Cheap flights from Chicago (CHI) to Caribbean

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How to find the cheapest flight from
Chicago (CHI) to Caribbean

How far in advance should I book a flight from Chicago to Caribbean?

Users have found that booking a flight from Chicago to Caribbean at least 19 days early can save you up to 7% on average compared to booking a flight this week. If booking 19 days before your flight isn’t an option for you, users have found flights from Chicago to Caribbean for as little as $262 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 $281 for flights departing within the next 3 days.

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

Flights from Chicago to Caribbean lean towards being more expensive in December. Prices are generally better when you fly from Chicago to Caribbean in August, with the cheapest ticket starting at $121.

Cheap flights from Chicago to Caribbean in April, May 2021

2 May - 6 May
$145pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
16 May - 19 May
$149pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
5 May - 13 May
$153pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
STT
Saint Thomas Island Cyril E King
STT
Saint Thomas Island Cyril E King
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to Caribbean 2021 flight deals

2 May - 6 May
$145pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
16 May - 19 May
$149pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
5 May - 13 May
$153pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
STT
Saint Thomas Island Cyril E King
STT
Saint Thomas Island Cyril E King
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Non-stop flights to Caribbean from Chicago

17 Apr - 1 May
$157pp
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
10 May - 14 May
$158pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl
9 May - 13 May
$159pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Caribbean

17 Apr - 1 May
$157pp
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
17 Apr - 30 Apr
$161pp
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
18 Apr - 21 Apr
$162pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to Caribbean from Chicago

4:00 am - 4:11 pm
United Airlines
1 Stop
11h 11m
ORD - SJU
United Airlines
$83
United
5:05 am - 9:49 pm
Multiple Airlines
2 Stops
15h 44m
ORD - SJU
Multiple Airlines
$92
SmartFares
11:45 am - 7:01 pm
Delta
1 Stop
6h 16m
MDW - SJU
Delta
$99
Delta

Related info for your journey

Flight FAQs

From Chicago to Caribbean

Are flight prices decreasing from Chicago to Caribbean due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Chicago and Caribbean for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from Chicago to Caribbean to control the spread of COVID-19?

New policies can now be found on Delta and Alaska Airlines to help keep travelers safe while flying. New policies for travelers booking flights from Chicago to Caribbean include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially distanced seating (for a limited time). Keep in mind that policies will vary by airline.

Which airlines flying from Chicago to Caribbean have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Chicago to Caribbean that may be offering flexible cancellation policies are United Airlines, American Airlines, and Spirit Airlines. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

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 $153, but on average you can expect to pay $162.

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 $192.

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 airlines that fly from Chicago to Caribbean?

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

What are the most popular routes from Chicago to Caribbean?

Most travelers choose Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago O'Hare Intl - Punta Cana or Chicago Midway - San Juan Luis Munoz Marin Intl when deciding on the best route from Chicago to Caribbean.

What are the cheapest Flights from Chicago to Caribbean?

The cheapest flight price from Chicago to Caribbean is $94. On average you can expect to pay $677. The most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $157.

What are the most reliable airlines from Chicago to Caribbean?

Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Caribbean on time: Air Canada(96%), United Airlines(96%), Air New Zealand(96%.)

How long is the flight from Chicago to Caribbean?

A quick flight from Chicago to Caribbean can take about 4h 46m. United Airlines provides one of the quickest options available for as low as $157. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What are the cheapest airlines flying from Chicago to Caribbean round-trip?

According to our current data, Spirit Airlines ($153), United Airlines ($157), and Frontier ($176) offers the cheapest pricing from Chicago to Caribbean.

What are the cheapest airlines to fly from Chicago to Caribbean one-way?

The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $60. However, be on the lookout for offers from United Airlines and Frontier, as they are both options that can get you from Chicago to Caribbean for a low price.

Destination points for flights from Chicago to Caribbean

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Destination information for Caribbean

Today's exchange rate
$1 = $1.00
Flight duration
5h 02m

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 9 airlines flying from Chicago to Caribbean

Airline Cheapest Average Flexibility On-time COVID-19 safety
Spirit Airlines
$112 $364 No cancel fee 65%
Aeromexico
$203 $371 No cancel fee N/A
Frontier
$90 $386 No cancel fee 62%
Copa Airlines
$199 $434 No cancel fee 70%
JetBlue
$151 $434 No cancel fee 62%
American Airlines
$185 $542 No cancel fee 71%
Delta
$163 $584 No cancel fee N/A
United Airlines
$183 $587 No cancel fee 69%
Air Canada
$272 $608 No cancel fee 67%
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