$117+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Sep 5 — Sep 121
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 August 6, 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 August 6, 2026.
This eDestinos deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:14 pm -
Nonstop5h 13m
Sun 8/3012:44 am -
Nonstop5h 00m
Deal found 8/2![Frontier logo]()
$179
This Frontier deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 8/287:14 pm -
Nonstop5h 13m
Sat 8/2912:44 am -
Nonstop5h 00m
Deal found 8/5![Frontier logo]()
$193
This eDestinos deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:14 pm -
Nonstop5h 13m
Sat 8/2912:44 am -
Nonstop5h 00m
Deal found 8/2![Frontier logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/168:45 am -
1 stop31h 00m
Sat 9/197:11 am -
1 stop8h 52m
Deal found 8/5![Frontier logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:45 am -
1 stop31h 00m
Wed 9/237:11 am -
1 stop29h 23m
Deal found 8/2![Frontier logo]()
$217
This Super.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/47:14 pm -
Nonstop5h 13m
Sun 9/612:44 am -
Nonstop5h 00m
Deal found 8/4![Frontier logo]()
$224
This eDestinos deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/37:14 pm -
Nonstop5h 13m
Sun 9/612:44 am -
Nonstop5h 00m
Deal found 8/5![Frontier logo]()
$229
This eDestinos deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 8/207:14 pm -
Nonstop5h 13m
Sat 8/2212:44 am -
Nonstop5h 00m
Deal found 8/6![Frontier logo]()
$234
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/116:00 am -
2 stops9h 30m
Sun 9/138:05 pm -
1 stop12h 05m
Deal found 8/5![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/510:25 am -
1 stop10h 20m
Tue 9/159:40 am -
1 stop7h 30m
Deal found 8/4![Southwest logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 11/45:30 pm -
1 stop18h 10m
Mon 11/1610:35 am -
2 stops30h 44m
Deal found 8/6![Frontier logo]()
$271
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/35:40 am -
1 stop7h 40m
Tue 11/31:20 pm -
1 stop7h 00m
Deal found 8/2![Southwest logo]()
$271
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 August 6, 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 August 6, 2026.
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1611:50 am -
1 stop6h 50m
Tue 9/2212:20 pm -
1 stop7h 50m
Deal found 8/3![Southwest logo]()
$276
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:59 pm -
1 stop7h 00m
Tue 9/2210:25 am -
1 stop12h 24m
Deal found 8/3![Delta logo]()
$276
This American Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:30 am -
2 stops10h 18m
Mon 10/126:00 am -
1 stop15h 57m
Deal found 8/2![American Airlines logo]()
$356
This JetBlue deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:00 pm -
1 stop7h 44m
Mon 8/316:00 am -
1 stop8h 59m
Deal found 8/1![JetBlue logo]()
$400
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 8/273:56 pm -
1 stop8h 03m
Wed 9/212:27 pm -
1 stop10h 23m
Deal found 8/4![United Airlines logo]()
$446
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:05 am -
2 stops10h 35m
Thu 10/82:50 pm -
2 stops8h 15m
Deal found 8/1![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/151:20 pm -
1 stop6h 50m
Sat 9/1911:45 am -
2 stops9h 15m
Deal found 8/4![Southwest logo]()
$320
This Delta deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 10/12:59 pm -
1 stop9h 43m
Sat 10/31:40 pm -
1 stop7h 39m
Deal found 8/6![Delta logo]()
$356
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/115:59 pm -
1 stop6h 43m
Sun 9/136:00 am -
1 stop9h 49m
Deal found 8/5![Delta logo]()
$356
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 10/215:05 am -
1 stop10h 35m
Sat 10/241:50 pm -
1 stop6h 40m
Deal found 8/4![Southwest logo]()
$326
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/45:49 pm -
1 stop7h 09m
Mon 9/76:00 am -
1 stop6h 42m
Deal found 8/5![Delta logo]()
$356
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/281:00 am -
2 stops12h 13m
Wed 9/306:15 am -
1 stop8h 27m
Deal found 8/2![United Airlines logo]()
$446
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 8/255:15 am -
2 stops7h 50m
Wed 9/912:45 pm -
1 stop8h 20m
Deal found 8/4![Southwest logo]()
$341
This United Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:25 am -
Nonstop5h 24m
Mon 11/28:52 am -
Nonstop4h 48m
Deal found 8/1![United Airlines logo]()
$457
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/165:15 am -
2 stops7h 50m
Sat 9/1911:45 am -
2 stops9h 15m
Deal found 8/5![Southwest logo]()
$345
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/43:56 pm -
Nonstop5h 09m
Sun 9/138:55 am -
Nonstop4h 49m
Deal found 8/6![United Airlines logo]()
$472
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/15:15 am -
1 stop8h 25m
Wed 9/237:15 am -
2 stops9h 55m
Deal found 8/4![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/112:35 pm -
2 stops8h 35m
Sun 9/139:00 pm -
1 stop11h 10m
Deal found 8/5![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/91:20 pm -
1 stop7h 35m
Tue 9/1510:15 am -
2 stops9h 45m
Deal found 8/4![Southwest logo]()
$356
This United Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:56 pm -
Nonstop5h 09m
Sun 9/138:55 am -
Nonstop4h 49m
Deal found 8/1![United Airlines logo]()
$547
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/288:55 am -
Nonstop4h 49m
Deal found 8/4![United Airlines logo]()
$547
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:55 pm -
1 stop13h 30m
Mon 8/249:20 am -
2 stops9h 45m
Deal found 8/3![Southwest logo]()
$380
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/192:50 pm -
1 stop8h 54m
Fri 9/2512:39 pm -
1 stop8h 40m
Deal found 8/1![Delta logo]()
$629
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:00 am -
1 stop9h 44m
Sun 9/66:09 pm -
2 stops18h 36m
Deal found 8/2![United Airlines logo]()
$578
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 8/111:45 pm -
2 stops9h 05m
Tue 8/2512:45 pm -
2 stops8h 15m
Deal found 8/5![Southwest logo]()
$431
This United Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/101:00 am -
2 stops13h 13m
Fri 9/115:59 pm -
2 stops18h 46m
Deal found 8/1![United Airlines logo]()
$607
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 12/196:35 am -
1 stop11h 15m
Sun 1/31:30 pm -
2 stops8h 40m
Deal found 8/4![Southwest logo]()
$436
This United Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/261:00 am -
2 stops11h 52m
Sat 8/296:30 am -
1 stop8h 12m
Deal found 8/1![United Airlines logo]()
$612
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/46:00 am -
2 stops9h 30m
Mon 9/71:00 pm -
2 stops8h 55m
Deal found 8/4![Southwest logo]()
$466
This United Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/34:55 pm -
1 stop7h 45m
Mon 9/711:15 am -
2 stops11h 35m
Deal found 8/1![United Airlines logo]()
$665
Last-minute flights from San Juan to IllinoisDiscover last-minute flight deals from San Juan to Illinois. Data last updated August 6, 2026 and is based on user searches.
Discover last-minute flight deals from San Juan to Illinois. Data last updated August 6, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 8/207:14 pm -
Nonstop5h 13m
Sat 8/2212:44 am -
Nonstop5h 00m
Deal found 8/6![Frontier logo]()
$234
This eDestinos deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:14 pm -
Nonstop5h 13m
Sun 8/3012:44 am -
Nonstop5h 00m
Deal found 8/2![Frontier logo]()
$179
This eDestinos deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:14 pm -
Nonstop5h 13m
Sat 8/2912:44 am -
Nonstop5h 00m
Deal found 8/2![Frontier logo]()
$206
This Frontier deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 8/287:14 pm -
Nonstop5h 13m
Sat 8/2912:44 am -
Nonstop5h 00m
Deal found 8/5![Frontier logo]()
$193
This Orbitz deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:14 pm -
Nonstop5h 13m
Sun 8/3012:44 am -
Nonstop5h 00m
Deal found 8/2![Frontier logo]()
$198
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 8/286:30 am -
2 stops8h 15m
Sat 8/2911:00 am -
1 stop6h 15m
Deal found 8/5![Southwest logo]()
$276
This eDestinos deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/37:14 pm -
Nonstop5h 13m
Sun 9/612:44 am -
Nonstop5h 00m
Deal found 8/5![Frontier logo]()
$229
This Super.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/47:14 pm -
Nonstop5h 13m
Sun 9/612:44 am -
Nonstop5h 00m
Deal found 8/4![Frontier logo]()
$224
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/510:25 am -
1 stop10h 20m
Tue 9/159:40 am -
1 stop7h 30m
Deal found 8/4![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/112:35 pm -
1 stop9h 10m
Sun 9/138:05 pm -
1 stop12h 05m
Deal found 8/5![Southwest logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/168:45 am -
1 stop31h 00m
Sat 9/197:11 am -
1 stop8h 52m
Deal found 8/5![Frontier logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:45 am -
1 stop31h 00m
Wed 9/237:11 am -
1 stop29h 23m
Deal found 8/2![Frontier logo]()
$217
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 August 6, 2026.
Search for one-way flight options from San Juan to Illinois. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 10/63:08 am -
2 stops31h 32m
Deal found 8/6![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 11/46:12 pm -
2 stops17h 28m
Deal found 8/4![Frontier logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/47:00 am -
2 stops31h 10m
Deal found 8/3![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:37 pm -
2 stops24h 45m
Deal found 8/2![Frontier logo]()
$125
This eDestinos deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/37:14 pm -
Nonstop5h 13m
Deal found 8/6![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:12 pm -
2 stops18h 28m
Deal found 8/2![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:12 pm -
1 stop23h 12m
Deal found 8/2![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:08 am -
2 stops35h 02m
Deal found 8/3![Frontier logo]()
$128
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/106:30 am -
2 stops8h 15m
Deal found 8/5![Southwest logo]()
$128
This Super.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:37 pm -
2 stops24h 45m
Deal found 8/4![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:00 am -
1 stop8h 45m
Deal found 8/3![Frontier logo]()
$133
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 August 6, 2026.
Round-trip from | $179 (eDestinos) |
|---|---|
One-way from | $117 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $287 |
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 August 6, 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 - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 9/16
11:50 am-5:40 pm
1 stop6h 50m
Chicago Midway
Tue 9/22
12:20 pm-9:10 pm
1 stop7h 50m
$276
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Wed 9/16
5:59 pm-11:59 pm
1 stop7h 00m
Chicago O'Hare Intl
Tue 9/22
10:25 am-11:49 pm
1 stop12h 24m
$276
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 10/6
5:05 am-2:40 pm
2 stops10h 35m
Chicago Midway
Thu 10/8
2:50 pm-12:05 am
2 stops8h 15m
$301
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 9/15
1:20 pm-7:10 pm
1 stop6h 50m
Chicago Midway
Sat 9/19
11:45 am-10:00 pm
2 stops9h 15m
$320
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 10/21
5:05 am-2:40 pm
1 stop10h 35m
Chicago Midway
Sat 10/24
1:50 pm-9:30 pm
1 stop6h 40m
$326
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 8/25
5:15 am-12:05 pm
2 stops7h 50m
Chicago Midway
Wed 9/9
12:45 pm-10:05 pm
1 stop8h 20m
$341
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 9/16
5:15 am-12:05 pm
2 stops7h 50m
Chicago Midway
Sat 9/19
11:45 am-10:00 pm
2 stops9h 15m
$345
San JuanSt. Louis
SJU San Juan Luis Munoz Marin Intl - STL Lambert-St Louis
SJUSTL
San Juan Luis Munoz Marin Intl
Tue 10/6
6:30 am-3:48 pm
2 stops10h 18m
Lambert-St Louis
Mon 10/12
6:00 am-10:57 pm
1 stop15h 57m
$356
San JuanSt. Louis
SJU San Juan Luis Munoz Marin Intl - STL Lambert-St Louis
SJUSTL
San Juan Luis Munoz Marin Intl
Thu 10/1
2:59 pm-11:42 pm
1 stop9h 43m
Lambert-St Louis
Sat 10/3
1:40 pm-10:19 pm
1 stop7h 39m
$356
San JuanSt. Louis
SJU San Juan Luis Munoz Marin Intl - STL Lambert-St Louis
SJUSTL
San Juan Luis Munoz Marin Intl
Fri 9/11
5:59 pm-11:42 pm
1 stop6h 43m
Lambert-St Louis
Sun 9/13
6:00 am-4:49 pm
1 stop9h 49m
$356
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, February is the cheapest month in which you can book a flight from San Juan to Illinois (average of $227). Flying from San Juan to Illinois in June is currently the most expensive (average of $447). 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 August 6, 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 28% 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 August 6, 2026.
The most flights from PR1 to USIL are scheduled on a Monday (9 on average). You will have fewer flight options on Tuesday, 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 $226 and $392 in August.The cheapest round-trip price found within the last 5 days was $179 on Frontier (Aug 27-Aug 30).
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 August 1, 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 August 6, 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.
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
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 August 6, 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 August 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$128 | Average$284 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$204 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$227 | Average$428 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$266 | Average$490 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$267 | Average$477 | FlexibilityNo cancel fee | On-time69% |