$103+ Cheap flights from Illinois to Puerto Rico
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Sep 7 — Sep 141
Round-trip
1 adult, Economy
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Find cheap flights from Illinois to Puerto Rico 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
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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 Illinois to Puerto Rico
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Cheapest flights from Illinois to Puerto RicoExplore the most affordable flight options available from Illinois to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 8, 2026.
Explore the most affordable flight options available from Illinois to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 8, 2026.
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.
Thu 9/177:11 am -
1 stop29h 23m
Thu 9/247:00 am -
1 stop8h 45m
Deal found 8/3![Frontier logo]()
$222
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.
Sat 9/512:44 am -
Nonstop5h 00m
Wed 9/168:45 am -
1 stop31h 00m
Deal found 8/7![Frontier logo]()
$223
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.
Tue 9/112:44 am -
Nonstop5h 00m
Wed 9/98:45 am -
1 stop31h 00m
Deal found 8/4![Frontier logo]()
$224
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am -
Nonstop5h 00m
Fri 9/47:14 pm -
Nonstop5h 13m
Deal found 8/6![Frontier logo]()
$225
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.
Thu 8/2712:44 am -
Nonstop5h 00m
Sat 8/297:14 pm -
Nonstop5h 13m
Deal found 8/4![Frontier logo]()
$226
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2912:44 am -
Nonstop5h 00m
Sat 9/57:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$228
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:44 am -
Nonstop5h 00m
Sat 8/295:00 pm -
1 stop7h 44m
Deal found 8/5![Multiple Airlines logo]()
$229
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.
Mon 8/1712:44 am -
Nonstop5h 00m
Mon 9/1411:23 am -
2 stops25h 28m
Deal found 8/3![Frontier logo]()
$230
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.
Sun 8/1612:44 am -
Nonstop5h 00m
Sat 8/227:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$231
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1712:44 am -
Nonstop5h 00m
Sat 8/227:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$233
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.
Sun 8/3012:44 am -
Nonstop5h 00m
Sat 9/122:32 pm -
1 stop9h 36m
Deal found 8/7![Multiple Airlines logo]()
$234
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:44 am -
Nonstop5h 00m
Fri 8/287:14 pm -
Nonstop5h 13m
Deal found 8/4![Frontier logo]()
$235
Best flights from Illinois to Puerto RicoDiscover carefully curated flight deals from Illinois to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 8, 2026.
Discover carefully curated flight deals from Illinois to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 8, 2026.
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.
Sat 9/198:55 am -
Nonstop4h 49m
Sat 9/261:25 pm -
1 stop10h 04m
Deal found 8/4![United Airlines logo]()
$252
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.
Mon 8/2411:15 am -
1 stop7h 50m
Sat 8/295:55 am -
2 stops8h 10m
Deal found 8/5![Southwest logo]()
$266
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:35 pm -
1 stop8h 24m
Fri 9/45:01 am -
1 stop9h 38m
Deal found 8/6![JetBlue logo]()
$304
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.
Sun 11/15:38 pm -
2 stops15h 06m
Thu 11/56:05 am -
2 stops12h 04m
Deal found 8/6![American Airlines logo]()
$346
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/163:50 pm -
1 stop17h 23m
Wed 9/2311:12 am -
1 stop24h 08m
Deal found 8/3![Frontier logo]()
$356
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:00 am -
1 stop9h 49m
Wed 9/307:00 am -
1 stop9h 54m
Deal found 8/4![Delta logo]()
$356
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:50 pm -
1 stop18h 04m
Sun 9/138:55 am -
2 stops15h 13m
Deal found 8/5![Multiple Airlines logo]()
$409
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:50 am -
1 stop10h 48m
Sat 9/121:00 am -
1 stop9h 13m
Deal found 8/3![United Airlines 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.
Tue 9/112:45 pm -
2 stops8h 15m
Fri 9/46:00 am -
2 stops9h 30m
Deal found 8/4![Southwest logo]()
$291
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/293:20 pm -
1 stop7h 39m
Fri 9/45:01 am -
1 stop9h 38m
Deal found 8/5![JetBlue logo]()
$304
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 8/282:55 pm -
1 stop7h 55m
Mon 8/318:55 pm -
1 stop13h 30m
Deal found 8/5![Southwest logo]()
$291
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.
Sun 1/317:21 pm -
1 stop17h 57m
Mon 2/86:00 am -
1 stop14h 31m
Deal found 8/7![American Airlines logo]()
$346
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.
Tue 10/201:40 pm -
2 stops8h 25m
Tue 10/275:05 am -
1 stop10h 35m
Deal found 8/3![Southwest logo]()
$301
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.
Wed 11/44:44 pm -
1 stop16h 13m
Mon 11/93:48 am -
1 stop22h 02m
Deal found 8/7![Frontier logo]()
$369
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.
Wed 9/910:40 am -
1 stop8h 58m
Wed 9/163:56 pm -
Nonstop5h 09m
Deal found 8/4![United Airlines logo]()
$342
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/236:02 am -
1 stop13h 37m
Wed 1/276:00 am -
1 stop10h 29m
Deal found 8/8![American Airlines logo]()
$346
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:50 pm -
1 stop18h 04m
Sun 9/1310:05 am -
1 stop25h 15m
Deal found 8/5![Frontier logo]()
$376
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:51 pm -
2 stops20h 49m
Mon 9/77:24 pm -
2 stops19h 57m
Deal found 8/5![American Airlines logo]()
$346
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.
Mon 10/193:45 pm -
1 stop8h 35m
Mon 10/268:50 pm -
1 stop12h 35m
Deal found 8/7![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.
Wed 9/166:16 am -
1 stop9h 33m
Sat 9/1912:56 pm -
1 stop9h 01m
Deal found 8/6![Delta logo]()
$426
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:00 am -
2 stops11h 38m
Fri 9/111:00 am -
2 stops10h 12m
Deal found 8/8![United Airlines logo]()
$356
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.
Sat 8/293:20 pm -
1 stop8h 13m
Tue 9/12:30 pm -
1 stop10h 14m
Deal found 8/7![JetBlue logo]()
$398
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:59 pm -
1 stop16h 10m
Sat 9/58:39 am -
2 stops16h 05m
Deal found 8/8![Multiple Airlines logo]()
$448
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.
Wed 9/1612:25 pm -
2 stops19h 59m
Sat 9/196:00 am -
2 stops12h 29m
Deal found 8/6![American Airlines logo]()
$351
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.
Tue 9/87:05 am -
2 stops18h 05m
Tue 9/2210:52 am -
1 stop13h 07m
Deal found 8/3![Frontier logo]()
$387
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.
Sat 9/511:00 am -
1 stop6h 20m
Sat 9/125:05 am -
2 stops9h 05m
Deal found 8/7![Southwest logo]()
$320
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:25 am -
2 stops12h 59m
Thu 11/58:05 am -
2 stops10h 42m
Deal found 8/3![United Airlines logo]()
$366
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.
Wed 1/206:00 am -
1 stop9h 20m
Sun 1/246:15 am -
1 stop10h 28m
Deal found 8/5![Delta logo]()
$456
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/32:35 pm -
1 stop8h 24m
Fri 9/45:01 am -
1 stop9h 38m
Deal found 8/4![JetBlue logo]()
$423
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:53 am -
2 stops10h 40m
Tue 9/87:03 am -
2 stops14h 12m
Deal found 8/3![American Airlines logo]()
$351
Last-minute flights from Illinois to Puerto RicoDiscover last-minute flight deals from Illinois to Puerto Rico. Data last updated August 8, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Puerto Rico. Data last updated August 8, 2026 and is based on user searches.
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.
Sun 8/1612:44 am -
Nonstop5h 00m
Sat 8/227:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$231
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.
Mon 8/1712:44 am -
Nonstop5h 00m
Mon 9/1411:23 am -
2 stops25h 28m
Deal found 8/3![Frontier logo]()
$230
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1712:44 am -
Nonstop5h 00m
Sat 8/227:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$233
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:44 am -
Nonstop5h 00m
Sat 8/295:00 pm -
1 stop7h 44m
Deal found 8/5![Multiple Airlines logo]()
$229
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:44 am -
Nonstop5h 00m
Fri 8/287:14 pm -
Nonstop5h 13m
Deal found 8/4![Frontier logo]()
$235
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am -
Nonstop5h 00m
Fri 9/47:14 pm -
Nonstop5h 13m
Deal found 8/6![Frontier logo]()
$225
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.
Thu 8/2712:44 am -
Nonstop5h 00m
Sat 8/297:14 pm -
Nonstop5h 13m
Deal found 8/4![Frontier logo]()
$226
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2912:44 am -
Nonstop5h 00m
Sat 9/57:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$228
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.
Sun 8/3012:44 am -
Nonstop5h 00m
Sat 9/122:32 pm -
1 stop9h 36m
Deal found 8/7![Multiple Airlines logo]()
$234
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.
Tue 9/112:44 am -
Nonstop5h 00m
Wed 9/98:45 am -
1 stop31h 00m
Deal found 8/4![Frontier logo]()
$224
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.
Sat 9/512:44 am -
Nonstop5h 00m
Wed 9/168:45 am -
1 stop31h 00m
Deal found 8/7![Frontier logo]()
$223
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.
Thu 9/177:11 am -
1 stop29h 23m
Thu 9/247:00 am -
1 stop8h 45m
Deal found 8/3![Frontier logo]()
$222
One-way flights from Illinois to Puerto RicoSearch for one-way flight options from Illinois to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated August 8, 2026.
Search for one-way flight options from Illinois to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated August 8, 2026.
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:44 am -
Nonstop5h 00m
Deal found 8/8![Frontier logo]()
$103
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.
Sat 9/267:11 am -
1 stop8h 52m
Deal found 8/3![Frontier logo]()
$105
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:45 am -
1 stop14h 53m
Deal found 8/7![Frontier logo]()
$107
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.
Sat 9/127:11 am -
1 stop29h 23m
Deal found 8/3![Frontier logo]()
$109
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 9/167:11 am -
1 stop29h 23m
Deal found 8/3![Frontier logo]()
$110
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.
Mon 8/3112:44 am -
Nonstop5h 00m
Deal found 8/4![Frontier logo]()
$112
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 8/2712:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$113
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$114
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1412:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$117
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 10/52:29 pm -
2 stops23h 48m
Deal found 8/6![Frontier logo]()
$117
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.
Wed 8/2612:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$118
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1512:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$119
Find flight deals from Illinois to Puerto Rico
Keep the following information in mind while searching for Illinois to Puerto Rico flight deals. Data was last updated August 8, 2026.
Round-trip from | $222 (Kiwi.com) |
|---|---|
One-way from | $103 (eDestinos) |
Popular in | December |
Cheapest in | August |
Average price | $322 |
Good round-trip deal | $315 or less |
Good one-way deal | $133 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois to Puerto Rico 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 8, 2026.
Use the filters below to find and compare flights from Illinois to Puerto Rico that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Sat 9/19
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Sat 9/26
1:25 pm-10:29 pm
1 stop10h 04m
$252
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Tue 9/1
8:50 am-8:38 pm
1 stop10h 48m
San Juan Luis Munoz Marin Intl
Sat 9/12
1:00 am-9:13 am
1 stop9h 13m
$256
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 8/24
11:15 am-8:05 pm
1 stop7h 50m
San Juan Luis Munoz Marin Intl
Sat 8/29
5:55 am-1:05 pm
2 stops8h 10m
$266
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 9/1
12:45 pm-10:00 pm
2 stops8h 15m
San Juan Luis Munoz Marin Intl
Fri 9/4
6:00 am-2:30 pm
2 stops9h 30m
$291
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Fri 8/28
2:55 pm-11:50 pm
1 stop7h 55m
San Juan Luis Munoz Marin Intl
Mon 8/31
8:55 pm-9:25 am
1 stop13h 30m
$291
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 10/20
1:40 pm-11:05 pm
2 stops8h 25m
San Juan Luis Munoz Marin Intl
Tue 10/27
5:05 am-2:40 pm
1 stop10h 35m
$301
ChicagoPonce
ORD Chicago O'Hare Intl - PSE Ponce Mercedita
ORDPSE
Chicago O'Hare Intl
Mon 8/31
2:35 pm-11:59 pm
1 stop8h 24m
Ponce Mercedita
Fri 9/4
5:01 am-1:39 pm
1 stop9h 38m
$304
ChicagoPonce
ORD Chicago O'Hare Intl - PSE Ponce Mercedita
ORDPSE
Chicago O'Hare Intl
Sat 8/29
3:20 pm-11:59 pm
1 stop7h 39m
Ponce Mercedita
Fri 9/4
5:01 am-1:39 pm
1 stop9h 38m
$304
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 10/19
3:45 pm-1:20 am
1 stop8h 35m
San Juan Luis Munoz Marin Intl
Mon 10/26
8:50 pm-8:25 am
1 stop12h 35m
$320
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Sat 9/5
11:00 am-6:20 pm
1 stop6h 20m
San Juan Luis Munoz Marin Intl
Sat 9/12
5:05 am-1:10 pm
2 stops9h 05m
$320
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Illinois to Puerto Rico
Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Illinois with our price prediction graph.
ORD-SJU
MDW-SJU
ORD-PSE
PIA-SJU
ORD-BQN
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 Illinois to Puerto Rico
USIL-PR0
ORD-SJU
MDW-SJU
ORD-PSE
PIA-SJU
What is the cheapest month to book a flight from Illinois to Puerto Rico?
Currently, August is the cheapest month in which you can book a flight from Illinois to Puerto Rico (average of $344). Flying from Illinois to Puerto Rico in December is currently the most expensive (average of $543). 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 IL to PR?
Find hourly flight availability from Illinois to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 8, 2026.
When flying from Illinois to Puerto Rico, 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 37% versus a flight in the morning.
Weekly flight availability from Illinois to Puerto Rico
Explore weekly flight availability from Illinois to Puerto Rico. 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 8, 2026.
The most flights from USIL to PR0 are scheduled on a Wednesday (10 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).
How far ahead should I book a flight from Illinois to Puerto Rico?
Booking 56 days in advance of your planned departure date is, on average, the best time to get cheap flights from Illinois to Puerto Rico. 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 Illinois to Puerto Rico?
Use this chart to determine the cheapest time to fly round-trip from Illinois to Puerto Rico. Price data was last updated on August 1, 2026.
Travelers seeking maximum savings on their Illinois to Puerto Rico flight should consider departing on Sunday evenings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Illinois to Puerto Rico. 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 Illinois to Puerto Rico
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Puerto Rico by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Illinois to Puerto Rico by cabin class
Find flights from Illinois to Puerto Rico, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Illinois and Puerto Rico flights
Browse other Illinois and Puerto Rico flight options. Last updated on August 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Puerto Rico
Find the right flight back to Illinois after your stay in Puerto Rico
Illinois to Puerto Rico flights
Consider these flights traveling from Illinois to Puerto Rico.
Top 6 airlines flying from Illinois to Puerto Rico
Discover the top 6 airlines that operate flights from Illinois to Puerto Rico. 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 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$359 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$486 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$327 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$263 | Average$518 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$295 | Average$588 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$296 | Average$490 | FlexibilityNo cancel fee | On-time63% |