30mSpirit Airlines
Deal found 5/13$64
Wed 5/2910:58 amORD - SJU
2 stops14h 33mSpirit Airlines
Deal found 5/13$72
Tue 5/289:15 pmORD - SJU
1 stop10h 10mMultiple Airlines
Deal found 5/13$73
Mon 8/266:32 pmORD - SJU
1 stop15h 56mSpirit Airlines
Deal found 5/13$76
Mon 5/209:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Deal found 5/13$83
Tue 6/49:15 pmORD - SJU
1 stop14h 47mSpirit Airlines
Deal found 5/13$85
Mon 5/209:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Deal found 5/12$86
Tue 5/216:10 amORD - SJU
1 stop15h 14mSpirit Airlines
Deal found 5/13$87

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 2,632,958 searches. Data last updated May 14, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$183 - $409

Route

Depart

Return

Price

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 5/20

1 stop14h 16m

San Juan Luis Munoz Marin Intl

Tue 5/28

1 stop13h 48m

$183

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 5/29

1 stop11h 50m

San Juan Luis Munoz Marin Intl

Wed 6/5

Nonstop5h 11m

$184

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 5/21

1 stop14h 16m

San Juan Luis Munoz Marin Intl

Tue 5/28

2 stops25h 38m

$185

Chicago O'Hare IntlSaint Thomas Island Cyril E King

ORD - STT

ORDSTT

Chicago O'Hare Intl

Wed 9/11

1 stop10h 32m

Saint Thomas Island Cyril E King

Tue 9/17

1 stop7h 35m

$186

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 5/20

1 stop14h 16m

San Juan Luis Munoz Marin Intl

Fri 5/31

1 stop8h 00m

$197

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Tue 6/4

1 stop16h 29m

San Juan Luis Munoz Marin Intl

Tue 6/11

2 stops11h 20m

$212

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 5/19

1 stop12h 45m

San Juan Luis Munoz Marin Intl

Thu 5/23

1 stop7h 08m

$263

Chicago O'Hare IntlNassau Intl

ORD - NAS

ORDNAS

Chicago O'Hare Intl

Wed 6/12

1 stop7h 40m

Nassau Intl

Tue 6/18

1 stop7h 51m

$351

Chicago O'Hare IntlPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 9/25

1 stop17h 17m

Punta Cana

Sun 9/29

1 stop18h 58m

$409

Flights are sorted by cheapest first

Deals found on 5/13

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

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 May 14, 2024.
Alaska Airlines
8.1
Very good
9,152 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.3

Overall

8.1

Crew

8.6

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

Alaska Airlines
8.1
Very good
9,152 reviews
Alaska Airlines
8.1
Very good
9,152 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.3

Overall

8.1

Crew

8.6

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

Delta
8.0
Very good
10,706 reviews
Alaska Airlines
8.1
Very good
9,152 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.3

Overall

8.1

Crew

8.6

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

Copa Airlines
8.0
Very good
2,718 reviews
Alaska Airlines
8.1
Very good
9,152 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.3

Overall

8.1

Crew

8.6

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

WestJet
7.5
Good
2,925 reviews
Alaska Airlines
8.1
Very good
9,152 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.3

Overall

8.1

Crew

8.6

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

Avianca
7.5
Good
3,772 reviews
Alaska Airlines
8.1
Very good
9,152 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.3

Overall

8.1

Crew

8.6

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

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 $183, but on average you can expect to pay $192.

  • Are there nonstop flights from Chicago to Caribbean for under $300 on Cheapflights?

    Cheapflights has at least 20 direct flights from Chicago to Caribbean under $300. A good price for a nonstop flight from Chicago to Caribbean is less than $228.

  • 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 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 are the most reliable airlines from Chicago to Caribbean?

    The top 3 most reliable airlines when flying from Chicago to Caribbean are American Airlines (94%), Alaska Airlines (93%) and United Airlines (84%).

  • What are the cheapest flights from Chicago to Caribbean?

    Looking for the cheapest flight from Chicago to Caribbean? While on average our users pay $527, our data indicates the cheapest price to be $87. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $125.

  • 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! Punta Cana Airport (PUJ), Santo Domingo Las Americas Airport (SDQ), 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 5/14.

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 2,632,958 searches. Data last updated May 14, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$329FlexibilityNo cancel feeOn-time62%
Search Frontier flights
Spirit AirlinesCheapest$132Average$386FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights
DeltaCheapest$137Average$618FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapest$153Average$602FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
JetBlueCheapest$172Average$549FlexibilityNo cancel feeOn-time62%
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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.
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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 May 14, 2024.
8%of flight departuresEarly morningMidnight to 6 am
92%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
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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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