$87+ Cheap flights from Illinois to Puerto Rico
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 4/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Apr 23 — Apr 301
Round-trip
1 adult, Economy
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Find cheap flights from Illinois to Puerto Rico with Cheapflights
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Cheapest flights from Illinois to Puerto RicoExplore the most affordable flight options available from Illinois to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 24, 2026.
Explore the most affordable flight options available from Illinois to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 24, 2026.
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 5/85:30 pm
ORD
- PSE
1 stop14h 37m
Frontier
Fri 5/159:47 am
PSE
- ORD
1 stop14h 26m
Frontier
Deal found 3/23![Frontier logo]()
$186
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.
Thu 5/145:30 pm
ORD
- BQN
1 stop7h 32m
Frontier
Sun 5/172:59 am
BQN
- ORD
1 stop21h 14m
Frontier
Deal found 3/20![Frontier logo]()
$196
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.
Wed 4/84:21 pm
ORD
- SJU
1 stop6h 41m
Multiple Airlines
Mon 4/131:29 am
SJU
- ORD
Nonstop5h 16m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$205
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.
Mon 4/279:14 am
MDW
- SJU
1 stop23h 40m
Frontier
Thu 4/303:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 3/20![Frontier logo]()
$205
This Frontier deal was found by Cheapflights users on 3/19. 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.
Tue 4/74:34 pm
ORD
- SJU
1 stop7h 18m
Frontier
Fri 4/173:23 pm
SJU
- ORD
1 stop8h 16m
Frontier
Deal found 3/19![Frontier logo]()
$206
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.
Fri 4/176:04 pm
ORD
- SJU
1 stop14h 50m
Frontier
Thu 4/2311:30 am
SJU
- ORD
1 stop13h 29m
Frontier
Deal found 3/23![Frontier logo]()
$207
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1011:55 am
ORD
- SJU
1 stop11h 30m
Multiple Airlines
Mon 4/131:29 am
SJU
- ORD
Nonstop5h 16m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$208
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.
Thu 4/303:52 pm
ORD
- SJU
1 stop25h 07m
Frontier
Mon 5/46:00 am
SJU
- ORD
1 stop18h 55m
Frontier
Deal found 3/22![Frontier logo]()
$209
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.
Sun 4/1212:29 pm
ORD
- SJU
Nonstop4h 31m
Multiple Airlines
Fri 4/173:23 pm
SJU
- ORD
1 stop8h 16m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$210
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:25 am
ORD
- SJU
1 stop9h 14m
Frontier
Sat 4/181:59 am
SJU
- ORD
1 stop12h 33m
Frontier
Deal found 3/20![Frontier logo]()
$211
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
MDW
- SJU
1 stop29h 13m
Frontier
Sat 4/183:21 am
SJU
- MDW
1 stop29h 43m
Frontier
Deal found 3/21![Frontier logo]()
$211
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Mon 4/131:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/20![Spirit Airlines logo]()
$212
Best flights from Illinois to Puerto RicoDiscover carefully curated flight deals from Illinois to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 24, 2026.
Discover carefully curated flight deals from Illinois to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 24, 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.
Fri 5/155:30 pm
ORD
- BQN
1 stop7h 32m
Frontier
Sat 5/234:28 pm
BQN
- ORD
1 stop7h 45m
Frontier
Deal found 3/24![Frontier logo]()
$221
This Spirit 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:00 am
ORD
- SJU
Nonstop4h 42m
Spirit Airlines
Tue 6/910:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Deal found 3/23![Spirit Airlines logo]()
$274
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.
Tue 4/219:50 am
ORD
- SJU
1 stop9h 34m
Delta
Fri 4/242:03 pm
SJU
- ORD
1 stop7h 37m
Delta
Deal found 3/20![Delta logo]()
$316
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2112:50 pm
MDW
- SJU
2 stops8h 50m
Southwest
Tue 4/285:35 am
SJU
- MDW
1 stop9h 10m
Southwest
Deal found 3/22![Southwest logo]()
$336
This American Airlines deal was found by Cheapflights users on 3/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:41 pm
MLI
- SJU
2 stops15h 07m
American Airlines
Tue 4/145:45 am
SJU
- MLI
2 stops13h 22m
American Airlines
Deal found 3/19![American Airlines logo]()
$357
This United Airlines deal was found by Cheapflights users on 3/19. 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.
Mon 5/47:45 am
STL
- SJU
2 stops12h 39m
United Airlines
Thu 5/73:56 pm
SJU
- STL
1 stop7h 49m
United Airlines
Deal found 3/19![United Airlines logo]()
$372
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.
Wed 4/84:21 pm
ORD
- PSE
1 stop18h 28m
Multiple Airlines
Wed 4/158:39 am
PSE
- ORD
2 stops14h 00m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$409
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:30 pm
ORD
- BQN
1 stop7h 32m
Frontier
Sat 5/162:59 am
BQN
- ORD
1 stop21h 14m
Frontier
Deal found 3/20![Frontier logo]()
$222
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.
Wed 4/14:21 pm
ORD
- BQN
1 stop8h 32m
Frontier
Sun 4/128:27 pm
BQN
- ORD
1 stop28h 09m
Frontier
Deal found 3/24![Frontier logo]()
$275
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:00 am
MDW
- SJU
1 stop9h 23m
Delta
Wed 5/66:15 am
SJU
- MDW
1 stop11h 11m
Delta
Deal found 3/21![Delta logo]()
$316
This American Airlines deal was found by Cheapflights users on 3/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:30 am
EVV
- SJU
1 stop8h 25m
American Airlines
Thu 8/278:00 am
SJU
- EVV
1 stop8h 55m
American Airlines
Deal found 3/19![American Airlines logo]()
$366
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:30 pm
ORD
- BQN
1 stop7h 32m
Frontier
Tue 5/262:59 am
BQN
- ORD
1 stop21h 14m
Frontier
Deal found 3/21![Frontier logo]()
$303
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.
Sun 5/37:25 am
STL
- SJU
1 stop7h 58m
Delta
Wed 5/62:03 pm
SJU
- STL
1 stop7h 41m
Delta
Deal found 3/20![Delta logo]()
$353
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.
Fri 5/81:00 pm
MDW
- SJU
1 stop9h 25m
Southwest
Sun 5/105:00 am
SJU
- MDW
2 stops9h 05m
Southwest
Deal found 3/23![Southwest logo]()
$391
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:56 pm
EVV
- SJU
2 stops14h 57m
American Airlines
Fri 4/2411:38 am
SJU
- EVV
2 stops13h 16m
American Airlines
Deal found 3/20![American Airlines logo]()
$366
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:30 pm
ORD
- BQN
1 stop7h 32m
Frontier
Sun 5/102:59 am
BQN
- ORD
1 stop21h 14m
Frontier
Deal found 3/22![Frontier logo]()
$303
This United Airlines deal was found by Cheapflights users on 3/19. 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.
Sat 4/189:16 am
STL
- SJU
2 stops13h 34m
United Airlines
Fri 4/241:00 am
SJU
- STL
2 stops12h 22m
United Airlines
Deal found 3/19![United Airlines logo]()
$415
This Spirit 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/218:00 am
ORD
- SJU
Nonstop4h 42m
Spirit Airlines
Mon 5/252:37 pm
SJU
- ORD
Nonstop5h 13m
Spirit Airlines
Deal found 3/21![Spirit Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 3/19. 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 4/286:04 am
ORD
- SJU
1 stop9h 27m
Delta
Sat 5/27:30 am
SJU
- ORD
1 stop10h 12m
Delta
Deal found 3/19![Delta logo]()
$366
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.
Sun 5/105:30 pm
ORD
- PSE
1 stop14h 32m
Frontier
Fri 5/159:47 am
PSE
- ORD
1 stop14h 26m
Frontier
Deal found 3/23![Frontier logo]()
$306
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.
Tue 5/56:35 am
MLI
- SJU
2 stops13h 03m
United Airlines
Wed 5/61:00 am
SJU
- MLI
2 stops12h 53m
United Airlines
Deal found 3/23![United Airlines logo]()
$416
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/99:05 am
MDW
- SJU
1 stop13h 10m
Southwest
Wed 5/135:35 am
SJU
- MDW
1 stop9h 10m
Southwest
Deal found 3/22![Southwest logo]()
$421
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.
Tue 4/78:56 pm
ORD
- MAZ
1 stop11h 46m
Multiple Airlines
Sat 4/114:36 pm
MAZ
- ORD
1 stop14h 09m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$472
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/294:21 pm
EVV
- SJU
2 stops17h 48m
American Airlines
Mon 9/73:50 pm
SJU
- EVV
1 stop6h 57m
American Airlines
Deal found 3/22![American Airlines logo]()
$391
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.
Sun 9/206:00 am
BMI
- SJU
1 stop7h 44m
United Airlines
Thu 9/243:56 pm
SJU
- BMI
1 stop9h 16m
United Airlines
Deal found 3/20![United Airlines logo]()
$416
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/185:30 pm
ORD
- PSE
1 stop14h 37m
Frontier
Mon 5/2510:02 am
PSE
- ORD
1 stop14h 11m
Frontier
Deal found 3/21![Frontier logo]()
$321
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:00 am
ORD
- SJU
2 stops16h 40m
Southwest
Fri 5/18:40 pm
SJU
- ORD
2 stops15h 50m
Southwest
Deal found 3/22![Southwest logo]()
$431
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:30 pm
ORD
- BQN
1 stop7h 32m
Multiple Airlines
Mon 5/115:01 am
BQN
- ORD
2 stops16h 52m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$477
This American Airlines deal was found by Cheapflights users on 3/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/14:33 pm
EVV
- SJU
2 stops17h 31m
American Airlines
Wed 7/1511:54 am
SJU
- EVV
2 stops13h 05m
American Airlines
Deal found 3/19![American Airlines logo]()
$411
This United Airlines deal was found by Cheapflights users on 3/19. 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.
Sun 9/205:45 am
PIA
- SJU
1 stop7h 59m
United Airlines
Thu 9/243:56 pm
SJU
- PIA
1 stop9h 23m
United Airlines
Deal found 3/19![United Airlines logo]()
$416
Last-minute flights from Illinois to Puerto RicoDiscover last-minute flight deals from Illinois to Puerto Rico. Data last updated March 24, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Puerto Rico. Data last updated March 24, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 3/19. 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.
Tue 4/74:34 pm
ORD
- SJU
1 stop7h 18m
Frontier
Fri 4/173:23 pm
SJU
- ORD
1 stop8h 16m
Frontier
Deal found 3/19![Frontier logo]()
$206
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Mon 4/131:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/20![Spirit Airlines logo]()
$212
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.
Tue 4/74:21 pm
ORD
- SJU
1 stop15h 57m
Multiple Airlines
Sat 4/1112:55 pm
SJU
- ORD
1 stop7h 56m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$214
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.
Wed 4/84:21 pm
ORD
- SJU
1 stop6h 41m
Multiple Airlines
Mon 4/131:29 am
SJU
- ORD
Nonstop5h 16m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$205
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1011:55 am
ORD
- SJU
1 stop11h 30m
Multiple Airlines
Mon 4/131:29 am
SJU
- ORD
Nonstop5h 16m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$208
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.
Sun 4/1212:29 pm
ORD
- SJU
Nonstop4h 31m
Multiple Airlines
Fri 4/173:23 pm
SJU
- ORD
1 stop8h 16m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$210
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:25 am
ORD
- SJU
1 stop9h 14m
Frontier
Sat 4/181:59 am
SJU
- ORD
1 stop12h 33m
Frontier
Deal found 3/20![Frontier logo]()
$211
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
MDW
- SJU
1 stop29h 13m
Frontier
Sat 4/183:21 am
SJU
- MDW
1 stop29h 43m
Frontier
Deal found 3/21![Frontier logo]()
$211
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.
Fri 4/176:04 pm
ORD
- SJU
1 stop14h 50m
Frontier
Thu 4/2311:30 am
SJU
- ORD
1 stop13h 29m
Frontier
Deal found 3/23![Frontier logo]()
$207
This Priceline deal was found by Cheapflights users on 3/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/179:14 am
MDW
- SJU
1 stop23h 40m
Frontier
Fri 4/243:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Deal found 3/19![Frontier logo]()
$214
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.
Mon 4/279:14 am
MDW
- SJU
1 stop23h 40m
Frontier
Thu 4/303:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 3/20![Frontier logo]()
$205
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.
Thu 4/303:52 pm
ORD
- SJU
1 stop25h 07m
Frontier
Mon 5/46:00 am
SJU
- ORD
1 stop18h 55m
Frontier
Deal found 3/22![Frontier logo]()
$209
One-way flights from Illinois to Puerto RicoSearch for one-way flight options from Illinois to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated March 24, 2026.
Search for one-way flight options from Illinois to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated March 24, 2026.
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/204:59 pm
STL
- SJU
1 stop8h 02m
Frontier
Deal found 3/21![Frontier logo]()
$87
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.
Sat 4/184:59 pm
STL
- SJU
1 stop8h 02m
Frontier
Deal found 3/23![Frontier logo]()
$88
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/174:59 pm
STL
- SJU
1 stop28h 49m
Frontier
Deal found 3/22![Frontier logo]()
$94
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/294:59 pm
STL
- SJU
1 stop8h 02m
Frontier
Deal found 3/20![Frontier logo]()
$97
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.
Sun 4/192:00 pm
ORD
- SJU
1 stop8h 59m
Frontier
Deal found 3/23![Frontier logo]()
$98
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.
Wed 5/63:55 pm
ORD
- BQN
1 stop9h 07m
Frontier
Deal found 3/23![Frontier logo]()
$98
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/35:30 am
MDW
- SJU
1 stop6h 56m
Frontier
Deal found 3/20![Frontier logo]()
$98
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.
Thu 5/1410:22 am
ORD
- SJU
1 stop13h 28m
Frontier
Deal found 3/22![Frontier logo]()
$100
This eDestinos deal was found by Cheapflights users on 3/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:25 am
ORD
- SJU
1 stop9h 14m
Frontier
Deal found 3/19![Frontier logo]()
$101
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/45:05 am
ORD
- SJU
1 stop12h 50m
Spirit Airlines
Deal found 3/21![Spirit Airlines logo]()
$102
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.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 3/20![Spirit Airlines logo]()
$103
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 4/176:04 pm
ORD
- SJU
1 stop27h 44m
Frontier
Deal found 3/23![Frontier logo]()
$104
Find flight deals from Illinois to Puerto Rico
Keep the following information in mind while searching for Illinois to Puerto Rico flight deals. Data was last updated March 24, 2026.
Round-trip from | $186 (Expedia) |
|---|---|
One-way from | $87 (Super.com) |
Popular in | December |
Cheapest in | October |
Average price | $416 |
Good round-trip deal | $315 or less |
Good one-way deal | $175 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois to Puerto Rico that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 24, 2026.
Use the filters below to find and compare flights from Illinois to Puerto Rico that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Fri 5/15
5:30 pm-2:02 am
1 stop7h 32m
Aguadilla Borinquen
Sat 5/23
4:28 pm-11:13 pm
1 stop7h 45m
$221
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Fri 5/8
5:30 pm-2:02 am
1 stop7h 32m
Aguadilla Borinquen
Sat 5/16
2:59 am-11:13 pm
1 stop21h 14m
$222
Quickest round-trip
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 6/5
8:00 am-1:42 pm
Nonstop4h 42m
San Juan Luis Munoz Marin Intl
Tue 6/9
10:59 am-3:08 pm
Nonstop5h 09m
$274
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Wed 4/1
4:21 pm-1:53 am
1 stop8h 32m
Aguadilla Borinquen
Sun 4/12
8:27 pm-11:36 pm
1 stop28h 09m
$275
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Fri 5/15
5:30 pm-2:02 am
1 stop7h 32m
Aguadilla Borinquen
Tue 5/26
2:59 am-11:13 pm
1 stop21h 14m
$303
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Fri 5/8
5:30 pm-2:02 am
1 stop7h 32m
Aguadilla Borinquen
Sun 5/10
2:59 am-11:13 pm
1 stop21h 14m
$303
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Sun 5/10
5:30 pm-9:02 am
1 stop14h 32m
Ponce Mercedita
Fri 5/15
9:47 am-11:13 pm
1 stop14h 26m
$306
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 4/21
9:50 am-8:24 pm
1 stop9h 34m
San Juan Luis Munoz Marin Intl
Fri 4/24
2:03 pm-8:40 pm
1 stop7h 37m
$316
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 4/28
6:00 am-4:23 pm
1 stop9h 23m
San Juan Luis Munoz Marin Intl
Wed 5/6
6:15 am-4:26 pm
1 stop11h 11m
$316
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Mon 5/18
5:30 pm-9:07 am
1 stop14h 37m
Ponce Mercedita
Mon 5/25
10:02 am-11:13 pm
1 stop14h 11m
$321
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Illinois to Puerto Rico
Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Illinois with our price prediction graph.
STL-SJU
ORD-SJU
ORD-BQN
MDW-SJU
ORD-PSE
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Illinois to Puerto Rico
USIL-PR0
STL-SJU
ORD-SJU
ORD-BQN
MDW-SJU
What is the cheapest month to book a flight from Illinois to Puerto Rico?
Currently, April is the cheapest month in which you can book a flight from Illinois to Puerto Rico (average of $91). Flying from Illinois to Puerto Rico in December is currently the most expensive (average of $224). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from IL to PR?
Find hourly flight availability from Illinois to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 24, 2026.
When flying from Illinois to Puerto Rico, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 25% versus a flight in the morning.
What is the cheapest day to fly from Illinois to Puerto Rico?
Use this chart to determine the cheapest time to fly round-trip from Illinois to Puerto Rico. Price data was last updated on March 23, 2026.
Travelers seeking maximum savings on their Illinois to Puerto Rico flight should consider departing on Tuesday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Illinois to Puerto Rico
Explore weekly flight availability from Illinois to Puerto Rico. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 24, 2026.
The most flights from USIL to PR0 are scheduled on a Saturday (16 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 on average).
Related info for your journey
Find useful and relevant information for your journey from Illinois to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
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Top destinations
Alternative routes for Illinois to Puerto Rico
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Puerto Rico by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Illinois to Puerto Rico by cabin class
Find flights from Illinois to Puerto Rico, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Illinois and Puerto Rico flights
Browse other Illinois and Puerto Rico flight options. Last updated on March 24, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Puerto Rico
Find the right flight back to Illinois after your stay in Puerto Rico
Illinois to Puerto Rico flights
Consider these flights traveling from Illinois to Puerto Rico.
Top 7 airlines flying from Illinois to Puerto Rico
Discover the top 7 airlines that operate flights from Illinois to Puerto Rico. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$114 | Average$296 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$236 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$132 | Average$420 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$139 | Average$315 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$225 | Average$609 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$254 | Average$499 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$377 | Average$488 | FlexibilityNo cancel fee | On-time63% |