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

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The best prices from Chicago to San Juan are usually found in August or July, booked 19 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

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
82.4 - 89.6 °F
PR1
Rainfall
1.3 - 5.8 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 to San Juan

One-way from

$92

One-way flight from Chicago 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 day to fly round-trip from Chicago to San Juan?

Users have found that flying from Chicago to San Juan on a Saturday typically leans towards higher prices. However, this doesn’t mean you still can’t find a deal. Flexibility with other aspects of your flight can still land a great price for your trip.

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

Travelers have found it’s best to book a flight 19 days in advance to save up to 7% 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 19 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 $262, or $281 for flights within the next 24 hours.

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 $313. You can even find prices in August for less than $313, as users have found deals to San Juan from as low as $121. 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 71%.

When is the cheapest time to fly from Chicago to San Juan (CHI - PR1)?

Unlike in the evening, when flights are generally more expensive, you can save up to 43% on flights from Chicago to San Juan by exploring options for tickets at noon.

Cheap flights from Chicago to San Juan in May, June 2021

The best prices found for CHI to SJU flights for May, June
17 May - 18 May
$140pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
17 May - 19 May
$141pp
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
18 May - 19 May
$144pp
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

Chicago to San Juan 2021 flight deals

Cheap flights to San Juan from Chicago found for this year
17 May - 18 May
$140pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
17 May - 19 May
$141pp
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
18 May - 19 May
$144pp
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

Non-stop flights to San Juan from Chicago

Save time with Chicago to San Juan direct flight deals
18 May - 19 May
$141pp
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
15 Sep - 21 Sep
$163pp
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
4 Oct - 12 Oct
$167pp
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
18 May - 19 May
$141pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
18 May - 19 May
$144pp
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
18 May - 20 May
$146pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl

One-way flights to San Juan from Chicago

The cheapest one-way flights from Chicago to San Juan
7:00 am - 7:52 pm
Delta
1 Stop
11h 52m
ORD - SJU
Delta
$92
Delta
2:00 am - 3:40 pm
Frontier
1 Stop
12h 40m
ORD - SJU
Frontier
$106
Kiwi.com
10:20 am - 4:06 pm
United Airlines
Nonstop
4h 46m
ORD - SJU
United Airlines
$108
United

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

Are flight prices decreasing from Chicago to San Juan 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 San Juan 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 San Juan to control the spread of COVID-19?

Alaska Airlines is one of the many airlines that have implemented additional safety measures to control the spread of COVID-19. New policies for travelers booking flights from Chicago to San Juan 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 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 $200 on Cheapflights?

Yes, there are multiple flights from Chicago to San Juan for under $200. The cheapest flight booked recently is on Multiple Airlines for just $141, but on average you can expect to pay $170.

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 $185.

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.

Is Chicago weather warmer or cooler than San Juan?

Our data indicates that the weather will be 90 °F on average in the month of June. The temperature in San Juan is typically hotter than in Chicago. If you're traveling when the temperature is at its warmest, push to plan early, as flight price and availability will have an impact on your travels. For the best results, search for flights well in advance or after peak season.

How long is the flight from Chicago to San Juan?

Frontier, Delta, and Spirit Airlines can get you from Chicago to San Juan in just under 4h 49m. Your travel time can differ by up to 1h 49m. Both multi-stop and nonstop flights can be found to your destination and back.

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

Delta, at $144, was found to be the cheapest airline from Chicago to San Juan.Alternate airlines to your destination round-trip include Frontier and Spirit Airlines. These flights start at 53% lower than the current average price 3 months from now.

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

$70 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Delta and Spirit Airlines, with prices starting from $72 and $73, respectively.

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
Flight duration
5h 07m
Average temperature for May in San Juan
87.8 °F
Avg rainfall for May in San Juan
3.6 ″

Airports servicing Chicago

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
Spirit Airlines
$112 $274 No cancel fee 65%
Frontier
$90 $342 No cancel fee 62%
JetBlue
$151 $369 No cancel fee 62%
American Airlines
$185 $461 No cancel fee 71%
Delta
$163 $463 No cancel fee N/A
United Airlines
$183 $515 No cancel fee 69%

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 72% of CHI to SJU departures
Morning 6 AM to noon 27% of CHI to SJU departures
Early morning Midnight to 6 AM 1% of CHI to SJU departures
Evening 6 PM to midnight 0% of CHI to SJU departures
Midnight
6 AM
Noon
6 PM
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