Cheap flights from Chicago (CHI) to Puerto Rico

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How to find the cheapest flight from
Chicago (CHI) to Puerto Rico

All the information you need to plan the best CHI to SJU flight in 2021: compare Chicago to Puerto Rico flight prices with the expected peak season, weather and rainfall in Puerto Rico.
When is the cheapest time to fly from Chicago to Puerto Rico (CHI - PR)?

When flying from Chicago to Puerto Rico, 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 Puerto Rico?

Find a great deal and save up to 13% by booking at least 18 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Puerto Rico within the next two weeks, with the cheapest ticket starting at $256.

What is the cheapest month to fly from Chicago to Puerto Rico?

August is one of the best times of the year to fly to Puerto Rico 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

Cheap flights from Chicago to Puerto Rico in October, November 2021

The best prices found for CHI to Puerto Rico flights for October, November
3 Nov - 6 Nov
$84pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
6 Nov - 13 Nov
$86pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
6 Nov - 9 Nov
$90pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to Puerto Rico 2021 flight deals

Cheap flights to Puerto Rico from Chicago found for this year
3 Nov - 6 Nov
$84pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
6 Nov - 13 Nov
$86pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
6 Nov - 9 Nov
$90pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl

Non-stop flights to Puerto Rico from Chicago

Save time with Chicago to Puerto Rico direct flight deals
22 Nov - 26 Nov
$123pp
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
22 Nov - 26 Nov
$125pp
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
12 Jan - 19 Jan
$128pp
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 Puerto Rico

Late deals on round-trip flights to Puerto Rico from Chicago, departing today and this week
30 Oct - 5 Nov
$84pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BQN
Aguadilla Borinquen
BQN
Aguadilla Borinquen
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
29 Oct - 2 Nov
$92pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BQN
Aguadilla Borinquen
BQN
Aguadilla Borinquen
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
30 Oct - 2 Nov
$97pp
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 Puerto Rico from Chicago

The cheapest one-way flights from Chicago to Puerto Rico
6:00 pm - 12:57 am
Frontier
Nonstop
4h 57m
ORD - SJU
Frontier
6:14 pm - 1:11 am
Frontier
Nonstop
4h 57m
ORD - SJU
Frontier
$64
SmartFares
12:40 pm - 9:39 pm
Spirit Airlines
1 Stop
6h 59m
ORD - BQN
Spirit Airlines
$41
FlyFar

Related info for your journey

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

Flight FAQs

From Chicago to Puerto Rico

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

Due to the rapidly changing circumstances due to COVID-19, airlines like United Airlines, American Airlines, and Spirit Airlines flying from Chicago to Puerto Rico have implemented new flexible cancellation policies.

Can I find flights from Chicago to Puerto Rico for under $100 on Cheapflights?

Yes, there are multiple flights from Chicago to Puerto Rico for under $100. The cheapest flight booked recently is on Frontier for just $84, but on average you can expect to pay $99.

Are there nonstop flights from Chicago to Puerto Rico for under $200 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Puerto Rico under $200. A good price for a nonstop flight from Chicago to Puerto Rico is less than $150.

Are there last-minute flights available from Chicago to Puerto Rico for under $100?

There are currently 20+ open flights from Chicago to Puerto Rico within the next 7 days for less than $100.

What days are nonstop flights available from Chicago to Puerto Rico?

Nonstop flights can be found on the following days: Friday, Saturday.

How many flights depart from Chicago to Puerto Rico on average per day?

3 flight departures from Chicago to Puerto Rico per day on average.
Morning (6am - Noon) - 100% of flight departures

How long is the flight from Chicago to Puerto Rico?

Frontier and Spirit Airlines can get you from Chicago to Puerto Rico in just under 8h 47m. Your travel time can differ by up to 10h 29m. The distance from Chicago to Puerto Rico is about 2085 mi. Both multi-stop and nonstop flights can be found to your destination and back.

What are the most popular routes from Chicago to Puerto Rico?

The most popular flight routes from Chicago to Puerto Rico are Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago Midway - San Juan Luis Munoz Marin Intl and Chicago O'Hare Intl - Aguadilla Borinquen.

What are the most reliable airlines from Chicago to Puerto Rico?

Before booking your flight to Puerto Rico from Chicago, check out the most reliable airlines to get you to your destination on time: Frontier (92%), Qatar Airways (86%), Air Canada( 86%).

What are the cheapest flights from Chicago to Puerto Rico?

On average you can expect to pay $676 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $93 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $91.

What are the most popular airlines that fly from Chicago to Puerto Rico?

When booking a flight from Chicago to Puerto Rico, you may want to consider flying on Major Airline, American Airlines or Alaska Airlines as they are the most popular for this route.

COVID Restrictions

View COVID Travel Restrictions for Puerto Rico

Do I need a COVID test to fly to Puerto Rico from Chicago?

Information is based on travel restrictions from Chicago to Puerto Rico

Most visitors from Chicago need to provide a negative COVID-19 test result and/or quarantine to enter Puerto Rico.

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) test taken 72 hours before departing to Puerto Rico.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Puerto Rico.

Documents
Travel Declaration Form - Must be completed prior to travel to Puerto Rico.


Do I need a test to fly back to Chicago from Puerto Rico?

Returning to Chicago from Puerto Rico

COVID-19 testing requirements
Visitors from Puerto Rico must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from Puerto Rico are not required to quarantine after entering Chicago.

Hide COVID Travel Restrictions for Puerto Rico

Destination points for flights from Chicago to Puerto Rico

Select to see more specific information for flights from Chicago to all places in Puerto Rico.

Destination information for Puerto Rico

Things to know before you go - useful duration and weather info for your trip from Chicago to Puerto Rico.
Today's exchange rate
$1 = $1.00

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Airports servicing

Culebra (CPX)
Mayagüez Eugenio M De Hostos (MAZ)
Ceiba J. Aponte de la Torre (NRR)
Ponce (PSE)
Vieques (VQS)

Top 6 airlines flying from Chicago to Puerto Rico

The chart below displays the airlines Cheapflights users traveling from Chicago to Puerto Rico 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 $342 No cancel fee 62%
Spirit Airlines
$112 $300 No cancel fee 65%
JetBlue
$139 $303 No cancel fee 62%
Delta
$163 $463 No cancel fee N/A
United Airlines
$183 $492 No cancel fee 69%
American Airlines
$185 $461 No cancel fee 71%
Home Caribbean Puerto Rico Cheap flights from Chicago to Puerto Rico