$118+ Cheap flights from Puerto Rico to Illinois
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Jul 22 — Jul 291
Round-trip
1 adult, Economy
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Find cheap flights from Puerto Rico to Illinois with Cheapflights
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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 June 22, 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 June 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/196:45 am
SJU
- ORD
1 stop31h 15m
Frontier
Sun 8/2312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/17![Frontier logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 9/27:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Mon 9/712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/17![Frontier logo]()
$234
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/195:10 pm
SJU
- ORD
1 stop7h 20m
American Airlines
Mon 8/245:00 am
ORD
- SJU
1 stop7h 24m
American Airlines
Deal found 6/17![American Airlines logo]()
$236
This United Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 9/53:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Tue 9/88:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 6/21![United Airlines logo]()
$237
This Frontier deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/207:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Mon 8/2412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/21![Frontier logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 9/57:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Tue 9/87:44 pm
ORD
- SJU
1 stop16h 32m
Frontier
Deal found 6/21![Frontier logo]()
$239
This Frontier deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/197:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Mon 8/2412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/21![Frontier logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/137:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Mon 8/3112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/21![Frontier logo]()
$241
This American Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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.
Thu 8/207:24 pm
SJU
- ORD
1 stop13h 10m
American Airlines
Sun 8/235:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 6/20![American Airlines logo]()
$242
This Trip.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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.
Wed 8/127:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Sat 8/1512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/19![Frontier logo]()
$244
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 8/1912:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Wed 8/2612:46 pm
MDW
- SJU
1 stop8h 43m
Delta
Deal found 6/19![Delta logo]()
$246
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/205:49 pm
SJU
- ORD
1 stop7h 08m
Delta
Sun 8/235:30 am
ORD
- SJU
1 stop7h 12m
Delta
Deal found 6/21![Delta logo]()
$246
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 June 22, 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 June 22, 2026.
This United Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 9/53:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Tue 9/88:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 6/21![United Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 8/1912:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Wed 8/2612:46 pm
MDW
- SJU
1 stop8h 43m
Delta
Deal found 6/19![Delta logo]()
$246
This Southwest deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:55 pm
SJU
- MDW
2 stops15h 30m
Southwest
Wed 9/236:15 am
MDW
- SJU
1 stop6h 20m
Southwest
Deal found 6/21![Southwest logo]()
$256
This Travelocity deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/158:37 pm
SJU
- STL
1 stop28h 22m
Frontier
Tue 7/214:09 pm
STL
- SJU
1 stop24h 22m
Frontier
Deal found 6/21![Frontier logo]()
$376
This Cheapflightsfares deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/215:01 am
BQN
- ORD
1 stop9h 38m
JetBlue
Sat 8/82:35 pm
ORD
- BQN
1 stop8h 58m
JetBlue
Deal found 6/19![JetBlue logo]()
$384
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 9/218:55 pm
SJU
- MDW
1 stop13h 30m
Southwest
Wed 9/307:30 am
MDW
- SJU
1 stop10h 30m
Southwest
Deal found 6/20![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 8/1912:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Fri 8/2812:46 pm
MDW
- SJU
1 stop8h 43m
Delta
Deal found 6/19![Delta logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/27:35 am
MAZ
- ORD
2 stops33h 18m
Multiple Airlines
Sun 7/512:44 am
ORD
- MAZ
1 stop11h 00m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$566
This United Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 9/161:00 am
SJU
- STL
2 stops11h 57m
United Airlines
Mon 9/216:00 am
STL
- SJU
1 stop7h 44m
United Airlines
Deal found 6/19![United Airlines logo]()
$336
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/127:00 am
SJU
- MDW
1 stop10h 15m
Delta
Tue 8/186:05 am
MDW
- SJU
1 stop9h 33m
Delta
Deal found 6/18![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/182:35 pm
SJU
- STL
2 stops8h 30m
Southwest
Sun 9/208:50 pm
STL
- SJU
1 stop13h 05m
Southwest
Deal found 6/17![Southwest logo]()
$336
This Super.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 9/234:23 pm
BQN
- ORD
1 stop8h 08m
JetBlue
Wed 9/306:00 am
ORD
- BQN
1 stop6h 56m
JetBlue
Deal found 6/17![JetBlue logo]()
$389
This Frontier deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 8/1212:13 pm
SJU
- STL
1 stop12h 46m
Frontier
Mon 8/174:09 pm
STL
- SJU
1 stop9h 06m
Frontier
Deal found 6/19![Frontier logo]()
$396
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 9/35:49 pm
SJU
- STL
1 stop7h 09m
Delta
Mon 9/77:00 am
STL
- SJU
1 stop8h 38m
Delta
Deal found 6/20![Delta logo]()
$336
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/111:20 pm
SJU
- STL
1 stop7h 35m
Southwest
Sun 8/163:30 pm
STL
- SJU
1 stop8h 00m
Southwest
Deal found 6/19![Southwest logo]()
$336
This JetBlue deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 9/234:23 pm
BQN
- ORD
1 stop8h 08m
JetBlue
Sat 9/261:00 pm
ORD
- BQN
1 stop8h 39m
JetBlue
Deal found 6/21![JetBlue logo]()
$393
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:49 pm
SJU
- STL
1 stop6h 32m
Delta
Tue 9/17:00 am
STL
- SJU
1 stop8h 38m
Delta
Deal found 6/21![Delta logo]()
$336
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1711:35 am
SJU
- STL
1 stop11h 50m
Southwest
Mon 9/212:25 pm
STL
- SJU
1 stop6h 45m
Southwest
Deal found 6/19![Southwest logo]()
$336
This deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/244:23 pm
BQN
- ORD
1 stop8h 08m
JetBlue
Fri 10/21:00 pm
ORD
- BQN
1 stop8h 39m
JetBlue
Deal found 6/17![JetBlue logo]()
$423
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:00 am
SJU
- MDW
1 stop10h 15m
Delta
Thu 8/2710:54 am
MDW
- SJU
1 stop10h 35m
Delta
Deal found 6/19![Delta logo]()
$358
This Frontier deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/1212:04 pm
BQN
- ORD
1 stop12h 06m
Frontier
Sun 7/265:13 pm
ORD
- BQN
1 stop7h 57m
Frontier
Deal found 6/22![Frontier logo]()
$486
This Southwest deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/138:55 pm
SJU
- STL
1 stop11h 50m
Southwest
Tue 8/256:30 am
STL
- SJU
2 stops8h 55m
Southwest
Deal found 6/21![Southwest logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 7/57:35 am
MAZ
- ORD
1 stop16h 52m
Multiple Airlines
Wed 7/812:44 am
ORD
- MAZ
1 stop14h 27m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$586
This Frontier deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 11/711:52 am
BQN
- ORD
1 stop13h 58m
Frontier
Sun 11/154:44 pm
ORD
- BQN
1 stop8h 09m
Frontier
Deal found 6/20![Frontier logo]()
$486
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/105:50 pm
SJU
- STL
1 stop7h 03m
Delta
Tue 7/141:22 pm
STL
- SJU
1 stop8h 08m
Delta
Deal found 6/18![Delta logo]()
$367
This United Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 9/2212:15 am
BQN
- ORD
1 stop8h 26m
United Airlines
Sat 9/267:15 am
ORD
- BQN
2 stops14h 54m
United Airlines
Deal found 6/19![United Airlines logo]()
$571
This Southwest deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:00 pm
SJU
- MDW
2 stops9h 15m
Southwest
Sun 10/41:15 pm
MDW
- SJU
2 stops9h 20m
Southwest
Deal found 6/21![Southwest logo]()
$426
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/137:00 am
SJU
- STL
1 stop8h 33m
Delta
Tue 8/257:00 am
STL
- SJU
1 stop8h 38m
Delta
Deal found 6/20![Delta logo]()
$405
This Southwest deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/3010:20 pm
SJU
- MDW
1 stop11h 55m
Southwest
Mon 8/31:00 pm
MDW
- SJU
2 stops10h 20m
Southwest
Deal found 6/21![Southwest logo]()
$426
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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.
Mon 8/1712:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Tue 8/2512:46 pm
MDW
- SJU
1 stop8h 43m
Delta
Deal found 6/19![Delta logo]()
$406
Last-minute flights from Puerto Rico to IllinoisDiscover last-minute flight deals from Puerto Rico to Illinois. Data last updated June 22, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Illinois. Data last updated June 22, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 6/267:00 am
SJU
- ORD
1 stop11h 42m
American Airlines
Tue 6/308:05 am
ORD
- SJU
1 stop13h 55m
American Airlines
Deal found 6/17![American Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 6/2610:20 pm
SJU
- MDW
1 stop12h 30m
Southwest
Mon 7/63:00 pm
MDW
- SJU
1 stop8h 35m
Southwest
Deal found 6/19![Southwest logo]()
$366
This eDestinos deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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.
Mon 6/296:00 am
SJU
- ORD
1 stop18h 19m
Frontier
Sat 7/412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/21![Frontier logo]()
$373
This United Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 6/302:05 am
SJU
- ORD
1 stop9h 56m
United Airlines
Sat 7/48:49 am
ORD
- SJU
Nonstop4h 55m
United Airlines
Deal found 6/17![United Airlines logo]()
$333
This eDestinos deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/16:00 am
SJU
- ORD
1 stop7h 24m
Frontier
Sun 7/512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/17![Frontier logo]()
$362
This Southwest deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/26:30 pm
SJU
- MDW
1 stop7h 10m
Southwest
Tue 7/74:40 pm
MDW
- SJU
1 stop6h 40m
Southwest
Deal found 6/21![Southwest logo]()
$356
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/105:50 pm
SJU
- STL
1 stop7h 03m
Delta
Tue 7/141:22 pm
STL
- SJU
1 stop8h 08m
Delta
Deal found 6/18![Delta logo]()
$367
This Travelocity deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/158:37 pm
SJU
- STL
1 stop28h 22m
Frontier
Tue 7/214:09 pm
STL
- SJU
1 stop24h 22m
Frontier
Deal found 6/21![Frontier logo]()
$376
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/1710:20 pm
SJU
- MDW
1 stop11h 30m
Southwest
Mon 7/205:10 pm
MDW
- SJU
1 stop7h 15m
Southwest
Deal found 6/19![Southwest logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/175:15 pm
SJU
- STL
1 stop16h 42m
Frontier
Mon 7/204:57 pm
STL
- SJU
2 stops30h 44m
Frontier
Deal found 6/21![Frontier logo]()
$364
This eDestinos deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/178:37 pm
SJU
- STL
1 stop28h 22m
Frontier
Fri 7/244:09 pm
STL
- SJU
1 stop14h 48m
Frontier
Deal found 6/17![Frontier logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/215:15 pm
SJU
- STL
1 stop16h 42m
Frontier
Tue 7/286:34 pm
STL
- SJU
2 stops29h 07m
Frontier
Deal found 6/21![Frontier logo]()
$359
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 June 22, 2026.
Search for one-way flight options from Puerto Rico to Illinois. Find affordable one-way fares based on user searches. Data last updated June 22, 2026.
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/2610:33 am
SJU
- ORD
1 stop15h 02m
American Airlines
Deal found 6/17![American Airlines logo]()
$118
This Frontier deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/137:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/21![Frontier logo]()
$119
This eDestinos deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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.
Tue 7/147:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/18![Frontier logo]()
$120
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/412:55 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 6/17![American Airlines logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/186:45 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 6/20![Frontier logo]()
$122
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 8/138:55 pm
SJU
- MDW
2 stops15h 30m
Southwest
Deal found 6/19![Southwest logo]()
$123
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/267:30 am
SJU
- ORD
1 stop10h 31m
Delta
Deal found 6/21![Delta logo]()
$123
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/147:00 am
SJU
- ORD
1 stop13h 46m
American Airlines
Deal found 6/18![American Airlines logo]()
$126
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/125:10 pm
SJU
- ORD
1 stop7h 20m
American Airlines
Deal found 6/18![American Airlines logo]()
$127
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 9/139:25 pm
SJU
- MDW
1 stop13h 35m
Southwest
Deal found 6/20![Southwest logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/177:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/19![Frontier logo]()
$128
This Travelocity deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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.
Fri 7/317:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/18![Frontier logo]()
$129
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 June 22, 2026.
Round-trip from | $233 (Kiwi.com) |
|---|---|
One-way from | $118 (American Airlines) |
Popular in | June |
Cheapest in | February |
Average price | $443 |
Good round-trip deal | $404 or less |
Good one-way deal | $191 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Puerto Rico to Illinois that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 22, 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
Quickest round-trip
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Sat 9/5
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Tue 9/8
8:55 am-2:44 pm
Nonstop4h 49m
$237
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 8/19
12:56 pm-10:36 pm
1 stop10h 40m
Chicago Midway
Wed 8/26
12:46 pm-10:29 pm
1 stop8h 43m
$246
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 9/17
8:55 pm-11:25 am
2 stops15h 30m
Chicago Midway
Wed 9/23
6:15 am-1:35 pm
1 stop6h 20m
$256
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mon 9/21
8:55 pm-9:25 am
1 stop13h 30m
Chicago Midway
Wed 9/30
7:30 am-7:00 pm
1 stop10h 30m
$256
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 8/19
12:56 pm-10:36 pm
1 stop10h 40m
Chicago Midway
Fri 8/28
12:46 pm-10:29 pm
1 stop8h 43m
$256
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 8/12
7:00 am-4:15 pm
1 stop10h 15m
Chicago Midway
Tue 8/18
6:05 am-4:38 pm
1 stop9h 33m
$316
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Wed 9/16
1:00 am-11:57 am
2 stops11h 57m
Lambert-St Louis
Mon 9/21
6:00 am-2:44 pm
1 stop7h 44m
$336
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Fri 9/18
2:35 pm-10:05 pm
2 stops8h 30m
Lambert-St Louis
Sun 9/20
8:50 pm-10:55 am
1 stop13h 05m
$336
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Thu 9/3
5:49 pm-11:58 pm
1 stop7h 09m
Lambert-St Louis
Mon 9/7
7:00 am-4:38 pm
1 stop8h 38m
$336
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Tue 8/11
1:20 pm-7:55 pm
1 stop7h 35m
Lambert-St Louis
Sun 8/16
3:30 pm-12:30 am
1 stop8h 00m
$336
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Puerto Rico to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Puerto Rico with our price prediction graph.
SJU-ORD
SJU-MDW
SJU-STL
BQN-ORD
MAZ-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Puerto Rico to Illinois
PR0-USIL
SJU-ORD
SJU-MDW
SJU-STL
BQN-ORD
What is the cheapest month to book a flight from Puerto Rico to Illinois?
Currently, May is the cheapest month in which you can book a flight from Puerto Rico to Illinois (average of $64). Flying from Puerto Rico to Illinois in June is currently the most expensive (average of $915). 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 June 22, 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 22% 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 June 22, 2026.
The most flights from PR0 to USIL are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 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 June 20, 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. Sunday mornings 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 June 22, 2026.
Read through reviews of airlines operating flights from Puerto Rico to Illinois, such as Southwest,United Airlines, andAmerican Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Puerto Rico to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Puerto Rico to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Puerto Rico to Illinois by cabin class
Find flights from Puerto Rico to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Puerto Rico and Illinois flights
Browse other Puerto Rico and Illinois flight options. Last updated on June 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Illinois
Find the right flight back to Puerto Rico after your stay in Illinois
Puerto Rico to Illinois flights
Consider these flights traveling from Puerto Rico to Illinois.
Top 6 airlines flying from Puerto Rico to Illinois
Discover the top 6 airlines that operate flights from Puerto Rico to Illinois. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$254 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$227 | Average$432 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$262 | Average$482 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$292 | Average$508 | FlexibilityNo cancel fee | On-time63% |