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)

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

$66

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 morning, when flights are generally more expensive, you can save up to 36% on flights from Chicago to San Juan by exploring options for tickets at noon.

Cheap flights from Chicago to San Juan in February, March 2021

8 Mar - 10 Mar
$85pp
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
1 Mar - 17 Mar
$86pp
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
13 Mar - 10 Apr
$87pp
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 San Juan 2021 flight deals

4 May - 10 May
$85pp
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
14 Apr - 17 Apr
$86pp
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
13 Mar - 10 Apr
$87pp
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 San Juan from Chicago

8 Mar - 16 Mar
$115pp
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
8 Mar - 13 Mar
$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
6 Mar - 10 Mar
$138pp
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

2 Mar - 9 Mar
$95pp
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 Mar - 9 Mar
$96pp
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
6 Mar - 9 Mar
$102pp
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 San Juan from Chicago

12:03 pm - 8:51 pm
Frontier
1 Stop
30h 48m
ORD - SJU
Frontier
$66
Kiwi.com
1:40 pm - 7:13 am
Spirit Airlines
1 Stop
14h 33m
ORD - SJU
Spirit Airlines
$73
FareScan
4:20 am - 10:49 pm
Multiple Airlines
2 Stops
17h 29m
ORD - SJU
Multiple Airlines
$74
Gotogate

Related info for your journey

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 and Delta are some 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 $100 on Cheapflights?

Yes, there are multiple flights from Chicago to San Juan for under $100. The cheapest flight booked recently is on Spirit Airlines for just $85, but on average you can expect to pay $94.

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 $156.

Are there last-minute flights available from Chicago to San Juan for under $100?

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

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

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

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

6 flight departures from Chicago to San Juan per day on average.
Morning (6am - Noon) - 50% of flight departures
Afternoon (Noon - 6pm) - 50% of flight departures

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?

Spirit Airlines and Delta can get you from Chicago to San Juan in just under 5h 58m. Your travel time can differ by up to 17m. There are 2085 mi between Chicago and San Juan. Both multi-stop and nonstop flights can be found to your destination and back.

What is the cheapest airline to fly from Chicago to San Juan round-trip?

Spirit Airlines, at $85, was found to be the cheapest airline from Chicago to San Juan.. This flight start at 72% lower than the current average price 3 months from now.

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

$42 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, with prices from $58.

Destination information for San Juan

Today's exchange rate
$1 = $1.00
Average temperature for February in San Juan
84.2 °F
Avg rainfall for February in San Juan
1.6 ″

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

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

Afternoon Noon to 6 PM 53% of CHI to SJU departures
Morning 6 AM to noon 46% 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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