$123+ Cheap flights from Chicago (CHI) 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Jul 23 — Jul 301
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Puerto Rico 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 Chicago to Puerto Rico
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Cheapest flights from Chicago to Puerto RicoExplore the most affordable flight options available from Chicago to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 23, 2026.
Explore the most affordable flight options available from Chicago to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 23, 2026.
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/154:59 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Fri 8/2812:55 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 6/19![American Airlines logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Mon 8/248:57 pm
SJU
- ORD
1 stop27h 11m
Frontier
Deal found 6/21![Frontier logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Thu 8/137:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/18![Frontier logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 8/77:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/18![Frontier logo]()
$260
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:54 am
ORD
- SJU
1 stop11h 35m
Delta
Wed 9/91:21 pm
SJU
- ORD
1 stop9h 16m
Delta
Deal found 6/22![Delta logo]()
$261
This Frontier deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Thu 8/137:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/20![Frontier logo]()
$263
This Super.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Wed 8/127:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/21![Frontier logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Mon 8/248:57 pm
SJU
- ORD
1 stop27h 11m
Frontier
Deal found 6/21![Frontier logo]()
$265
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:40 am
ORD
- SJU
1 stop8h 58m
Delta
Sat 8/292:31 pm
SJU
- ORD
1 stop6h 59m
Delta
Deal found 6/22![Delta logo]()
$266
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:05 am
MDW
- SJU
1 stop9h 33m
Delta
Fri 9/412:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Deal found 6/22![Delta logo]()
$266
This American Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Thu 9/31:38 pm
SJU
- ORD
1 stop11h 57m
American Airlines
Deal found 6/21![American Airlines logo]()
$267
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:40 am
ORD
- SJU
1 stop8h 58m
United Airlines
Sun 9/61:00 am
SJU
- ORD
1 stop9h 13m
United Airlines
Deal found 6/22![United Airlines logo]()
$268
Best flights from Chicago to Puerto RicoDiscover carefully curated flight deals from Chicago to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 23, 2026.
Discover carefully curated flight deals from Chicago to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 23, 2026.
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:40 am
ORD
- SJU
1 stop8h 58m
Delta
Sat 8/225:49 pm
SJU
- ORD
1 stop7h 08m
Delta
Deal found 6/22![Delta logo]()
$266
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:20 am
MDW
- SJU
2 stops9h 45m
Southwest
Sun 9/139:25 pm
SJU
- MDW
1 stop13h 35m
Southwest
Deal found 6/20![Southwest logo]()
$296
This United Airlines deal was found by Cheapflights users on 6/23. 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.
Sun 7/52:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Tue 7/72:05 am
SJU
- ORD
1 stop9h 15m
United Airlines
Deal found 6/23![United Airlines logo]()
$337
This JetBlue deal was found by Cheapflights users on 6/23. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/223:20 pm
ORD
- PSE
1 stop7h 39m
JetBlue
Tue 9/15:01 am
PSE
- ORD
1 stop9h 38m
JetBlue
Deal found 6/23![JetBlue logo]()
$357
This United deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:55 am
ORD
- MAZ
1 stop23h 47m
Multiple Airlines
Thu 8/274:36 pm
MAZ
- ORD
1 stop28h 29m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$440
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/181:50 pm
ORD
- BQN
2 stops11h 20m
Frontier
Sat 8/112:19 pm
BQN
- ORD
1 stop11h 51m
Frontier
Deal found 6/20![Frontier logo]()
$483
This KAYAK deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/66:36 am
ORD
- SJU
1 stop15h 21m
American Airlines
Fri 7/107:25 am
SJU
- ORD
1 stop10h 21m
American Airlines
Deal found 6/18![American Airlines logo]()
$484
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2711:23 am
ORD
- SJU
1 stop10h 06m
Delta
Fri 9/412:56 pm
SJU
- ORD
1 stop12h 01m
Delta
Deal found 6/22![Delta logo]()
$276
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:54 am
ORD
- SJU
1 stop11h 35m
Delta
Tue 8/1812:56 pm
SJU
- ORD
1 stop8h 59m
Delta
Deal found 6/22![Delta logo]()
$276
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2512:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Sun 8/305:00 am
SJU
- MDW
2 stops8h 55m
Southwest
Deal found 6/22![Southwest logo]()
$306
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:05 am
MDW
- SJU
1 stop9h 33m
Delta
Tue 9/112:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Deal found 6/18![Delta logo]()
$276
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:00 pm
MDW
- SJU
2 stops8h 50m
Southwest
Mon 8/246:00 am
SJU
- MDW
2 stops9h 30m
Southwest
Deal found 6/18![Southwest logo]()
$326
This JetBlue deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:35 pm
ORD
- PSE
1 stop8h 24m
JetBlue
Wed 9/25:01 am
PSE
- ORD
1 stop9h 38m
JetBlue
Deal found 6/22![JetBlue logo]()
$371
This United Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2711:15 am
ORD
- SJU
1 stop9h 09m
United Airlines
Mon 6/294:55 pm
SJU
- ORD
1 stop7h 36m
United Airlines
Deal found 6/21![United Airlines logo]()
$383
This JetBlue deal was found by Cheapflights users on 6/23. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:35 pm
ORD
- PSE
1 stop8h 24m
JetBlue
Wed 9/25:01 am
PSE
- ORD
1 stop9h 38m
JetBlue
Deal found 6/23![JetBlue logo]()
$373
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:33 am
ORD
- SJU
1 stop10h 56m
Delta
Sun 8/302:59 pm
SJU
- ORD
1 stop6h 56m
Delta
Deal found 6/18![Delta logo]()
$316
This United Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/262:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Sun 6/281:00 am
SJU
- ORD
1 stop9h 00m
United Airlines
Deal found 6/18![United Airlines logo]()
$407
This JetBlue deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/72:35 pm
ORD
- PSE
1 stop8h 24m
JetBlue
Tue 8/115:01 am
PSE
- ORD
1 stop9h 38m
JetBlue
Deal found 6/18![JetBlue logo]()
$373
This CheapOair deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:00 am
ORD
- BQN
1 stop6h 56m
Multiple Airlines
Fri 10/3010:52 am
BQN
- ORD
1 stop13h 58m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$482
This Frontier deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/185:13 pm
ORD
- BQN
1 stop7h 57m
Frontier
Sun 7/2612:04 pm
BQN
- ORD
1 stop12h 06m
Frontier
Deal found 6/22![Frontier logo]()
$486
This Cheapflightsfares deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/172:35 pm
ORD
- PSE
1 stop8h 24m
JetBlue
Wed 7/225:01 am
PSE
- ORD
1 stop9h 38m
JetBlue
Deal found 6/18![JetBlue logo]()
$379
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:05 am
MDW
- SJU
1 stop9h 33m
Delta
Tue 9/12:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Deal found 6/21![Delta logo]()
$346
This United Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Tue 9/153:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 6/21![United Airlines logo]()
$437
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/69:15 am
MDW
- SJU
1 stop13h 25m
Southwest
Thu 7/910:20 pm
SJU
- MDW
2 stops12h 40m
Southwest
Deal found 6/22![Southwest logo]()
$439
This Frontier deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/44:59 pm
ORD
- BQN
1 stop8h 06m
Frontier
Sun 7/1212:04 pm
BQN
- ORD
1 stop12h 06m
Frontier
Deal found 6/22![Frontier logo]()
$486
This Cheapflightsfares deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:35 pm
ORD
- PSE
1 stop8h 24m
JetBlue
Tue 8/45:01 am
PSE
- ORD
1 stop9h 38m
JetBlue
Deal found 6/22![JetBlue logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/912:44 am
ORD
- MAZ
1 stop7h 58m
Multiple Airlines
Thu 8/137:35 am
MAZ
- ORD
1 stop16h 52m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$521
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:05 am
MDW
- SJU
1 stop6h 37m
Delta
Sat 9/57:00 am
SJU
- MDW
1 stop9h 44m
Delta
Deal found 6/22![Delta logo]()
$358
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/102:25 pm
MDW
- SJU
1 stop8h 15m
Southwest
Tue 7/145:30 am
SJU
- MDW
1 stop8h 15m
Southwest
Deal found 6/22![Southwest logo]()
$439
This United Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Mon 9/142:55 pm
SJU
- ORD
1 stop10h 33m
United Airlines
Deal found 6/19![United Airlines logo]()
$462
Last-minute flights from Chicago to Puerto RicoDiscover last-minute flight deals from Chicago to Puerto Rico. Data last updated June 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Puerto Rico. Data last updated June 23, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Wed 7/157:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/22![Frontier logo]()
$267
This Super.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Wed 7/87:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/22![Frontier logo]()
$268
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/48:02 pm
ORD
- SJU
1 stop8h 27m
United Airlines
Fri 7/102:05 am
SJU
- ORD
1 stop9h 15m
United Airlines
Deal found 6/22![United Airlines logo]()
$286
This Frontier deal was found by Cheapflights users on 6/23. 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 7/412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sat 7/117:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/23![Frontier logo]()
$292
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:30 am
MDW
- SJU
1 stop8h 15m
Southwest
Thu 7/96:30 am
SJU
- MDW
1 stop10h 25m
Southwest
Deal found 6/18![Southwest logo]()
$336
This eDestinos deal was found by Cheapflights users on 6/23. 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.
Sun 7/512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Wed 7/157:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/23![Frontier logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 7/147:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/20![Frontier logo]()
$277
This Frontier deal was found by Cheapflights users on 6/23. 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 7/512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sat 7/117:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/23![Frontier logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 7/177:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/18![Frontier logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 7/147:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/20![Frontier logo]()
$291
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/205:10 pm
MDW
- SJU
1 stop7h 15m
Southwest
Fri 7/3110:20 pm
SJU
- MDW
1 stop11h 30m
Southwest
Deal found 6/19![Southwest logo]()
$316
This Super.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 7/317:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/18![Frontier logo]()
$287
One-way flights from Chicago to Puerto RicoSearch for one-way flight options from Chicago to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated June 23, 2026.
Search for one-way flight options from Chicago to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated June 23, 2026.
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:33 am
ORD
- SJU
1 stop10h 56m
Delta
Deal found 6/18![Delta logo]()
$123
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:05 am
MDW
- SJU
1 stop6h 37m
Delta
Deal found 6/18![Delta logo]()
$123
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 6/18![American Airlines logo]()
$124
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:00 am
ORD
- SJU
1 stop7h 38m
American Airlines
Deal found 6/19![American Airlines logo]()
$126
This American Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:45 am
ORD
- SJU
1 stop14h 39m
American Airlines
Deal found 6/22![American Airlines logo]()
$127
This American Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:29 pm
ORD
- SJU
1 stop14h 55m
American Airlines
Deal found 6/22![American Airlines logo]()
$128
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/181:00 pm
MDW
- SJU
1 stop8h 50m
Southwest
Deal found 6/20![Southwest logo]()
$128
This Frontier deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/21![Frontier logo]()
$129
This eDestinos deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/20![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/21![Frontier logo]()
$131
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:54 am
ORD
- SJU
1 stop11h 35m
Delta
Deal found 6/19![Delta logo]()
$133
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2210:56 am
MDW
- SJU
1 stop10h 33m
Delta
Deal found 6/22![Delta logo]()
$133
Find flight deals from Chicago to Puerto Rico
Keep the following information in mind while searching for Chicago to Puerto Rico flight deals. Data was last updated June 23, 2026.
Round-trip from | $257 (American Airlines) |
|---|---|
One-way from | $123 (Delta) |
Popular in | December |
Cheapest in | January |
Average price | $460 |
Good round-trip deal | $376 or less |
Good one-way deal | $204 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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 June 23, 2026.
Use the filters below to find and compare flights from Chicago to Puerto Rico that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 8/15
6:40 am-4:38 pm
1 stop8h 58m
San Juan Luis Munoz Marin Intl
Sat 8/22
5:49 pm-11:57 pm
1 stop7h 08m
$266
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 8/27
11:23 am-10:29 pm
1 stop10h 06m
San Juan Luis Munoz Marin Intl
Fri 9/4
12:56 pm-11:57 pm
1 stop12h 01m
$276
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 8/14
9:54 am-10:29 pm
1 stop11h 35m
San Juan Luis Munoz Marin Intl
Tue 8/18
12:56 pm-8:55 pm
1 stop8h 59m
$276
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 8/28
6:05 am-4:38 pm
1 stop9h 33m
San Juan Luis Munoz Marin Intl
Tue 9/1
12:56 pm-10:36 pm
1 stop10h 40m
$276
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 9/10
9:20 am-8:05 pm
2 stops9h 45m
San Juan Luis Munoz Marin Intl
Sun 9/13
9:25 pm-10:00 am
1 stop13h 35m
$296
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 8/25
12:45 pm-10:00 pm
2 stops8h 15m
San Juan Luis Munoz Marin Intl
Sun 8/30
5:00 am-12:55 pm
2 stops8h 55m
$306
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 8/26
10:33 am-10:29 pm
1 stop10h 56m
San Juan Luis Munoz Marin Intl
Sun 8/30
2:59 pm-8:55 pm
1 stop6h 56m
$316
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 8/20
1:00 pm-10:50 pm
2 stops8h 50m
San Juan Luis Munoz Marin Intl
Mon 8/24
6:00 am-2:30 pm
2 stops9h 30m
$326
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 7/5
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Tue 7/7
2:05 am-10:20 am
1 stop9h 15m
$337
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 8/29
6:05 am-4:38 pm
1 stop9h 33m
San Juan Luis Munoz Marin Intl
Tue 9/1
2:59 pm-10:36 pm
1 stop8h 37m
$346
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Puerto Rico
Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Chicago with our price prediction graph.
ORD-SJU
MDW-SJU
ORD-PSE
ORD-MAZ
ORD-BQN
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 Chicago to Puerto Rico
CHI-PR0
ORD-SJU
MDW-SJU
ORD-PSE
ORD-MAZ
What is the cheapest month to book a flight from Chicago to Puerto Rico?
Currently, April is the cheapest month in which you can book a flight from Chicago to Puerto Rico (average of $315). Flying from Chicago to Puerto Rico in December is currently the most expensive (average of $635). 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 CHI to PR?
Find hourly flight availability from Chicago 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 June 23, 2026.
When flying from Chicago 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 34% versus a flight in the morning.
Weekly flight availability from Chicago to Puerto Rico
Explore weekly flight availability from Chicago 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 June 23, 2026.
The most flights from CHI to PR0 are scheduled on a Saturday (10 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (9 on average).
How often are flights from Chicago to Puerto Rico delayed?
About 22% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 138 minutes.
What is the most punctual flight time for Chicago to Puerto Rico flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Puerto Rico flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 19% of flights being delayed.
How far ahead should I book a flight from Chicago to Puerto Rico?
The best time to book flights from Chicago to Puerto Rico is 90 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Chicago to Puerto Rico?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Puerto Rico. Price data was last updated on June 20, 2026.
Travelers seeking maximum savings on their Chicago to Puerto Rico flight should consider departing on Saturday evenings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Puerto Rico
Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated June 23, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to Puerto Rico to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Chicago 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.
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Alternative routes for Chicago 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 Chicago to Puerto Rico by cabin class
Find flights from Chicago to Puerto Rico, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Puerto Rico flights
Browse other Chicago and Puerto Rico flight options. Last updated on June 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Chicago to Puerto Rico
Discover the top 6 airlines that operate flights from Chicago 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 June 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$325 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$448 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$234 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$261 | Average$524 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$301 | Average$503 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$352 | Average$486 | FlexibilityNo cancel fee | On-time63% |