$119+ Cheap flights from Puerto Rico to Chicago (CHI)
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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Sep 23 — Sep 301
Round-trip
1 adult, Economy
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Find cheap flights from Puerto Rico to Chicago 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 Puerto Rico to Chicago
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Cheapest flights from Puerto Rico to ChicagoExplore the most affordable flight options available from Puerto Rico to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 24, 2026.
Explore the most affordable flight options available from Puerto Rico to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 24, 2026.
This CheapOair deal was found by Cheapflights users on 8/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:14 pm -
Nonstop5h 13m
Sat 9/512:44 am -
Nonstop5h 00m
Deal found 8/24![Frontier logo]()
$182
This Super.com deal was found by Cheapflights users on 8/20. 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.
Thu 8/277:14 pm -
Nonstop5h 13m
Mon 8/3112:44 am -
Nonstop5h 00m
Deal found 8/20![Frontier logo]()
$184
This Expedia deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:14 pm -
Nonstop5h 13m
Sun 8/3012:44 am -
Nonstop5h 00m
Deal found 8/24![Frontier logo]()
$186
This CheapOair deal was found by Cheapflights users on 8/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:14 pm -
Nonstop5h 13m
Sat 8/2912:44 am -
Nonstop5h 00m
Deal found 8/24![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:14 pm -
Nonstop5h 13m
Wed 9/97:11 am -
1 stop29h 23m
Deal found 8/19![Frontier logo]()
$189
This eDestinos deal was found by Cheapflights users on 8/23. 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.
Thu 8/277:14 pm -
Nonstop5h 13m
Sun 8/3012:44 am -
Nonstop5h 00m
Deal found 8/23![Frontier logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:14 pm -
Nonstop5h 13m
Wed 9/97:11 am -
1 stop29h 23m
Deal found 8/19![Frontier logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:14 pm -
Nonstop5h 13m
Sat 9/127:11 am -
1 stop8h 52m
Deal found 8/19![Frontier logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:14 pm -
Nonstop5h 13m
Thu 9/107:11 am -
1 stop29h 23m
Deal found 8/19![Frontier logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/57:14 pm -
Nonstop5h 13m
Wed 9/237:11 am -
1 stop29h 23m
Deal found 8/20![Frontier logo]()
$214
This eDestinos deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:14 pm -
Nonstop5h 13m
Tue 9/112:44 am -
Nonstop5h 00m
Deal found 8/22![Frontier logo]()
$215
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:00 am -
2 stops9h 30m
Tue 9/296:15 am -
1 stop6h 15m
Deal found 8/21![Southwest logo]()
$226
Best flights from Puerto Rico to ChicagoDiscover carefully curated flight deals from Puerto Rico to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 24, 2026.
Discover carefully curated flight deals from Puerto Rico to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 24, 2026.
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:35 pm -
1 stop9h 10m
Tue 9/2212:20 pm -
1 stop8h 45m
Deal found 8/23![Southwest logo]()
$246
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:56 pm -
Nonstop5h 09m
Mon 9/215:00 am -
1 stop7h 45m
Deal found 8/23![United Airlines logo]()
$252
This Cheapflightsfares deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/73:20 pm -
1 stop10h 24m
Sun 11/152:35 pm -
1 stop8h 58m
Deal found 8/24![JetBlue logo]()
$415
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 10/1310:52 am -
1 stop21h 39m
Sun 10/187:44 pm -
2 stops37h 13m
Deal found 8/23![Frontier logo]()
$417
This Southwest deal was found by Cheapflights users on 8/22. 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.
Wed 10/148:15 am -
2 stops12h 05m
Sat 10/172:40 pm -
1 stop6h 30m
Deal found 8/22![Southwest logo]()
$246
This CheapOair deal was found by Cheapflights users on 8/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:22 pm -
1 stop22h 24m
Sun 11/158:24 pm -
2 stops15h 57m
Deal found 8/24![Multiple Airlines logo]()
$522
This Southwest deal was found by Cheapflights users on 8/20. 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 9/246:30 am -
2 stops8h 15m
Wed 9/3012:45 pm -
2 stops8h 20m
Deal found 8/20![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:30 am -
1 stop10h 45m
Mon 10/52:15 pm -
1 stop9h 05m
Deal found 8/21![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 8/22. 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 9/182:35 pm -
1 stop9h 10m
Tue 9/2212:20 pm -
1 stop8h 45m
Deal found 8/22![Southwest logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
Wed 9/92:44 am -
2 stops16h 39m
Mon 9/143:50 pm -
1 stop17h 04m
Deal found 8/20![Frontier logo]()
$422
This United Airlines deal was found by Cheapflights users on 8/23. 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.
Wed 10/147:00 am -
1 stop10h 41m
Sat 10/178:55 am -
Nonstop4h 49m
Deal found 8/23![United Airlines logo]()
$422
This United Airlines deal was found by Cheapflights users on 8/19. 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 11/58:05 am -
1 stop8h 33m
Sun 11/158:52 am -
Nonstop4h 48m
Deal found 8/19![United Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:35 am -
2 stops8h 40m
Thu 10/82:50 pm -
2 stops8h 15m
Deal found 8/21![Southwest logo]()
$326
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/91:00 am -
1 stop7h 41m
Tue 9/228:55 am -
Nonstop4h 49m
Deal found 8/20![United Airlines logo]()
$422
This Expedia deal was found by Cheapflights users on 8/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/33:10 am -
1 stop20h 58m
Tue 9/85:29 pm -
1 stop15h 45m
Deal found 8/19![Frontier logo]()
$466
This JetBlue deal was found by Cheapflights users on 8/22. 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.
Fri 9/254:23 pm -
1 stop7h 45m
Mon 9/286:00 am -
1 stop6h 56m
Deal found 8/22![JetBlue logo]()
$530
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:00 am -
2 stops8h 25m
Mon 9/143:15 pm -
1 stop6h 55m
Deal found 8/23![Southwest logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 8/23. 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.
Mon 9/77:35 am -
1 stop16h 52m
Fri 9/113:50 pm -
2 stops23h 21m
Deal found 8/23![Multiple Airlines logo]()
$555
This Southwest deal was found by Cheapflights users on 8/23. 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 9/1111:35 am -
1 stop7h 25m
Mon 9/143:15 pm -
1 stop6h 55m
Deal found 8/23![Southwest logo]()
$331
This United Airlines deal was found by Cheapflights users on 8/22. 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.
Wed 9/303:56 pm -
Nonstop5h 09m
Sat 10/248:55 am -
Nonstop4h 49m
Deal found 8/22![United Airlines logo]()
$443
This Expedia deal was found by Cheapflights users on 8/23. 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 10/135:01 am -
2 stops15h 13m
Sun 10/188:04 pm -
2 stops16h 22m
Deal found 8/23![JetBlue logo]()
$548
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:30 am -
2 stops8h 55m
Mon 10/261:20 pm -
2 stops8h 45m
Deal found 8/23![Southwest logo]()
$346
This United Airlines deal was found by Cheapflights users on 8/23. 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.
Wed 10/287:05 am -
2 stops14h 28m
Sat 10/319:00 am -
2 stops13h 36m
Deal found 8/23![United Airlines logo]()
$465
This Southwest deal was found by Cheapflights users on 8/23. 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.
Wed 9/231:45 pm -
1 stop8h 20m
Sat 9/2611:45 am -
2 stops9h 15m
Deal found 8/23![Southwest logo]()
$346
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/184:55 pm -
2 stops15h 42m
Sat 9/267:45 pm -
2 stops17h 00m
Deal found 8/20![United Airlines logo]()
$488
This Southwest deal was found by Cheapflights users on 8/20. 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 9/46:30 am -
2 stops8h 15m
Tue 9/87:30 am -
1 stop10h 35m
Deal found 8/20![Southwest logo]()
$366
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:25 pm -
2 stops24h 45m
Wed 10/287:15 am -
2 stops15h 21m
Deal found 8/21![United Airlines logo]()
$490
This Trip.com deal was found by Cheapflights users on 8/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2310:52 am -
2 stops13h 51m
Fri 11/201:29 pm -
1 stop11h 06m
Deal found 8/22![Frontier logo]()
$760
This United Airlines deal was found by Cheapflights users on 8/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:00 am -
2 stops17h 02m
Sat 10/179:50 pm -
2 stops14h 55m
Deal found 8/24![United Airlines logo]()
$497
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/223:56 pm -
Nonstop5h 09m
Tue 10/278:52 am -
Nonstop4h 48m
Deal found 8/23![United Airlines logo]()
$507
Last-minute flights from Puerto Rico to ChicagoDiscover last-minute flight deals from Puerto Rico to Chicago. Data last updated August 24, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Chicago. Data last updated August 24, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:00 am -
2 stops9h 30m
Mon 8/312:55 pm -
1 stop7h 55m
Deal found 8/23![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 8/22. 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 9/11:45 pm -
1 stop8h 15m
Wed 9/28:30 am -
1 stop8h 40m
Deal found 8/22![Southwest logo]()
$266
This CheapOair deal was found by Cheapflights users on 8/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:14 pm -
Nonstop5h 13m
Sat 9/512:44 am -
Nonstop5h 00m
Deal found 8/24![Frontier logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 9/27:14 pm -
Nonstop5h 13m
Thu 9/103:50 pm -
1 stop16h 45m
Deal found 8/21![Frontier logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 9/27:14 pm -
Nonstop5h 13m
Tue 9/153:50 pm -
1 stop9h 02m
Deal found 8/21![Frontier logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 9/27:14 pm -
Nonstop5h 13m
Fri 9/113:50 pm -
1 stop9h 02m
Deal found 8/21![Frontier logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:14 pm -
Nonstop5h 13m
Wed 9/97:11 am -
1 stop29h 23m
Deal found 8/19![Frontier logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 9/37:14 pm -
Nonstop5h 13m
Sun 9/65:55 am -
1 stop11h 54m
Deal found 8/22![Frontier logo]()
$231
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:00 am -
1 stop7h 45m
Fri 9/112:55 pm -
1 stop8h 00m
Deal found 8/21![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:05 am -
2 stops9h 05m
Tue 9/1512:35 pm -
2 stops8h 30m
Deal found 8/21![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 8/20. 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 9/172:35 pm -
1 stop9h 10m
Tue 9/2212:20 pm -
1 stop8h 45m
Deal found 8/20![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:00 am -
2 stops9h 30m
Tue 9/296:15 am -
1 stop6h 15m
Deal found 8/21![Southwest logo]()
$226
One-way flights from Puerto Rico to ChicagoSearch for one-way flight options from Puerto Rico to Chicago. Find affordable one-way fares based on user searches. Data last updated August 24, 2026.
Search for one-way flight options from Puerto Rico to Chicago. Find affordable one-way fares based on user searches. Data last updated August 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
Wed 9/98:45 am -
1 stop31h 00m
Deal found 8/20![Frontier logo]()
$119
This CheapOair deal was found by Cheapflights users on 8/22. 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 8/287:14 pm -
Nonstop5h 13m
Deal found 8/22![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
Wed 9/238:45 am -
1 stop31h 00m
Deal found 8/20![Frontier logo]()
$121
This American Airlines deal was found by Cheapflights users on 8/19. 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 9/512:55 am -
Nonstop5h 05m
Deal found 8/19![American Airlines logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:00 am -
1 stop10h 37m
Deal found 8/21![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 8/23. 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.
Thu 10/227:00 am -
1 stop9h 36m
Deal found 8/23![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:00 am -
1 stop9h 37m
Deal found 8/24![Frontier logo]()
$127
This Southwest deal was found by Cheapflights users on 8/19. 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.
Wed 9/211:50 am -
1 stop6h 50m
Deal found 8/19![Southwest logo]()
$128
This American Airlines deal was found by Cheapflights users on 8/19. 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 9/23:44 pm -
1 stop8h 46m
Deal found 8/19![American Airlines logo]()
$128
This American Airlines deal was found by Cheapflights users on 8/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:55 am -
Nonstop5h 05m
Deal found 8/24![American Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:00 am -
1 stop8h 45m
Deal found 8/24![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:45 am -
2 stops34h 00m
Deal found 8/23![Frontier logo]()
$134
Find flight deals from Puerto Rico to Chicago
Keep the following information in mind while searching for Puerto Rico to Chicago flight deals. Data was last updated August 24, 2026.
Round-trip from | $184 |
|---|---|
One-way from | $119 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $287 |
Good round-trip deal | $346 or less |
Good one-way deal | $204 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Puerto Rico to Chicago 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 7,457,451 searches. Data last updated August 24, 2026.
Use the filters below to find and compare flights from Puerto Rico to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 9/17
2:35 pm-10:45 pm
1 stop9h 10m
Chicago Midway
Tue 9/22
12:20 pm-10:05 pm
1 stop8h 45m
$246
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 10/14
8:15 am-7:20 pm
2 stops12h 05m
Chicago Midway
Sat 10/17
2:40 pm-10:10 pm
1 stop6h 30m
$246
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 9/24
6:30 am-1:45 pm
2 stops8h 15m
Chicago Midway
Wed 9/30
12:45 pm-10:05 pm
2 stops8h 20m
$246
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Fri 9/11
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Mon 9/21
5:00 am-1:45 pm
1 stop7h 45m
$252
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 10/1
6:30 am-4:15 pm
1 stop10h 45m
Chicago Midway
Mon 10/5
2:15 pm-12:20 am
1 stop9h 05m
$266
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 9/18
2:35 pm-10:45 pm
1 stop9h 10m
Chicago Midway
Tue 9/22
12:20 pm-10:05 pm
1 stop8h 45m
$266
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Sun 10/4
6:35 am-2:15 pm
2 stops8h 40m
Chicago Midway
Thu 10/8
2:50 pm-12:05 am
2 stops8h 15m
$326
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 9/10
5:00 am-12:25 pm
2 stops8h 25m
Chicago Midway
Mon 9/14
3:15 pm-11:10 pm
1 stop6h 55m
$331
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 9/11
11:35 am-6:00 pm
1 stop7h 25m
Chicago Midway
Mon 9/14
3:15 pm-11:10 pm
1 stop6h 55m
$331
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 10/22
5:30 am-1:25 pm
2 stops8h 55m
Chicago Midway
Mon 10/26
1:20 pm-11:05 pm
2 stops8h 45m
$346
Showing 1-10 of 57 resultsSorted by cheapest first
Best time to book a flight from Puerto Rico to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Puerto Rico with our price prediction graph.
SJU-MDW
SJU-ORD
BQN-ORD
MAZ-ORD
BQN-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Puerto Rico to Chicago
PR0-CHI
SJU-MDW
SJU-ORD
BQN-ORD
MAZ-ORD
What is the cheapest month to book a flight from Puerto Rico to Chicago?
Currently, February is the cheapest month in which you can book a flight from Puerto Rico to Chicago (average of $221). Flying from Puerto Rico to Chicago in June is currently the most expensive (average of $447). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from PR to CHI?
Find hourly flight availability from Puerto Rico to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 24, 2026.
When flying from Puerto Rico to Chicago, 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 27% versus a flight in the afternoon.
Weekly flight availability from Puerto Rico to Chicago
Explore weekly flight availability from Puerto Rico to Chicago. 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 24, 2026.
The most flights from PR0 to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 on average).
How often are flights from Puerto Rico to Chicago delayed?
About 9% of weekly flights between Puerto Rico and Chicago have experienced delays in the past year, with the average delay time being 184 minutes.
What is the most punctual flight time for Puerto Rico to Chicago flights?
Historically, flights departing at night 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 Saturday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Puerto Rico to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 4% of flights being delayed.
How far ahead should I book a flight from Puerto Rico to Chicago?
Booking 81 days in advance of your planned departure date is, on average, the best time to get cheap flights from Puerto Rico to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Puerto Rico to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Puerto Rico to Chicago. Price data was last updated on August 22, 2026.
Travelers seeking maximum savings on their Puerto Rico to Chicago flight should consider departing on Sunday at noon when fares are most often at their lowest. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated August 24, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines from Puerto Rico to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Puerto Rico to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Puerto Rico to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 24, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Puerto Rico to Chicago by cabin class
Find flights from Puerto Rico to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Puerto Rico and Chicago flights
Browse other Puerto Rico and Chicago flight options. Last updated on August 24, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Puerto Rico to Chicago
Discover the top 6 airlines that operate flights from Puerto Rico to Chicago. 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 7,457,451 searches. Data last updated August 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$128 | Average$284 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$216 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$227 | Average$425 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$266 | Average$484 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$268 | Average$470 | FlexibilityNo cancel fee | On-time69% |