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
Add another flight clear all

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

Home Caribbean Puerto Rico San Juan Cheap flights from Chicago to San Juan

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 2022: compare Chicago to San Juan flight prices with the expected peak season, weather and rainfall in San Juan.
CHI - SJU
Price
$181 - $557
SJU
Temperature
77 - 82.4 °F
SJU
Rainfall
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

$110

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?

The best pricing can be found in the month of August. Prices to San Juan from Chicago average $307. You can even find prices in August for less than $307, as users have found deals to San Juan from as low as $118. The month of December appears to be one of the more expensive times to travel to San Juan from Chicago. Flying in the targeted month can save you up to 81%.

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

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 San Juan 1-2 weeks in advance for as low as $256, or $302 for flights within the next 24 hours.

When is the cheapest time to fly from Chicago to San Juan (CHI - SJU)?

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.

Cheap flights from Chicago to San Juan in May, June 2022

The best prices found for CHI to SJU flights for May, June
31 May - 7 Jun
$276pp
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
   
2 STOPS
ORD
Chicago O'Hare Intl
31 May - 9 Aug
$294pp
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
8 Jun - 24 Aug
$301pp
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

Chicago to San Juan 2022 flight deals

Cheap flights to San Juan from Chicago found for this year
1 Nov - 9 Nov
$219pp
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
24 Aug - 31 Aug
$228pp
ORD
Chicago O'Hare Intl
Spirit Airlines
   
2 STOPS
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
24 Oct - 30 Oct
$229pp
MDW
Chicago Midway
Delta
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Delta
 
1 STOP
MDW
Chicago Midway

Non-stop flights to San Juan from Chicago

Save time with Chicago to San Juan direct flight deals
1 Nov - 9 Nov
$288pp
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
1 Nov - 9 Nov
$299pp
ORD
Chicago O'Hare Intl
Multiple 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
16 Nov - 6 Dec
$308pp
ORD
Chicago O'Hare Intl
Multiple 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

Last minute flights from Chicago to San Juan

Late deals on round-trip flights to San Juan from Chicago, departing today and this week
31 May - 7 Jun
$276pp
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
   
2 STOPS
ORD
Chicago O'Hare Intl
31 May - 9 Aug
$294pp
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
31 May - 3 Jun
$315pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
American Airlines
 
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
1:40 am - 12:15 pm
Delta
1 Stop
9h 35m
ORD - SJU
Delta
$110
Delta
8:05 am - 7:55 pm
United Airlines
1 Stop
10h 50m
ORD - SJU
United Airlines
$160
United
2:30 am - 5:42 pm
American Airlines
2 Stops
14h 12m
ORD - SJU
American Airlines
$185

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 Frontier, American Airlines, and United 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 $300 on Cheapflights?

Yes, there are multiple flights from Chicago to San Juan for under $300. The cheapest flight booked recently is on Delta for just $219, but on average you can expect to pay $241.

Are there nonstop flights from Chicago to San Juan for under $300 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to San Juan under $300. A good price for a nonstop flight from Chicago to San Juan is less than $345.

Are there last-minute flights available from Chicago to San Juan for under $300?

There are currently 20+ open flights from Chicago to San Juan within the next 7 days for less than $300.

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 $219. Other airlines that can offer you cheap pricing are Spirit Airlines, from $228, and United Airlines, from $259. Delta is priced at 28% lower than the current average price of a flight leaving 3 months from now.

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

$105 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 Delta and United Airlines, with prices starting from $110 and $114, respectively.

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

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

What are the cheapest flights from Chicago to San Juan?

Looking at all options, your cheapest flight can be booked for $26. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $219 on average our data indicates $900 when flying from Chicago to San Juan.

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: Qatar Airways (94%), Air Canada (90%), Air New Zealand (90%).

Related searches

Flights to San Juan from Chicago
Flights to Chicago Flights to San Juan Flights from Chicago

Other flights from Chicago

Chicago to Knoxville Chicago to Asheville Chicago to Myrtle Beach Chicago to New Orleans Chicago to Fort Lauderdale

Other flights to San Juan

New York to San Juan Philadelphia to San Juan Newark to San Juan Boston to San Juan Orlando to San Juan

Rent a Car

Car Rentals in San Juan Car Rentals at Luis Munoz Marin Intl Car Rentals at Ponce Car Rentals at Singapore

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 can enter San Juan without restrictions.

COVID-19 testing requirements
Visitors from Chicago are not required to present a negative COVID-19 PCR test or antigen result upon entering 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 are not required to present a negative COVID-19 PCR test or antigen result upon entering 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 May in San Juan
87.8 °F
Avg rainfall for May in San Juan
3.6 ″

Airports servicing Chicago

O'Hare Intl (ORD)
Midway (MDW)
Rockford (RFD)

Airports servicing San Juan

Luis Munoz Marin Intl (SJU)
San Juan Isla Grande (SIG)

Top 8 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
Juneyao Airlines 		$12 $22 No cancel fee 66%

We couldn't confirm the COVID-19 safety measures taken by Juneyao Airlines. Please check directly on their website for additional information.
Spirit Airlines 		$85 $179 No cancel fee 65%
JetBlue 		$101 $263 No cancel fee 62%
Frontier 		$117 $349 No cancel fee 62%
United Airlines 		$124 $577 No cancel fee 69%
Delta 		$124 $472 No cancel fee N/A
American Airlines 		$174 $401 No cancel fee 71%
Alaska Airlines 		$325 $509 No cancel fee 75%

Popular flight searches

Check out other popular destinations found by fellow travelers in 2022.

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 61% of CHI to SJU departures
Evening 6 PM to midnight 20% of CHI to SJU departures
Early morning Midnight to 6 AM 18% of CHI to SJU departures
Morning 6 AM to noon 1% 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
5 daily flights
Monday
5 daily flights
Tuesday
5 daily flights
Wednesday
5 daily flights
Thursday
5 daily flights
Friday
5 daily flights
Saturday
4 daily flights
Home Caribbean Puerto Rico San Juan Cheap flights from Chicago to San Juan