Cheap flights from Chicago (CHI) to San Juan (SJU)

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

How to find the cheapest flight from
Chicago (CHI) to San Juan (SJU)

All the information you need to plan the best CHI to SJU flight in 2021: compare Chicago to San Juan flight prices with the expected peak season, weather and rainfall in San Juan.
CHI - PR1
Price
$181 - $557
PR1
Temperature
77 - 82.4 °F
PR1
Precipitation
2.2 - 6.1 inches

Popular in

December

High demand for flights, 45% potential price rise

Cheapest in

August

Best time to find cheap flights, 41% potential price drop

Round-trip from

$181

From Chicago (CHI) to San Juan

One-way from

$41

One-way flight from Chicago (CHI) to San Juan

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest month to fly from Chicago to San Juan?

August is one of the best times of the year to fly to San Juan 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 San Juan (CHI - PR1)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to San Juan as you normally would.

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

To save on the cost of your flight from Chicago to San Juan, book at least 18 days before your planned departure. Booking around this time can save you about 13% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $256 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $302.

Cheap flights from Chicago to San Juan in October, November 2021

The best prices found for CHI to SJU flights for October, November
13 Nov - 15 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
9 Nov - 12 Nov
$91pp
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
13 Nov - 15 Nov
$99pp
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

Chicago to San Juan 2021 flight deals

Cheap flights to San Juan from Chicago found for this year
13 Nov - 15 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
9 Nov - 12 Nov
$91pp
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
4 Dec - 8 Dec
$99pp
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

Non-stop flights to San Juan from Chicago

Save time with Chicago to San Juan direct flight deals
21 Nov - 25 Nov
$124pp
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
16 Jan - 20 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
22 Nov - 25 Nov
$144pp
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 San Juan

Late deals on round-trip flights to San Juan from Chicago, departing today and this week
3 Nov - 6 Nov
$109pp
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
2 Nov - 9 Nov
$117pp
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 - 12 Nov
$122pp
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

One-way flights to San Juan from Chicago

The cheapest one-way flights from Chicago to San Juan
6:00 pm - 12:57 am
Frontier
Nonstop
4h 57m
ORD - SJU
Frontier
$62
JustFly
6:14 pm - 1:11 am
Frontier
Nonstop
4h 57m
ORD - SJU
Frontier
$75
Kiwi.com
8:57 am - 9:58 pm
Frontier
1 Stop
11h 01m
ORD - SJU
Frontier

Related info for your journey

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

Flight FAQs

From Chicago to San Juan

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

Some of the carriers operating flights from Chicago to San Juan 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 San Juan for under $100 on Cheapflights?

Yes, there are multiple flights from Chicago to San Juan for under $100. The cheapest flight booked recently is on Frontier for just $84, but on average you can expect to pay $106.

Are there nonstop flights from Chicago to San Juan for under $200 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to San Juan under $200. A good price for a nonstop flight from Chicago to San Juan is less than $167.

Are there last-minute flights available from Chicago to San Juan for under $200?

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

What days are nonstop flights available from Chicago to San Juan?

Days when nonstop flights are available for this flight are: Sunday, Friday, Saturday.

How many flights depart from Chicago to San Juan on average per day?

Travelers can expect 6 flights from Chicago to San Juan on average per day.
Morning (6am - Noon) - 100% of flight departures

How long is the flight from Chicago to San Juan?

There are many flights that can get you from Chicago to San Juan in 17h 33m. Fly via Frontier or Spirit Airlines to get the fastest option. The distance between Chicago and San Juan is about 2085 mi. This flight may include one or multiple stops.

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

Cheapflights users have booked flights from Chicago to San Juan round-trip from $84. Another airline that can offer you cheap pricing is Spirit Airlines. Frontier is priced at 72% lower than the current average price of a flight leaving 3 months from now.

What are the most reliable airlines from Chicago to San Juan?

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 San Juan on time: Frontier (92%), Qatar Airways (86%), Air Canada (86%).

What are the cheapest flights from Chicago to San Juan?

Looking at all options, your cheapest flight can be booked for $93. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $109 on average our data indicates $676 when flying from Chicago to San Juan

What are the most popular airlines that fly from Chicago to San Juan?

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

COVID Restrictions

View COVID Travel Restrictions for San Juan, Puerto Rico

Do I need a COVID test to fly to San Juan from Chicago?

Information is based on travel restrictions from Chicago to San Juan

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

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

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering San Juan.

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


Do I need a test to fly back to Chicago from San Juan?

Returning to Chicago from San Juan

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

Quarantine requirements
Visitors from San Juan are not required to quarantine after entering Chicago.

Hide COVID Travel Restrictions for San Juan, Puerto Rico

Destination information for San Juan

Things to know before you go - useful duration and weather info for your trip from Chicago to San Juan.
Today's exchange rate
$1 = $1.00
Average temperature for October in San Juan
87.8 °F
Avg rainfall for October in San Juan
5.8 ″

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Airports servicing San Juan

San Juan Isla Grande (SIG)

Top 6 airlines flying from Chicago to San Juan

The chart below displays the airlines Cheapflights users traveling from Chicago to San Juan 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 $274 No cancel fee 65%
JetBlue
$151 $369 No cancel fee 62%
Delta
$163 $463 No cancel fee N/A
United Airlines
$183 $515 No cancel fee 69%
American Airlines
$185 $461 No cancel fee 71%

Hourly flight availability from Chicago to San Juan

See what time of day planes typically take off from Chicago towards San Juan.
Afternoon Noon to 6 PM 70% of CHI to SJU departures
Morning 6 AM to noon 30% of CHI to SJU departures
Early morning Midnight to 6 AM 0% of CHI to SJU departures
Evening 6 PM to midnight 0% of CHI to SJU departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Chicago to San Juan
See how many times per day planes take to the skies headed from Chicago to San Juan.
Sunday
4 daily flights
Monday
4 daily flights
Tuesday
6 daily flights
Wednesday
6 daily flights
Thursday
4 daily flights
Friday
5 daily flights
Saturday
5 daily flights
Home Caribbean Puerto Rico San Juan Cheap flights from Chicago to San Juan