$108+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Jun 8 — Jun 151
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
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from 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 May 9, 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 May 9, 2026.
This Orbitz deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz 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 8/2412:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 5/4![Frontier logo]()
$173
This deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:00 am
SJU
- ORD
1 stop7h 25m
Frontier
Fri 8/1412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 5/5![Frontier logo]()
$192
This eDestinos deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:00 am
SJU
- ORD
1 stop7h 25m
Frontier
Tue 8/1112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 5/5![Frontier logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/44:05 pm
SJU
- ORD
1 stop8h 14m
Frontier
Fri 8/1412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 5/5![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Tue 9/86:55 am
ORD
- SJU
2 stops16h 49m
Frontier
Deal found 5/6![Frontier logo]()
$214
This eDestinos deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/134:05 pm
SJU
- ORD
1 stop18h 06m
Frontier
Wed 8/195:30 pm
ORD
- SJU
1 stop13h 39m
Frontier
Deal found 5/4![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/37:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Sat 8/812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 5/4![Frontier logo]()
$217
This American Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:59 am
SJU
- ORD
Nonstop5h 01m
American Airlines
Mon 9/76:34 am
ORD
- SJU
1 stop14h 50m
American Airlines
Deal found 5/9![American Airlines logo]()
$222
This eDestinos deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/227:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Mon 5/2512:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 5/4![Frontier logo]()
$224
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:49 pm
SJU
- ORD
1 stop7h 09m
Delta
Wed 8/126:00 am
ORD
- SJU
1 stop9h 33m
Delta
Deal found 5/7![Delta logo]()
$226
This eDestinos deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/134:05 pm
SJU
- STL
1 stop8h 54m
Frontier
Tue 8/253:33 pm
STL
- SJU
1 stop12h 22m
Frontier
Deal found 5/4![Frontier logo]()
$234
This Travelocity deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/134:05 pm
SJU
- STL
1 stop8h 54m
Frontier
Wed 8/264:10 pm
STL
- SJU
1 stop14h 59m
Frontier
Deal found 5/4![Frontier logo]()
$238
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 May 9, 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 May 9, 2026.
This Orbitz deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:59 am
BQN
- ORD
1 stop21h 15m
Frontier
Fri 8/285:30 pm
ORD
- BQN
1 stop7h 34m
Frontier
Deal found 5/4![Frontier logo]()
$276
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:15 am
SJU
- MDW
1 stop7h 50m
Southwest
Tue 8/256:15 am
MDW
- SJU
1 stop6h 20m
Southwest
Deal found 5/8![Southwest logo]()
$296
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1312:56 pm
SJU
- MDW
1 stop10h 19m
Delta
Mon 7/206:00 am
MDW
- SJU
1 stop9h 45m
Delta
Deal found 5/5![Delta logo]()
$356
This JetBlue deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:01 am
BQN
- ORD
1 stop9h 38m
JetBlue
Sat 8/292:35 pm
ORD
- BQN
1 stop8h 58m
JetBlue
Deal found 5/6![JetBlue logo]()
$379
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:00 am
SJU
- ORD
1 stop9h 00m
United Airlines
Wed 6/242:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 5/4![United Airlines logo]()
$432
This Priceline deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:59 am
BQN
- ORD
1 stop21h 15m
Multiple Airlines
Fri 8/286:00 am
ORD
- BQN
2 stops30h 26m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$446
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:00 am
SJU
- STL
1 stop9h 50m
Southwest
Sun 9/138:50 pm
STL
- SJU
1 stop13h 05m
Southwest
Deal found 5/8![Southwest logo]()
$336
This eDestinos deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:41 pm
SJU
- STL
2 stops39h 11m
Frontier
Sat 8/295:33 pm
STL
- SJU
2 stops30h 11m
Frontier
Deal found 5/6![Frontier logo]()
$342
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:35 am
SJU
- STL
2 stops9h 20m
Southwest
Sun 9/138:50 pm
STL
- SJU
1 stop11h 20m
Southwest
Deal found 5/6![Southwest logo]()
$373
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:00 am
SJU
- MDW
1 stop11h 15m
Delta
Tue 7/216:00 am
MDW
- SJU
1 stop9h 45m
Delta
Deal found 5/7![Delta logo]()
$426
This Frontier deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2512:28 pm
BQN
- ORD
1 stop11h 46m
Frontier
Sat 8/295:30 pm
ORD
- BQN
1 stop7h 34m
Frontier
Deal found 5/4![Frontier logo]()
$406
This United Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/231:00 am
SJU
- ORD
1 stop9h 43m
United Airlines
Mon 6/292:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 5/8![United Airlines logo]()
$455
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/89:45 pm
SJU
- MDW
1 stop13h 00m
Southwest
Tue 10/137:50 am
MDW
- SJU
1 stop6h 00m
Southwest
Deal found 5/5![Southwest logo]()
$396
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/255:41 pm
SJU
- STL
1 stop6h 56m
Delta
Thu 10/11:30 pm
STL
- SJU
1 stop7h 30m
Delta
Deal found 5/6![Delta logo]()
$441
This Gotogate deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/263:06 am
SJU
- STL
1 stop21h 43m
Frontier
Sat 7/114:09 pm
STL
- SJU
1 stop9h 02m
Frontier
Deal found 5/6![Frontier logo]()
$417
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/167:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Mon 6/292:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 5/7![United Airlines logo]()
$478
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/204:36 pm
MAZ
- ORD
1 stop31h 10m
Multiple Airlines
Sun 5/247:52 pm
ORD
- MAZ
2 stops15h 52m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$542
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Sat 8/296:05 am
MDW
- SJU
1 stop9h 32m
Delta
Deal found 5/4![Delta logo]()
$466
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2510:00 am
SJU
- STL
2 stops9h 25m
Southwest
Thu 10/12:05 pm
STL
- SJU
2 stops9h 30m
Southwest
Deal found 5/8![Southwest logo]()
$427
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/181:00 am
SJU
- ORD
1 stop9h 00m
United Airlines
Thu 6/252:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 5/5![United Airlines logo]()
$517
This Priceline deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/23:00 am
BQN
- ORD
1 stop21h 19m
Frontier
Sun 7/125:13 pm
ORD
- BQN
1 stop7h 52m
Frontier
Deal found 5/8![Frontier logo]()
$473
This Southwest deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1110:20 pm
SJU
- MDW
1 stop12h 40m
Southwest
Sun 6/142:40 pm
MDW
- SJU
2 stops9h 00m
Southwest
Deal found 5/9![Southwest logo]()
$445
This JetBlue deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:30 am
SJU
- ORD
1 stop8h 46m
JetBlue
Tue 5/2610:45 am
ORD
- SJU
1 stop11h 08m
JetBlue
Deal found 5/8![JetBlue logo]()
$660
This United Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/261:00 am
SJU
- STL
2 stops12h 13m
United Airlines
Mon 8/316:00 am
STL
- SJU
1 stop7h 44m
United Airlines
Deal found 5/6![United Airlines logo]()
$520
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/18:35 pm
SJU
- MDW
1 stop13h 40m
Southwest
Tue 7/74:40 pm
MDW
- SJU
1 stop6h 35m
Southwest
Deal found 5/7![Southwest logo]()
$460
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/277:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Sat 7/48:49 am
ORD
- SJU
Nonstop4h 55m
United Airlines
Deal found 5/4![United Airlines logo]()
$525
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/209:25 pm
SJU
- MDW
1 stop12h 05m
Southwest
Sat 6/275:05 pm
MDW
- SJU
1 stop7h 10m
Southwest
Deal found 5/8![Southwest logo]()
$466
This eDestinos deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/212:59 am
BQN
- MDW
2 stops33h 05m
Frontier
Fri 5/296:00 am
MDW
- BQN
2 stops43h 02m
Frontier
Deal found 5/7![Frontier logo]()
$589
This United Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Sat 7/112:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 5/6![United Airlines logo]()
$577
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1010:20 pm
SJU
- MDW
1 stop11h 30m
Southwest
Fri 7/241:30 pm
MDW
- SJU
2 stops9h 35m
Southwest
Deal found 5/5![Southwest logo]()
$486
Last-minute flights from Puerto Rico to IllinoisDiscover last-minute flight deals from Puerto Rico to Illinois. Data last updated May 9, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Illinois. Data last updated May 9, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/121:25 pm
SJU
- ORD
1 stop11h 13m
American Airlines
Sat 5/168:46 pm
ORD
- SJU
1 stop13h 02m
American Airlines
Deal found 5/5![American Airlines logo]()
$273
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/122:42 pm
SJU
- ORD
1 stop9h 56m
American Airlines
Fri 5/158:46 pm
ORD
- SJU
1 stop13h 02m
American Airlines
Deal found 5/4![American Airlines logo]()
$276
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/142:35 pm
SJU
- ORD
1 stop6h 39m
Delta
Mon 5/189:49 am
ORD
- SJU
1 stop9h 41m
Delta
Deal found 5/4![Delta logo]()
$266
This eDestinos deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/216:30 am
SJU
- ORD
1 stop13h 14m
Frontier
Mon 5/2512:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 5/4![Frontier logo]()
$282
This eDestinos deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/227:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Mon 5/2512:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 5/4![Frontier logo]()
$224
This eDestinos deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Sat 5/307:52 pm
ORD
- SJU
1 stop7h 09m
Frontier
Deal found 5/4![Frontier logo]()
$259
This CheapOair deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sat 5/3012:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 5/4![Frontier logo]()
$268
This eDestinos deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:30 am
SJU
- ORD
1 stop13h 14m
Frontier
Tue 6/164:59 pm
ORD
- SJU
1 stop23h 00m
Frontier
Deal found 5/4![Frontier logo]()
$290
This Mytrip deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/186:00 am
SJU
- ORD
1 stop7h 24m
Frontier
Sun 7/512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 5/7![Frontier logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/196:45 pm
SJU
- ORD
1 stop25h 02m
Frontier
Thu 6/254:59 pm
ORD
- SJU
1 stop13h 56m
Frontier
Deal found 5/5![Frontier logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:00 am
SJU
- ORD
1 stop31h 24m
Frontier
Sun 7/512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 5/4![Frontier logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:00 am
SJU
- ORD
1 stop31h 24m
Frontier
Mon 6/2910:16 am
ORD
- SJU
1 stop12h 13m
Frontier
Deal found 5/5![Frontier logo]()
$271
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 May 9, 2026.
Search for one-way flight options from Puerto Rico to Illinois. Find affordable one-way fares based on user searches. Data last updated May 9, 2026.
This Mytrip deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 5/4![Frontier logo]()
$108
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:42 pm
SJU
- MDW
1 stop8h 33m
Delta
Deal found 5/7![Delta logo]()
$113
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:42 pm
SJU
- ORD
1 stop8h 26m
Delta
Deal found 5/7![Delta logo]()
$113
This eDestinos deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 5/7![Frontier logo]()
$117
This Frontier deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:31 pm
SJU
- STL
1 stop6h 28m
Frontier
Deal found 5/6![Frontier logo]()
$118
This Expedia deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:00 am
SJU
- ORD
1 stop7h 25m
Frontier
Deal found 5/4![Frontier logo]()
$118
This Frontier deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/307:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 5/5![Frontier logo]()
$119
This Frontier deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:31 pm
SJU
- STL
1 stop6h 28m
Frontier
Deal found 5/6![Frontier logo]()
$120
This Frontier deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:00 am
SJU
- ORD
1 stop7h 25m
Frontier
Deal found 5/5![Frontier logo]()
$120
This Super.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 5/4![Frontier logo]()
$121
This Expedia deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/107:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 5/4![Frontier logo]()
$122
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1312:56 pm
SJU
- MDW
1 stop10h 19m
Delta
Deal found 5/5![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 May 9, 2026.
Round-trip from | $192 |
|---|---|
One-way from | $108 (Mytrip) |
Popular in | December |
Cheapest in | February |
Average price | $327 |
Good round-trip deal | $276 or less |
Good one-way deal | $166 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 May 9, 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
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Thu 8/20
2:59 am-11:14 pm
1 stop21h 15m
Chicago O'Hare Intl
Fri 8/28
5:30 pm-2:04 am
1 stop7h 34m
$276
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 8/18
5:15 am-12:05 pm
1 stop7h 50m
Chicago Midway
Tue 8/25
6:15 am-1:35 pm
1 stop6h 20m
$296
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Wed 9/9
6:00 am-2:50 pm
1 stop9h 50m
Lambert-St Louis
Sun 9/13
8:50 pm-10:55 am
1 stop13h 05m
$336
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Wed 8/26
6:41 pm-8:52 am
2 stops39h 11m
Lambert-St Louis
Sat 8/29
5:33 pm-12:44 am
2 stops30h 11m
$342
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mon 7/13
12:56 pm-10:15 pm
1 stop10h 19m
Chicago Midway
Mon 7/20
6:00 am-4:45 pm
1 stop9h 45m
$356
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Fri 9/11
11:35 am-7:55 pm
2 stops9h 20m
Lambert-St Louis
Sun 9/13
8:50 pm-9:10 am
1 stop11h 20m
$373
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Tue 8/25
5:01 am-1:39 pm
1 stop9h 38m
Chicago O'Hare Intl
Sat 8/29
2:35 pm-12:33 am
1 stop8h 58m
$379
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 10/8
9:45 pm-9:45 am
1 stop13h 00m
Chicago Midway
Tue 10/13
7:50 am-2:50 pm
1 stop6h 00m
$396
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Tue 8/25
12:28 pm-11:14 pm
1 stop11h 46m
Chicago O'Hare Intl
Sat 8/29
5:30 pm-2:04 am
1 stop7h 34m
$406
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Fri 6/26
3:06 am-11:49 pm
1 stop21h 43m
Lambert-St Louis
Sat 7/11
4:09 pm-2:11 am
1 stop9h 02m
$417
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-MDW
SJU-ORD
SJU-STL
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
BQN-ORD
SJU-MDW
SJU-ORD
SJU-STL
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 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 July is currently the most expensive (average of $575). 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 May 9, 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 46% versus a flight in the afternoon.
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 May 9, 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 afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 May 9, 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).
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 May 9, 2026.
Read through reviews of airlines operating flights from Puerto Rico to Illinois, such as United Airlines,JetBlue, andAmerican Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.6
Comfort
7.3
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.6
Comfort
7.3
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.6
Comfort
7.3
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.6
Comfort
7.3
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.6
Comfort
7.3
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.6
Comfort
7.3
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
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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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 May 9, 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 7 airlines flying from Puerto Rico to Illinois
Discover the top 7 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 May 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$116 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$121 | Average$265 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$128 | Average$254 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$254 | Average$484 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$257 | Average$440 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$292 | Average$512 | FlexibilityNo cancel fee | On-time63% |