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$107+ Cheap flights from O'Hare Intl (ORD) to San Juan

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Jun 6 — Jun 131
Sat 6/6
Sat 6/13
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to San Juan are usually found in September or August, booked 57 days in advance, depart on a Tuesday or Monday and return on a Friday

Cheap flight deals from O'Hare Intl to San Juan

Cheapest flights from O'Hare Intl to San Juan
Explore the most affordable flight options available from O'Hare Intl to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 7, 2026.

This Frontier deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:44 am
ORD
-
SJU
Nonstop4h 57m
Frontier
Thu 7/97:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 5/2$218
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/612:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Wed 7/86:00 am
SJU
-
ORD
1 stop7h 25m
Frontier
Deal found 5/2$219
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/612:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Tue 7/77:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 5/2$220
This Trip.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/193:55 pm
ORD
-
SJU
1 stop9h 13m
Frontier
Wed 5/277:04 pm
SJU
-
ORD
Nonstop5h 22m
Frontier
Deal found 5/2$221
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:14 pm
ORD
-
SJU
Nonstop4h 53m
American Airlines
Tue 8/187:14 pm
SJU
-
ORD
1 stop13h 20m
American Airlines
Deal found 5/6$222
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/1212:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Mon 8/37:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 5/5$223
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/188:05 am
ORD
-
SJU
1 stop7h 00m
Frontier
Mon 8/37:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 5/5$224
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/191:48 pm
ORD
-
SJU
1 stop7h 41m
Delta
Wed 9/22:40 pm
SJU
-
ORD
1 stop10h 17m
Delta
Deal found 5/7$226
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:14 pm
ORD
-
SJU
Nonstop4h 53m
American Airlines
Wed 9/26:51 am
SJU
-
ORD
1 stop8h 24m
American Airlines
Deal found 5/5$227
This Orbitz deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1412:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Sat 8/229:24 am
SJU
-
ORD
1 stop14h 50m
Frontier
Deal found 5/2$228
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:29 am
ORD
-
SJU
Nonstop4h 57m
Frontier
Mon 9/76:00 am
SJU
-
ORD
1 stop7h 25m
Frontier
Deal found 5/5$229
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1712:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Sat 8/226:11 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Deal found 5/5$230

Find flight deals from O'Hare Intl to San Juan

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to San Juan (PR1). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 7, 2026.

Round-trip from

$218
(Frontier)

One-way from

$107
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$371
From Chicago O'Hare Intl to San Juan
Search Deals
One-way flight from Chicago O'Hare Intl to San Juan
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($55 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in May 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to San Juan that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 7, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to San Juan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 5/12

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

Wed 5/20

3:56 pm-8:15 pm

Nonstop5h 19m

$349

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/1

6:00 am-4:46 pm

1 stop9h 46m

San Juan Luis Munoz Marin Intl

Sat 8/8

7:43 pm-11:38 pm

Nonstop4h 55m

$382

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 6/17

5:00 am-1:45 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Tue 6/23

1:00 am-9:00 am

1 stop9h 00m

$490

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 6/10

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

Tue 6/16

7:40 am-11:53 am

Nonstop5h 13m

$502

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 6/29

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

Fri 7/3

7:40 am-11:53 am

Nonstop5h 13m

$517

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 7/18

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

Sun 7/26

7:40 am-11:53 am

Nonstop5h 13m

$545

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 5/24

2:00 pm-9:10 am

2 stops18h 10m

San Juan Luis Munoz Marin Intl

Thu 5/28

5:35 am-9:55 pm

2 stops17h 20m

$571

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 5/18

6:00 am-11:40 pm

2 stops16h 40m

San Juan Luis Munoz Marin Intl

Fri 5/22

5:35 am-9:55 pm

2 stops17h 20m

$578

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 6/19

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

Fri 6/26

7:40 am-11:53 am

Nonstop5h 13m

$597

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/16

1:55 pm-9:05 am

2 stops18h 10m

San Juan Luis Munoz Marin Intl

Wed 5/20

5:05 am-9:55 pm

2 stops17h 50m

$607

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

Showing 1-10 of 22 resultsSorted by cheapest first
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Best time to book a flight from O'Hare Intl to San Juan

Have a flexible travel schedule? Discover the best time to fly to San Juan from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to San Juan

How far ahead should I book a flight from Chicago O'Hare Intl Airport to San Juan?

To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to San Juan, you should look to book at least 56 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to San Juan?

Currently, August is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to San Juan (average of $115). Flying from Chicago O'Hare Intl Airport to San Juan in July is currently the most expensive (average of $560). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ORD to SJU?

Find hourly flight availability from O'Hare Intl to San Juan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 7, 2026.

It’s optimal to fly from Chicago O'Hare Intl Airport to San Juan in the evening. By choosing this option you can save up to 22% on the cost of your flight, compared to a flight at noon.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to San Juan?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to San Juan. Price data was last updated on May 2, 2026.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to San Juan flight should consider departing on Monday afternoons when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago O'Hare Intl Airport to San Juan

Explore weekly flight availability from O'Hare Intl to San Juan. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 7, 2026.

The most flights from ORD to PR1 are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 on average).

How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to San Juan?

How often are flights from Chicago to San Juan delayed?

About 21% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 144 minutes.

What is the most punctual flight time for Chicago to San Juan flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Thursday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to San Juan flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 19% of flights being delayed.

Reviews of airlines servicing San Juan

Get insights into the airlines that provide service to San Juan. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San Juan. Reviews last updated May 7, 2026.
See what other customers who have flown with United Airlines,American Airlines, andJetBlue from Chicago O'Hare Intl Airport to San Juan have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,692 reviews

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
United Airlines
7.4
Good
9,692 reviews
United Airlines
7.4
Good
9,692 reviews

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
American Airlines
7.1
Good
11,669 reviews
United Airlines
7.4
Good
9,692 reviews

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
JetBlue
7.1
Good
2,979 reviews
United Airlines
7.4
Good
9,692 reviews

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
Spirit Airlines
6.3
Okay
8,637 reviews
United Airlines
7.4
Good
9,692 reviews

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
Frontier
5.6
Fair
2,964 reviews
United Airlines
7.4
Good
9,692 reviews

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Overall

7.4

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to San Juan. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago O'Hare Intl Airport to San Juan?

    A quick flight from Chicago O'Hare Intl Airport to San Juan can take about 4h 56m. United Airlines provides one of the quickest options available for as low as $349. Chicago O'Hare Intl Airport and San Juan are separated by a distance of 2073 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to San Juan round-trip?

    Flying on JetBlue is currently your cheapest option to San Juan, with prices starting at $119. Additional round-trip tickets that might be worth considering are offered by Frontier and Spirit Airlines, with the lowest prices starting at $121 and $138, respectively. JetBlue is 69% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to San Juan one-way?

    $75 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on Spirit Airlines and Frontier, with prices starting from $90 and $95, respectively.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to San Juan?

    Before booking your flight to San Juan from Chicago O'Hare Intl Airport, check out the most reliable airlines to get you to your destination on time: Qatar Airways (95%), American Airlines (81%), Alaska Airlines( 79%).

  • What are the cheapest flights from Chicago O'Hare Intl Airport to San Juan?

    Looking for the cheapest flight from Chicago O'Hare Intl Airport to San Juan? While on average our users pay $650, our data indicates the cheapest price to be $98. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $157.

  • Where are the most common layover locations when flying from Chicago O'Hare Intl Airport to San Juan?

    Most of the time, Chicago O'Hare Intl Airport to San Juan flights that have layovers will stop in New York.

  • What are some popular things to do or see while on a layover in New York?

    Times Square, New York City Center, and Madison Square Garden are the most popular attractions in New York if you're in need of something to do during your layover. Times Square, New York City Center, and Madison Square Garden are located about 13.6 mi, 13.6 mi, and 13.6 mi, respectively from New York John F Kennedy Intl. Those landing in New York looking to spend some time exploring during their layover can rent a car for about $67 per day.

  • Where are the least popular layover locations for Chicago O'Hare Intl Airport to San Juan flights?

    Chicago O'Hare Intl Airport to San Juan flights have a layover in Orlando least often.

  • Can I find deals for flights from O'Hare Intl to San Juan that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to San Juan flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to San Juan?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to San Juan.

  • Can I find deals for business class flights from O'Hare Intl to San Juan?

    Yes. Cheapflights offers flight deals from O'Hare Intl to San Juan by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to San Juan?

    Currently, August is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to San Juan (average of $115). Flying from Chicago O'Hare Intl Airport to San Juan in July is currently the most expensive (average of $560). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for O'Hare Intl to San Juan

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Ponce flights

Top 7 airlines flying from O'Hare Intl to San Juan

Discover the top 7 airlines that operate flights from O'Hare Intl to San Juan. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$119Average$235FlexibilityNo cancel feeOn-time62%
FrontierCheapest$121Average$293FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$138Average$313FlexibilityNo cancel feeOn-time65%
DeltaCheapest$143Average$347FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$255Average$505FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$311Average$512FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$376Average$484FlexibilityNo cancel feeOn-time63%

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