$112+ Cheap flights from Illinois to Puerto Rico
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Nov 1 — Nov 81
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
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 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 October 2, 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 October 2, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/319:51 am -
1 stop24h 01m
Wed 11/412:22 pm -
1 stop22h 24m
Deal found 10/2![Frontier logo]()
$210
This Frontier deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/136:00 am -
1 stop9h 06m
Mon 10/197:44 pm -
1 stop13h 07m
Deal found 9/27![Frontier logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/206:00 am -
2 stops33h 26m
Tue 11/33:59 pm -
1 stop22h 52m
Deal found 9/30![Frontier logo]()
$219
This CheapOair deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:21 am -
1 stop8h 45m
Tue 11/33:59 pm -
1 stop9h 48m
Deal found 9/30![Frontier logo]()
$219
This Cheapflightsfares deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/85:35 am -
1 stop18h 38m
Fri 12/187:25 am -
1 stop7h 25m
Deal found 9/28![Frontier logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 10/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:00 am -
1 stop15h 28m
Fri 11/66:15 am -
1 stop18h 28m
Deal found 10/1![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/309:51 am -
1 stop14h 59m
Mon 11/26:15 am -
1 stop18h 28m
Deal found 9/27![Frontier logo]()
$222
This Frontier deal was found by Cheapflights users on 10/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 am -
1 stop9h 06m
Wed 10/216:42 pm -
1 stop13h 49m
Deal found 10/1![Frontier logo]()
$223
This CheapOair deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:21 am -
1 stop8h 45m
Thu 10/293:59 pm -
1 stop8h 48m
Deal found 9/30![Frontier logo]()
$223
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:42 pm -
1 stop21h 35m
Tue 11/177:26 pm -
1 stop23h 37m
Deal found 9/29![Frontier logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 12/1212:28 pm -
1 stop10h 39m
Wed 12/163:50 am -
1 stop17h 12m
Deal found 9/28![Frontier logo]()
$224
This Cheapflightsfares deal was found by Cheapflights users on 10/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:11 pm -
1 stop12h 04m
Sun 11/112:59 am -
1 stop23h 44m
Deal found 10/1![Frontier logo]()
$225
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 October 2, 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 October 2, 2026.
This JetBlue deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/302:42 pm -
1 stop6h 27m
Tue 11/35:30 pm -
1 stop8h 27m
Deal found 9/27![JetBlue logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 10/2. 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 10/2510:20 am -
1 stop26h 11m
Sat 10/313:47 pm -
1 stop19h 43m
Deal found 10/2![Multiple Airlines logo]()
$237
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/291:30 pm -
1 stop6h 52m
Tue 11/34:55 pm -
Nonstop5h 31m
Deal found 9/29![United Airlines logo]()
$242
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/271:40 pm -
2 stops8h 30m
Tue 11/35:40 am -
2 stops9h 15m
Deal found 9/27![Southwest logo]()
$246
This Delta deal was found by Cheapflights users on 10/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/411:00 am -
1 stop10h 50m
Sat 2/136:15 am -
1 stop12h 07m
Deal found 10/2![Delta logo]()
$386
This American Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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.
Mon 11/92:34 pm -
2 stops18h 11m
Sat 11/1410:32 am -
2 stops15h 27m
Deal found 9/30![American Airlines logo]()
$386
This Frontier deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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.
Sun 11/225:40 am -
1 stop6h 54m
Mon 11/233:29 pm -
1 stop11h 13m
Deal found 9/28![Frontier logo]()
$416
This JetBlue deal was found by Cheapflights users on 10/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:00 am -
1 stop7h 09m
Fri 12/46:38 am -
1 stop8h 52m
Deal found 10/2![JetBlue logo]()
$237
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:07 pm -
1 stop9h 29m
Fri 11/64:55 pm -
Nonstop5h 31m
Deal found 9/29![United Airlines logo]()
$242
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Sat 11/72:30 pm -
1 stop8h 06m
Fri 11/132:05 am -
1 stop9h 40m
Deal found 10/1![United Airlines logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 10/2. 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 10/1810:30 am -
1 stop26h 01m
Thu 10/227:20 am -
1 stop25h 34m
Deal found 10/2![Multiple Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/63:20 pm -
1 stop6h 50m
Tue 10/135:05 am -
2 stops10h 35m
Deal found 9/29![Southwest logo]()
$286
This JetBlue deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 12/52:59 pm -
1 stop9h 00m
Sat 12/126:01 am -
1 stop9h 29m
Deal found 9/27![JetBlue logo]()
$294
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/273:25 pm -
1 stop7h 25m
Sat 10/317:45 am -
2 stops10h 00m
Deal found 9/28![Southwest logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/299:40 am -
1 stop26h 06m
Sat 10/313:55 am -
2 stops10h 27m
Deal found 9/28![Multiple Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 10/2. 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.
Tue 10/66:25 am -
1 stop8h 17m
Sat 10/312:05 am -
1 stop8h 57m
Deal found 10/2![United Airlines logo]()
$301
This American Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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.
Mon 11/96:01 am -
1 stop16h 15m
Fri 11/1311:35 am -
2 stops14h 24m
Deal found 9/30![American Airlines logo]()
$386
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/79:30 am -
2 stops10h 05m
Wed 10/148:15 am -
1 stop7h 30m
Deal found 9/30![Southwest logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/89:40 am -
1 stop26h 51m
Wed 10/148:45 am -
1 stop25h 05m
Deal found 9/27![Multiple Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 11/86:01 am -
1 stop16h 15m
Fri 11/1311:35 am -
2 stops14h 24m
Deal found 9/30![American Airlines logo]()
$386
This FlightHub deal was found by Cheapflights users on 10/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:15 am -
2 stops16h 30m
Sun 12/63:47 am -
2 stops19h 55m
Deal found 10/1![Frontier logo]()
$428
This United Airlines deal was found by Cheapflights users on 10/2. 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.
Tue 10/278:52 am -
Nonstop4h 48m
Sat 10/317:25 am -
Nonstop5h 22m
Deal found 10/2![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 10/2. 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.
Sat 10/172:40 pm -
1 stop6h 35m
Sun 10/185:40 pm -
1 stop7h 00m
Deal found 10/2![Southwest logo]()
$350
This American Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 1/196:37 pm -
2 stops16h 35m
Fri 1/2910:32 am -
2 stops9h 34m
Deal found 9/28![American Airlines logo]()
$386
This JetBlue deal was found by Cheapflights users on 10/1. 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.
Wed 10/212:55 pm -
1 stop10h 11m
Tue 10/272:25 pm -
1 stop10h 32m
Deal found 10/1![JetBlue logo]()
$398
This Cheapflightsfares deal was found by Cheapflights users on 10/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:58 pm -
1 stop12h 54m
Sun 10/189:43 am -
1 stop22h 48m
Deal found 10/1![Frontier logo]()
$451
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/252:16 pm -
Nonstop4h 44m
Sat 10/316:40 am -
1 stop9h 11m
Deal found 9/29![United Airlines logo]()
$342
This FlightHub deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/510:26 am -
2 stops21h 33m
Thu 11/195:01 am -
1 stop10h 31m
Deal found 9/30![Multiple Airlines logo]()
$377
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:35 am -
2 stops8h 15m
Fri 11/65:35 am -
2 stops8h 45m
Deal found 9/29![Southwest logo]()
$356
This CheapOair deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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.
Mon 10/267:00 am -
1 stop16h 11m
Mon 11/25:01 am -
1 stop10h 53m
Deal found 9/27![JetBlue logo]()
$410
Last-minute flights from Illinois to Puerto RicoDiscover last-minute flight deals from Illinois to Puerto Rico. Data last updated October 2, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Puerto Rico. Data last updated October 2, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/104:41 pm -
1 stop21h 38m
Mon 10/127:44 pm -
1 stop13h 07m
Deal found 9/30![Frontier logo]()
$226
This Frontier deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/136:00 am -
1 stop9h 06m
Mon 10/197:44 pm -
1 stop13h 07m
Deal found 9/27![Frontier logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/206:00 am -
2 stops33h 26m
Tue 11/33:59 pm -
1 stop22h 52m
Deal found 9/30![Frontier logo]()
$219
This CheapOair deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:21 am -
1 stop8h 45m
Tue 11/33:59 pm -
1 stop9h 48m
Deal found 9/30![Frontier logo]()
$219
This CheapOair deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:21 am -
1 stop8h 45m
Thu 10/293:59 pm -
1 stop8h 48m
Deal found 9/30![Frontier logo]()
$223
This Frontier deal was found by Cheapflights users on 10/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 am -
1 stop9h 06m
Wed 10/216:42 pm -
1 stop13h 49m
Deal found 10/1![Frontier logo]()
$223
This Cheapflightsfares deal was found by Cheapflights users on 10/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:11 pm -
1 stop12h 04m
Sun 11/112:59 am -
1 stop23h 44m
Deal found 10/1![Frontier logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/277:50 pm -
2 stops18h 27m
Thu 12/33:59 pm -
1 stop11h 00m
Deal found 9/30![Frontier logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/309:51 am -
1 stop14h 59m
Sun 11/17:26 pm -
1 stop15h 20m
Deal found 9/27![Frontier logo]()
$222
This Cheapflightsfares deal was found by Cheapflights users on 10/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/319:51 am -
1 stop24h 01m
Wed 11/412:22 pm -
1 stop22h 24m
Deal found 10/2![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 10/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:00 am -
1 stop15h 28m
Fri 11/66:15 am -
1 stop18h 28m
Deal found 10/1![Frontier logo]()
$221
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:42 pm -
1 stop21h 35m
Tue 11/177:26 pm -
1 stop23h 37m
Deal found 9/29![Frontier logo]()
$224
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 October 2, 2026.
Search for one-way flight options from Illinois to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated October 2, 2026.
This Super.com deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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.
Sat 10/174:41 pm -
1 stop16h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Frontier logo]()
$112
This Priceline deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 11/99:51 am -
1 stop23h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Frontier logo]()
$112
This Super.com deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/76:25 am -
1 stop7h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Frontier logo]()
$112
This Frontier deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/168:11 pm -
1 stop12h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$114
This Frontier deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:21 am -
1 stop8h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/299:40 am -
1 stop26h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 11/86:00 am -
1 stop15h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 10/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:00 am -
1 stop15h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Frontier logo]()
$117
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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.
Sun 10/116:00 am -
1 stop18h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$118
This JetBlue deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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.
Tue 10/271:00 pm -
1 stop10h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![JetBlue logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 11/110:20 am -
1 stop25h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Multiple Airlines logo]()
$121
This FlightHub deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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.
Wed 11/49:51 am -
1 stop23h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$121
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 October 2, 2026.
Round-trip from | $210 (Cheapflightsfares) |
|---|---|
One-way from | $112 (Super.com) |
Popular in | December |
Cheapest in | August |
Average price | $423 |
Good round-trip deal | $336 or less |
Good one-way deal | $162 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 7,457,451 searches. Data last updated October 2, 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
Fri 10/16
4:41 pm-10:19 am
1 stop16h 38m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$112
ChicagoSan Juan
RFD Chicago Greater Rockford - SJU San Juan Luis Munoz Marin Intl
RFDSJU
Chicago Greater Rockford
Thu 10/29
9:40 am-12:46 pm
1 stop26h 06m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$117
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Sat 10/31
1:00 pm-12:13 am
1 stop10h 13m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$119
Quickest round-trip
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Sun 10/25
2:16 pm-8:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$119
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 11/24
8:35 pm-9:50 am
1 stop11h 15m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$123
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Wed 11/18
1:00 pm-1:13 am
1 stop10h 13m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$123
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Wed 11/11
9:21 am-9:24 pm
1 stop10h 03m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$123
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Fri 11/13
1:00 pm-1:13 am
1 stop10h 13m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$123
ChicagoAguadilla
ORD Chicago O'Hare Intl - BQN Aguadilla Borinquen
ORDBQN
Chicago O'Hare Intl
Wed 11/11
7:15 am-10:52 am
2 stops25h 37m
Aguadilla Borinquen
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$124
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Tue 10/27
1:50 pm-11:44 pm
1 stop8h 54m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$125
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-BQN
ORD-SJU
MDW-SJU
RFD-SJU
MLI-SJU
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-BQN
ORD-SJU
MDW-SJU
RFD-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 $332). Flying from Illinois to Puerto Rico in December is currently the most expensive (average of $532). 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 October 2, 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 33% 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 October 2, 2026.
The most flights from USIL to PR0 are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).
How far ahead should I book a flight from Illinois to Puerto Rico?
Booking 88 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 September 26, 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
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
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Return Flight Options
Top destinations
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 October 2, 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 7,457,451 searches. Data last updated October 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$376 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$491 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$484 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$262 | Average$524 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$276 | Average$488 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$287 | Average$554 | FlexibilityNo cancel fee | On-time71% |