HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news

Cheap flights from Chicago (CHI) to Caribbean from $81

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 8/12. 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 21 — May 281
From?
To?
Tue 5/21
Tue 5/28
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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 2,637,452 searches. Data last updated May 16, 2024.
Tue 8/205:00 amORD - SJU
1 stop13h 11mSpirit Airlines
Tue 8/2712:28 pmSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 5/15$114
Tue 8/207:27 amORD - SJU
1 stop10h 30mSpirit Airlines
Tue 8/2712:28 pmSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 5/15$127
Thu 5/309:03 amORD - SJU
1 stop8h 54mSpirit Airlines
Mon 6/39:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/15$129
Wed 9/1110:33 amORD - SJU
1 stop7h 38mSpirit Airlines
Sat 9/2112:28 pmSJU - ORD
1 stop9h 04mSpirit Airlines
Deal found 5/14$131
Tue 9/1010:33 amORD - SJU
1 stop7h 38mSpirit Airlines
Tue 9/1712:28 pmSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 5/15$135
Tue 8/2010:33 amORD - SJU
1 stop7h 38mSpirit Airlines
Tue 8/274:01 pmSJU - ORD
Nonstop5h 13mSpirit Airlines
Deal found 5/15$137
Mon 9/166:32 pmORD - SJU
1 stop15h 56mSpirit Airlines
Sat 9/2112:28 pmSJU - ORD
1 stop9h 04mSpirit Airlines
Deal found 5/15$148
Tue 8/207:03 amORD - SJU
2 stops10h 54mSpirit Airlines
Tue 8/2712:28 pmSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 5/15$152
Thu 5/3010:03 amORD - SJU
1 stop7h 54mSpirit Airlines
Mon 6/39:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/15$153

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 2,637,452 searches. Data last updated May 16, 2024.
Wed 6/127:00 amORD - NAS
1 stop6h 40mDelta
Tue 6/183:55 pmNAS - ORD
1 stop7h 51mDelta
Deal found 5/16$351
Fri 7/123:47 pmMDW - SJU
1 stop6h 12mDelta
Sat 7/276:10 amSJU - MDW
1 stop9h 47mDelta
Deal found 5/15$373
Sat 5/255:57 pmORD - SXM
1 stop18h 43mDelta
Thu 5/303:10 pmSXM - ORD
1 stop18h 07mDelta
Deal found 5/15$857

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 2,637,452 searches. Prices were last updated on May 16, 2024.
Thu 5/3011:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Mon 6/39:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/15$184
Fri 5/3111:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Tue 6/49:07 pmSJU - ORD
1 stop13h 54mSpirit Airlines
Deal found 5/15$185
Tue 6/118:50 pmORD - SJU
1 stop15h 12mSpirit Airlines
Mon 6/178:06 pmSJU - ORD
1 stop14h 55mSpirit Airlines
Deal found 5/15$187
Sat 6/111:05 amORD - SJU
1 stop12h 42mMultiple Airlines
Wed 6/59:06 pmSJU - ORD
1 stop13h 55mMultiple Airlines
Deal found 5/15$188
Mon 6/35:25 pmORD - SJU
1 stop24h 32mSpirit Airlines
Tue 7/239:15 pmSJU - ORD
1 stop13h 08mSpirit Airlines
Deal found 5/15$189
Sun 6/26:32 amORD - SJU
1 stop28h 11mSpirit Airlines
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/15$191
Sat 6/111:05 amORD - SJU
1 stop12h 42mMultiple Airlines
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mMultiple Airlines
Deal found 5/15$192
Thu 5/309:03 amORD - SJU
1 stop8h 54mSpirit Airlines
Tue 6/412:32 pmSJU - ORD
1 stop10h 24mSpirit Airlines
Deal found 5/15$193
Tue 6/45:41 pmORD - STT
1 stop14h 59mSpirit Airlines
Tue 6/1110:30 amSTT - ORD
1 stop6h 58mSpirit Airlines
Deal found 5/15$194

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 2,637,452 searches. Data last updated May 16, 2024.
Tue 7/27:36 amORD - SJU
1 stop10h 29mSpirit Airlines
Tue 7/99:06 pmSJU - ORD
1 stop13h 17mSpirit Airlines
Deal found 5/15$183
Thu 5/3011:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Mon 6/39:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/15$184
Fri 5/3111:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Tue 6/49:07 pmSJU - ORD
1 stop13h 54mSpirit Airlines
Deal found 5/15$185
Tue 8/207:03 amORD - SJU
2 stops10h 54mSpirit Airlines
Sat 8/2412:28 pmSJU - ORD
1 stop9h 04mSpirit Airlines
Deal found 5/15$186
Wed 8/2811:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Tue 9/106:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/15$187
Sat 6/111:05 amORD - SJU
1 stop12h 42mMultiple Airlines
Wed 6/59:06 pmSJU - ORD
1 stop13h 55mMultiple Airlines
Deal found 5/15$188
Mon 6/35:25 pmORD - SJU
1 stop24h 32mSpirit Airlines
Tue 7/239:15 pmSJU - ORD
1 stop13h 08mSpirit Airlines
Deal found 5/15$189
Mon 9/165:35 pmORD - SJU
1 stop16h 53mSpirit Airlines
Sat 9/216:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/15$190
Sun 6/26:32 amORD - SJU
1 stop28h 11mSpirit Airlines
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/15$191

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 2,637,452 searches. Data last updated May 16, 2024.
Tue 9/1011:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Tue 9/176:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/15$177
Tue 8/209:23 amORD - SJU
Nonstop4h 48mSpirit Airlines
Tue 8/274:01 pmSJU - ORD
Nonstop5h 13mSpirit Airlines
Deal found 5/15$182
Wed 8/2811:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Tue 9/106:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/15$187
Fri 5/3111:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Tue 6/46:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 5/14$196
Wed 9/1111:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Sat 9/216:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/14$201
Tue 8/209:23 amORD - SJU
Nonstop4h 48mSpirit Airlines
Tue 8/274:01 pmSJU - ORD
Nonstop5h 13mSpirit Airlines
Deal found 5/15$202
Fri 5/3111:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/14$204
Wed 8/289:23 amORD - SJU
Nonstop4h 48mSpirit Airlines
Sat 9/76:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/15$213
Wed 6/510:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Wed 6/126:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/15$215

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 2,637,452 searches. Data last updated May 16, 2024.
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Wed 5/299:07 pmSJU - ORD
2 stops20h 21mSpirit Airlines
Deal found 5/14$194
Tue 5/215:56 pmORD - SJU
1 stop7h 13mMultiple Airlines
Sat 5/2512:32 pmSJU - ORD
1 stop9h 00mMultiple Airlines
Deal found 5/15$197
Sat 5/256:40 pmORD - SJU
1 stop15h 52mSpirit Airlines
Mon 6/39:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/15$198
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Wed 5/2912:32 pmSJU - ORD
3 stops22h 23mSpirit Airlines
Deal found 5/14$200
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Fri 5/319:00 pmSJU - ORD
3 stops22h 23mSpirit Airlines
Deal found 5/14$201
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Thu 5/3011:07 pmSJU - ORD
1 stop11h 48mSpirit Airlines
Deal found 5/14$204
Sat 5/2511:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Mon 6/39:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/15$205
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Fri 5/319:00 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Deal found 5/14$206
Tue 5/219:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Fri 5/319:00 pmSJU - ORD
2 stops22h 23mSpirit Airlines
Deal found 5/14$210

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 2,637,452 searches. Data last updated May 16, 2024.
Mon 8/126:26 amORD - PUJ
Nonstop4h 41mFrontier
Deal found 5/14$81
Sat 8/106:59 amORD - PUJ
Nonstop4h 41mFrontier
Deal found 5/14$82
Tue 6/47:00 amORD - SJU
2 stops10h 57mSpirit Airlines
Deal found 5/15$87
Thu 5/3010:03 amORD - SJU
1 stop7h 54mSpirit Airlines
Deal found 5/14$88
Wed 5/298:09 pmORD - SJU
1 stop21h 48mSpirit Airlines
Deal found 5/14$89
Tue 6/49:57 amORD - SJU
1 stop8h 00mSpirit Airlines
Deal found 5/15$90
Mon 6/35:25 pmORD - SJU
1 stop24h 32mSpirit Airlines
Deal found 5/15$91
Wed 10/25:00 amORD - SXM
1 stop7h 44mSpirit Airlines
Deal found 5/15$91
Wed 5/297:20 amORD - SJU
2 stops18h 45mSpirit Airlines
Deal found 5/15$95

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 2,637,452 searches. Data last updated May 16, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$114 - $351

Route

Depart

Return

Price

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/20

1 stop13h 11m

San Juan Luis Munoz Marin Intl

Tue 8/27

1 stop10h 28m

$114

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/20

1 stop10h 30m

San Juan Luis Munoz Marin Intl

Tue 8/27

1 stop10h 28m

$127

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 5/30

1 stop8h 54m

San Juan Luis Munoz Marin Intl

Mon 6/3

1 stop13h 48m

$129

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 9/11

1 stop7h 38m

San Juan Luis Munoz Marin Intl

Sat 9/21

1 stop9h 04m

$131

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 5/29

1 stop12h 52m

San Juan Luis Munoz Marin Intl

Tue 6/4

1 stop13h 54m

$171

Chicago O'Hare IntlPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 7/7

Nonstop4h 44m

Punta Cana

Tue 8/6

Nonstop5h 03m

$179

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 6/1

1 stop8h 29m

San Juan Luis Munoz Marin Intl

Tue 6/4

1 stop13h 54m

$179

Chicago O'Hare IntlNassau Intl

ORD - NAS

ORDNAS

Chicago O'Hare Intl

Wed 6/19

1 stop7h 33m

Nassau Intl

Tue 6/25

1 stop14h 25m

$350

Chicago O'Hare IntlNassau Intl

ORD - NAS

ORDNAS

Chicago O'Hare Intl

Wed 6/12

1 stop6h 40m

Nassau Intl

Tue 6/18

1 stop7h 51m

$351

Flights are sorted by cheapest first

Deals found on 5/15

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 16, 2024.
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Food

7.4

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Delta
8.0
Very good
10,673 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Food

7.4

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

JetBlue
7.6
Good
4,472 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Food

7.4

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

WestJet
7.5
Good
2,919 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Food

7.4

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Avianca
7.5
Good
3,765 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Food

7.4

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

United Airlines
7.4
Good
10,924 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Food

7.4

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

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 $114, but on average you can expect to pay $152.

  • 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 $213.

  • 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 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 $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 $114.

  • 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 5/15.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.

O'Hare Intl to Cancún flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Seattle flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Orlando flights
O'Hare Intl to Newark flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Denver flights
O'Hare Intl to Heathrow flights
O'Hare Intl to Mexico City flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Boston flights
O'Hare Intl to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Miami flights
O'Hare Intl to Tampa flights
Midway to Newark flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Athens flights
Midway to Cancún flights
Midway to LaGuardia flights
O'Hare Intl to Charles de Gaulle flights
O'Hare Intl to Dublin flights
O'Hare Intl to Atlanta flights
O'Hare Intl to Reagan-National flights
Midway to John F Kennedy Intl flights
Midway to Seattle flights
O'Hare Intl to Haneda flights
O'Hare Intl to London City flights
O'Hare Intl to Baltimore flights
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Gatwick flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to San Diego flights
Midway to Atlanta flights
O'Hare Intl to Madrid flights
Midway to Mexico City flights
O'Hare Intl to Frederic Chopin flights
O'Hare Intl to Narita flights
O'Hare Intl to Istanbul flights
O'Hare Intl to Austin flights
O'Hare Intl to Ontario flights
O'Hare Intl to Cozumel flights
Midway to Los Angeles flights
O'Hare Intl to Barcelona-El Prat flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to Nashville flights
O'Hare Intl to Portland flights

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 2,637,452 searches. Data last updated May 16, 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%
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$405Average$452FlexibilityNo cancel feeOn-time76%
Search Lufthansa flights
Los Angeles to Chicago flights
Phoenix to Seattle flights
Houston to New Orleans flights
Detroit to Miami flights
Seattle to Salt Lake City flights
Hartford to Orlando flights
Seattle to Los Angeles flights
Los Angeles to Oakland, California flights
Los Angeles to Dallas flights
Honolulu to Maui flights
New York to Jamaica flights
Chicago to Middle East 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.
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 May 16, 2024.
18%of flight departuresEarly morningMidnight to 6 am
82%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Book a flight to one of these trending destinations

User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Flights to Montes Claros
Flights to Girona Costa Brava
Flights to Naxos
Flights to Bourgas
Flights to Hyannis Barnstable
Flights to Samos
Flights to Reggio Calabria Tito Menniti
Flights to Devils Lake
Flights to Ningbo Lishe Intl
Flights to Pellston Emmet County
Flights to Provincetown
Flights to Cortez Montezuma County
Flights to Ohrid
Flights to Oran Es Senia
Flights to Menorca/Mahon
Flights to Hakodate
Flights to Ordu/Giresun
Flights to Laayoune Hassan I
Flights to Cornwall Newquay
Flights to Melilla
Flights to Rennes St Jacques
Flights to Parikia Paros
Flights to Constanţa Mihail Kogalniceanu
Flights to Miyakojima Hirara

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.

100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines