Cheap flights from Chicago (CHI) to Caribbean from $46

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 6/11. 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. 2 — jun. 91

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

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 2,740,132 searches. Data last updated mayo 28, 2024.
mar. 8/277:27 amORD - SJU
1 stop10h 30mSpirit Airlines
mié. 8/284:01 pmSJU - ORD
Nonstop5h 13mSpirit Airlines
Deal found 5/28$115
mar. 9/107:27 amORD - SJU
1 stop10h 30mSpirit Airlines
mar. 9/247:57 pmSJU - ORD
1 stop14h 36mSpirit Airlines
Deal found 5/27$120
mar. 8/275:00 amORD - SJU
1 stop13h 11mSpirit Airlines
mar. 8/271:00 amSJU - ORD
2 stops17h 27mSpirit Airlines
Deal found 5/28$122
lun. 8/265:35 pmORD - SJU
1 stop16h 53mSpirit Airlines
mié. 8/284:01 pmSJU - ORD
Nonstop5h 13mSpirit Airlines
Deal found 5/28$125
mar. 8/207:27 amORD - SJU
1 stop10h 30mSpirit Airlines
mar. 8/2712:28 pmSJU - ORD
1 stop20h 57mSpirit Airlines
Deal found 5/28$128
mar. 8/275:00 amORD - SJU
1 stop13h 11mSpirit Airlines
mar. 8/271:00 amSJU - ORD
3 stops20h 35mSpirit Airlines
Deal found 5/28$129
lun. 8/266:32 pmORD - SJU
1 stop15h 56mSpirit Airlines
mar. 8/278:02 pmSJU - ORD
1 stop14h 31mSpirit Airlines
Deal found 5/28$130
mar. 8/2010:33 amORD - SJU
1 stop7h 38mSpirit Airlines
mar. 8/276:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/27$132
mar. 9/107:27 amORD - SJU
1 stop10h 30mSpirit Airlines
mar. 9/246:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/27$133

Cheap Delta flights from Chicago to Caribbean

Explore cheap flight options specifically provided by Delta 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 2,740,132 searches. Data last updated mayo 28, 2024.
mié. 6/127:00 amORD - NAS
1 stop6h 40mDelta
mar. 6/183:55 pmNAS - ORD
1 stop7h 51mDelta
Deal found 5/27$351
mar. 6/47:09 amORD - NAS
2 stops8h 20mDelta
mar. 6/112:20 pmNAS - ORD
2 stops7h 38mDelta
Deal found 5/28$356
lun. 8/2612:35 pmMDW - SJU
1 stop8h 32mDelta
mié. 8/2812:56 pmSJU - MDW
1 stop9h 50mDelta
Deal found 5/28$359
mar. 6/256:00 amORD - NAS
1 stop7h 40mDelta
vie. 7/53:55 pmNAS - ORD
1 stop7h 47mDelta
Deal found 5/27$412

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 2,740,132 searches. Prices were last updated on mayo 28, 2024.
lun. 6/108:57 pmORD - SJU
2 stops21h 18mSpirit Airlines
lun. 6/1712:30 pmSJU - ORD
1 stop20h 51mSpirit Airlines
Deal found 5/28$192
mar. 6/49:15 pmORD - SJU
1 stop14h 47mSpirit Airlines
lun. 6/103:33 amSJU - ORD
1 stop16h 32mSpirit Airlines
Deal found 5/26$193
mar. 6/116:40 pmORD - SJU
1 stop16h 01mSpirit Airlines
dom. 6/165:40 amSJU - ORD
1 stop27h 44mSpirit Airlines
Deal found 5/27$194
mié. 6/268:50 pmORD - SJU
1 stop22h 35mSpirit Airlines
mar. 7/26:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/27$195
mar. 6/117:00 amORD - SJU
3 stops27h 41mSpirit Airlines
mar. 6/189:06 pmSJU - ORD
2 stops20h 01mSpirit Airlines
Deal found 5/27$196
mar. 6/49:15 pmORD - SJU
1 stop20h 50mSpirit Airlines
mar. 6/113:49 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 5/26$197
mar. 6/1110:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
mar. 6/186:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/27$198
mar. 6/49:15 pmORD - SJU
1 stop14h 47mSpirit Airlines
mar. 6/115:51 pmSJU - ORD
3 stops20h 49mSpirit Airlines
Deal found 5/28$199
mié. 6/55:45 pmORD - SJU
1 stop16h 45mSpirit Airlines
mié. 6/1212:41 pmSJU - ORD
1 stop21h 23mSpirit Airlines
Deal found 5/27$200

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 2,740,132 searches. Data last updated mayo 28, 2024.
mar. 9/105:00 amORD - STT
1 stop10h 32mSpirit Airlines
mar. 9/1710:27 amSTT - ORD
1 stop14h 33mSpirit Airlines
Deal found 5/27$173
mar. 9/105:00 amORD - STT
1 stop10h 32mSpirit Airlines
mar. 9/1710:27 amSTT - ORD
1 stop8h 00mSpirit Airlines
Deal found 5/28$174
lun. 6/108:57 pmORD - SJU
2 stops21h 18mSpirit Airlines
lun. 6/1712:30 pmSJU - ORD
1 stop20h 51mSpirit Airlines
Deal found 5/28$192
mar. 6/49:15 pmORD - SJU
1 stop14h 47mSpirit Airlines
lun. 6/103:33 amSJU - ORD
1 stop16h 32mSpirit Airlines
Deal found 5/26$193
mar. 8/205:00 amORD - STT
1 stop10h 32mSpirit Airlines
mar. 8/2710:27 amSTT - ORD
1 stop8h 00mSpirit Airlines
Deal found 5/26$194
mar. 6/116:40 pmORD - SJU
1 stop16h 01mSpirit Airlines
dom. 6/165:40 amSJU - ORD
1 stop27h 44mSpirit Airlines
Deal found 5/27$194
sáb. 8/313:25 pmORD - SJU
1 stop26h 32mSpirit Airlines
mié. 9/115:51 amSJU - ORD
2 stops14h 06mSpirit Airlines
Deal found 5/28$195
vie. 8/239:23 amORD - SJU
Nonstop4h 48mSpirit Airlines
mar. 8/276:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/27$196
mar. 6/49:15 pmORD - SJU
1 stop20h 50mSpirit Airlines
mar. 6/113:49 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 5/26$197

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 2,740,132 searches. Data last updated mayo 28, 2024.
mar. 7/210:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
sáb. 7/66:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/27$195
vie. 8/239:23 amORD - SJU
Nonstop4h 48mSpirit Airlines
mar. 8/276:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/27$196
dom. 6/99:15 amORD - SJU
Nonstop4h 48mSpirit Airlines
mié. 6/126:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/27$197
mar. 6/1110:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
mar. 6/186:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/27$198
vie. 8/2311:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
mié. 8/286:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/28$199
mié. 6/2610:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
mar. 7/26:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/27$201
mié. 6/2610:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
mar. 7/26:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/27$202
dom. 8/259:23 amORD - SJU
Nonstop4h 48mSpirit Airlines
mié. 8/286:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/28$204
dom. 8/259:23 amORD - SJU
Nonstop4h 48mSpirit Airlines
mar. 8/276:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/28$209

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 2,740,132 searches. Data last updated mayo 28, 2024.
mar. 6/49:15 pmORD - SJU
1 stop14h 47mSpirit Airlines
lun. 6/103:33 amSJU - ORD
1 stop16h 32mSpirit Airlines
Deal found 5/26$193
mar. 6/49:15 pmORD - SJU
1 stop20h 50mSpirit Airlines
mar. 6/113:49 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 5/26$197
mar. 6/49:15 pmORD - SJU
1 stop14h 47mSpirit Airlines
mar. 6/115:51 pmSJU - ORD
3 stops20h 49mSpirit Airlines
Deal found 5/28$199
mié. 6/55:45 pmORD - SJU
1 stop16h 45mSpirit Airlines
mié. 6/1212:41 pmSJU - ORD
1 stop21h 23mSpirit Airlines
Deal found 5/27$200
mié. 6/511:01 amORD - SJU
2 stops34h 17mSpirit Airlines
mié. 6/122:00 pmSJU - ORD
1 stop27h 44mSpirit Airlines
Deal found 5/28$202
mar. 6/49:15 pmORD - SJU
1 stop14h 47mSpirit Airlines
mar. 6/115:40 amSJU - ORD
2 stops14h 25mSpirit Airlines
Deal found 5/26$205
vie. 6/710:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
mié. 6/122:00 pmSJU - ORD
1 stop20h 04mSpirit Airlines
Deal found 5/27$209
lun. 6/35:25 pmORD - SJU
1 stop24h 32mSpirit Airlines
mié. 6/52:00 pmSJU - ORD
1 stop20h 04mSpirit Airlines
Deal found 5/28$210
jue. 6/69:37 pmORD - SJU
2 stops26h 44mSpirit Airlines
mié. 6/125:40 amSJU - ORD
1 stop27h 44mSpirit Airlines
Deal found 5/27$211

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 2,740,132 searches. Data last updated mayo 28, 2024.
mar. 6/116:40 pmORD - SJU
1 stop16h 01mSpirit Airlines
Deal found 5/27$46
mar. 6/49:15 pmORD - SJU
1 stop14h 47mSpirit Airlines
Deal found 5/27$47
lun. 9/236:32 pmORD - SJU
1 stop15h 56mSpirit Airlines
Deal found 5/26$56
mar. 6/118:50 pmORD - SJU
1 stop15h 12mSpirit Airlines
Deal found 5/28$60
mar. 8/206:32 pmORD - SJU
1 stop15h 56mSpirit Airlines
Deal found 5/27$63
mar. 6/1110:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Deal found 5/27$69
lun. 6/109:10 pmORD - SJU
1 stop29h 00mSpirit Airlines
Deal found 5/27$71
mié. 8/2110:33 amORD - SJU
1 stop7h 38mSpirit Airlines
Deal found 5/27$73
lun. 9/95:35 pmORD - SJU
2 stops22h 40mSpirit Airlines
Deal found 5/27$75

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 2,740,132 searches. Data last updated mayo 28, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$115 - $351

Route

Depart

Return

Price

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 8/27

1 stop10h 30m

San Juan Luis Munoz Marin Intl

mié. 8/28

Nonstop5h 13m

$115

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 9/10

1 stop10h 30m

San Juan Luis Munoz Marin Intl

mar. 9/24

1 stop14h 36m

$120

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 8/27

1 stop13h 11m

San Juan Luis Munoz Marin Intl

mar. 8/27

2 stops17h 27m

$122

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

lun. 8/26

1 stop16h 53m

San Juan Luis Munoz Marin Intl

mié. 8/28

Nonstop5h 13m

$125

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 8/20

1 stop10h 30m

San Juan Luis Munoz Marin Intl

mar. 8/27

1 stop20h 57m

$128

Chicago MidwayPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

lun. 7/8

1 stop22h 49m

Punta Cana

jue. 7/11

1 stop12h 56m

$215

Chicago O'Hare IntlPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mar. 7/2

1 stop9h 02m

Punta Cana

vie. 7/12

1 stop9h 03m

$241

Chicago O'Hare IntlPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

sáb. 8/24

1 stop17h 05m

Punta Cana

jue. 8/29

Nonstop5h 00m

$284

Chicago O'Hare IntlNassau Intl

ORD - NAS

ORDNAS

Chicago O'Hare Intl

mié. 6/12

1 stop6h 40m

Nassau Intl

mar. 6/18

1 stop7h 51m

$351

Flights are sorted by cheapest first

Deals found on 5/28

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 mayo 28, 2024.
8.1
Very good
9,192 reviews

Overall

8.1

Food

7.3

Entertainment

7.3

Boarding

8.2

Comfort

7.9

Crew

8.6

Reviews

1 / 10

Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.

8.1
Very good
9,192 reviews
8.1
Very good
9,192 reviews

Overall

8.1

Food

7.3

Entertainment

7.3

Boarding

8.2

Comfort

7.9

Crew

8.6

Reviews

1 / 10

Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.

8.0
Very good
10,502 reviews
8.1
Very good
9,192 reviews

Overall

8.1

Food

7.3

Entertainment

7.3

Boarding

8.2

Comfort

7.9

Crew

8.6

Reviews

1 / 10

Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.

7.9
Good
1,528 reviews
8.1
Very good
9,192 reviews

Overall

8.1

Food

7.3

Entertainment

7.3

Boarding

8.2

Comfort

7.9

Crew

8.6

Reviews

1 / 10

Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.

7.6
Good
4,383 reviews
8.1
Very good
9,192 reviews

Overall

8.1

Food

7.3

Entertainment

7.3

Boarding

8.2

Comfort

7.9

Crew

8.6

Reviews

1 / 10

Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.

Avelo Airlines
7.5
Good
69 reviews
8.1
Very good
9,192 reviews

Overall

8.1

Food

7.3

Entertainment

7.3

Boarding

8.2

Comfort

7.9

Crew

8.6

Reviews

1 / 10

Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.

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 $115, but on average you can expect to pay $133.

  • 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 $215.

  • 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?

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

    The top 3 most reliable airlines when flying from Chicago to Caribbean are Alaska Airlines (93%), American Airlines (92%) and United Airlines (83%).

  • What are the cheapest flights from Chicago to Caribbean?

    Looking for the cheapest flight from Chicago to Caribbean? While on average our users pay $600, our data indicates the cheapest price to be $105. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $120.

  • 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 5/28.

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

  • When is the best time 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 $248). 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

Browse thousands of different options on Cheapflights for your next trip

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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.

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 2,740,132 searches. Data last updated mayo 28, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$329FlexibilityNo cancel feeOn-time62%
Search Frontier flights
Spirit AirlinesCheapest$130Average$384FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights
DeltaCheapest$135Average$615FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapest$152Average$609FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
JetBlueCheapest$172Average$545FlexibilityNo cancel feeOn-time62%
Search JetBlue flights
AeromexicoCheapest$262Average$548FlexibilityNo cancel feeOn-timeN/A
Search Aeromexico flights
Air CanadaCheapest$283Average$846FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Alaska AirlinesCheapest$288Average$620FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
American AirlinesCheapest$291Average$611FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
LufthansaCheapest$404Average$446FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights

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.

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 mayo 28, 2024.
17%of flight departures