$89+ Cheap flights from San Juan to Illinois
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Oct 21 — Oct 281
Round-trip
1 adult, Economy
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1. Tell us where you want to go
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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 September 21, 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 September 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/217:15 am -
2 stops11h 25m
Fri 10/236:35 pm -
1 stop20h 31m
Deal found 9/17![Frontier logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 9/18. 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.
Thu 10/293:59 pm -
1 stop26h 41m
Wed 11/116:44 pm -
2 stops40h 41m
Deal found 9/18![Frontier logo]()
$214
This CheapOair deal was found by Cheapflights users on 9/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:11 pm -
1 stop7h 32m
Mon 10/266:15 am -
1 stop8h 51m
Deal found 9/20![Frontier logo]()
$220
This CheapOair deal was found by Cheapflights users on 9/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:00 am -
1 stop9h 30m
Sat 10/318:00 am -
1 stop28h 25m
Deal found 9/18![Frontier logo]()
$221
This Frontier deal was found by Cheapflights users on 9/16. 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 10/85:11 pm -
1 stop7h 32m
Tue 10/136:21 am -
1 stop8h 45m
Deal found 9/16![Frontier logo]()
$222
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:12 pm -
Nonstop5h 21m
Fri 11/275:01 am -
1 stop6h 58m
Deal found 9/17![Frontier logo]()
$223
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:15 am -
1 stop17h 24m
Wed 10/289:51 am -
1 stop14h 59m
Deal found 9/17![Frontier logo]()
$224
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:12 pm -
Nonstop5h 21m
Mon 11/3011:53 pm -
Nonstop4h 39m
Deal found 9/17![Frontier logo]()
$228
This FlightHub deal was found by Cheapflights users on 9/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:00 am -
1 stop12h 10m
Sun 12/610:38 am -
1 stop26h 21m
Deal found 9/21![Frontier logo]()
$229
This FlightHub deal was found by Cheapflights users on 9/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:55 am -
1 stop17h 52m
Sun 11/228:42 pm -
1 stop27h 42m
Deal found 9/18![Frontier logo]()
$230
This FlightHub deal was found by Cheapflights users on 9/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:42 pm -
1 stop13h 49m
Mon 10/128:11 pm -
1 stop28h 42m
Deal found 9/19![Frontier logo]()
$230
This CheapOair deal was found by Cheapflights users on 9/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/148:45 am -
1 stop7h 45m
Wed 10/218:04 am -
1 stop28h 27m
Deal found 9/19![Frontier logo]()
$231
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 September 21, 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 September 21, 2026.
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Wed 10/213:56 pm -
Nonstop5h 09m
Mon 10/268:52 am -
Nonstop4h 48m
Deal found 9/16![United Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 12/77:00 am -
1 stop11h 17m
Thu 12/101:02 pm -
1 stop8h 11m
Deal found 9/16![Delta logo]()
$306
This Southwest deal was found by Cheapflights users on 9/20. 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.
Wed 10/216:35 am -
2 stops9h 50m
Mon 10/261:20 pm -
2 stops8h 50m
Deal found 9/20![Southwest logo]()
$321
This Mytrip deal was found by Cheapflights users on 9/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:15 am -
2 stops11h 25m
Sun 10/184:30 pm -
2 stops30h 24m
Deal found 9/16![Frontier logo]()
$351
This American Airlines deal was found by Cheapflights users on 9/18. 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.
Tue 10/66:30 am -
1 stop16h 29m
Mon 10/126:00 am -
1 stop15h 57m
Deal found 9/18![American Airlines logo]()
$486
This United Airlines deal was found by Cheapflights users on 9/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:25 am -
Nonstop5h 22m
Tue 11/32:16 pm -
Nonstop4h 44m
Deal found 9/20![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 9/18. 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 11/65:50 pm -
1 stop7h 25m
Sun 11/88:40 pm -
1 stop11h 50m
Deal found 9/18![Southwest logo]()
$321
This United Airlines deal was found by Cheapflights users on 9/18. 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.
Tue 11/104:55 pm -
Nonstop5h 31m
Wed 11/112:16 pm -
Nonstop4h 44m
Deal found 9/18![United Airlines logo]()
$301
This Southwest deal was found by Cheapflights users on 9/20. 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.
Fri 1/226:15 am -
2 stops10h 30m
Mon 1/2511:10 am -
1 stop8h 50m
Deal found 9/20![Southwest logo]()
$330
This United Airlines deal was found by Cheapflights users on 9/21. 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 10/293:55 pm -
Nonstop5h 31m
Sun 11/12:16 pm -
Nonstop4h 44m
Deal found 9/21![United Airlines logo]()
$305
This Delta deal was found by Cheapflights users on 9/18. 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 10/307:15 am -
1 stop10h 13m
Wed 11/1112:29 pm -
1 stop8h 46m
Deal found 9/18![Delta logo]()
$396
This United Airlines deal was found by Cheapflights users on 9/21. 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.
Mon 10/267:25 am -
Nonstop5h 22m
Fri 10/302:16 pm -
Nonstop4h 44m
Deal found 9/21![United Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 9/16. 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.
Sat 10/107:50 am -
1 stop8h 35m
Tue 10/137:05 pm -
1 stop13h 05m
Deal found 9/16![Southwest logo]()
$356
This Delta deal was found by Cheapflights users on 9/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:59 pm -
1 stop7h 24m
Tue 10/2710:14 am -
1 stop11h 04m
Deal found 9/20![Delta logo]()
$396
This United Airlines deal was found by Cheapflights users on 9/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:56 pm -
Nonstop5h 09m
Sun 9/276:25 am -
1 stop8h 17m
Deal found 9/19![United Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 9/19. 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 11/196:10 am -
1 stop10h 50m
Mon 11/304:00 pm -
2 stops7h 45m
Deal found 9/19![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 9/18. 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 12/46:10 am -
2 stops8h 45m
Sun 12/612:45 pm -
2 stops10h 20m
Deal found 9/18![Southwest logo]()
$390
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:56 pm -
Nonstop5h 09m
Mon 9/285:00 am -
1 stop7h 45m
Deal found 9/21![United Airlines logo]()
$417
This Southwest deal was found by Cheapflights users on 9/19. 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 11/185:40 am -
2 stops9h 15m
Mon 11/304:00 pm -
2 stops7h 45m
Deal found 9/19![Southwest logo]()
$437
This Delta deal was found by Cheapflights users on 9/19. 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.
Thu 9/247:00 am -
1 stop7h 23m
Wed 9/307:05 am -
1 stop8h 44m
Deal found 9/19![Delta logo]()
$602
This United Airlines deal was found by Cheapflights users on 9/18. 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.
Wed 11/184:55 pm -
Nonstop5h 31m
Tue 12/12:16 pm -
Nonstop4h 44m
Deal found 9/18![United Airlines logo]()
$419
This Southwest deal was found by Cheapflights users on 9/20. 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.
Sun 10/188:25 pm -
1 stop12h 15m
Tue 10/273:00 pm -
1 stop5h 55m
Deal found 9/20![Southwest logo]()
$447
This United Airlines deal was found by Cheapflights users on 9/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:25 am -
Nonstop5h 22m
Wed 12/210:35 am -
1 stop9h 47m
Deal found 9/19![United Airlines logo]()
$424
This Southwest deal was found by Cheapflights users on 9/17. 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.
Thu 2/116:10 am -
2 stops11h 30m
Sun 2/1411:10 am -
1 stop8h 50m
Deal found 9/17![Southwest logo]()
$459
This United Airlines deal was found by Cheapflights users on 9/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/304:55 pm -
1 stop7h 37m
Sun 10/48:55 am -
Nonstop4h 49m
Deal found 9/19![United Airlines logo]()
$446
This Southwest deal was found by Cheapflights users on 9/18. 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.
Sun 11/85:35 am -
2 stops8h 45m
Thu 11/1212:45 pm -
1 stop10h 25m
Deal found 9/18![Southwest logo]()
$471
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Mon 11/28:25 am -
Nonstop5h 22m
Fri 11/62:16 pm -
Nonstop4h 44m
Deal found 9/17![United Airlines logo]()
$467
This Southwest deal was found by Cheapflights users on 9/18. 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 11/192:25 pm -
1 stop9h 05m
Sat 11/2812:50 pm -
1 stop9h 30m
Deal found 9/18![Southwest logo]()
$471
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Fri 11/132:05 am -
1 stop10h 43m
Thu 12/32:16 pm -
Nonstop4h 44m
Deal found 9/17![United Airlines logo]()
$472
This Southwest deal was found by Cheapflights users on 9/17. 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 10/25:30 am -
1 stop12h 40m
Tue 10/611:25 am -
1 stop10h 45m
Deal found 9/17![Southwest logo]()
$506
Last-minute flights from San Juan to IllinoisDiscover last-minute flight deals from San Juan to Illinois. Data last updated September 21, 2026 and is based on user searches.
Discover last-minute flight deals from San Juan to Illinois. Data last updated September 21, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 9/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/68:45 am -
1 stop7h 35m
Tue 10/136:00 am -
1 stop9h 06m
Deal found 9/19![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/68:45 am -
1 stop7h 35m
Mon 10/128:11 pm -
1 stop28h 42m
Deal found 9/19![Frontier logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Wed 10/78:45 am -
1 stop7h 35m
Mon 10/128:11 pm -
1 stop28h 42m
Deal found 9/19![Frontier logo]()
$223
This FlightHub deal was found by Cheapflights users on 9/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:42 pm -
1 stop13h 49m
Mon 10/128:11 pm -
1 stop28h 42m
Deal found 9/19![Frontier logo]()
$230
This CheapOair deal was found by Cheapflights users on 9/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/148:45 am -
1 stop7h 45m
Wed 10/218:04 am -
1 stop28h 27m
Deal found 9/19![Frontier logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/217:15 am -
2 stops11h 25m
Fri 10/236:35 pm -
1 stop20h 31m
Deal found 9/17![Frontier logo]()
$183
This CheapOair deal was found by Cheapflights users on 9/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:00 am -
1 stop9h 30m
Sat 10/318:00 am -
1 stop28h 25m
Deal found 9/18![Frontier logo]()
$221
This JetBlue deal was found by Cheapflights users on 9/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:00 pm -
1 stop10h 10m
Sat 10/311:00 pm -
1 stop10h 13m
Deal found 9/17![JetBlue logo]()
$233
This CheapOair deal was found by Cheapflights users on 9/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:11 pm -
1 stop7h 32m
Mon 10/266:15 am -
1 stop8h 51m
Deal found 9/20![Frontier logo]()
$220
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:15 am -
1 stop17h 24m
Wed 10/289:51 am -
1 stop14h 59m
Deal found 9/17![Frontier logo]()
$224
This JetBlue deal was found by Cheapflights users on 9/21. 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 10/231:00 pm -
1 stop10h 10m
Wed 10/281:00 pm -
1 stop10h 13m
Deal found 9/21![JetBlue logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 9/18. 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.
Thu 10/293:59 pm -
1 stop26h 41m
Wed 11/116:44 pm -
2 stops40h 41m
Deal found 9/18![Frontier logo]()
$214
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 September 21, 2026.
Search for one-way flight options from San Juan to Illinois. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/18. 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.
Thu 12/35:01 am -
1 stop32h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/2012:59 am -
2 stops17h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 11/183:59 pm -
1 stop28h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$104
This OneTravel deal was found by Cheapflights users on 9/16. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:11 pm -
1 stop7h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$114
This Cheapflightsfares deal was found by Cheapflights users on 9/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:00 am -
1 stop9h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:15 am -
2 stops35h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$117
This Super.com deal was found by Cheapflights users on 9/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:00 pm -
1 stop10h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![JetBlue logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Tue 10/138:45 am -
2 stops33h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 11/247:12 pm -
Nonstop5h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$118
This JetBlue deal was found by Cheapflights users on 9/18. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:00 pm -
1 stop10h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![JetBlue logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Tue 10/1312:59 am -
2 stops17h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$120
This FlightHub deal was found by Cheapflights users on 9/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2210:21 pm -
1 stop28h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$121
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 September 21, 2026.
Round-trip from | $183 (Kiwi.com) |
|---|---|
One-way from | $89 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $276 |
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 7,457,451 searches. Data last updated September 21, 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 San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Fri 12/18
6:15 am-1:30 pm
1 stop9h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$119
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Tue 10/27
3:55 pm-8:26 pm
Nonstop5h 31m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$119
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Sat 12/12
6:01 am-1:30 pm
1 stop9h 29m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$119
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Fri 10/16
1:00 pm-10:10 pm
1 stop10h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$119
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 12/8
6:10 am-3:00 pm
1 stop10h 50m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$123
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 12/3
2:25 pm-9:30 pm
1 stop9h 05m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$123
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Sat 12/19
2:52 pm-11:39 pm
1 stop10h 47m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$123
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Tue 10/13
2:37 pm-11:30 pm
1 stop9h 53m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$123
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 11/10
7:00 am-11:59 am
1 stop6h 59m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$125
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Fri 10/23
5:59 pm-11:57 pm
1 stop6h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$125
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-STL
SJU-MDW
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 Illinois
PR1-USIL
SJU-STL
SJU-MDW
SJU-ORD
What is the cheapest month to book a flight from San Juan to Illinois?
Currently, February is the cheapest month in which you can book a flight from San Juan to Illinois (average of $218). Flying from San Juan to Illinois in June is currently the most expensive (average of $446). 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 September 21, 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 29% 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 September 21, 2026.
The most flights from PR1 to USIL are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).
How much does it cost to fly round-trip from San Juan to Illinois?
Airfare is below average for this route at the moment.
San Juan to Illinois flights typically cost between $250 and $444 in October.The cheapest round-trip price found within the last 5 days was $221 on Frontier (Oct 22-Oct 31).
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 September 19, 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. Wednesday at noon 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 September 21, 2026.
See what other customers who have flown with Southwest,United Airlines, andJetBlue 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.
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
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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Alternative routes for San Juan to Illinois
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Complete your trip
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Search flights from San Juan to Illinois by cabin class
Find flights from San Juan to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
San Juan and Illinois flights
Browse other San Juan and Illinois flight options. Last updated on September 21, 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 7,457,451 searches. Data last updated September 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$265 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$216 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$226 | Average$411 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$262 | Average$462 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$476 | FlexibilityNo cancel fee | On-time63% |