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$98+ 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 3/31. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Apr 21 — Apr 281
Tue 4/21
Tue 4/28
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 May, booked 40 days in advance, depart on a Monday or Tuesday 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 March 22, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 3/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:10 pm
ORD
-
SJU
1 stop16h 39m
Spirit Airlines
Wed 4/1510:59 am
SJU
-
ORD
Nonstop5h 09m
Spirit Airlines
Deal found 3/17$202
This CheapOair deal was found by Cheapflights users on 3/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:17 am
ORD
-
SJU
1 stop10h 38m
Spirit Airlines
Wed 4/1510:59 am
SJU
-
ORD
Nonstop5h 09m
Spirit Airlines
Deal found 3/18$203
This Kiwi.com deal was found by Cheapflights users on 3/21. 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.
Wed 4/84:21 pm
ORD
-
SJU
1 stop6h 41m
Multiple Airlines
Mon 4/131:29 am
SJU
-
ORD
Nonstop5h 16m
Multiple Airlines
Deal found 3/21$205
This Frontier deal was found by Cheapflights users on 3/19. 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.
Tue 4/74:34 pm
ORD
-
SJU
1 stop7h 18m
Frontier
Fri 4/173:23 pm
SJU
-
ORD
1 stop8h 16m
Frontier
Deal found 3/19$206
This CheapOair deal was found by Cheapflights users on 3/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:30 pm
ORD
-
SJU
1 stop13h 34m
Frontier
Sat 5/166:41 pm
SJU
-
ORD
1 stop15h 56m
Frontier
Deal found 3/20$207
This Priceline deal was found by Cheapflights users on 3/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1011:55 am
ORD
-
SJU
1 stop11h 30m
Multiple Airlines
Mon 4/131:29 am
SJU
-
ORD
Nonstop5h 16m
Multiple Airlines
Deal found 3/21$208
This Priceline deal was found by Cheapflights users on 3/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:30 pm
ORD
-
SJU
1 stop13h 34m
Frontier
Fri 5/296:00 am
SJU
-
ORD
1 stop7h 37m
Frontier
Deal found 3/20$209
This Priceline deal was found by Cheapflights users on 3/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1310:55 am
ORD
-
SJU
1 stop12h 03m
Multiple Airlines
Thu 4/306:00 am
SJU
-
ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/17$210
This Priceline deal was found by Cheapflights users on 3/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:25 am
ORD
-
SJU
1 stop9h 14m
Frontier
Wed 4/1511:05 am
SJU
-
ORD
1 stop27h 48m
Frontier
Deal found 3/20$211
This Cheapflightsfares deal was found by Cheapflights users on 3/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
-
SJU
1 stop12h 03m
Spirit Airlines
Mon 4/131:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/20$212
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 4/117:17 am
ORD
-
SJU
1 stop10h 38m
Spirit Airlines
Wed 4/1510:59 am
SJU
-
ORD
Nonstop5h 09m
Spirit Airlines
Deal found 3/18$214

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 March 22, 2026.

Round-trip from

$202
(Cheapflightsfares)

One-way from

$98
(WAYA)

Popular in

December

Cheapest in

September

Average price

$435
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 ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 22, 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
Quickest round-trip

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 5/5

8:49 am-2:44 pm

Nonstop4h 55m

San Juan Luis Munoz Marin Intl

Tue 5/12

7:40 am-11:53 am

Nonstop5h 13m

$363

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 5/4

4:15 pm-10:35 am

2 stops17h 20m

San Juan Luis Munoz Marin Intl

Wed 5/13

5:05 am-9:55 pm

2 stops17h 50m

$366

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 5/4

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

Sat 5/9

3:56 pm-8:15 pm

Nonstop5h 19m

$457

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

8:40 pm-12:50 pm

2 stops17h 10m

$461

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 5/4

8:49 am-2:44 pm

Nonstop4h 55m

San Juan Luis Munoz Marin Intl

Mon 5/18

7:40 am-11:53 am

Nonstop5h 13m

$464

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/9

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

Sat 5/16

7:40 am-11:53 am

Nonstop5h 13m

$466

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 4/16

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

Mon 4/20

7:40 am-11:53 am

Nonstop5h 13m

$472

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/2

1:55 pm-11:40 pm

2 stops8h 45m

San Juan Luis Munoz Marin Intl

Sat 5/9

5:15 am-3:30 pm

2 stops11h 15m

$476

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 4/20

2:40 pm-11:55 pm

2 stops8h 15m

San Juan Luis Munoz Marin Intl

Sat 4/25

5:45 am-3:30 pm

2 stops10h 45m

$479

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 4/29

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

Mon 5/4

7:40 am-11:53 am

Nonstop5h 13m

$495

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/22

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?

Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to San Juan. Price data was last updated on March 13, 2026.

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 40 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, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to San Juan (average of $124). Flying from Chicago O'Hare Intl Airport to San Juan in December is currently the most expensive (average of $224). 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 March 22, 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 25% 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 March 14, 2026.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to San Juan flight should consider departing on Tuesday evenings 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 March 22, 2026.

The most flights from ORD to PR1 are scheduled on a Saturday (16 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 on average).

How often are flights from Chicago to San Juan delayed?

About 19% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 141 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, American Airlines have had the lowest number of delays on this route, with just 17% 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 March 22, 2026.
See what other customers who have flown with United Airlines,JetBlue, andAmerican Airlines 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
9,459 reviews

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,459 reviews
United Airlines
7.4
Good
9,459 reviews

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
JetBlue
7.2
Good
2,911 reviews
United Airlines
7.4
Good
9,459 reviews

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.1
Good
11,485 reviews
United Airlines
7.4
Good
9,459 reviews

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Spirit Airlines
6.3
Okay
8,533 reviews
United Airlines
7.4
Good
9,459 reviews

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Frontier
5.7
Fair
3,020 reviews
United Airlines
7.4
Good
9,459 reviews

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 55m. United Airlines provides one of the quickest options available for as low as $363. 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 Frontier is currently your cheapest option to San Juan, with prices starting at $112. Additional round-trip tickets that might be worth considering are offered by JetBlue and Spirit Airlines, with the lowest prices starting at $119 and $138, respectively. Frontier is 70% 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 $89 and $98, 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 (92%), Alaska Airlines (88%), American Airlines( 87%).

  • 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 $591, our data indicates the cheapest price to be $118. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $203.

  • 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 $64 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, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to San Juan (average of $124). Flying from Chicago O'Hare Intl Airport to San Juan in December is currently the most expensive (average of $224). 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.

See more FAQs

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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 March 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$112Average$284FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$119Average$236FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$138Average$313FlexibilityNo cancel feeOn-time65%
DeltaCheapest$143Average$347FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$254Average$497FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$312Average$521FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$377Average$484FlexibilityNo cancel feeOn-time63%

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