$115+ Cheap flights from Puerto Rico 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 10 — Sep 171
Round-trip
1 adult, Economy
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Find cheap flights from Puerto Rico to Illinois with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Puerto Rico to Illinois
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Cheapest flights from Puerto Rico to IllinoisExplore the most affordable flight options available from Puerto Rico to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 11, 2026.
Explore the most affordable flight options available from Puerto Rico to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 9/177:00 am -
1 stop8h 45m
Wed 9/307:11 am -
1 stop29h 23m
Deal found 8/9![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/177:00 am -
1 stop8h 45m
Sun 9/207:11 am -
1 stop29h 23m
Deal found 8/10![Frontier logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/247:00 am -
1 stop8h 45m
Sun 9/277:11 am -
1 stop29h 23m
Deal found 8/10![Frontier logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/107:00 am -
1 stop8h 45m
Wed 9/167:11 am -
1 stop29h 23m
Deal found 8/7![Frontier logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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
Sat 9/267:11 am -
1 stop8h 52m
Deal found 8/10![Frontier logo]()
$205
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.
Fri 9/47:14 pm -
Nonstop5h 13m
Sat 9/127:11 am -
1 stop8h 52m
Deal found 8/6![Frontier logo]()
$206
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.
Mon 9/287:00 am -
1 stop8h 45m
Wed 9/307:11 am -
1 stop29h 23m
Deal found 8/6![Frontier logo]()
$208
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.
Fri 9/257:00 am -
1 stop8h 45m
Wed 9/307:11 am -
1 stop29h 23m
Deal found 8/6![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/107:00 am -
1 stop8h 45m
Sun 9/137:11 am -
1 stop29h 23m
Deal found 8/10![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/247:00 am -
1 stop8h 45m
Sat 9/267:11 am -
1 stop8h 52m
Deal found 8/10![Frontier logo]()
$211
This eDestinos deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 8/10![Frontier logo]()
$215
This Faresmojo deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:35 pm -
1 stop8h 55m
Mon 9/144:55 pm -
1 stop6h 00m
Deal found 8/10![JetBlue logo]()
$228
Best flights from Puerto Rico to IllinoisDiscover carefully curated flight deals from Puerto Rico to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 11, 2026.
Discover carefully curated flight deals from Puerto Rico to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 11, 2026.
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 9/252:35 pm -
1 stop9h 10m
Tue 9/296:15 am -
1 stop6h 15m
Deal found 8/9![Southwest logo]()
$256
This JetBlue deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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.
Mon 9/142:32 pm -
1 stop9h 36m
Tue 9/156:00 am -
1 stop8h 23m
Deal found 8/7![JetBlue logo]()
$300
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/173:56 pm -
Nonstop5h 09m
Sun 9/208:55 am -
Nonstop4h 49m
Deal found 8/10![United Airlines logo]()
$301
This Priceline deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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.
Mon 8/313:10 am -
1 stop20h 58m
Tue 9/153:50 pm -
1 stop17h 24m
Deal found 8/7![Frontier logo]()
$356
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 10/202:54 pm -
1 stop10h 15m
Tue 10/276:20 pm -
1 stop14h 26m
Deal found 8/7![American Airlines logo]()
$356
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 12/224:19 pm -
1 stop8h 59m
Tue 12/2911:51 am -
1 stop9h 29m
Deal found 8/7![Delta logo]()
$401
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/711:52 am -
1 stop13h 58m
Sun 11/152:35 pm -
1 stop8h 58m
Deal found 8/6![Multiple Airlines logo]()
$427
This Sun Country Air deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/245:20 pm -
1 stop27h 25m
Mon 12/287:40 pm -
1 stop18h 39m
Deal found 8/9![Sun Country Air logo]()
$523
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:00 am -
2 stops9h 30m
Tue 9/2212:20 pm -
1 stop8h 45m
Deal found 8/6![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:30 am -
1 stop9h 35m
Tue 9/19:40 am -
1 stop10h 25m
Deal found 8/8![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/186:00 am -
2 stops9h 30m
Tue 9/2212:20 pm -
1 stop7h 50m
Deal found 8/8![Southwest logo]()
$291
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:35 pm -
1 stop18h 49m
Thu 10/15:00 am -
1 stop9h 40m
Deal found 8/6![American Airlines logo]()
$364
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/33:10 am -
1 stop20h 58m
Mon 9/143:50 pm -
1 stop8h 59m
Deal found 8/6![Frontier logo]()
$396
This JetBlue deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 8/292:30 pm -
1 stop10h 14m
Mon 8/312:35 pm -
1 stop8h 58m
Deal found 8/8![JetBlue logo]()
$398
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/102:35 pm -
1 stop8h 55m
Sun 9/203:30 pm -
1 stop8h 05m
Deal found 8/11![Southwest logo]()
$300
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/244:55 pm -
1 stop7h 37m
Mon 9/288:55 am -
Nonstop4h 49m
Deal found 8/10![United Airlines logo]()
$426
This CheapOair deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/18:39 am -
2 stops16h 05m
Tue 9/153:50 pm -
1 stop17h 24m
Deal found 8/7![Multiple Airlines logo]()
$428
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 10/225:30 am -
2 stops8h 15m
Mon 10/263:45 pm -
1 stop8h 35m
Deal found 8/7![Southwest logo]()
$301
This Cheapflightsfares deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:01 am -
1 stop9h 38m
Sun 11/152:35 pm -
1 stop8h 58m
Deal found 8/10![JetBlue logo]()
$405
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/2411:08 am -
1 stop12h 51m
Mon 9/287:28 pm -
2 stops37h 46m
Deal found 8/8![Frontier logo]()
$428
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 9/14:36 pm -
1 stop7h 51m
Sun 9/612:44 am -
1 stop7h 58m
Deal found 8/6![Multiple Airlines logo]()
$429
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/186:00 am -
2 stops9h 30m
Sun 9/208:05 pm -
1 stop12h 05m
Deal found 8/8![Southwest logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 9/2411:08 am -
1 stop12h 51m
Sun 9/2711:15 am -
1 stop21h 58m
Deal found 8/9![Frontier logo]()
$428
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 8/7![United Airlines logo]()
$472
This CheapOair deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/49:52 pm -
2 stops17h 32m
Mon 9/79:10 pm -
1 stop28h 00m
Deal found 8/10![Multiple Airlines logo]()
$453
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/83:56 pm -
Nonstop5h 09m
Wed 10/148:55 am -
Nonstop4h 49m
Deal found 8/10![United Airlines logo]()
$479
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 10/305:30 am -
2 stops8h 55m
Sun 11/112:55 pm -
2 stops11h 10m
Deal found 8/9![Southwest logo]()
$345
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/291:00 am -
2 stops14h 17m
Fri 10/26:15 am -
1 stop8h 27m
Deal found 8/7![United Airlines logo]()
$486
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 10/88:50 pm -
1 stop12h 55m
Wed 10/144:40 pm -
1 stop6h 05m
Deal found 8/10![Southwest logo]()
$345
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/176:00 am -
2 stops9h 30m
Sun 9/202:45 pm -
2 stops8h 50m
Deal found 8/8![Southwest logo]()
$361
Last-minute flights from Puerto Rico to IllinoisDiscover last-minute flight deals from Puerto Rico to Illinois. Data last updated August 11, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Illinois. Data last updated August 11, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 8/10![Frontier logo]()
$215
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.
Fri 9/47:14 pm -
Nonstop5h 13m
Sat 9/127:11 am -
1 stop8h 52m
Deal found 8/6![Frontier logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/107:00 am -
1 stop8h 45m
Wed 9/167:11 am -
1 stop29h 23m
Deal found 8/7![Frontier logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/107:00 am -
1 stop8h 45m
Sun 9/137:11 am -
1 stop29h 23m
Deal found 8/10![Frontier logo]()
$210
This Faresmojo deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:35 pm -
1 stop8h 55m
Mon 9/144:55 pm -
1 stop6h 00m
Deal found 8/10![JetBlue logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 9/177:00 am -
1 stop8h 45m
Wed 9/307:11 am -
1 stop29h 23m
Deal found 8/9![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/177:00 am -
1 stop8h 45m
Sun 9/207:11 am -
1 stop29h 23m
Deal found 8/10![Frontier logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/247:00 am -
1 stop8h 45m
Sun 9/277:11 am -
1 stop29h 23m
Deal found 8/10![Frontier logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/247:00 am -
1 stop8h 45m
Sat 9/267:11 am -
1 stop8h 52m
Deal found 8/10![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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
Sat 9/267:11 am -
1 stop8h 52m
Deal found 8/10![Frontier logo]()
$205
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.
Fri 9/257:00 am -
1 stop8h 45m
Wed 9/307:11 am -
1 stop29h 23m
Deal found 8/6![Frontier logo]()
$209
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.
Mon 9/287:00 am -
1 stop8h 45m
Wed 9/307:11 am -
1 stop29h 23m
Deal found 8/6![Frontier logo]()
$208
One-way flights from Puerto Rico to IllinoisSearch for one-way flight options from Puerto Rico to Illinois. Find affordable one-way fares based on user searches. Data last updated August 11, 2026.
Search for one-way flight options from Puerto Rico to Illinois. Find affordable one-way fares based on user searches. Data last updated August 11, 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]()
$115
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/1810:16 am -
2 stops11h 28m
Deal found 8/10![American Airlines logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 -
2 stops49h 55m
Deal found 8/10![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/78:24 pm -
2 stops39h 16m
Deal found 8/11![Frontier logo]()
$124
This Faresmojo deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/67:00 am -
1 stop9h 44m
Deal found 8/10![JetBlue logo]()
$126
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 8/10. Clicking the “Pick Dates” 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 9/104:39 pm -
2 stops21h 31m
Deal found 8/10![Frontier logo]()
$127
This Trip.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am -
2 stops17h 03m
Deal found 8/9![Frontier logo]()
$127
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/106:00 am -
2 stops9h 30m
Deal found 8/10![Southwest logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 -
2 stops34h 06m
Deal found 8/7![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 9/52:14 pm -
1 stop29h 25m
Deal found 8/9![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:12 pm -
2 stops17h 28m
Deal found 8/11![Frontier logo]()
$130
Find flight deals from Puerto Rico to Illinois
Keep the following information in mind while searching for Puerto Rico to Illinois flight deals. Data was last updated August 11, 2026.
Round-trip from | $188 (Kiwi.com) |
|---|---|
One-way from | $115 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $302 |
Good round-trip deal | $325 or less |
Good one-way deal | $173 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Puerto Rico 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 11, 2026.
Use the filters below to find and compare flights from Puerto Rico 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
Fri 9/25
2:35 pm-10:45 pm
1 stop9h 10m
Chicago Midway
Tue 9/29
6:15 am-1:30 pm
1 stop6h 15m
$256
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 9/17
6:00 am-2:30 pm
2 stops9h 30m
Chicago Midway
Tue 9/22
12:20 pm-10:05 pm
1 stop8h 45m
$276
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 8/28
5:30 am-2:05 pm
1 stop9h 35m
Chicago Midway
Tue 9/1
9:40 am-9:05 pm
1 stop10h 25m
$286
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 9/18
6:00 am-2:30 pm
2 stops9h 30m
Chicago Midway
Tue 9/22
12:20 pm-9:10 pm
1 stop7h 50m
$291
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Mon 9/14
2:32 pm-11:08 pm
1 stop9h 36m
Chicago O'Hare Intl
Tue 9/15
6:00 am-3:23 pm
1 stop8h 23m
$300
San JuanSt. Louis
SJU San Juan Luis Munoz Marin Intl - STL Lambert-St Louis
SJUSTL
San Juan Luis Munoz Marin Intl
Thu 9/10
2:35 pm-10:30 pm
1 stop8h 55m
Lambert-St Louis
Sun 9/20
3:30 pm-12:35 am
1 stop8h 05m
$300
Quickest round-trip
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Thu 9/17
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Sun 9/20
8:55 am-2:44 pm
Nonstop4h 49m
$301
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 10/22
5:30 am-12:45 pm
2 stops8h 15m
Chicago Midway
Mon 10/26
3:45 pm-1:20 am
1 stop8h 35m
$301
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 9/18
6:00 am-2:30 pm
2 stops9h 30m
Chicago Midway
Sun 9/20
8:05 pm-9:10 am
1 stop12h 05m
$310
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 10/30
5:30 am-1:25 pm
2 stops8h 55m
Chicago Midway
Sun 11/1
12:55 pm-2:05 am
2 stops11h 10m
$345
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Puerto Rico to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Puerto Rico with our price prediction graph.
SJU-STL
SJU-MDW
SJU-ORD
BQN-ORD
MAZ-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 Puerto Rico to Illinois
PR0-USIL
SJU-STL
SJU-MDW
SJU-ORD
BQN-ORD
What is the cheapest month to book a flight from Puerto Rico to Illinois?
Currently, February is the cheapest month in which you can book a flight from Puerto Rico to Illinois (average of $220). Flying from Puerto Rico 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 PR to IL?
Find hourly flight availability from Puerto Rico 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 11, 2026.
When flying from Puerto Rico to Illinois, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 27% versus a flight in the afternoon.
Weekly flight availability from Puerto Rico to Illinois
Explore weekly flight availability from Puerto Rico 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 11, 2026.
The most flights from PR0 to USIL are scheduled on a Monday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 on average).
How far ahead should I book a flight from Puerto Rico to Illinois?
To ensure you get the cheapest price possible for a flight from Puerto Rico to Illinois, you should look to book at least 81 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Puerto Rico to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Puerto Rico to Illinois. Price data was last updated on August 8, 2026.
Travelers seeking maximum savings on their Puerto Rico 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 11, 2026.
Read through reviews of airlines operating flights from Puerto Rico to Illinois, such as Southwest,United Airlines, andAmerican Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
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 Puerto Rico to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Puerto Rico to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Puerto Rico to Illinois by cabin class
Find flights from Puerto Rico to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Puerto Rico and Illinois flights
Browse other Puerto Rico and Illinois flight options. Last updated on August 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Illinois
Find the right flight back to Puerto Rico after your stay in Illinois
Puerto Rico to Illinois flights
Consider these flights traveling from Puerto Rico to Illinois.
Top 6 airlines flying from Puerto Rico to Illinois
Discover the top 6 airlines that operate flights from Puerto Rico 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 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$128 | Average$283 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$204 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$227 | Average$427 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$266 | Average$490 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$267 | Average$476 | FlexibilityNo cancel fee | On-time69% |