$96+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Mar 4 — Mar 111
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 67 days in advance, depart on a Friday or Thursday and return on a Monday
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 February 2, 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 February 2, 2026.
This Travelocity deal was found by Cheapflights users on 1/30. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Mon 3/98:16 pm
ORD
- SJU
1 stop17h 15m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$134
This Orbitz deal was found by Cheapflights users on 1/31. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2711:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Mon 3/28:16 pm
ORD
- SJU
1 stop17h 15m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$144
This Orbitz deal was found by Cheapflights users on 2/1. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Sat 3/78:16 pm
ORD
- SJU
1 stop16h 15m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$146
This Orbitz deal was found by Cheapflights users on 1/31. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1912:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Mon 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$147
This Expedia deal was found by Cheapflights users on 2/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/51:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Sat 2/712:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$149
This Orbitz deal was found by Cheapflights users on 1/31. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1111:32 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Wed 3/1810:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$156
This Cheapflightsfares deal was found by Cheapflights users on 2/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Tue 3/38:16 pm
ORD
- SJU
1 stop17h 15m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$157
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 February 2, 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 February 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/30. 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.
Tue 3/106:39 pm
SJU
- ORD
1 stop16h 00m
Multiple Airlines
Wed 3/1810:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$182
This CheapOair deal was found by Cheapflights users on 2/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/711:03 am
SJU
- ORD
1 stop23h 47m
Spirit Airlines
Mon 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Fri 2/2711:52 am
SJU
- ORD
1 stop8h 26m
Multiple Airlines
Sun 3/19:18 am
ORD
- SJU
1 stop14h 51m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$188
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2711:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Mon 3/28:42 pm
ORD
- SJU
2 stops16h 49m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$205
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Tue 3/38:42 pm
ORD
- SJU
2 stops16h 49m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$205
This CheapOair deal was found by Cheapflights users on 1/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2211:07 am
SJU
- ORD
1 stop8h 08m
Spirit Airlines
Sat 4/256:34 pm
ORD
- SJU
1 stop29h 46m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$209
This Priceline deal was found by Cheapflights users on 2/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1712:32 pm
SJU
- ORD
Nonstop5h 16m
Multiple Airlines
Sat 2/218:15 am
ORD
- SJU
1 stop8h 44m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$236
This OneTravel deal was found by Cheapflights users on 2/1. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:52 am
SJU
- ORD
1 stop23h 47m
Spirit Airlines
Sun 3/112:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$210
This OneTravel deal was found by Cheapflights users on 2/1. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3111:03 am
SJU
- ORD
1 stop23h 47m
Spirit Airlines
Tue 4/78:56 pm
ORD
- SJU
Nonstop4h 33m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$223
This OneTravel deal was found by Cheapflights users on 2/1. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1811:03 am
SJU
- ORD
1 stop8h 28m
Spirit Airlines
Mon 3/238:58 pm
ORD
- SJU
2 stops13h 51m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$228
This Cheapflightsfares deal was found by Cheapflights users on 2/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Sun 3/812:22 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$238
Last-minute flights from San Juan to O'Hare IntlDiscover last-minute flight deals from San Juan to O'Hare Intl. Data last updated February 2, 2026 and is based on user searches.
Discover last-minute flight deals from San Juan to O'Hare Intl. Data last updated February 2, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 2/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/51:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Sat 2/712:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$149
This eDestinos deal was found by Cheapflights users on 2/1. 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.
Wed 2/114:40 pm
SJU
- ORD
1 stop9h 07m
Spirit Airlines
Wed 3/47:00 am
ORD
- SJU
1 stop6h 31m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$169
This Orbitz deal was found by Cheapflights users on 1/31. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1912:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Mon 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$147
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Tue 3/35:15 am
ORD
- SJU
1 stop8h 16m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$136
This Orbitz deal was found by Cheapflights users on 1/31. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Sat 2/288:16 pm
ORD
- SJU
1 stop17h 15m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$173
This Orbitz deal was found by Cheapflights users on 1/31. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2711:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Mon 3/28:16 pm
ORD
- SJU
1 stop17h 15m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$144
This Expedia deal was found by Cheapflights users on 2/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/287:00 am
SJU
- ORD
1 stop12h 03m
Spirit Airlines
Mon 3/212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$167
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 February 2, 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 February 2, 2026.
This Trip.com deal was found by Cheapflights users on 1/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/710:53 am
SJU
- ORD
1 stop14h 06m
Frontier
Deal found 1/31![Frontier logo]()
$96
This Expedia deal was found by Cheapflights users on 2/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/287:00 am
SJU
- ORD
1 stop12h 03m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$97
This Cheapflightsfares deal was found by Cheapflights users on 1/31. 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.
Fri 3/612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$100
This Travelocity deal was found by Cheapflights users on 2/2. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/164:11 pm
SJU
- ORD
1 stop7h 42m
Frontier
Deal found 2/2![Frontier logo]()
$101
This Cheapflightsfares deal was found by Cheapflights users on 2/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/232:15 am
SJU
- ORD
1 stop17h 00m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$102
This Orbitz deal was found by Cheapflights users on 2/2. 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.
Wed 2/1811:52 am
SJU
- ORD
1 stop7h 54m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$103
This Cheapflightsfares deal was found by Cheapflights users on 2/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1912:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$104
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/411:52 am
SJU
- ORD
2 stops22h 02m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$105
This Expedia deal was found by Cheapflights users on 2/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:30 am
SJU
- ORD
1 stop27h 45m
Frontier
Deal found 2/2![Frontier logo]()
$107
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1411:03 am
SJU
- ORD
2 stops23h 09m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Thu 2/2612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$110
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2811:07 am
SJU
- ORD
1 stop8h 08m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$111
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 February 2, 2026.
Round-trip from | $134 (Travelocity) |
|---|---|
One-way from | $96 (Trip.com) |
Popular in | November |
Cheapest in | February |
Average price | $210 |
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 February 2, 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
San Juan
Fly to
O'Hare Intl
Route
Depart
Return
Price
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 3/10
6:39 pm-9:39 am
1 stop16h 00m
Chicago O'Hare Intl
Wed 3/18
10:55 am-11:58 pm
1 stop12h 03m
$182
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 2/27
11:52 am-6:18 pm
1 stop8h 26m
Chicago O'Hare Intl
Sun 3/1
9:18 am-2:09 am
1 stop14h 51m
$188
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 4/7
11:03 am-9:50 am
1 stop23h 47m
Chicago O'Hare Intl
Mon 4/13
10:55 am-11:58 pm
1 stop12h 03m
$196
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 2/27
11:52 am-6:18 pm
1 stop8h 26m
Chicago O'Hare Intl
Mon 3/2
8:42 pm-3:31 pm
2 stops16h 49m
$205
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 2/26
11:52 am-6:18 pm
1 stop8h 26m
Chicago O'Hare Intl
Tue 3/3
8:42 pm-3:31 pm
2 stops16h 49m
$205
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 4/22
11:07 am-6:15 pm
1 stop8h 08m
Chicago O'Hare Intl
Sat 4/25
6:34 pm-1:20 am
1 stop29h 46m
$209
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 2/26
11:52 am-9:39 am
1 stop23h 47m
Chicago O'Hare Intl
Sun 3/1
12:17 pm-6:49 pm
Nonstop4h 32m
$210
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 3/31
11:03 am-9:50 am
1 stop23h 47m
Chicago O'Hare Intl
Tue 4/7
8:56 pm-2:29 am
Nonstop4h 33m
$223
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 3/18
11:03 am-6:31 pm
1 stop8h 28m
Chicago O'Hare Intl
Mon 3/23
8:58 pm-11:49 am
2 stops13h 51m
$228
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 2/17
12:32 pm-3:48 pm
Nonstop5h 16m
Chicago O'Hare Intl
Sat 2/21
8:15 am-6:59 pm
1 stop8h 44m
$236
Showing 1-10 of 21 results
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
How far ahead should I book a flight from San Juan to Chicago O'Hare Intl Airport?
Use this chart to determine the optimal time to book a round-trip flight from San Juan to O'Hare Intl. Price data was last updated on January 30, 2026.
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 67 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 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 $120). Flying from San Juan to Chicago O'Hare Intl Airport in December is currently the most expensive (average of $157). 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 February 2, 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 47% on the flight price compared to flying in the afternoon, which is usually more expensive.
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 January 31, 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. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 February 2, 2026.
The most flights from PR1 to ORD are scheduled on a Monday (12 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 on average).
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 171 minutes.
What is the most punctual flight time for San Juan to Chicago 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 San Juan to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 5% of flights being delayed.
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 February 2, 2026.
Get a feel of what it's like to fly with United Airlines, American Airlines, and JetBlue 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
7.7
Comfort
7.3
Crew
8.1
Overall
7.4
Entertainment
7.1
Food
6.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Boarding
7.7
Comfort
7.3
Crew
8.1
Overall
7.4
Entertainment
7.1
Food
6.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Boarding
7.7
Comfort
7.3
Crew
8.1
Overall
7.4
Entertainment
7.1
Food
6.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Boarding
7.7
Comfort
7.3
Crew
8.1
Overall
7.4
Entertainment
7.1
Food
6.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Boarding
7.7
Comfort
7.3
Crew
8.1
Overall
7.4
Entertainment
7.1
Food
6.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Boarding
7.7
Comfort
7.3
Crew
8.1
Overall
7.4
Entertainment
7.1
Food
6.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
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 locationsSchaumburg
Rosemont
Naperville
Gurnee
Elgin
Hoffman Estates
Beloit
Delavan
Oak Brook
Des Plaines
Downers Grove
Elk Grove Village
Skokie
Libertyville
Lake Geneva
Waukegan
Bridgeview
Kenosha
Warrenville
Aurora
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Alternative routes for San Juan to O'Hare Intl
See prices for flight routes from nearby airports that may be better suited for you.
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 February 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$116 | Average$538 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$120 | Average$266 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$131 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$137 | Average$258 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$256 | Average$481 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$258 | Average$483 | FlexibilityNo cancel fee | On-time71% |