HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news

Cheap flights from Caribbean to Chicago (CHI) from $75

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.
SJU — CHI
Jun 10 — Jun 171
From?
To?
Mon 6/10
Mon 6/17
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 Caribbean to Chicago?

Users have found that booking a flight from Caribbean to Chicago at least 16 days early can save you up to 85% on average compared to booking a flight this week. If booking 16 days before your flight isn’t an option for you, users have found flights from Caribbean to Chicago for as little as $238 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $312 for flights departing within the next 3 days.

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

Flights from Caribbean to Chicago lean towards being more expensive in March. Prices are generally better when you fly from Caribbean to Chicago in January, with the cheapest ticket starting at $122.

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

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

Cheap Caribbean to Chicago flights in June & July 2024

Find cheap flight options from Caribbean to Chicago specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Prices were last updated on June 5, 2024.
Tue 7/212:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Tue 7/98:50 pmORD - SJU
1 stop14h 41mSpirit Airlines
Deal found 6/5$136
Tue 7/212:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Thu 7/1110:02 amORD - SJU
1 stop9h 23mSpirit Airlines
Deal found 6/4$167
Tue 7/212:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Thu 7/1110:02 amORD - SJU
1 stop9h 23mSpirit Airlines
Deal found 6/4$169
Tue 7/22:59 pmSJU - ORD
1 stop7h 11mSpirit Airlines
Tue 7/98:50 pmORD - SJU
1 stop14h 41mSpirit Airlines
Deal found 6/4$170
Tue 7/26:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Tue 7/98:50 pmORD - SJU
1 stop14h 41mSpirit Airlines
Deal found 6/5$174
Tue 7/26:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Thu 7/1110:02 amORD - SJU
1 stop9h 23mSpirit Airlines
Deal found 6/4$176
Wed 6/123:49 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Sun 6/306:40 pmORD - SJU
1 stop15h 50mSpirit Airlines
Deal found 6/4$180
Thu 6/2012:30 pmSJU - ORD
1 stop21h 34mSpirit Airlines
Tue 6/258:50 pmORD - SJU
1 stop21h 15mSpirit Airlines
Deal found 6/4$181
Thu 7/48:06 pmSJU - ORD
1 stop14h 55mSpirit Airlines
Wed 7/105:00 amORD - SJU
1 stop11h 43mSpirit Airlines
Deal found 6/4$182

Caribbean to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Caribbean and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 5, 2024.
Tue 8/208:50 pmSJU - ORD
Nonstop4h 59mSpirit Airlines
Sat 8/246:50 amORD - SJU
1 stop6h 48mSpirit Airlines
Deal found 6/5$173
Tue 7/26:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Tue 7/98:50 pmORD - SJU
1 stop14h 41mSpirit Airlines
Deal found 6/5$174
Wed 8/148:59 pmSJU - ORD
Nonstop4h 59mSpirit Airlines
Wed 8/217:00 amORD - SJU
1 stop6h 45mSpirit Airlines
Deal found 6/4$175
Tue 7/26:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Thu 7/1110:02 amORD - SJU
1 stop9h 23mSpirit Airlines
Deal found 6/4$176
Thu 9/57:57 pmSJU - ORD
1 stop14h 36mSpirit Airlines
Sun 9/86:32 pmORD - SJU
1 stop15h 56mSpirit Airlines
Deal found 6/4$179
Tue 8/201:52 amSJU - ORD
2 stops14h 05mSpirit Airlines
Wed 8/282:10 pmORD - SJU
Nonstop4h 47mSpirit Airlines
Deal found 6/3$180
Tue 8/201:52 amSJU - ORD
2 stops14h 05mSpirit Airlines
Tue 8/272:10 pmORD - SJU
Nonstop4h 47mSpirit Airlines
Deal found 6/3$181
Tue 8/278:59 pmSJU - ORD
Nonstop4h 59mSpirit Airlines
Sat 8/318:08 pmORD - SJU
1 stop17h 37mSpirit Airlines
Deal found 6/4$182
Tue 7/28:06 pmSJU - ORD
2 stops22h 01mSpirit Airlines
Tue 7/98:50 pmORD - SJU
1 stop14h 41mSpirit Airlines
Deal found 6/5$183

Caribbean to Chicago flights leaving soon

Find last-minute flight options from Caribbean to Chicago 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 3,050,429 searches. Data last updated June 5, 2024.
Wed 6/123:49 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Sun 6/306:40 pmORD - SJU
1 stop15h 50mSpirit Airlines
Deal found 6/4$180
Wed 6/123:49 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Sun 6/309:24 amORD - SJU
1 stop10h 01mSpirit Airlines
Deal found 6/5$191
Wed 6/126:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Sun 6/309:15 amORD - SJU
Nonstop4h 48mSpirit Airlines
Deal found 6/4$199
Tue 6/1112:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Sun 6/306:40 pmORD - SJU
1 stop15h 50mSpirit Airlines
Deal found 6/4$203
Wed 6/123:49 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Thu 6/139:24 amORD - SJU
1 stop8h 41mSpirit Airlines
Deal found 6/4$215
Tue 6/1112:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Sun 6/309:15 amORD - SJU
Nonstop4h 48mSpirit Airlines
Deal found 6/4$222
Wed 6/123:49 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Sun 6/3010:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Deal found 6/5$223
Wed 6/123:49 pmSJU - ORD
Nonstop5h 11mMultiple Airlines
Fri 6/145:58 pmORD - SJU
1 stop21h 52mMultiple Airlines
Deal found 6/4$224
Thu 6/138:30 pmSJU - ORD
1 stop13h 44mSpirit Airlines
Wed 6/1911:01 amORD - SJU
2 stops31h 04mSpirit Airlines
Deal found 6/4$231

One-way flights to Chicago from Caribbean

Search for one-way flight options from Caribbean to Chicago. 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 3,050,429 searches. Data last updated June 5, 2024.
Tue 6/1112:41 pmSJU - ORD
1 stop29h 59mSpirit Airlines
Deal found 6/4$75
Wed 8/217:54 pmSJU - ORD
1 stop15h 01mSpirit Airlines
Deal found 6/4$78
Wed 8/217:54 pmSJU - ORD
1 stop15h 01mSpirit Airlines
Deal found 6/4$81
Tue 6/189:06 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Deal found 6/4$82
Tue 6/189:06 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Deal found 6/4$83
Wed 6/263:49 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 6/4$84
Thu 6/138:30 pmSJU - ORD
1 stop13h 44mSpirit Airlines
Deal found 6/5$86
Sat 6/2212:41 pmSJU - ORD
1 stop8h 08mSpirit Airlines
Deal found 6/4$89
Thu 7/48:06 pmSJU - ORD
1 stop14h 55mSpirit Airlines
Deal found 6/5$90

Find flights from Caribbean to Chicago within your budget

Customize your flight search to find flights from Caribbean to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 5, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$136 - $357

Route

Depart

Return

Price

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 7/2

1 stop9h 29m

Chicago O'Hare Intl

Tue 7/9

1 stop14h 41m

$136

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 8/14

Nonstop4h 59m

Chicago O'Hare Intl

Mon 8/26

1 stop17h 30m

$139

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 9/11

1 stop15h 16m

Chicago O'Hare Intl

Wed 9/25

1 stop6h 45m

$148

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 6/20

1 stop13h 23m

Chicago O'Hare Intl

Sat 6/22

1 stop28h 27m

$201

Punta CanaChicago Midway

PUJ - MDW

PUJMDW

Punta Cana

Tue 7/9

1 stop27h 01m

Chicago Midway

Tue 7/16

1 stop11h 17m

$229

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Mon 8/19

1 stop10h 19m

Chicago O'Hare Intl

Sat 8/24

1 stop9h 35m

$256

Punta CanaChicago O'Hare Intl

PUJ - ORD

PUJORD

Punta Cana

Wed 10/23

1 stop16h 01m

Chicago O'Hare Intl

Sun 10/27

Nonstop4h 28m

$311

San Juan Luis Munoz Marin IntlChicago Midway

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/31

1 stop9h 50m

Chicago Midway

Tue 11/5

1 stop9h 04m

$344

Montego Bay Sangster IntlChicago O'Hare Intl

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Thu 7/4

Nonstop4h 30m

Chicago O'Hare Intl

Tue 7/9

Nonstop4h 00m

$357

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 Caribbean to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Caribbean with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 5, 2024.
Delta
8.0
Very good
10,368 reviews

Boarding

8.2

Comfort

7.9

Crew

8.6

Food

7.4

Entertainment

8.0

Overall

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Delta
8.0
Very good
10,368 reviews
Delta
8.0
Very good
10,368 reviews

Boarding

8.2

Comfort

7.9

Crew

8.6

Food

7.4

Entertainment

8.0

Overall

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Copa Airlines
8.0
Very good
2,568 reviews
Delta
8.0
Very good
10,368 reviews

Boarding

8.2

Comfort

7.9

Crew

8.6

Food

7.4

Entertainment

8.0

Overall

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

KLM
7.9
Good
1,493 reviews
Delta
8.0
Very good
10,368 reviews

Boarding

8.2

Comfort

7.9

Crew

8.6

Food

7.4

Entertainment

8.0

Overall

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

JetBlue
7.6
Good
4,316 reviews
Delta
8.0
Very good
10,368 reviews

Boarding

8.2

Comfort

7.9

Crew

8.6

Food

7.4

Entertainment

8.0

Overall

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Aeromexico
7.6
Good
2,447 reviews
Delta
8.0
Very good
10,368 reviews

Boarding

8.2

Comfort

7.9

Crew

8.6

Food

7.4

Entertainment

8.0

Overall

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Related info for your journey

Find useful and relevant information for your journey from Caribbean to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find flights from Caribbean to Chicago for under $200 on Cheapflights?

    Yes, there are multiple flights from Caribbean to Chicago for under $200. The cheapest flight booked recently is on Spirit Airlines for just $136, but on average you can expect to pay $163.

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

    Cheapflights has at least 20 direct flights from Caribbean to Chicago under $200. A good price for a nonstop flight from Caribbean to Chicago is less than $220.

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

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

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

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

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

    The top 3 most reliable airlines when flying from Caribbean to Chicago are Air Canada (85%), United Airlines (85%) and Air New Zealand (85%).

  • What are the cheapest flights from Caribbean to Chicago?

    While on average a flight from Caribbean to Chicago is generally $347, our data shows the cheapest flight currently is $109. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $139 for that flight.

  • What does SJU to ORD mean?

    Great question - SJU to ORD just means San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport. Now you’ll know what these unique codes when you look for flights! Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

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

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

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Caribbean to Chicago that allow pets onboard?

    Many airlines flying from Caribbean to Chicago 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 Caribbean to Chicago?

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

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

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

    Before booking your flight from Caribbean to Chicago check out the most popular airlines for this route: American Airlines, JetBlue or Delta.

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

    Currently, February is the cheapest month in which you can book a flight from Caribbean to Chicago (average of $244). Flying from Caribbean to Chicago in July is currently the most expensive (average of $324). 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

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

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

Newark to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Seattle to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Newark to Midway flights
Boston to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Baltimore to O'Hare Intl flights
Orlando to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Atlanta to Midway flights
Philadelphia to O'Hare Intl flights
Tampa to O'Hare Intl flights
Austin to O'Hare Intl flights
Ontario to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
LaGuardia to Midway flights
Seattle to Midway flights
Burbank to O'Hare Intl flights
Los Angeles to Midway flights
Baltimore to Midway flights
Dulles Intl to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Denver to O'Hare Intl flights
Dulles Intl to Midway flights
San Diego to O'Hare Intl flights
Oakland to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Miami to O'Hare Intl flights
Reagan-National to Midway flights
Boston to Midway flights
Mexico City to O'Hare Intl flights
Hobby to Midway flights
George Bush Intcntl to O'Hare Intl flights
Frankfurt to O'Hare Intl flights
Minneapolis to Midway flights
Hobby to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Ontario to Midway flights
Salt Lake City to O'Hare Intl flights
Portland to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Hartford to O'Hare Intl flights
San Jose to O'Hare Intl flights

Top 7 airlines flying from Caribbean to Chicago

Discover the top 7 airlines that operate flights from Caribbean to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 5, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$112Average$332FlexibilityNo cancel feeOn-time65%
FrontierCheapest$114Average$264FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$149Average$513FlexibilityNo cancel feeOn-time69%
DeltaCheapest$160Average$494FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$168Average$310FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$279Average$538FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$359Average$568FlexibilityNo cancel feeOn-time70%
New York to Paris flights
Denver to Dallas flights
San Francisco to New Delhi flights
Phoenix to Hawaii flights
Nashville to Orlando flights
Austin to Dallas flights
Charlotte to Los Angeles flights
USA to India flights
Orlando to Dallas flights
Los Angeles to Mumbai flights
San Francisco to San Diego flights
Caribbean to Charlottesville flights

Search flights from Caribbean to Chicago by cabin class

Find flights from Caribbean to Chicago, 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 Caribbean to Chicago

Find hourly flight availability from Caribbean to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 5, 2024.
6%of flight departuresEarly morningMidnight to 6 am
10%of flight departuresMorning6 am to noon
84%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 Gaziantep
Flights to Miyakojima Hirara
Flights to Figari-Sud Corse
Flights to Mason City
Flights to Komatsu
Flights to Sendai
Flights to Rhinelander Oneida County
Flights to Constanţa Mihail Kogalniceanu
Flights to Brainerd Crow Wing County
Flights to Reus
Flights to Virac
Flights to Neiva La Marguita
Flights to Pellston Emmet County
Flights to Urumqi
Flights to Bastia Poretta
Flights to Samos
Flights to Hyannis Barnstable
Flights to Provincetown
Flights to Alghero-Fertilia
Flights to Laayoune Hassan I
Flights to Devils Lake
Flights to Vava'u Lupepau'U
Flights to Hakodate
Flights to Edremit/Korfez

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 Caribbean to Chicago?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Caribbean today with Cheapflights!

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

Cheapflights helps you find that perfect flight to Chicago from Caribbean by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

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

Cheapflights does show flights with no change fees to all users. To see these options for flights from Caribbean to Chicago, users can toggle the no change fees filter when performing a flight search.

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

Yes! Start tracking prices for Caribbean to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your 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