Cheap flights from Chicago (CHI) to Caribbean

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

All the information you need to plan the best CHI to SJU flight in 2022: compare Chicago to Caribbean flight prices with the expected peak season, weather and rainfall in Caribbean.
What is the cheapest month to fly from Chicago to Caribbean?

August is one of the best times of the year to fly to Caribbean from Chicago. Prices for August average $307 per person but you can even find prices for as low as $118. The most expensive prices can be found in the month of December. Opting for a August flight can save you 81% on your journey compared to booking in August

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.

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

Travelers have found it’s best to book a flight 18 days in advance to save up to 13% 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 18 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 $256, or $302 for flights within the next 24 hours.

Cheap flights from Chicago to Caribbean in January, February 2022

The best prices found for CHI to Caribbean flights for January, February
25 Jan - 2 Feb
$104pp
ORD
Chicago O'Hare Intl
Spirit 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
26 Jan - 1 Feb
$105pp
ORD
Chicago O'Hare Intl
Spirit 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
8 Feb - 16 Feb
$106pp
ORD
Chicago O'Hare Intl
Spirit 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

Chicago to Caribbean 2022 flight deals

Cheap flights to Caribbean from Chicago found for this year
26 Apr - 3 May
$103pp
ORD
Chicago O'Hare Intl
Spirit 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
25 Jan - 2 Feb
$104pp
ORD
Chicago O'Hare Intl
Spirit 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
26 Jan - 1 Feb
$105pp
ORD
Chicago O'Hare Intl
Spirit 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

Non-stop flights to Caribbean from Chicago

Save time with Chicago to Caribbean direct flight deals
23 Feb - 2 Mar
$127pp
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl
23 Feb - 1 Mar
$129pp
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl
23 Feb - 24 Feb
$133pp
ORD
Chicago O'Hare Intl
Frontier
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

Late deals on round-trip flights to Caribbean from Chicago, departing today and this week
25 Jan - 2 Feb
$104pp
ORD
Chicago O'Hare Intl
Spirit 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
26 Jan - 1 Feb
$105pp
ORD
Chicago O'Hare Intl
Spirit 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
25 Jan - 27 Jan
$114pp
ORD
Chicago O'Hare Intl
Spirit 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

The cheapest one-way flights from Chicago to Caribbean
1:34 am - 10:23 am
Frontier
1 Stop
7h 49m
ORD - NAS
Frontier
$75
Flights by SU
2:51 am - 11:27 am
Spirit Airlines
1 Stop
6h 36m
ORD - SJU
Spirit Airlines
$76
FareScan
12:40 am - 11:04 am
JetBlue
1 Stop
9h 24m
ORD - NAS
JetBlue

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Chicago</span> to <span class="emphasized">Caribbean</span> flights.

Flight FAQs

From Chicago to Caribbean

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 $103, but on average you can expect to pay $119.

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 $148.

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 cheapest airlines to fly from Chicago to Caribbean one-way?

$48 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and JetBlue, with prices starting from $52 and $77, respectively.

What are the cheapest flights from Chicago to Caribbean?

Looking for the cheapest flight from Chicago to Caribbean? While on average our users pay $612, our data indicates the cheapest price to be $61. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $103.

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?

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 reliable airlines from Chicago to Caribbean?

The top 3 most reliable airlines when flying from Chicago to Caribbean are Qatar Airways (93%), Air Canada (91%) and Air New Zealand (91%).

Destination information for Caribbean

Things to know before you go - useful duration and weather info for your trip from Chicago to Caribbean.
Today's exchange rate
$1 = $1.00
Flight duration from Chicago to Caribbean
4h 54m

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Top 10 airlines flying from Chicago to Caribbean

The chart below displays the airlines Cheapflights users traveling from Chicago to Caribbean choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Frontier
$90 $386 No cancel fee 62%
Spirit Airlines
$112 $367 No cancel fee 65%
JetBlue
$151 $452 No cancel fee 62%
Delta
$163 $597 No cancel fee N/A
United Airlines
$183 $562 No cancel fee 69%
American Airlines
$185 $539 No cancel fee 71%
Copa Airlines
$199 $432 No cancel fee 70%
Aeromexico
$203 $371 No cancel fee N/A
Air Canada
$272 $608 No cancel fee 67%
Avianca
$502 $571 No cancel fee 71%
Home Caribbean Cheap flights from Chicago to Caribbean