$113+ Cheap flights from Puerto Rico to Illinois
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Oct 30 — Nov 61
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 September 30, 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 September 30, 2026.
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:22 pm -
1 stop22h 24m
Sun 11/159:51 am -
1 stop23h 41m
Deal found 9/27![Frontier logo]()
$210
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:00 am -
1 stop12h 10m
Fri 12/410:38 am -
1 stop26h 21m
Deal found 9/28![Frontier logo]()
$224
This OneTravel deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:11 pm -
1 stop7h 32m
Wed 10/216:21 am -
1 stop8h 45m
Deal found 9/26![Frontier logo]()
$225
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.
Thu 10/1512:59 am -
1 stop22h 40m
Mon 10/194:41 pm -
1 stop22h 45m
Deal found 9/29![Frontier logo]()
$225
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.
Thu 10/85:11 pm -
1 stop7h 32m
Tue 10/136:21 am -
1 stop8h 45m
Deal found 9/29![Frontier logo]()
$226
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.
Thu 10/810:39 am -
1 stop8h 14m
Mon 10/128:11 pm -
1 stop28h 42m
Deal found 9/29![Frontier logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/206:42 pm -
1 stop14h 09m
Sun 10/256:00 am -
1 stop18h 17m
Deal found 9/26![Frontier logo]()
$227
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.
Thu 10/87:20 am -
1 stop11h 33m
Tue 10/136:00 am -
1 stop9h 06m
Deal found 9/29![Frontier logo]()
$228
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/224:24 pm -
1 stop19h 57m
Sat 10/247:44 pm -
2 stops16h 47m
Deal found 9/30![Frontier logo]()
$229
This Priceline deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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.
Fri 10/166:15 am -
1 stop17h 24m
Wed 10/218:04 am -
1 stop28h 27m
Deal found 9/26![Frontier logo]()
$230
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:57 am -
1 stop22h 49m
Mon 11/169:51 am -
1 stop23h 01m
Deal found 9/28![Frontier logo]()
$231
This OneTravel 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:30 am -
1 stop12h 21m
Sun 10/116:24 am -
1 stop8h 42m
Deal found 9/29![Frontier logo]()
$231
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 September 30, 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 September 30, 2026.
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:57 am -
1 stop22h 49m
Mon 11/169:51 am -
1 stop23h 01m
Deal found 9/28![Frontier logo]()
$231
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:00 pm -
1 stop10h 10m
Wed 10/281:00 pm -
1 stop10h 13m
Deal found 9/28![JetBlue logo]()
$232
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.
Tue 10/203:56 pm -
Nonstop5h 09m
Wed 11/49:21 am -
1 stop10h 03m
Deal found 9/29![United Airlines logo]()
$306
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.
Wed 10/283:35 pm -
1 stop7h 25m
Sun 11/18:40 pm -
1 stop13h 10m
Deal found 9/28![Southwest logo]()
$330
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.
Fri 12/46:00 am -
2 stops12h 17m
Mon 12/74:18 pm -
2 stops16h 26m
Deal found 9/30![American Airlines logo]()
$386
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/133:20 am -
1 stop11h 30m
Sun 10/186:58 pm -
1 stop12h 54m
Deal found 9/29![Multiple Airlines logo]()
$432
This Cheapflightsfares deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/1110:52 am -
1 stop21h 39m
Thu 10/156:58 pm -
1 stop13h 59m
Deal found 9/25![Frontier logo]()
$339
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 10/2912:09 am -
1 stop10h 36m
Mon 11/22:30 pm -
1 stop7h 27m
Deal found 9/29![United Airlines logo]()
$350
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/292:59 pm -
1 stop8h 34m
Sun 11/16:04 am -
1 stop6h 45m
Deal found 9/28![Delta logo]()
$728
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.
Thu 10/155:00 am -
2 stops8h 10m
Mon 10/194:30 pm -
2 stops7h 55m
Deal found 9/29![Southwest logo]()
$380
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 1/211:09 am -
1 stop8h 43m
Wed 1/2712:40 pm -
1 stop9h 17m
Deal found 9/29![United Airlines logo]()
$350
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.
Fri 12/410:45 am -
2 stops9h 40m
Wed 12/912:50 pm -
2 stops9h 55m
Deal found 9/29![Southwest logo]()
$385
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 1/141:09 am -
1 stop9h 53m
Sat 1/302:25 pm -
1 stop7h 32m
Deal found 9/29![United Airlines logo]()
$390
This Southwest deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/118:25 pm -
1 stop13h 20m
Thu 10/153:45 pm -
1 stop8h 40m
Deal found 9/25![Southwest logo]()
$409
This CheapOair deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/203:20 am -
1 stop11h 30m
Wed 11/47:28 pm -
2 stops36h 31m
Deal found 9/26![Multiple Airlines logo]()
$501
This Mytrip deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/511:57 am -
2 stops14h 24m
Mon 11/910:26 am -
2 stops22h 26m
Deal found 9/26![Frontier logo]()
$478
This Southwest deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/810:50 pm -
1 stop10h 55m
Sun 10/113:15 pm -
2 stops8h 00m
Deal found 9/25![Southwest logo]()
$409
This Priceline deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/1210:52 am -
1 stop21h 59m
Fri 10/162:55 pm -
2 stops42h 29m
Deal found 9/26![Multiple Airlines logo]()
$505
This United Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:25 am -
Nonstop5h 22m
Fri 10/302:16 pm -
Nonstop4h 44m
Deal found 9/25![United Airlines logo]()
$459
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.
Fri 12/253:47 am -
1 stop23h 22m
Wed 12/302:31 pm -
1 stop23h 42m
Deal found 9/28![Frontier logo]()
$526
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.
Thu 12/106:10 am -
1 stop10h 50m
Fri 1/11:15 pm -
2 stops8h 05m
Deal found 9/28![Southwest logo]()
$464
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/223:47 pm -
1 stop21h 08m
Sun 11/295:11 pm -
1 stop19h 37m
Deal found 9/29![American Airlines logo]()
$695
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/238:20 pm -
2 stops36h 20m
Tue 12/298:59 pm -
2 stops23h 33m
Deal found 9/29![Alaska Airlines logo]()
$1,390
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/194:55 pm -
Nonstop5h 31m
Mon 11/232:16 pm -
Nonstop4h 44m
Deal found 9/28![United Airlines logo]()
$477
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.
Mon 10/125:30 am -
2 stops8h 55m
Fri 10/163:45 pm -
1 stop7h 40m
Deal found 9/27![Southwest logo]()
$466
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/53:59 pm -
1 stop8h 34m
Sun 11/810:59 am -
1 stop10h 19m
Deal found 9/29![Delta logo]()
$785
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/55:00 am -
1 stop13h 16m
Mon 1/1111:41 am -
1 stop10h 00m
Deal found 9/29![American Airlines logo]()
$714
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.
Tue 1/121:09 am -
1 stop9h 53m
Fri 1/2912:40 pm -
1 stop9h 17m
Deal found 9/29![United Airlines logo]()
$488
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.
Wed 10/145:05 am -
2 stops8h 20m
Sun 10/183:15 pm -
2 stops8h 00m
Deal found 9/29![Southwest logo]()
$466
This United Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/168:25 am -
Nonstop5h 22m
Wed 12/210:35 am -
1 stop9h 47m
Deal found 9/25![United Airlines logo]()
$506
Last-minute flights from Puerto Rico to IllinoisDiscover last-minute flight deals from Puerto Rico to Illinois. Data last updated September 30, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Illinois. Data last updated September 30, 2026 and is based on user searches.
This OneTravel 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:30 am -
1 stop12h 21m
Sun 10/116:24 am -
1 stop8h 42m
Deal found 9/29![Frontier logo]()
$231
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.
Thu 10/85:11 pm -
1 stop7h 32m
Tue 10/136:21 am -
1 stop8h 45m
Deal found 9/29![Frontier logo]()
$226
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.
Thu 10/810:39 am -
1 stop8h 14m
Mon 10/128:11 pm -
1 stop28h 42m
Deal found 9/29![Frontier logo]()
$226
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.
Thu 10/87:20 am -
1 stop11h 33m
Tue 10/136:00 am -
1 stop9h 06m
Deal found 9/29![Frontier logo]()
$228
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.
Thu 10/1512:59 am -
1 stop22h 40m
Mon 10/194:41 pm -
1 stop22h 45m
Deal found 9/29![Frontier logo]()
$225
This OneTravel deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:11 pm -
1 stop7h 32m
Wed 10/216:21 am -
1 stop8h 45m
Deal found 9/26![Frontier logo]()
$225
This Priceline deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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.
Fri 10/166:15 am -
1 stop17h 24m
Wed 10/218:04 am -
1 stop28h 27m
Deal found 9/26![Frontier logo]()
$230
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.
Mon 10/197:44 pm -
1 stop13h 07m
Thu 10/226:00 am -
1 stop18h 17m
Deal found 9/28![Frontier logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/206:42 pm -
1 stop14h 09m
Sun 10/256:00 am -
1 stop18h 17m
Deal found 9/26![Frontier logo]()
$227
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/224:24 pm -
1 stop19h 57m
Sat 10/247:44 pm -
2 stops16h 47m
Deal found 9/30![Frontier logo]()
$229
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:00 pm -
1 stop10h 10m
Wed 10/281:00 pm -
1 stop10h 13m
Deal found 9/29![JetBlue logo]()
$232
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:00 pm -
1 stop10h 10m
Sat 10/311:00 pm -
1 stop10h 13m
Deal found 9/28![JetBlue logo]()
$233
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 September 30, 2026.
Search for one-way flight options from Puerto Rico to Illinois. Find affordable one-way fares based on user searches. Data last updated September 30, 2026.
This Frontier deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/105:11 pm -
1 stop7h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Frontier logo]()
$113
This Frontier deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/56:30 am -
1 stop12h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Frontier logo]()
$114
This Priceline deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/56:30 am -
1 stop12h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Frontier logo]()
$114
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/145:11 pm -
1 stop7h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Frontier logo]()
$116
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/163:55 pm -
1 stop16h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/226:15 am -
1 stop17h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Frontier logo]()
$117
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 10/1012:59 am -
1 stop22h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Frontier logo]()
$118
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:25 am -
1 stop8h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![JetBlue logo]()
$119
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/274:52 pm -
2 stops25h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$120
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.
Sun 12/208:46 pm -
1 stop23h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$121
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/23:28 am -
2 stops19h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$122
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/244:10 pm -
1 stop8h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Delta logo]()
$123
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 September 30, 2026.
Round-trip from | $210 (Cheapflightsfares) |
|---|---|
One-way from | $113 (Frontier) |
Popular in | June |
Cheapest in | February |
Average price | $277 |
Good round-trip deal | $319 or less |
Good one-way deal | $205 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 7,457,451 searches. Data last updated September 30, 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 - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Wed 10/28
7:25 am-11:47 am
Nonstop5h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$119
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Mon 12/21
5:03 am-8:42 am
Nonstop5h 39m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$119
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Fri 11/13
8:25 am-11:47 am
Nonstop5h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$119
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Tue 10/27
3:55 pm-8:26 pm
Nonstop5h 31m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$119
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 11/12
6:05 am-2:25 pm
2 stops10h 20m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$123
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 12/24
4:10 pm-10:22 pm
1 stop8h 12m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$123
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Tue 12/22
6:24 pm-11:33 pm
1 stop7h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$123
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 11/5
6:05 am-2:25 pm
2 stops10h 20m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$123
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Fri 12/25
7:40 am-4:25 pm
1 stop10h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$123
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Sat 12/12
6:01 am-1:30 pm
1 stop9h 29m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$124
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.
BQN-ORD
SJU-ORD
SJU-MDW
SJU-PIA
PSE-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
BQN-ORD
SJU-ORD
SJU-MDW
SJU-PIA
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 $218). 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 September 30, 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 29% 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 September 30, 2026.
The most flights from PR0 to USIL are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).
How 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 September 26, 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 September 30, 2026.
Read through reviews of airlines operating flights from Puerto Rico to Illinois, such as Southwest,United Airlines, andJetBlue. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from 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
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Top destinations
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 September 30, 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 7,457,451 searches. Data last updated September 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$538 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$265 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$219 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$226 | Average$408 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$264 | Average$461 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$476 | FlexibilityNo cancel fee | On-time63% |