$105+ 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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Sep 6 — Sep 131
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 August 7, 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 August 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:11 am -
1 stop29h 23m
Thu 9/247:00 am -
1 stop8h 45m
Deal found 8/3![Frontier logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:44 am -
Nonstop5h 00m
Wed 9/168:45 am -
1 stop31h 00m
Deal found 8/7![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:44 am -
Nonstop5h 00m
Wed 9/98:45 am -
1 stop31h 00m
Deal found 8/4![Frontier logo]()
$224
This Super.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am -
Nonstop5h 00m
Fri 9/47:14 pm -
Nonstop5h 13m
Deal found 8/6![Frontier logo]()
$225
This Super.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 8/3112:44 am -
Nonstop5h 00m
Sun 9/67:14 pm -
Nonstop5h 13m
Deal found 8/2![Frontier logo]()
$226
This Expedia deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 8/2912:44 am -
Nonstop5h 00m
Sat 9/57:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$228
This Orbitz deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:44 am -
Nonstop5h 00m
Sat 8/295:00 pm -
1 stop7h 44m
Deal found 8/5![Multiple Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1712:44 am -
Nonstop5h 00m
Mon 9/1411:23 am -
2 stops25h 28m
Deal found 8/3![Frontier logo]()
$230
This Super.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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.
Sun 8/1612:44 am -
Nonstop5h 00m
Sat 8/227:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$231
This Frontier deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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.
Mon 8/1712:44 am -
Nonstop5h 00m
Sat 8/227:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$233
This CheapOair deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3012:44 am -
Nonstop5h 00m
Sat 9/122:32 pm -
1 stop9h 36m
Deal found 8/7![Multiple Airlines logo]()
$234
This FlightHub deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:44 am -
Nonstop5h 00m
Fri 8/287:14 pm -
Nonstop5h 13m
Deal found 8/4![Frontier logo]()
$235
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 August 7, 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 August 7, 2026.
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2411:15 am -
1 stop7h 50m
Sat 8/295:55 am -
2 stops8h 10m
Deal found 8/5![Southwest logo]()
$266
This JetBlue deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:35 pm -
1 stop8h 24m
Fri 9/45:01 am -
1 stop9h 38m
Deal found 8/6![JetBlue logo]()
$304
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/910:40 am -
1 stop8h 58m
Wed 9/163:56 pm -
Nonstop5h 09m
Deal found 8/4![United Airlines logo]()
$342
This Priceline deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/163:50 pm -
1 stop17h 23m
Wed 9/2311:12 am -
1 stop24h 08m
Deal found 8/3![Frontier logo]()
$356
This FlightHub deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:13 pm -
1 stop7h 57m
Sat 8/295:01 am -
1 stop10h 23m
Deal found 8/6![Multiple Airlines logo]()
$461
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 8/241:00 pm -
1 stop8h 50m
Tue 9/12:25 pm -
1 stop7h 20m
Deal found 8/2![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:55 pm -
1 stop7h 55m
Mon 8/318:55 pm -
1 stop13h 30m
Deal found 8/5![Southwest logo]()
$291
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/25:00 am -
1 stop7h 45m
Tue 9/81:00 am -
1 stop9h 44m
Deal found 8/2![United Airlines logo]()
$346
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/19:40 am -
1 stop7h 30m
Fri 9/46:00 am -
2 stops9h 30m
Deal found 8/4![Southwest logo]()
$291
This Super.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 8/255:59 pm -
1 stop7h 11m
Sun 8/3012:04 pm -
1 stop12h 04m
Deal found 8/2![Frontier logo]()
$376
This Orbitz deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:20 pm -
1 stop7h 39m
Sat 9/128:55 am -
2 stops15h 13m
Deal found 8/6![JetBlue logo]()
$377
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:40 am -
1 stop8h 58m
Tue 9/224:20 pm -
1 stop9h 08m
Deal found 8/2![United Airlines logo]()
$346
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:30 am -
1 stop10h 35m
Wed 9/238:20 am -
2 stops9h 30m
Deal found 8/2![Southwest logo]()
$301
This CheapTickets deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapTickets is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:50 pm -
1 stop17h 23m
Sat 9/2611:12 am -
1 stop12h 47m
Deal found 8/5![Frontier logo]()
$389
This FlightHub deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/132:35 pm -
1 stop8h 24m
Tue 11/1710:30 am -
2 stops15h 14m
Deal found 8/5![JetBlue logo]()
$396
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:50 pm -
1 stop12h 35m
Fri 9/115:00 am -
2 stops8h 25m
Deal found 8/6![Southwest logo]()
$320
This Travelocity deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:44 pm -
1 stop13h 18m
Thu 9/310:47 am -
1 stop13h 21m
Deal found 8/5![Frontier logo]()
$396
This JetBlue deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/293:20 pm -
1 stop8h 13m
Tue 9/15:01 am -
1 stop9h 38m
Deal found 8/4![JetBlue logo]()
$408
This Expedia deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/133:50 pm -
1 stop16h 28m
Sun 9/2010:05 am -
1 stop13h 54m
Deal found 8/4![Frontier logo]()
$396
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:55 am -
Nonstop4h 49m
Sat 9/123:56 pm -
Nonstop5h 09m
Deal found 8/5![United Airlines logo]()
$437
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3010:40 am -
2 stops9h 00m
Sat 9/58:20 am -
2 stops9h 25m
Deal found 8/3![Southwest logo]()
$345
This United deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:00 am -
2 stops11h 21m
Wed 9/301:06 pm -
2 stops11h 21m
Deal found 8/4![Multiple Airlines logo]()
$574
This Expedia deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:00 pm -
2 stops16h 01m
Sun 9/138:55 am -
2 stops15h 13m
Deal found 8/5![JetBlue logo]()
$450
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 11/42:16 pm -
Nonstop4h 44m
Wed 11/184:55 pm -
Nonstop5h 31m
Deal found 8/2![United Airlines logo]()
$457
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/224:15 pm -
2 stops8h 05m
Tue 10/278:15 am -
1 stop7h 30m
Deal found 8/4![Southwest logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:44 am -
1 stop7h 58m
Tue 8/254:36 pm -
1 stop7h 51m
Deal found 8/6![Multiple Airlines logo]()
$584
This CheapOair deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 10/73:50 pm -
1 stop17h 07m
Fri 10/3010:52 am -
1 stop13h 58m
Deal found 8/2![Frontier logo]()
$446
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:55 am -
Nonstop4h 49m
Sat 10/173:56 pm -
Nonstop5h 09m
Deal found 8/4![United Airlines logo]()
$457
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 10/143:25 pm -
1 stop7h 20m
Sat 10/245:40 am -
1 stop11h 30m
Deal found 8/2![Southwest logo]()
$345
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/148:55 am -
Nonstop4h 49m
Fri 9/183:56 pm -
Nonstop5h 09m
Deal found 8/6![United Airlines logo]()
$457
Last-minute flights from Chicago to Puerto RicoDiscover last-minute flight deals from Chicago to Puerto Rico. Data last updated August 7, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Puerto Rico. Data last updated August 7, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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.
Sun 8/1612:44 am -
Nonstop5h 00m
Sat 8/227:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1712:44 am -
Nonstop5h 00m
Mon 9/1411:23 am -
2 stops25h 28m
Deal found 8/3![Frontier logo]()
$230
This Frontier deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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.
Mon 8/1712:44 am -
Nonstop5h 00m
Sat 8/227:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$233
This Orbitz deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:44 am -
Nonstop5h 00m
Sat 8/295:00 pm -
1 stop7h 44m
Deal found 8/5![Multiple Airlines logo]()
$229
This FlightHub deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:44 am -
Nonstop5h 00m
Fri 8/287:14 pm -
Nonstop5h 13m
Deal found 8/4![Frontier logo]()
$235
This Super.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am -
Nonstop5h 00m
Fri 9/47:14 pm -
Nonstop5h 13m
Deal found 8/6![Frontier logo]()
$225
This Expedia deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 8/2912:44 am -
Nonstop5h 00m
Sat 9/57:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$228
This CheapOair deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3012:44 am -
Nonstop5h 00m
Sat 9/122:32 pm -
1 stop9h 36m
Deal found 8/7![Multiple Airlines logo]()
$234
This Super.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 8/3112:44 am -
Nonstop5h 00m
Sun 9/67:14 pm -
Nonstop5h 13m
Deal found 8/2![Frontier logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:44 am -
Nonstop5h 00m
Wed 9/98:45 am -
1 stop31h 00m
Deal found 8/4![Frontier logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:44 am -
Nonstop5h 00m
Wed 9/168:45 am -
1 stop31h 00m
Deal found 8/7![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:11 am -
1 stop29h 23m
Thu 9/247:00 am -
1 stop8h 45m
Deal found 8/3![Frontier logo]()
$222
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 August 7, 2026.
Search for one-way flight options from Chicago to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated August 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:11 am -
1 stop8h 52m
Deal found 8/3![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:11 am -
1 stop29h 23m
Deal found 8/3![Frontier logo]()
$109
This eDestinos deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 8/2912:44 am -
Nonstop5h 00m
Deal found 8/2![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:11 am -
1 stop29h 23m
Deal found 8/2![Frontier logo]()
$111
This Super.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:44 am -
Nonstop5h 00m
Deal found 8/4![Frontier logo]()
$112
This Super.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 8/2712:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$113
This Frontier deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/112:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$114
This eDestinos deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 8/1412:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$117
This Super.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 8/2612:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$118
This Frontier deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 8/1512:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:11 am -
1 stop29h 23m
Deal found 8/2![Frontier logo]()
$120
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:45 pm -
2 stops8h 15m
Deal found 8/4![Southwest logo]()
$128
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 August 7, 2026.
Round-trip from | $222 (Kiwi.com) |
|---|---|
One-way from | $105 (Kiwi.com) |
Popular in | December |
Cheapest in | August |
Average price | $322 |
Good round-trip deal | $315 or less |
Good one-way deal | $130 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 August 7, 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
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 8/24
11:15 am-8:05 pm
1 stop7h 50m
San Juan Luis Munoz Marin Intl
Sat 8/29
5:55 am-1:05 pm
2 stops8h 10m
$266
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 8/24
1:00 pm-10:50 pm
1 stop8h 50m
San Juan Luis Munoz Marin Intl
Tue 9/1
2:25 pm-8:45 pm
1 stop7h 20m
$276
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Fri 8/28
2:55 pm-11:50 pm
1 stop7h 55m
San Juan Luis Munoz Marin Intl
Mon 8/31
8:55 pm-9:25 am
1 stop13h 30m
$291
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 9/1
9:40 am-6:10 pm
1 stop7h 30m
San Juan Luis Munoz Marin Intl
Fri 9/4
6:00 am-2:30 pm
2 stops9h 30m
$291
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Wed 9/16
7:30 am-7:05 pm
1 stop10h 35m
San Juan Luis Munoz Marin Intl
Wed 9/23
8:20 am-4:50 pm
2 stops9h 30m
$301
ChicagoPonce
ORD Chicago O'Hare Intl - PSE Ponce Mercedita
ORDPSE
Chicago O'Hare Intl
Mon 8/31
2:35 pm-11:59 pm
1 stop8h 24m
Ponce Mercedita
Fri 9/4
5:01 am-1:39 pm
1 stop9h 38m
$304
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Fri 9/4
7:50 pm-9:25 am
1 stop12h 35m
San Juan Luis Munoz Marin Intl
Fri 9/11
5:00 am-12:25 pm
2 stops8h 25m
$320
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Wed 9/9
10:40 am-8:38 pm
1 stop8h 58m
San Juan Luis Munoz Marin Intl
Wed 9/16
3:56 pm-8:05 pm
Nonstop5h 09m
$342
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Sun 8/30
10:40 am-8:40 pm
2 stops9h 00m
San Juan Luis Munoz Marin Intl
Sat 9/5
8:20 am-4:45 pm
2 stops9h 25m
$345
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Thu 10/22
4:15 pm-1:20 am
2 stops8h 05m
San Juan Luis Munoz Marin Intl
Tue 10/27
8:15 am-2:45 pm
1 stop7h 30m
$345
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.
MDW-SJU
ORD-PSE
ORD-SJU
ORD-BQN
ORD-CPX
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
MDW-SJU
ORD-PSE
ORD-SJU
ORD-BQN
What is the cheapest month to book a flight from Chicago to Puerto Rico?
Currently, August is the cheapest month in which you can book a flight from Chicago to Puerto Rico (average of $340). Flying from Chicago to Puerto Rico in December is currently the most expensive (average of $542). 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 August 7, 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 37% 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 August 7, 2026.
The most flights from CHI to PR0 are scheduled on a Wednesday (10 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).
How often are flights from Chicago to Puerto Rico delayed?
About 23% 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?
Wednesday tends to have the lowest number of delays on this route, whereas Sunday 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 18% 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 56 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 August 1, 2026.
Travelers seeking maximum savings on their Chicago to Puerto Rico flight should consider departing on Sunday 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 August 7, 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.
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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
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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 August 7, 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 August 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$357 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$486 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$327 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$262 | Average$523 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$302 | Average$494 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$346 | Average$490 | FlexibilityNo cancel fee | On-time63% |