$127+ Cheap flights from San Juan to O'Hare Intl (ORD)
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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Sep 3 — Sep 101
Round-trip
1 adult, Economy
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Find cheap flights from San Juan to O'Hare Intl with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from San Juan to Chicago O'Hare Intl are usually found in February or January, booked 82 days in advance, depart on a Thursday or Friday and return on a Tuesday
Cheap flight deals from San Juan to O'Hare Intl
Cheapest
Best
Last-minute
One-way
Cheapest flights from San Juan to O'Hare IntlExplore the most affordable flight options available from San Juan to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 4, 2026.
Explore the most affordable flight options available from San Juan to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 4, 2026.
This eDestinos deal was found by Cheapflights users on 8/2. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:14 pm -
Nonstop5h 13m
Sun 8/3012:44 am -
Nonstop5h 00m
Deal found 8/2![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 9/238:45 am -
1 stop31h 00m
Wed 9/307:11 am -
1 stop29h 23m
Deal found 7/31![Frontier logo]()
$180
This eDestinos deal was found by Cheapflights users on 7/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:14 pm -
Nonstop5h 13m
Mon 8/3112:44 am -
Nonstop5h 00m
Deal found 7/30![Frontier logo]()
$183
This Frontier deal was found by Cheapflights users on 7/30. 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.
Sat 8/297:14 pm -
Nonstop5h 13m
Sun 8/3012:44 am -
Nonstop5h 00m
Deal found 7/30![Frontier logo]()
$198
This eDestinos deal was found by Cheapflights users on 8/2. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:14 pm -
Nonstop5h 13m
Sat 8/2912:44 am -
Nonstop5h 00m
Deal found 8/2![Frontier logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Wed 9/168:45 am -
1 stop31h 00m
Wed 9/237:11 am -
1 stop29h 23m
Deal found 8/2![Frontier logo]()
$217
This Super.com deal was found by Cheapflights users on 8/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:14 pm -
Nonstop5h 13m
Fri 9/412:44 am -
Nonstop5h 00m
Deal found 8/1![Frontier logo]()
$224
This Frontier deal was found by Cheapflights users on 7/31. 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 9/47:14 pm -
Nonstop5h 13m
Sun 9/612:44 am -
Nonstop5h 00m
Deal found 7/31![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 9/98:45 am -
1 stop31h 00m
Wed 9/237:11 am -
1 stop29h 23m
Deal found 8/3![Frontier logo]()
$229
Best flights from San Juan to O'Hare IntlDiscover carefully curated flight deals from San Juan to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 4, 2026.
Discover carefully curated flight deals from San Juan to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 4, 2026.
This United Airlines deal was found by Cheapflights users on 8/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/81:00 am -
1 stop9h 13m
Tue 9/228:55 am -
Nonstop4h 49m
Deal found 8/3![United Airlines logo]()
$252
This Delta deal was found by Cheapflights users on 8/3. 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 9/165:59 pm -
1 stop7h 00m
Tue 9/2210:25 am -
1 stop12h 24m
Deal found 8/3![Delta logo]()
$276
This United Airlines deal was found by Cheapflights users on 8/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/43:56 pm -
Nonstop5h 09m
Fri 9/118:55 am -
Nonstop4h 49m
Deal found 8/3![United Airlines logo]()
$377
This United Airlines deal was found by Cheapflights users on 7/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/163:56 pm -
Nonstop5h 09m
Mon 10/198:55 am -
Nonstop4h 49m
Deal found 7/31![United Airlines logo]()
$377
This United Airlines deal was found by Cheapflights users on 7/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/31:00 am -
1 stop7h 42m
Thu 10/88:55 am -
Nonstop4h 49m
Deal found 7/30![United Airlines logo]()
$456
This United Airlines deal was found by Cheapflights users on 8/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/173:56 pm -
Nonstop5h 09m
Mon 9/218:55 am -
Nonstop4h 49m
Deal found 8/1![United Airlines logo]()
$457
This United Airlines deal was found by Cheapflights users on 7/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:56 pm -
Nonstop5h 09m
Wed 10/78:55 am -
Nonstop4h 49m
Deal found 7/30![United Airlines logo]()
$507
This United Airlines deal was found by Cheapflights users on 8/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:56 pm -
Nonstop5h 09m
Mon 9/288:55 am -
Nonstop4h 49m
Deal found 8/2![United Airlines logo]()
$547
This United Airlines deal was found by Cheapflights users on 8/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/133:56 pm -
Nonstop5h 09m
Wed 9/168:55 am -
Nonstop4h 49m
Deal found 8/1![United Airlines logo]()
$582
This United Airlines deal was found by Cheapflights users on 8/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/261:00 am -
2 stops11h 52m
Mon 8/315:30 am -
1 stop9h 12m
Deal found 8/1![United Airlines logo]()
$612
This United Airlines deal was found by Cheapflights users on 8/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:00 am -
2 stops11h 46m
Mon 8/248:50 am -
1 stop10h 48m
Deal found 8/3![United Airlines logo]()
$700
This United Airlines deal was found by Cheapflights users on 7/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/244:55 pm -
Nonstop5h 31m
Mon 12/282:16 pm -
Nonstop4h 44m
Deal found 7/31![United Airlines logo]()
$727
Last-minute flights from San Juan to O'Hare IntlDiscover last-minute flight deals from San Juan to O'Hare Intl. Data last updated August 4, 2026 and is based on user searches.
Discover last-minute flight deals from San Juan to O'Hare Intl. Data last updated August 4, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Tue 8/116:00 am -
1 stop31h 15m
Sun 8/1612:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$283
This CheapOair deal was found by Cheapflights users on 7/31. 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.
Tue 8/115:00 pm -
1 stop7h 44m
Mon 8/2412:44 am -
Nonstop5h 00m
Deal found 7/31![Multiple Airlines logo]()
$320
This Cheapflightsfares deal was found by Cheapflights users on 7/31. 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.
Wed 8/125:05 am -
1 stop9h 34m
Wed 8/192:35 pm -
1 stop7h 45m
Deal found 7/31![JetBlue logo]()
$298
This CheapOair deal was found by Cheapflights users on 7/31. 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.
Wed 8/125:05 am -
1 stop9h 34m
Tue 8/1812:44 am -
Nonstop5h 00m
Deal found 7/31![Multiple Airlines logo]()
$314
This eDestinos deal was found by Cheapflights users on 8/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:14 pm -
Nonstop5h 13m
Sun 8/3012:44 am -
Nonstop5h 00m
Deal found 8/1![Frontier logo]()
$256
This Frontier deal was found by Cheapflights users on 8/3. 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.
Thu 8/137:14 pm -
Nonstop5h 13m
Mon 8/1712:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$268
This eDestinos deal was found by Cheapflights users on 7/31. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1310:48 pm -
1 stop25h 22m
Sun 8/2312:44 am -
Nonstop5h 00m
Deal found 7/31![Frontier logo]()
$292
This Expedia deal was found by Cheapflights users on 8/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:14 pm -
Nonstop5h 13m
Sat 8/1512:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$313
One-way flights from San Juan to O'Hare IntlSearch for one-way flight options from San Juan to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
Search for one-way flight options from San Juan to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 11/16:12 pm -
1 stop23h 12m
Deal found 8/1![Frontier logo]()
$127
This Super.com deal was found by Cheapflights users on 8/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$130
This Frontier deal was found by Cheapflights users on 7/30. 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.
Wed 8/267:14 pm -
Nonstop5h 13m
Deal found 7/30![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 9/257:00 am -
1 stop8h 45m
Deal found 8/3![Frontier logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 10/27:00 am -
1 stop8h 45m
Deal found 8/3![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 10/23:08 am -
2 stops12h 09m
Deal found 7/30![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Thu 10/295:12 pm -
1 stop23h 12m
Deal found 8/2![Frontier logo]()
$137
This Frontier deal was found by Cheapflights users on 8/3. 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.
Thu 9/37:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$139
Find flight deals from San Juan to O'Hare Intl
Discover tips and strategies to find the most affordable flight options for your journey from San Juan (PR1) to O'Hare Intl (ORD). 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 August 4, 2026.
Round-trip from | $179 (eDestinos) |
|---|---|
One-way from | $127 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $307 |
Cheapflights Fare Finder
Customize your flight search to find flights from San Juan to O'Hare Intl 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 August 4, 2026.
Use the filters below to find and compare flights from San Juan to Chicago O'Hare Intl Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 9/8
1:00 am-9:13 am
1 stop9h 13m
Chicago O'Hare Intl
Tue 9/22
8:55 am-2:44 pm
Nonstop4h 49m
$252
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 9/16
5:59 pm-11:59 pm
1 stop7h 00m
Chicago O'Hare Intl
Tue 9/22
10:25 am-11:49 pm
1 stop12h 24m
$276
Quickest round-trip
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 9/4
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Fri 9/11
8:55 am-2:44 pm
Nonstop4h 49m
$377
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 10/16
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Mon 10/19
8:55 am-2:44 pm
Nonstop4h 49m
$377
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Sat 10/3
1:00 am-7:42 am
1 stop7h 42m
Chicago O'Hare Intl
Thu 10/8
8:55 am-2:44 pm
Nonstop4h 49m
$456
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 9/17
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Mon 9/21
8:55 am-2:44 pm
Nonstop4h 49m
$457
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Sat 10/3
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Wed 10/7
8:55 am-2:44 pm
Nonstop4h 49m
$507
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 9/25
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Mon 9/28
8:55 am-2:44 pm
Nonstop4h 49m
$547
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Sun 9/13
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Wed 9/16
8:55 am-2:44 pm
Nonstop4h 49m
$582
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 8/26
1:00 am-11:52 am
2 stops11h 52m
Chicago O'Hare Intl
Mon 8/31
5:30 am-3:42 pm
1 stop9h 12m
$612
Showing 1-10 of 23 resultsSorted by cheapest first
Best time to book a flight from San Juan to O'Hare Intl
Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from San Juan with our price prediction graph.
PR1-ORD
SJU-ORD
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 San Juan to Chicago O'Hare Intl Airport
PR1-ORD
SJU-ORD
What is the cheapest month to book a flight from San Juan to Chicago O'Hare Intl Airport?
Currently, February is the cheapest month in which you can book a flight from San Juan to Chicago O'Hare Intl Airport (average of $232). Flying from San Juan to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $439). 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 SJU to ORD?
Find hourly flight availability from San Juan to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 4, 2026.
It’s typically best to fly out from San Juan to Chicago O'Hare Intl Airport in the evening. Doing so could potentially save you 17% on the flight price compared to flying in the morning, which is usually more expensive.
Weekly flight availability from San Juan to Chicago O'Hare Intl Airport
Explore weekly flight availability from San Juan to O'Hare Intl. 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 August 4, 2026.
The most flights from PR1 to ORD are scheduled on a Monday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 on average).
How much does it cost to fly round-trip from San Juan to Chicago O'Hare Intl Airport?
Airfare is below average for this route at the moment.
San Juan to Chicago O'Hare Intl Airport flights typically cost between $227 and $400 in August.The cheapest round-trip price found within the last 5 days was $179 on Frontier (Aug 27-Aug 30).
How often are flights from San Juan to Chicago delayed?
About 9% of weekly flights between San Juan and Chicago have experienced delays in the past year, with the average delay time being 187 minutes.
What is the most punctual flight time for San Juan to Chicago flights?
Historically, flights departing at night 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 Tuesday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on San Juan to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 4% of flights being delayed.
How far ahead should I book a flight from San Juan to Chicago O'Hare Intl Airport?
To ensure you get the cheapest price possible for a flight from San Juan to Chicago O'Hare Intl Airport, you should look to book at least 81 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 day to fly from San Juan to Chicago O'Hare Intl Airport?
Use this chart to determine the cheapest time to fly round-trip from San Juan to O'Hare Intl. Price data was last updated on August 1, 2026.
Travelers seeking maximum savings on their San Juan to Chicago O'Hare Intl Airport flight should consider departing on Sunday at noon when fares are most often at their lowest. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing O'Hare Intl
Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated August 4, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andJetBlue from San Juan to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Crew
8.5
Comfort
7.8
Overall
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Boarding
8.1
Crew
8.5
Comfort
7.8
Overall
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Boarding
8.1
Crew
8.5
Comfort
7.8
Overall
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Boarding
8.1
Crew
8.5
Comfort
7.8
Overall
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Boarding
8.1
Crew
8.5
Comfort
7.8
Overall
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Boarding
8.1
Crew
8.5
Comfort
7.8
Overall
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Related info for your journey
Find useful and relevant information for your journey from San Juan to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago O'Hare Intl Airport?
Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locationsBenton Harbor
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Top 6 airlines flying from San Juan to O'Hare Intl
Discover the top 6 airlines that operate flights from San Juan to O'Hare Intl. 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 August 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$128 | Average$284 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$204 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$227 | Average$428 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$267 | Average$477 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$292 | Average$427 | FlexibilityNo cancel fee | On-time63% |