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

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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)

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 41 days in advance to save up to 11% 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 41 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 $380, or $415 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 September. Prices to San Juan from Chicago average $380. You can even find prices in September for less than $380, as users have found deals to San Juan from as low as $194. 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 41%.

Cheap flights from Chicago to San Juan in July, August 2020

The best prices found for CHI to SJU flights for July, August
21 Jul - 28 Jul
$149pp
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
27 Jul - 3 Aug
$153pp
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
   
2 STOPS
ORD
Chicago O'Hare Intl
29 Jul - 18 Aug
$154pp
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 2020 flight deals

Cheap flights to San Juan from Chicago found for this year
5 Aug - 11 Aug
$142pp
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
   
2 STOPS
ORD
Chicago O'Hare Intl
4 Aug - 9 Aug
$145pp
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
   
2 STOPS
ORD
Chicago O'Hare Intl
3 Aug - 12 Aug
$146pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
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
9 Nov - 12 Nov
$259pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl
28 Jul - 11 Aug
$267pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
18 Nov - 5 Dec
$276pp
ORD
Chicago O'Hare Intl
Multiple Airlines
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
26 Jun - 9 Jul
$198pp
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
28 Jun - 3 Jul
$208pp
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
26 Jun - 3 Jul
$209pp
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

One-way flights to San Juan from Chicago

The cheapest one-way flights from Chicago to San Juan
4:14 pm - 6:54 am
Spirit Airlines
1 Stop
13h 40m
ORD - SJU
Spirit Airlines
$68
FlightNetwork
5:11 am - 4:51 pm
Spirit Airlines
1 Stop
10h 40m
ORD - SJU
Spirit Airlines
$74
FlyFar
5:14 am - 10:24 pm
Spirit Airlines
1 Stop
16h 10m
ORD - SJU
Spirit Airlines
$80
FlyFar

Related info for your journey

Useful info, stats and facts about Chicago to San Juan 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.

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 Spirit Airlines for just $142, but on average you can expect to pay $155.

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 $317.

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.

How popular is this flight route?

This flight path from Chicago to San Juan was viewed by 763 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

What is the cheapest airline for this route?

While looking for the best option consider Delta Air Lines, Inc., our data currently shows that they have the cheapest flight available for the flight path. When traveling from Chicago to San Juan, generally 159 flights depart for this route daily.

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.

Related searches

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Rent a Car

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Destination information for San Juan

Things to know before you go. Useful info for your trip from Chicago to San Juan
Today's exchange rate
$1 = $1.00
Average temperature for July in San Juan
89.6 °F
Avg rainfall for July in San Juan
4.7 ″

Airports servicing Chicago

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

Airports servicing San Juan

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

Popular flight searches

Check out other popular destinations found by fellow travelers

Hourly flight availability from Chicago to San Juan

Morning 6 AM to noon 100% of CHI to SJU departures
Early morning Midnight to 6 AM 0% of CHI to SJU departures
Afternoon Noon to 6 PM 0% of CHI to SJU departures
Evening 6 PM to midnight 0% of CHI to SJU departures
Midnight
6 AM
Noon
6 PM