$94+ 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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Apr 24 — May 11
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 March 25, 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 March 25, 2026.
This eDestinos deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 4/2910:54 am
SJU
- STL
1 stop13h 25m
Frontier
Sat 5/24:59 pm
STL
- SJU
1 stop8h 02m
Frontier
Deal found 3/24![Frontier logo]()
$159
This eDestinos deal was found by Cheapflights users on 3/21. 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.
Sat 4/188:00 am
SJU
- STL
1 stop16h 19m
Frontier
Sat 4/254:59 pm
STL
- SJU
1 stop8h 02m
Frontier
Deal found 3/21![Frontier logo]()
$168
This eDestinos deal was found by Cheapflights users on 3/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:07 pm
SJU
- ORD
1 stop22h 50m
Frontier
Sun 4/124:21 pm
ORD
- SJU
1 stop26h 39m
Frontier
Deal found 3/20![Frontier logo]()
$168
This Expedia deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/173:23 pm
SJU
- ORD
1 stop8h 16m
Frontier
Mon 4/205:48 pm
ORD
- SJU
1 stop14h 12m
Frontier
Deal found 3/23![Frontier logo]()
$176
This eDestinos deal was found by Cheapflights users on 3/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:31 pm
SJU
- ORD
1 stop27h 43m
Frontier
Sun 4/2612:38 pm
ORD
- SJU
1 stop10h 21m
Frontier
Deal found 3/20![Frontier logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 3/21. 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 4/163:31 pm
SJU
- ORD
1 stop9h 13m
Frontier
Sun 4/193:52 pm
ORD
- SJU
1 stop25h 07m
Frontier
Deal found 3/21![Frontier logo]()
$183
This Priceline deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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.
Sat 4/113:21 am
SJU
- STL
1 stop29h 30m
Frontier
Tue 4/144:59 pm
STL
- SJU
1 stop8h 02m
Frontier
Deal found 3/24![Frontier logo]()
$186
This Priceline deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/96:07 pm
SJU
- MDW
1 stop20h 54m
Frontier
Mon 4/135:30 am
MDW
- SJU
1 stop13h 30m
Frontier
Deal found 3/23![Frontier logo]()
$186
This CheapOair deal was found by Cheapflights users on 3/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/13:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Mon 5/48:41 am
MDW
- SJU
1 stop16h 20m
Frontier
Deal found 3/25![Frontier logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 5/66:41 pm
SJU
- ORD
1 stop15h 56m
Frontier
Wed 5/133:55 pm
ORD
- SJU
1 stop9h 13m
Frontier
Deal found 3/23![Frontier logo]()
$188
This eDestinos deal was found by Cheapflights users on 3/21. 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.
Wed 4/1511:05 am
SJU
- ORD
1 stop27h 48m
Frontier
Sun 4/193:52 pm
ORD
- SJU
1 stop25h 07m
Frontier
Deal found 3/21![Frontier logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 5/136:41 pm
SJU
- ORD
1 stop15h 56m
Frontier
Wed 5/203:55 pm
ORD
- SJU
1 stop24h 17m
Frontier
Deal found 3/24![Frontier logo]()
$193
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 March 25, 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 March 25, 2026.
This Frontier deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 5/1412:28 pm
BQN
- ORD
1 stop11h 45m
Frontier
Mon 5/185:30 pm
ORD
- BQN
1 stop7h 32m
Frontier
Deal found 3/24![Frontier logo]()
$196
This Spirit deal was found by Cheapflights users on 3/22. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2110:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Tue 4/2810:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Deal found 3/22![Spirit Airlines logo]()
$274
This Delta deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 5/195:43 pm
SJU
- STL
1 stop7h 16m
Delta
Tue 6/21:27 pm
STL
- SJU
1 stop6h 03m
Delta
Deal found 3/24![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 7/226:00 am
SJU
- MDW
1 stop7h 20m
Southwest
Tue 7/2812:00 pm
MDW
- SJU
1 stop6h 45m
Southwest
Deal found 3/24![Southwest logo]()
$326
This United Airlines deal was found by Cheapflights users on 3/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:20 am
SJU
- STL
2 stops14h 53m
United Airlines
Mon 5/47:45 am
STL
- SJU
2 stops12h 39m
United Airlines
Deal found 3/22![United Airlines logo]()
$406
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/211:19 pm
MAZ
- ORD
1 stop26h 49m
Multiple Airlines
Tue 4/2810:00 am
ORD
- MAZ
1 stop7h 43m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$428
This Cheapflightsfares deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 4/31:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Sat 5/210:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Deal found 3/24![Spirit Airlines logo]()
$308
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/165:35 am
SJU
- MDW
2 stops8h 35m
Southwest
Wed 4/229:25 am
MDW
- SJU
1 stop10h 40m
Southwest
Deal found 3/23![Southwest logo]()
$346
This Delta deal was found by Cheapflights users on 3/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:15 am
SJU
- MDW
1 stop11h 11m
Delta
Tue 4/2810:41 am
MDW
- SJU
1 stop8h 43m
Delta
Deal found 3/22![Delta logo]()
$366
This United Airlines deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/301:00 am
SJU
- ORD
1 stop8h 44m
United Airlines
Tue 5/52:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 3/23![United Airlines logo]()
$408
This Southwest deal was found by Cheapflights users on 3/21. 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.
Wed 7/85:30 am
SJU
- MDW
1 stop8h 15m
Southwest
Wed 7/2212:05 pm
MDW
- SJU
1 stop6h 40m
Southwest
Deal found 3/21![Southwest logo]()
$376
This Kiwi.com deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 4/84:36 pm
MAZ
- ORD
1 stop14h 09m
Multiple Airlines
Sun 4/1210:55 am
ORD
- MAZ
2 stops21h 47m
Multiple Airlines
Deal found 3/24![Multiple Airlines logo]()
$430
This eDestinos deal was found by Cheapflights users on 3/22. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:38 am
BQN
- MDW
2 stops20h 41m
Frontier
Wed 5/612:04 pm
MDW
- BQN
2 stops22h 27m
Frontier
Deal found 3/22![Frontier logo]()
$432
This United Airlines deal was found by Cheapflights users on 3/21. 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.
Fri 4/171:00 am
SJU
- STL
2 stops10h 45m
United Airlines
Sat 4/2510:09 am
STL
- SJU
1 stop9h 29m
United Airlines
Deal found 3/21![United Airlines logo]()
$411
This Southwest deal was found by Cheapflights users on 3/20. 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.
Thu 4/308:40 pm
SJU
- MDW
1 stop13h 35m
Southwest
Mon 5/41:25 pm
MDW
- SJU
2 stops9h 30m
Southwest
Deal found 3/20![Southwest logo]()
$386
This eDestinos deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 5/292:59 am
BQN
- ORD
2 stops29h 56m
Frontier
Sat 6/131:50 pm
ORD
- BQN
2 stops20h 43m
Frontier
Deal found 3/23![Frontier logo]()
$444
This Priceline deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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.
Sat 5/306:30 am
BQN
- ORD
2 stops26h 30m
Multiple Airlines
Sat 6/135:30 pm
ORD
- BQN
1 stop7h 34m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$444
This United Airlines deal was found by Cheapflights users on 3/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/243:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Sun 4/262:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 3/20![United Airlines logo]()
$437
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/181:10 pm
SJU
- MDW
Nonstop5h 10m
Southwest
Mon 4/201:00 pm
MDW
- SJU
1 stop9h 25m
Southwest
Deal found 3/23![Southwest logo]()
$402
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/202:38 am
BQN
- ORD
2 stops32h 45m
Multiple Airlines
Tue 4/2810:31 am
ORD
- BQN
1 stop14h 12m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$463
This Expedia deal was found by Cheapflights users on 3/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/182:48 am
BQN
- ORD
1 stop22h 11m
Frontier
Sun 4/266:00 am
ORD
- BQN
1 stop18h 43m
Frontier
Deal found 3/20![Frontier logo]()
$489
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/98:40 pm
SJU
- ORD
2 stops17h 10m
Southwest
Mon 4/132:40 pm
ORD
- SJU
2 stops8h 15m
Southwest
Deal found 3/23![Southwest logo]()
$406
This United Airlines deal was found by Cheapflights users on 3/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/163:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Sat 9/198:51 am
ORD
- SJU
1 stop10h 47m
United Airlines
Deal found 3/20![United Airlines logo]()
$472
This Mytrip deal was found by Cheapflights users on 3/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/64:36 pm
MAZ
- ORD
1 stop14h 09m
Multiple Airlines
Fri 4/108:56 pm
ORD
- MAZ
1 stop11h 46m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$476
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 6/55:30 am
SJU
- MDW
2 stops9h 35m
Southwest
Mon 6/151:00 pm
MDW
- SJU
2 stops10h 15m
Southwest
Deal found 3/24![Southwest logo]()
$421
This eDestinos deal was found by Cheapflights users on 3/22. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/202:38 am
BQN
- ORD
2 stops28h 30m
Frontier
Tue 4/2811:07 am
ORD
- BQN
2 stops37h 36m
Frontier
Deal found 3/22![Frontier logo]()
$517
This United Airlines deal was found by Cheapflights users on 3/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Tue 4/282:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 3/22![United Airlines logo]()
$477
This Kiwi.com deal was found by Cheapflights users on 3/20. 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.
Sat 4/182:48 am
BQN
- ORD
2 stops41h 02m
Multiple Airlines
Sun 4/2610:31 am
ORD
- BQN
1 stop14h 12m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$512
This Southwest deal was found by Cheapflights users on 3/20. 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.
Tue 7/215:00 am
SJU
- STL
2 stops14h 25m
Southwest
Thu 7/301:50 pm
STL
- SJU
1 stop9h 35m
Southwest
Deal found 3/20![Southwest logo]()
$428
This United Airlines deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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.
Fri 4/173:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Wed 4/222:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 3/23![United Airlines logo]()
$497
Last-minute flights from Puerto Rico to IllinoisDiscover last-minute flight deals from Puerto Rico to Illinois. Data last updated March 25, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Illinois. Data last updated March 25, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 3/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/33:16 am
SJU
- STL
1 stop21h 09m
Frontier
Wed 4/84:59 pm
STL
- SJU
1 stop8h 02m
Frontier
Deal found 3/20![Frontier logo]()
$196
This eDestinos deal was found by Cheapflights users on 3/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:07 pm
SJU
- ORD
1 stop22h 50m
Frontier
Sun 4/124:21 pm
ORD
- SJU
1 stop26h 39m
Frontier
Deal found 3/20![Frontier logo]()
$168
This Priceline deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/96:07 pm
SJU
- MDW
1 stop20h 54m
Frontier
Mon 4/135:30 am
MDW
- SJU
1 stop13h 30m
Frontier
Deal found 3/23![Frontier logo]()
$186
This Priceline deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 4/103:16 am
SJU
- STL
1 stop21h 09m
Frontier
Tue 4/284:59 pm
STL
- SJU
1 stop8h 02m
Frontier
Deal found 3/24![Frontier logo]()
$186
This eDestinos deal was found by Cheapflights users on 3/21. 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.
Wed 4/1511:05 am
SJU
- ORD
1 stop27h 48m
Frontier
Sun 4/193:52 pm
ORD
- SJU
1 stop25h 07m
Frontier
Deal found 3/21![Frontier logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 3/21. 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 4/163:31 pm
SJU
- ORD
1 stop9h 13m
Frontier
Sun 4/193:52 pm
ORD
- SJU
1 stop25h 07m
Frontier
Deal found 3/21![Frontier logo]()
$183
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/163:31 pm
SJU
- ORD
1 stop9h 13m
Frontier
Thu 4/233:08 pm
ORD
- SJU
1 stop7h 21m
Frontier
Deal found 3/23![Frontier logo]()
$186
This Expedia deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/173:23 pm
SJU
- ORD
1 stop8h 16m
Frontier
Mon 4/205:48 pm
ORD
- SJU
1 stop14h 12m
Frontier
Deal found 3/23![Frontier logo]()
$176
This eDestinos deal was found by Cheapflights users on 3/21. 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.
Sat 4/188:00 am
SJU
- STL
1 stop16h 19m
Frontier
Sat 4/254:59 pm
STL
- SJU
1 stop8h 02m
Frontier
Deal found 3/21![Frontier logo]()
$168
This eDestinos deal was found by Cheapflights users on 3/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:31 pm
SJU
- ORD
1 stop27h 43m
Frontier
Sun 4/2612:38 pm
ORD
- SJU
1 stop10h 21m
Frontier
Deal found 3/20![Frontier logo]()
$178
This eDestinos deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 4/2910:54 am
SJU
- STL
1 stop13h 25m
Frontier
Sat 5/24:59 pm
STL
- SJU
1 stop8h 02m
Frontier
Deal found 3/24![Frontier logo]()
$159
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/303:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Mon 5/46:00 am
MDW
- SJU
1 stop7h 13m
Frontier
Deal found 3/23![Frontier logo]()
$196
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 March 25, 2026.
Search for one-way flight options from Puerto Rico to Illinois. Find affordable one-way fares based on user searches. Data last updated March 25, 2026.
This Orbitz deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:00 am
SJU
- STL
1 stop19h 21m
Frontier
Deal found 3/23![Frontier logo]()
$94
This Priceline deal was found by Cheapflights users on 3/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:30 am
SJU
- STL
1 stop17h 55m
Frontier
Deal found 3/20![Frontier logo]()
$98
This Expedia deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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.
Sun 4/128:27 pm
BQN
- ORD
1 stop28h 09m
Frontier
Deal found 3/24![Frontier logo]()
$104
This CheapOair deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/69:10 pm
SJU
- STL
1 stop27h 15m
Frontier
Deal found 3/23![Frontier logo]()
$117
This Priceline deal was found by Cheapflights users on 3/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/294:35 pm
SJU
- ORD
1 stop19h 28m
Frontier
Deal found 3/20![Frontier logo]()
$117
This CheapOair deal was found by Cheapflights users on 3/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/146:09 pm
SJU
- ORD
1 stop30h 04m
Frontier
Deal found 3/20![Frontier logo]()
$118
This Trip.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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.
Tue 4/213:08 am
SJU
- MDW
1 stop29h 18m
Frontier
Deal found 3/23![Frontier logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 3/20. 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.
Sat 5/166:00 am
SJU
- ORD
1 stop18h 13m
Frontier
Deal found 3/20![Frontier logo]()
$119
This eDestinos deal was found by Cheapflights users on 3/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Deal found 3/20![Frontier logo]()
$120
This Delta deal was found by Cheapflights users on 3/20. 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.
Wed 4/226:15 am
SJU
- STL
1 stop10h 17m
Delta
Deal found 3/20![Delta logo]()
$121
This eDestinos deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 4/26:07 pm
SJU
- ORD
1 stop22h 50m
Frontier
Deal found 3/24![Frontier logo]()
$121
This Super.com deal was found by Cheapflights users on 3/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/163:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 3/22![Frontier logo]()
$122
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 March 25, 2026.
Round-trip from | $159 (eDestinos) |
|---|---|
One-way from | $94 (Orbitz) |
Popular in | December |
Cheapest in | February |
Average price | $359 |
Good round-trip deal | $325 or less |
Good one-way deal | $193 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 March 25, 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 5/14
12:28 pm-11:13 pm
1 stop11h 45m
Chicago O'Hare Intl
Mon 5/18
5:30 pm-2:02 am
1 stop7h 32m
$196
Quickest round-trip
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 4/21
10:59 am-3:08 pm
Nonstop5h 09m
Chicago O'Hare Intl
Tue 4/28
10:00 am-3:39 pm
Nonstop4h 39m
$274
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 4/3
1:29 am-5:45 am
Nonstop5h 16m
Chicago O'Hare Intl
Sat 5/2
10:00 am-3:39 pm
Nonstop4h 39m
$308
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Tue 5/19
5:43 pm-11:59 pm
1 stop7h 16m
Lambert-St Louis
Tue 6/2
1:27 pm-8:30 pm
1 stop6h 03m
$316
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 7/22
6:00 am-12:20 pm
1 stop7h 20m
Chicago Midway
Tue 7/28
12:00 pm-7:45 pm
1 stop6h 45m
$326
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 4/16
5:35 am-1:10 pm
2 stops8h 35m
Chicago Midway
Wed 4/22
9:25 am-9:05 pm
1 stop10h 40m
$346
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 4/21
6:15 am-4:26 pm
1 stop11h 11m
Chicago Midway
Tue 4/28
10:41 am-8:24 pm
1 stop8h 43m
$366
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 7/8
5:30 am-12:45 pm
1 stop8h 15m
Chicago Midway
Wed 7/22
12:05 pm-7:45 pm
1 stop6h 40m
$376
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 4/30
8:40 pm-9:15 am
1 stop13h 35m
Chicago Midway
Mon 5/4
1:25 pm-11:55 pm
2 stops9h 30m
$386
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 4/18
1:10 pm-5:20 pm
Nonstop5h 10m
Chicago Midway
Mon 4/20
1:00 pm-11:25 pm
1 stop9h 25m
$402
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-STL
SJU-ORD
SJU-MDW
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-STL
SJU-ORD
SJU-MDW
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 $113). Flying from Puerto Rico to Illinois in December is currently the most expensive (average of $157). 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 March 25, 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 50% 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 March 23, 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 March 25, 2026.
The most flights from PR0 to USIL are scheduled on a Tuesday (15 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (7 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 March 25, 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.
Overall
7.4
Comfort
7.3
Food
6.6
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Overall
7.4
Comfort
7.3
Food
6.6
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Overall
7.4
Comfort
7.3
Food
6.6
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Overall
7.4
Comfort
7.3
Food
6.6
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Overall
7.4
Comfort
7.3
Food
6.6
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Overall
7.4
Comfort
7.3
Food
6.6
Crew
8.1
Entertainment
7.1
Boarding
7.7
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
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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 March 25, 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 March 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$64 | Average$259 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$122 | Average$268 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$131 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$256 | Average$483 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$257 | Average$446 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$292 | Average$499 | FlexibilityNo cancel fee | On-time63% |