$118+ Cheap flights from San Juan to Illinois
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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Jul 20 — Jul 271
Round-trip
1 adult, Economy
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Cheapest flights from San Juan to IllinoisExplore the most affordable flight options available from San Juan to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 20, 2026.
Explore the most affordable flight options available from San Juan to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 20, 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 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 9/36:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Sun 9/612:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/16![Frontier 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 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 8/228:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 6/15![United Airlines logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:45 am
SJU
- ORD
1 stop31h 15m
Frontier
Sun 8/2312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/17![Frontier logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Mon 9/712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/17![Frontier logo]()
$234
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.
Tue 8/258:20 am
SJU
- MDW
1 stop7h 25m
Southwest
Mon 8/315:00 am
MDW
- SJU
1 stop7h 45m
Southwest
Deal found 6/15![Southwest logo]()
$236
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:10 pm
SJU
- ORD
1 stop8h 25m
American Airlines
Sat 8/296:59 pm
ORD
- SJU
1 stop13h 44m
American Airlines
Deal found 6/17![American Airlines logo]()
$236
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:24 pm
SJU
- ORD
1 stop13h 10m
American Airlines
Wed 8/265:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 6/17![American Airlines logo]()
$237
This Frontier deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Sun 9/612:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/17![Frontier logo]()
$238
Best flights from San Juan to IllinoisDiscover carefully curated flight deals from San Juan to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 20, 2026.
Discover carefully curated flight deals from San Juan to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 20, 2026.
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:30 am
SJU
- MDW
1 stop9h 35m
Southwest
Mon 9/73:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 6/19![Southwest logo]()
$246
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:24 pm
SJU
- ORD
1 stop13h 10m
American Airlines
Mon 8/316:00 am
ORD
- SJU
1 stop9h 11m
American Airlines
Deal found 6/19![American Airlines logo]()
$246
This Priceline deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Sun 8/3012:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/19![Frontier logo]()
$254
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Fri 8/2812:46 pm
MDW
- SJU
1 stop8h 43m
Delta
Deal found 6/19![Delta logo]()
$256
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 8/231:00 am
SJU
- ORD
1 stop9h 13m
United Airlines
Mon 8/315:30 am
ORD
- SJU
1 stop9h 12m
United Airlines
Deal found 6/15![United Airlines logo]()
$272
This JetBlue deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/134:58 pm
SJU
- ORD
1 stop7h 46m
JetBlue
Mon 8/177:00 am
ORD
- SJU
1 stop10h 51m
JetBlue
Deal found 6/19![JetBlue logo]()
$416
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 8/216:00 am
SJU
- MDW
1 stop7h 40m
Southwest
Sun 8/238:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Deal found 6/15![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:55 pm
SJU
- MDW
1 stop12h 50m
Southwest
Sat 8/227:50 am
MDW
- SJU
2 stops7h 50m
Southwest
Deal found 6/18![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:00 am
SJU
- MDW
1 stop10h 15m
Delta
Tue 8/186:05 am
MDW
- SJU
1 stop9h 33m
Delta
Deal found 6/18![Delta logo]()
$316
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 6/267:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Tue 6/306:29 pm
ORD
- SJU
1 stop10h 00m
United Airlines
Deal found 6/16![United Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:49 pm
SJU
- STL
1 stop7h 09m
Delta
Mon 9/77:00 am
STL
- SJU
1 stop8h 38m
Delta
Deal found 6/17![Delta logo]()
$336
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 9/245:30 am
SJU
- STL
2 stops10h 40m
Southwest
Wed 9/309:35 am
STL
- SJU
1 stop8h 25m
Southwest
Deal found 6/15![Southwest logo]()
$326
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/63:50 pm
SJU
- STL
1 stop8h 41m
American Airlines
Mon 10/126:08 pm
STL
- SJU
1 stop15h 57m
American Airlines
Deal found 6/19![American Airlines logo]()
$405
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/105:50 pm
SJU
- STL
1 stop7h 03m
Delta
Tue 7/141:22 pm
STL
- SJU
1 stop8h 08m
Delta
Deal found 6/18![Delta logo]()
$367
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:05 pm
SJU
- STL
1 stop8h 25m
Southwest
Mon 10/197:50 pm
STL
- SJU
1 stop12h 15m
Southwest
Deal found 6/19![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/111:20 pm
SJU
- STL
1 stop7h 35m
Southwest
Sun 8/163:30 pm
STL
- SJU
1 stop8h 00m
Southwest
Deal found 6/19![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:30 am
SJU
- STL
2 stops10h 40m
Southwest
Mon 9/2111:40 am
STL
- SJU
2 stops9h 30m
Southwest
Deal found 6/19![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/182:35 pm
SJU
- STL
2 stops8h 30m
Southwest
Sun 9/208:50 pm
STL
- SJU
1 stop13h 05m
Southwest
Deal found 6/17![Southwest logo]()
$336
This United Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/52:55 pm
SJU
- ORD
1 stop11h 04m
United Airlines
Tue 9/81:00 pm
ORD
- SJU
2 stops9h 50m
United Airlines
Deal found 6/18![United Airlines logo]()
$590
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/121:20 pm
SJU
- MDW
1 stop6h 50m
Southwest
Sun 8/168:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Deal found 6/19![Southwest logo]()
$336
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 9/175:30 am
SJU
- STL
2 stops10h 40m
Southwest
Tue 9/2210:15 am
STL
- SJU
2 stops9h 50m
Southwest
Deal found 6/16![Southwest logo]()
$372
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 stop11h 30m
Southwest
Mon 6/2911:35 am
MDW
- SJU
1 stop11h 50m
Southwest
Deal found 6/18![Southwest logo]()
$386
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 7/2410:20 pm
SJU
- MDW
1 stop11h 30m
Southwest
Mon 7/272:30 pm
MDW
- SJU
1 stop8h 50m
Southwest
Deal found 6/15![Southwest logo]()
$441
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 6/17![Southwest logo]()
$451
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:30 am
SJU
- ORD
2 stops11h 59m
Delta
Sun 9/137:00 am
ORD
- SJU
2 stops14h 00m
Delta
Deal found 6/19![Delta logo]()
$3,394
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/241:19 pm
SJU
- ORD
1 stop9h 33m
Delta
Mon 8/3110:30 am
ORD
- SJU
2 stops10h 59m
Delta
Deal found 6/18![Delta logo]()
$3,394
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:30 am
SJU
- ORD
2 stops9h 47m
Delta
Sun 8/307:05 am
ORD
- SJU
2 stops14h 24m
Delta
Deal found 6/19![Delta logo]()
$3,394
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:00 am
SJU
- ORD
2 stops12h 03m
Delta
Sat 8/2211:22 am
ORD
- SJU
2 stops11h 30m
Delta
Deal found 6/18![Delta logo]()
$3,394
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:00 am
SJU
- ORD
2 stops13h 12m
Delta
Tue 8/251:00 pm
ORD
- SJU
1 stop9h 52m
Delta
Deal found 6/16![Delta logo]()
$3,403
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/246:00 am
SJU
- ORD
2 stops13h 03m
Delta
Mon 8/38:05 am
ORD
- SJU
2 stops14h 47m
Delta
Deal found 6/19![Delta logo]()
$3,403
Last-minute flights from San Juan to IllinoisDiscover last-minute flight deals from San Juan to Illinois. Data last updated June 20, 2026 and is based on user searches.
Discover last-minute flight deals from San Juan to Illinois. Data last updated June 20, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Sat 6/2711:15 am
ORD
- SJU
1 stop9h 09m
United Airlines
Deal found 6/17![United Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 stop8h 56m
American Airlines
Tue 6/308:05 am
ORD
- SJU
1 stop13h 55m
American Airlines
Deal found 6/19![American Airlines logo]()
$316
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 American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 stop8h 56m
American Airlines
Sat 6/278:00 am
ORD
- SJU
1 stop13h 45m
American Airlines
Deal found 6/19![American Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:47 pm
SJU
- ORD
1 stop11h 47m
American Airlines
Sat 6/2711:40 am
ORD
- SJU
1 stop10h 20m
American Airlines
Deal found 6/19![American Airlines logo]()
$333
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/257:00 am
SJU
- ORD
1 stop11h 42m
American Airlines
Tue 6/308:05 am
ORD
- SJU
1 stop13h 55m
American Airlines
Deal found 6/19![American Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/267:00 am
SJU
- ORD
1 stop11h 42m
American Airlines
Tue 6/308:05 am
ORD
- SJU
1 stop13h 55m
American Airlines
Deal found 6/17![American Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Mon 7/63:00 pm
MDW
- SJU
1 stop8h 35m
Southwest
Deal found 6/19![Southwest logo]()
$366
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.
Mon 6/296:00 am
SJU
- ORD
1 stop18h 19m
Frontier
Mon 7/2012:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/16![Frontier logo]()
$367
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/105:50 pm
SJU
- STL
1 stop7h 03m
Delta
Tue 7/141:22 pm
STL
- SJU
1 stop8h 08m
Delta
Deal found 6/18![Delta logo]()
$367
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1710:20 pm
SJU
- MDW
1 stop11h 30m
Southwest
Mon 7/205:10 pm
MDW
- SJU
1 stop7h 15m
Southwest
Deal found 6/19![Southwest logo]()
$346
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/235:15 pm
SJU
- STL
1 stop16h 42m
Frontier
Sun 7/266:34 pm
STL
- SJU
2 stops42h 26m
Frontier
Deal found 6/16![Frontier logo]()
$369
One-way flights from San Juan to IllinoisSearch for one-way flight options from San Juan to Illinois. Find affordable one-way fares based on user searches. Data last updated June 20, 2026.
Search for one-way flight options from San Juan to Illinois. Find affordable one-way fares based on user searches. Data last updated June 20, 2026.
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:33 am
SJU
- ORD
1 stop15h 02m
American Airlines
Deal found 6/17![American Airlines logo]()
$118
This eDestinos deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 6/18![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 Kiwi.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:45 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 6/19![Frontier logo]()
$122
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:55 pm
SJU
- MDW
2 stops15h 30m
Southwest
Deal found 6/19![Southwest logo]()
$123
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/237:24 pm
SJU
- ORD
1 stop13h 10m
American Airlines
Deal found 6/19![American Airlines logo]()
$123
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:00 am
SJU
- ORD
1 stop13h 46m
American Airlines
Deal found 6/18![American Airlines logo]()
$126
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 7/177:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/16![Frontier logo]()
$127
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:35 pm
SJU
- MDW
1 stop9h 05m
Southwest
Deal found 6/20![Southwest logo]()
$128
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/78:55 pm
SJU
- MDW
1 stop13h 30m
Southwest
Deal found 6/19![Southwest logo]()
$133
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
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:26 am
SJU
- STL
2 stops27h 31m
Frontier
Deal found 6/18![Frontier logo]()
$152
Find flight deals from San Juan to Illinois
Keep the following information in mind while searching for San Juan to Illinois flight deals. Data was last updated June 20, 2026.
Round-trip from | $225 (Kiwi.com) |
|---|---|
One-way from | $118 (American Airlines) |
Popular in | June |
Cheapest in | February |
Average price | $412 |
Cheapflights Fare Finder
Customize your flight search to find flights from San Juan to Illinois 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 20, 2026.
Use the filters below to find and compare flights from San Juan to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 9/3
5:30 am-2:05 pm
1 stop9h 35m
Chicago Midway
Mon 9/7
3:15 pm-11:05 pm
1 stop6h 50m
$246
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 8/20
7:24 pm-7:34 am
1 stop13h 10m
Chicago O'Hare Intl
Mon 8/31
6:00 am-4:11 pm
1 stop9h 11m
$246
Quickest round-trip
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 8/20
7:14 pm-11:27 pm
Nonstop5h 13m
Chicago O'Hare Intl
Sun 8/30
12:44 am-6:44 am
Nonstop5h 00m
$254
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 8/19
12:56 pm-10:36 pm
1 stop10h 40m
Chicago Midway
Fri 8/28
12:46 pm-10:29 pm
1 stop8h 43m
$256
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 8/21
6:00 am-12:40 pm
1 stop7h 40m
Chicago Midway
Sun 8/23
8:05 pm-9:10 am
1 stop12h 05m
$256
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 8/13
8:55 pm-8:45 am
1 stop12h 50m
Chicago Midway
Sat 8/22
7:50 am-4:40 pm
2 stops7h 50m
$256
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Sun 8/23
1:00 am-9:13 am
1 stop9h 13m
Chicago O'Hare Intl
Mon 8/31
5:30 am-3:42 pm
1 stop9h 12m
$272
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 8/12
7:00 am-4:15 pm
1 stop10h 15m
Chicago Midway
Tue 8/18
6:05 am-4:38 pm
1 stop9h 33m
$316
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Thu 9/24
5:30 am-3:10 pm
2 stops10h 40m
Lambert-St Louis
Wed 9/30
9:35 am-7:00 pm
1 stop8h 25m
$326
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Thu 9/3
5:49 pm-11:58 pm
1 stop7h 09m
Lambert-St Louis
Mon 9/7
7:00 am-4:38 pm
1 stop8h 38m
$336
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from San Juan to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from San Juan with our price prediction graph.
SJU-ORD
SJU-MDW
SJU-STL
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 Illinois
PR1-USIL
SJU-ORD
SJU-MDW
SJU-STL
What is the cheapest month to book a flight from San Juan to Illinois?
Currently, May is the cheapest month in which you can book a flight from San Juan to Illinois (average of $64). Flying from San Juan to Illinois in June is currently the most expensive (average of $915). 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 IL?
Find hourly flight availability from San Juan to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 20, 2026.
One of the essential ways to save on airfare from San Juan to Illinois is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 22% on airfare.
Weekly flight availability from San Juan to Illinois
Explore weekly flight availability from San Juan to Illinois. 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 20, 2026.
The most flights from PR1 to USIL 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 Illinois?
How far ahead should I book a flight from San Juan to Illinois?
Booking 81 days in advance of your planned departure date is, on average, the best time to get cheap flights from San Juan to Illinois. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from San Juan to Illinois?
Use this chart to determine the cheapest time to fly round-trip from San Juan to Illinois. Price data was last updated on June 13, 2026.
Travelers seeking maximum savings on their San Juan to Illinois 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 Illinois
Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated June 20, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from San Juan to Illinois have to say. 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.
Overall
7.9
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from San Juan to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
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San Juan and Illinois flights
Browse other San Juan and Illinois flight options. Last updated on June 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from San Juan to Illinois
Discover the top 6 airlines that operate flights from San Juan to Illinois. 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 20, 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% |