$99+ 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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Jun 3 — Jun 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 Friday or Thursday and return on a Tuesday
Cheap flight deals from San Juan to O'Hare Intl
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Best
Last-minute
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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 May 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 May 4, 2026.
This Priceline deal was found by Cheapflights users on 4/29. 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.
Sat 5/237:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sat 5/307:52 pm
ORD
- SJU
1 stop7h 09m
Frontier
Deal found 4/29![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Sat 5/307:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sun 5/3112:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 5/1![Frontier logo]()
$171
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.
Sat 8/16:00 am
SJU
- ORD
1 stop7h 25m
Frontier
Sat 8/1512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 5/2![Frontier logo]()
$172
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.
Sun 8/24:05 pm
SJU
- ORD
1 stop8h 00m
Frontier
Sat 8/1512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 5/2![Frontier logo]()
$182
This Frontier deal was found by Cheapflights users on 4/30. 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 5/237:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sun 5/2412:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/30![Frontier logo]()
$183
This eDestinos deal was found by Cheapflights users on 4/30. 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.
Sat 5/166:30 am
SJU
- ORD
1 stop13h 14m
Frontier
Sat 5/307:52 pm
ORD
- SJU
1 stop7h 09m
Frontier
Deal found 4/30![Frontier logo]()
$189
This eDestinos deal was found by Cheapflights users on 5/1. 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.
Fri 5/1511:00 am
SJU
- ORD
1 stop13h 59m
Frontier
Sun 5/1710:22 am
ORD
- SJU
1 stop12h 35m
Frontier
Deal found 5/1![Frontier logo]()
$196
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2111:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Sun 5/244:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$198
This eDestinos deal was found by Cheapflights users on 5/1. 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.
Sat 5/236:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Tue 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 5/1![Frontier logo]()
$201
This Orbitz deal was found by Cheapflights users on 4/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2011:01 am
SJU
- ORD
Nonstop5h 10m
Multiple Airlines
Tue 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$202
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 May 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 May 4, 2026.
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/131:06 pm
SJU
- ORD
1 stop9h 14m
Delta
Tue 8/186:00 am
ORD
- SJU
1 stop9h 31m
Delta
Deal found 4/30![Delta logo]()
$226
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Sat 8/17:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Sun 8/168:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 5/1![United Airlines logo]()
$307
This Delta deal was found by Cheapflights users on 5/3. 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.
Thu 8/62:11 pm
SJU
- ORD
1 stop7h 11m
Delta
Tue 8/185:28 am
ORD
- SJU
1 stop10h 09m
Delta
Deal found 5/3![Delta logo]()
$256
This Southwest deal was found by Cheapflights users on 5/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:40 pm
SJU
- ORD
2 stops17h 10m
Southwest
Mon 5/186:00 am
ORD
- SJU
2 stops16h 40m
Southwest
Deal found 5/3![Southwest logo]()
$518
This Delta deal was found by Cheapflights users on 5/3. 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.
Thu 8/62:11 pm
SJU
- ORD
1 stop7h 11m
Delta
Mon 8/108:02 am
ORD
- SJU
1 stop7h 35m
Delta
Deal found 5/3![Delta logo]()
$286
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/117:30 am
SJU
- ORD
1 stop7h 49m
Delta
Wed 8/198:15 am
ORD
- SJU
1 stop7h 20m
Delta
Deal found 4/30![Delta logo]()
$346
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Fri 5/157:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Mon 5/182:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 4/30![United Airlines logo]()
$457
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Tue 6/92:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 5/2![United Airlines logo]()
$473
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/217:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Wed 5/272:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 5/2![United Airlines logo]()
$495
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Tue 5/197:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Tue 5/192:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 5/1![United Airlines logo]()
$507
This United Airlines deal was found by Cheapflights users on 5/3. 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 10/83:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Tue 10/138:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 5/3![United Airlines logo]()
$547
This United Airlines deal was found by Cheapflights users on 5/3. 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 6/267:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Sun 7/52:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 5/3![United Airlines logo]()
$590
Last-minute flights from San Juan to O'Hare IntlDiscover last-minute flight deals from San Juan to O'Hare Intl. Data last updated May 4, 2026 and is based on user searches.
Discover last-minute flight deals from San Juan to O'Hare Intl. Data last updated May 4, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 4/29. 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 5/94:59 pm
SJU
- ORD
Nonstop5h 15m
Multiple Airlines
Sat 5/165:30 pm
ORD
- SJU
1 stop13h 34m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$203
This Orbitz deal was found by Cheapflights users on 4/29. 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.
Sat 5/94:59 pm
SJU
- ORD
Nonstop5h 15m
Multiple Airlines
Thu 5/143:44 pm
ORD
- SJU
1 stop24h 32m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 5/94:59 pm
SJU
- ORD
Nonstop5h 15m
Multiple Airlines
Fri 5/2912:33 am
ORD
- SJU
Nonstop4h 51m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$225
This Frontier deal was found by Cheapflights users on 4/29. 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 5/96:30 am
SJU
- ORD
1 stop13h 14m
Frontier
Sat 5/165:30 pm
ORD
- SJU
1 stop13h 34m
Frontier
Deal found 4/29![Frontier logo]()
$226
This Priceline deal was found by Cheapflights users on 4/29. 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.
Sat 5/93:33 pm
SJU
- ORD
1 stop8h 40m
Frontier
Fri 5/2912:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/29![Frontier logo]()
$227
This Priceline deal was found by Cheapflights users on 4/29. 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.
Sat 5/96:30 am
SJU
- ORD
1 stop13h 14m
Frontier
Thu 5/143:44 pm
ORD
- SJU
1 stop24h 32m
Frontier
Deal found 4/29![Frontier logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Wed 5/132:56 pm
SJU
- ORD
1 stop19h 31m
Frontier
Sun 5/1710:22 am
ORD
- SJU
1 stop12h 35m
Frontier
Deal found 5/1![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Thu 5/1411:39 am
SJU
- ORD
Nonstop5h 10m
Multiple Airlines
Mon 5/185:30 pm
ORD
- SJU
1 stop7h 38m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$224
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 5/1411:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Sun 5/174:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/29![Spirit Airlines logo]()
$228
This eDestinos deal was found by Cheapflights users on 4/30. 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.
Thu 5/147:00 am
SJU
- ORD
1 stop8h 39m
Frontier
Mon 5/185:30 pm
ORD
- SJU
1 stop18h 45m
Frontier
Deal found 4/30![Frontier logo]()
$232
This eDestinos deal was found by Cheapflights users on 4/30. 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.
Thu 5/1411:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Mon 5/185:05 am
ORD
- SJU
1 stop12h 54m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$237
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 May 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 May 4, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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.
Sat 5/234:59 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 5/1![Spirit Airlines logo]()
$99
This Spirit deal was found by Cheapflights users on 4/30. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2211:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$100
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.
Sat 5/307:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 5/2![Frontier logo]()
$101
This Super.com deal was found by Cheapflights users on 4/29. 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 5/233:03 am
SJU
- ORD
1 stop21h 10m
Frontier
Deal found 4/29![Frontier logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 5/2911:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/29![Spirit Airlines logo]()
$105
This eDestinos deal was found by Cheapflights users on 5/1. 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 7/167:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 5/1![Frontier logo]()
$108
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2312:59 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 4/30![American Airlines logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 6/56:00 am
SJU
- ORD
1 stop7h 24m
Frontier
Deal found 4/30![Frontier logo]()
$110
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:59 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 5/1![American Airlines logo]()
$111
This eDestinos deal was found by Cheapflights users on 5/1. 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.
Sat 5/236:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Deal found 5/1![Frontier logo]()
$112
This Delta deal was found by Cheapflights users on 5/3. 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.
Thu 7/912:56 pm
SJU
- ORD
1 stop10h 12m
Delta
Deal found 5/3![Delta logo]()
$113
This Priceline deal was found by Cheapflights users on 4/29. 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 5/123:03 am
SJU
- ORD
1 stop21h 10m
Frontier
Deal found 4/29![Frontier logo]()
$114
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 May 4, 2026.
Round-trip from | $165 (Priceline) |
|---|---|
One-way from | $99 (Cheapflightsfares) |
Popular in | November |
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 May 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
Thu 8/13
1:06 pm-9:20 pm
1 stop9h 14m
Chicago O'Hare Intl
Tue 8/18
6:00 am-4:31 pm
1 stop9h 31m
$226
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 8/6
2:11 pm-8:22 pm
1 stop7h 11m
Chicago O'Hare Intl
Tue 8/18
5:28 am-4:37 pm
1 stop10h 09m
$256
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 8/6
2:11 pm-8:22 pm
1 stop7h 11m
Chicago O'Hare Intl
Mon 8/10
8:02 am-4:37 pm
1 stop7h 35m
$286
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Sat 8/1
7:40 am-11:53 am
Nonstop5h 13m
Chicago O'Hare Intl
Sun 8/16
8:55 am-2:44 pm
Nonstop4h 49m
$307
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 8/11
7:30 am-2:19 pm
1 stop7h 49m
Chicago O'Hare Intl
Wed 8/19
8:15 am-4:35 pm
1 stop7h 20m
$346
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 5/15
7:40 am-11:53 am
Nonstop5h 13m
Chicago O'Hare Intl
Mon 5/18
2:38 pm-8:34 pm
Nonstop4h 56m
$457
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 6/2
7:40 am-11:53 am
Nonstop5h 13m
Chicago O'Hare Intl
Tue 6/9
2:38 pm-8:34 pm
Nonstop4h 56m
$473
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 5/21
7:40 am-11:53 am
Nonstop5h 13m
Chicago O'Hare Intl
Wed 5/27
2:38 pm-8:34 pm
Nonstop4h 56m
$495
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 5/19
7:40 am-11:53 am
Nonstop5h 13m
Chicago O'Hare Intl
Tue 5/19
2:38 pm-8:34 pm
Nonstop4h 56m
$507
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 5/14
8:40 pm-12:50 pm
2 stops17h 10m
Chicago O'Hare Intl
Mon 5/18
6:00 am-11:40 pm
2 stops16h 40m
$518
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
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 month to book a flight from San Juan to Chicago O'Hare Intl Airport?
Currently, May is the cheapest month in which you can book a flight from San Juan to Chicago O'Hare Intl Airport (average of $64). Flying from San Juan to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $117). 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 May 4, 2026.
It’s typically best to fly out from San Juan to Chicago O'Hare Intl Airport at noon. Doing so could potentially save you 43% 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 May 2, 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 May 4, 2026.
The most flights from PR1 to ORD are scheduled on a Monday (9 on average). You will have fewer flight options on Thursday, 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?
How often are flights from San Juan to Chicago delayed?
About 8% of weekly flights between San Juan and Chicago have experienced delays in the past year, with the average delay time being 188 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 Saturday 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.
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 May 4, 2026.
Get a feel of what it's like to fly with United Airlines,JetBlue, andAmerican Airlines 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.
Crew
8.1
Boarding
7.7
Food
6.6
Comfort
7.3
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Crew
8.1
Boarding
7.7
Food
6.6
Comfort
7.3
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Crew
8.1
Boarding
7.7
Food
6.6
Comfort
7.3
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Crew
8.1
Boarding
7.7
Food
6.6
Comfort
7.3
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Crew
8.1
Boarding
7.7
Food
6.6
Comfort
7.3
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Crew
8.1
Boarding
7.7
Food
6.6
Comfort
7.3
Entertainment
7.1
Overall
7.4
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 locationsRosemont
Schaumburg
Naperville
Lake Geneva
Gurnee
Delavan
Downers Grove
Oakbrook Terrace
Benton Harbor
Hoffman Estates
Des Plaines
Oak Brook
South Holland
Libertyville
Warrenville
Elk Grove Village
Bridgeview
Great Lakes
Lansing
Arlington Heights
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Other flights to O'Hare Intl
Explore flights to O'Hare Intl departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 4, 2026.
San Juan and O'Hare Intl flights
Browse other San Juan and O'Hare Intl flight options. Last updated on May 4, 2026.
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Top 7 airlines flying from San Juan to O'Hare Intl
Discover the top 7 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 May 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$116 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$121 | Average$265 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$128 | Average$254 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$254 | Average$484 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$257 | Average$440 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$292 | Average$457 | FlexibilityNo cancel fee | On-time63% |