$118+ Cheap flights from San Juan to Chicago (CHI)
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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Jul 16 — Jul 231
Round-trip
1 adult, Economy
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Find cheap flights from San Juan to Chicago 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 are usually found in February or September, booked 23 days in advance, depart on a Thursday or Friday and return on a Monday
Cheap flight deals from San Juan to Chicago
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Best
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Cheapest flights from San Juan to ChicagoExplore the most affordable flight options available from San Juan to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 16, 2026.
Explore the most affordable flight options available from San Juan to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/15. 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 8/76:00 am
SJU
- ORD
1 stop31h 15m
Frontier
Sat 8/1512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/15![Frontier logo]()
$225
This United Airlines deal was found by Cheapflights users on 6/12. 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 9/33:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Sun 9/68:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 6/12![United Airlines logo]()
$227
This Frontier deal was found by Cheapflights users on 6/15. 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 8/266:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Tue 9/112:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/15![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 6/15. 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 8/216:00 am
SJU
- ORD
1 stop31h 25m
Frontier
Fri 9/412:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/15![Frontier logo]()
$229
This Frontier deal was found by Cheapflights users on 6/16. 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 8/276:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Fri 8/2812:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/16![Frontier logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 8/66:00 am
SJU
- ORD
1 stop31h 15m
Frontier
Fri 8/712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/12![Frontier logo]()
$231
This American Airlines deal was found by Cheapflights users on 6/16. 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 8/201:38 pm
SJU
- ORD
1 stop10h 52m
American Airlines
Tue 8/255:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 6/16![American Airlines logo]()
$232
This Frontier deal was found by Cheapflights users on 6/13. 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 8/127:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Fri 8/1412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/13![Frontier logo]()
$233
This Southwest deal was found by Cheapflights users on 6/12. 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.
Mon 8/316:00 am
SJU
- MDW
2 stops9h 30m
Southwest
Mon 9/73:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 6/12![Southwest logo]()
$236
This American Airlines deal was found by Cheapflights users on 6/16. 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 8/277:24 pm
SJU
- ORD
1 stop13h 10m
American Airlines
Mon 8/315:00 am
ORD
- SJU
1 stop8h 38m
American Airlines
Deal found 6/16![American Airlines logo]()
$236
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/261:38 pm
SJU
- ORD
1 stop11h 57m
American Airlines
Wed 9/25:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 6/16![American Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 7/296:00 am
SJU
- ORD
1 stop31h 15m
Frontier
Fri 8/712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/12![Frontier logo]()
$238
Best flights from San Juan to ChicagoDiscover carefully curated flight deals from San Juan to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 16, 2026.
Discover carefully curated flight deals from San Juan to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 16, 2026.
This United Airlines deal was found by Cheapflights users on 6/13. 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 9/33:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Sat 9/510:40 am
ORD
- SJU
1 stop8h 58m
United Airlines
Deal found 6/13![United Airlines logo]()
$232
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Mon 8/246:05 am
MDW
- SJU
1 stop9h 33m
Delta
Deal found 6/12![Delta logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 8/66:00 am
SJU
- ORD
1 stop31h 15m
Frontier
Mon 8/1012:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/11![Frontier logo]()
$287
This Southwest deal was found by Cheapflights users on 6/12. 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.
Mon 8/316:00 am
SJU
- MDW
2 stops9h 30m
Southwest
Mon 9/712:15 pm
MDW
- SJU
2 stops9h 50m
Southwest
Deal found 6/12![Southwest logo]()
$321
This JetBlue deal was found by Cheapflights users on 6/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:50 am
SJU
- ORD
1 stop7h 49m
JetBlue
Wed 8/127:00 am
ORD
- SJU
1 stop10h 51m
JetBlue
Deal found 6/13![JetBlue logo]()
$413
This United Airlines deal was found by Cheapflights users on 6/14. 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 9/44:55 pm
SJU
- ORD
1 stop7h 45m
United Airlines
Tue 9/85:00 am
ORD
- SJU
1 stop7h 53m
United Airlines
Deal found 6/14![United Airlines logo]()
$265
This United Airlines deal was found by Cheapflights users on 6/11. 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 8/67:20 am
SJU
- ORD
1 stop8h 09m
United Airlines
Tue 8/115:30 am
ORD
- SJU
1 stop9h 12m
United Airlines
Deal found 6/11![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 6/13. 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.
Mon 7/1310:20 pm
SJU
- MDW
1 stop12h 30m
Southwest
Mon 7/205:10 pm
MDW
- SJU
1 stop7h 15m
Southwest
Deal found 6/13![Southwest logo]()
$386
This Delta deal was found by Cheapflights users on 6/12. 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 9/22:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Mon 9/76:05 am
MDW
- SJU
1 stop9h 33m
Delta
Deal found 6/12![Delta logo]()
$396
This Southwest deal was found by Cheapflights users on 6/13. 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.
Tue 8/45:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Sun 8/91:10 pm
MDW
- SJU
2 stops8h 35m
Southwest
Deal found 6/13![Southwest logo]()
$396
This United Airlines deal was found by Cheapflights users on 6/16. 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 6/251:00 am
SJU
- ORD
1 stop7h 42m
United Airlines
Tue 6/306:29 pm
ORD
- SJU
1 stop10h 00m
United Airlines
Deal found 6/16![United Airlines logo]()
$412
This Southwest deal was found by Cheapflights users on 6/11. 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.
Wed 7/158:35 pm
SJU
- MDW
2 stops14h 25m
Southwest
Tue 7/214:40 pm
MDW
- SJU
1 stop6h 40m
Southwest
Deal found 6/11![Southwest logo]()
$416
This Southwest deal was found by Cheapflights users on 6/14. 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.
Sat 8/19:25 pm
SJU
- MDW
1 stop12h 05m
Southwest
Sat 8/87:50 am
MDW
- SJU
2 stops9h 15m
Southwest
Deal found 6/14![Southwest logo]()
$416
This United Airlines deal was found by Cheapflights users on 6/12. 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 6/257:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Tue 6/302:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 6/12![United Airlines logo]()
$417
This United Airlines deal was found by Cheapflights users on 6/16. 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 6/197:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Sat 6/206:30 am
ORD
- SJU
1 stop8h 12m
United Airlines
Deal found 6/16![United Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 6/15. 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.
Fri 7/175:30 am
SJU
- MDW
2 stops9h 35m
Southwest
Mon 7/202:30 pm
MDW
- SJU
1 stop8h 50m
Southwest
Deal found 6/15![Southwest logo]()
$426
This Southwest deal was found by Cheapflights users on 6/16. 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.
Fri 6/2610:20 pm
SJU
- MDW
1 stop12h 30m
Southwest
Tue 6/3012:00 pm
MDW
- SJU
1 stop11h 45m
Southwest
Deal found 6/16![Southwest logo]()
$456
This United Airlines deal was found by Cheapflights users on 6/12. 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 9/34:55 pm
SJU
- ORD
1 stop7h 45m
United Airlines
Sun 9/68:08 pm
ORD
- SJU
2 stops16h 37m
United Airlines
Deal found 6/12![United Airlines logo]()
$463
This Southwest deal was found by Cheapflights users on 6/15. 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.
Fri 10/96:30 am
SJU
- MDW
2 stops8h 40m
Southwest
Wed 10/1412:25 pm
MDW
- SJU
2 stops8h 50m
Southwest
Deal found 6/15![Southwest logo]()
$466
This United Airlines deal was found by Cheapflights users on 6/15. 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 8/192:20 pm
SJU
- ORD
1 stop10h 06m
United Airlines
Sat 8/224:00 pm
ORD
- SJU
2 stops19h 54m
United Airlines
Deal found 6/15![United Airlines logo]()
$476
This Southwest deal was found by Cheapflights users on 6/12. 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 10/86:30 am
SJU
- MDW
2 stops8h 40m
Southwest
Mon 10/127:45 am
MDW
- SJU
2 stops7h 45m
Southwest
Deal found 6/12![Southwest logo]()
$466
This United Airlines deal was found by Cheapflights users on 6/13. 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 6/237:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Tue 6/232:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 6/13![United Airlines logo]()
$492
This United Airlines deal was found by Cheapflights users on 6/15. 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 6/217:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Wed 6/242:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 6/15![United Airlines logo]()
$524
Last-minute flights from San Juan to ChicagoDiscover last-minute flight deals from San Juan to Chicago. Data last updated June 16, 2026 and is based on user searches.
Discover last-minute flight deals from San Juan to Chicago. Data last updated June 16, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/15. 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.
Fri 6/196:30 pm
SJU
- MDW
1 stop7h 10m
Southwest
Mon 6/225:10 pm
MDW
- SJU
1 stop7h 10m
Southwest
Deal found 6/15![Southwest logo]()
$371
This United Airlines deal was found by Cheapflights users on 6/14. 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 6/231:25 pm
SJU
- ORD
1 stop8h 35m
United Airlines
Sat 6/272:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 6/14![United Airlines logo]()
$395
This United Airlines deal was found by Cheapflights users on 6/12. 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 6/237:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Wed 6/242:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 6/12![United Airlines logo]()
$398
This United Airlines deal was found by Cheapflights users on 6/16. 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 6/231:00 am
SJU
- ORD
1 stop7h 42m
United Airlines
Wed 7/811:07 am
ORD
- SJU
1 stop9h 17m
United Airlines
Deal found 6/16![United Airlines logo]()
$403
This United Airlines deal was found by Cheapflights users on 6/15. 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 6/247:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Mon 6/296:40 pm
ORD
- SJU
1 stop9h 49m
United Airlines
Deal found 6/15![United Airlines logo]()
$357
This United Airlines deal was found by Cheapflights users on 6/12. 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 6/241:00 am
SJU
- ORD
1 stop7h 42m
United Airlines
Wed 7/12:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 6/12![United Airlines logo]()
$392
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/246:21 am
SJU
- ORD
1 stop14h 05m
American Airlines
Mon 7/138:00 am
ORD
- SJU
1 stop13h 59m
American Airlines
Deal found 6/12![American Airlines logo]()
$406
This Southwest deal was found by Cheapflights users on 6/12. 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 6/2510:20 pm
SJU
- MDW
1 stop12h 40m
Southwest
Sat 6/2712:50 pm
MDW
- SJU
2 stops10h 15m
Southwest
Deal found 6/12![Southwest logo]()
$386
This eDestinos deal was found by Cheapflights users on 6/12. 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 6/254:05 pm
SJU
- ORD
1 stop8h 14m
Frontier
Sun 6/287:52 am
ORD
- SJU
1 stop7h 06m
Frontier
Deal found 6/12![Frontier logo]()
$390
This Southwest deal was found by Cheapflights users on 6/16. 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 7/96:30 am
SJU
- MDW
1 stop8h 15m
Southwest
Mon 7/135:10 pm
MDW
- SJU
1 stop7h 15m
Southwest
Deal found 6/16![Southwest logo]()
$396
This Southwest deal was found by Cheapflights users on 6/14. 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.
Wed 7/225:00 am
SJU
- MDW
1 stop7h 00m
Southwest
Wed 8/127:30 am
MDW
- SJU
1 stop10h 30m
Southwest
Deal found 6/14![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 6/14. 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.
Tue 7/285:00 am
SJU
- MDW
1 stop10h 00m
Southwest
Wed 8/512:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Deal found 6/14![Southwest logo]()
$401
One-way flights from San Juan to ChicagoSearch for one-way flight options from San Juan to Chicago. Find affordable one-way fares based on user searches. Data last updated June 16, 2026.
Search for one-way flight options from San Juan to Chicago. Find affordable one-way fares based on user searches. Data last updated June 16, 2026.
This Southwest deal was found by Cheapflights users on 6/12. 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.
Sun 8/169:25 pm
SJU
- MDW
1 stop13h 35m
Southwest
Deal found 6/12![Southwest logo]()
$118
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:56 pm
SJU
- ORD
1 stop8h 59m
Delta
Deal found 6/12![Delta logo]()
$118
This Frontier deal was found by Cheapflights users on 6/12. 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 8/216:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 6/12![Frontier logo]()
$119
This eDestinos deal was found by Cheapflights users on 6/16. 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.
Tue 7/147:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/16![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 6/15. 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 8/46:00 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 6/15![Frontier logo]()
$121
This Southwest deal was found by Cheapflights users on 6/15. 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.
Fri 8/285:30 am
SJU
- MDW
1 stop9h 35m
Southwest
Deal found 6/15![Southwest logo]()
$123
This Super.com deal was found by Cheapflights users on 6/16. 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.
Fri 7/317:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/16![Frontier logo]()
$128
This Mytrip deal was found by Cheapflights users on 6/15. 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.
Fri 7/177:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/15![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 9/16:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 6/12![Frontier logo]()
$131
This eDestinos deal was found by Cheapflights users on 6/16. 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 7/97:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/16![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 6/15. 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
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 6/15![Frontier logo]()
$137
This Southwest deal was found by Cheapflights users on 6/15. 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 6/2510:20 pm
SJU
- MDW
1 stop11h 55m
Southwest
Deal found 6/15![Southwest logo]()
$138
Find flight deals from San Juan to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from San Juan (PR1) to Chicago (CHI). 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 June 16, 2026.
Round-trip from | $225 (Kiwi.com) |
|---|---|
One-way from | $118 (Southwest) |
Popular in | June |
Cheapest in | February |
Average price | $412 |
Cheapflights Fare Finder
Customize your flight search to find flights from San Juan to Chicago 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 June 16, 2026.
Use the filters below to find and compare flights from San Juan to Chicago 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 9/3
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Sat 9/5
10:40 am-8:38 pm
1 stop8h 58m
$232
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 9/4
4:55 pm-11:40 pm
1 stop7h 45m
Chicago O'Hare Intl
Tue 9/8
5:00 am-1:53 pm
1 stop7h 53m
$265
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 8/19
2:59 pm-10:36 pm
1 stop8h 37m
Chicago Midway
Mon 8/24
6:05 am-4:38 pm
1 stop9h 33m
$266
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 8/6
7:20 am-2:29 pm
1 stop8h 09m
Chicago O'Hare Intl
Tue 8/11
5:30 am-3:42 pm
1 stop9h 12m
$277
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 8/6
6:00 am-12:15 pm
1 stop31h 15m
Chicago O'Hare Intl
Mon 8/10
12:44 am-6:44 am
Nonstop5h 00m
$287
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mon 8/31
6:00 am-2:30 pm
2 stops9h 30m
Chicago Midway
Mon 9/7
12:15 pm-11:05 pm
2 stops9h 50m
$321
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mon 7/13
10:20 pm-9:50 am
1 stop12h 30m
Chicago Midway
Mon 7/20
5:10 pm-1:25 am
1 stop7h 15m
$386
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 9/2
2:59 pm-10:36 pm
1 stop8h 37m
Chicago Midway
Mon 9/7
6:05 am-4:38 pm
1 stop9h 33m
$396
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 8/4
5:15 am-12:05 pm
2 stops7h 50m
Chicago Midway
Sun 8/9
1:10 pm-10:45 pm
2 stops8h 35m
$396
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 6/25
1:00 am-7:42 am
1 stop7h 42m
Chicago O'Hare Intl
Tue 6/30
6:29 pm-5:29 am
1 stop10h 00m
$412
Showing 1-10 of 43 resultsSorted by cheapest first
Best time to book a flight from San Juan to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from San Juan with our price prediction graph.
PR1-CHI
SJU-ORD
SJU-MDW
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
PR1-CHI
SJU-ORD
SJU-MDW
What is the cheapest month to book a flight from San Juan to Chicago?
Currently, May is the cheapest month in which you can book a flight from San Juan to Chicago (average of $64). Flying from San Juan to Chicago in June is currently the most expensive (average of $887). 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 CHI?
Find hourly flight availability from San Juan to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 16, 2026.
When flying from San Juan to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 22% versus a flight in the afternoon.
Weekly flight availability from San Juan to Chicago
Explore weekly flight availability from San Juan to Chicago. 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 June 16, 2026.
The most flights from PR1 to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 on average).
How much does it cost to fly round-trip from San Juan to Chicago?
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 183 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 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.
How far ahead should I book a flight from San Juan to Chicago?
To ensure you get the cheapest price possible for a flight from San Juan to Chicago, 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?
Use this chart to determine the cheapest time to fly round-trip from San Juan to Chicago. Price data was last updated on June 13, 2026.
Travelers seeking maximum savings on their San Juan to Chicago flight should consider departing on Sunday at noon when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated June 16, 2026.
Read reviews from past customers who have flown United Airlines,American Airlines, andJetBlue from San Juan to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.1
Comfort
7.3
Food
6.6
Boarding
7.7
Overall
7.4
Crew
8.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Entertainment
7.1
Comfort
7.3
Food
6.6
Boarding
7.7
Overall
7.4
Crew
8.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Entertainment
7.1
Comfort
7.3
Food
6.6
Boarding
7.7
Overall
7.4
Crew
8.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Entertainment
7.1
Comfort
7.3
Food
6.6
Boarding
7.7
Overall
7.4
Crew
8.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Entertainment
7.1
Comfort
7.3
Food
6.6
Boarding
7.7
Overall
7.4
Crew
8.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Related info for your journey
Find useful and relevant information for your journey from San Juan to Chicago. 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?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Alternative routes for San Juan to Chicago
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 16, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from San Juan to Chicago by cabin class
Find flights from San Juan to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
San Juan and Chicago flights
Browse other San Juan and Chicago flight options. Last updated on June 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from San Juan to Chicago
Discover the top 6 airlines that operate flights from San Juan to Chicago. 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 June 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$252 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$227 | Average$432 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$263 | Average$483 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$292 | Average$508 | FlexibilityNo cancel fee | On-time63% |