$114+ Cheap flights from Puerto Rico to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Nov 29 — Dec 61
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 October 30, 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 October 30, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:25 am -
1 stop9h 31m
Sun 12/65:24 pm -
1 stop6h 49m
Deal found 10/25![Frontier logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:55 pm -
1 stop9h 52m
Mon 11/231:16 pm -
1 stop10h 20m
Deal found 10/25![Frontier logo]()
$229
This Cheapflightsfares deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Mon 11/303:47 am -
1 stop23h 12m
Wed 12/95:24 pm -
1 stop18h 35m
Deal found 10/28![Frontier logo]()
$230
This Cheapflightsfares deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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.
Thu 11/193:55 pm -
1 stop9h 52m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 10/27![Frontier logo]()
$230
This Cheapflightsfares deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/43:43 am -
1 stop7h 35m
Tue 12/85:24 pm -
1 stop15h 13m
Deal found 10/27![Frontier logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/215:19 am -
1 stop10h 26m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 10/27![Frontier logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/235:19 am -
1 stop10h 25m
Fri 12/45:24 pm -
1 stop6h 47m
Deal found 10/26![Frontier logo]()
$231
This Priceline deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Tue 12/13:47 am -
1 stop23h 12m
Wed 12/95:24 pm -
1 stop18h 35m
Deal found 10/28![Frontier logo]()
$232
This Frontier deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Wed 12/23:43 am -
1 stop12h 58m
Sat 12/512:28 pm -
1 stop10h 39m
Deal found 10/28![Frontier logo]()
$232
This Frontier deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/226:00 am -
1 stop11h 57m
Fri 11/275:26 pm -
1 stop7h 07m
Deal found 10/27![Frontier logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/227:17 am -
1 stop14h 30m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 10/27![Frontier logo]()
$233
This Cheapflightsfares deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Thu 11/197:00 am -
1 stop10h 37m
Mon 11/304:00 pm -
1 stop26h 37m
Deal found 10/28![Frontier logo]()
$234
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 October 30, 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 October 30, 2026.
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 1/147:25 am -
2 stops9h 20m
Sun 1/173:35 pm -
1 stop7h 00m
Deal found 10/29![Southwest logo]()
$286
This Cheapflightsfares deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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.
Mon 12/73:47 am -
1 stop13h 43m
Tue 12/155:24 pm -
1 stop7h 28m
Deal found 10/27![Frontier logo]()
$342
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/38:25 am -
Nonstop5h 24m
Tue 12/82:16 pm -
Nonstop4h 44m
Deal found 10/28![United Airlines logo]()
$397
This Priceline deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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.
Tue 11/109:39 pm -
2 stops42h 03m
Tue 11/179:51 am -
1 stop23h 26m
Deal found 10/27![Multiple Airlines logo]()
$411
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/135:50 pm -
1 stop7h 25m
Tue 11/174:25 pm -
1 stop6h 25m
Deal found 10/27![Southwest logo]()
$298
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/54:00 pm -
1 stop9h 00m
Tue 11/101:20 pm -
1 stop7h 05m
Deal found 10/27![Southwest logo]()
$306
This Cheapflightsfares deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Sun 12/62:54 pm -
1 stop20h 24m
Sun 12/205:01 am -
1 stop7h 25m
Deal found 10/28![Frontier logo]()
$362
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/710:55 am -
1 stop8h 30m
Mon 11/163:00 pm -
1 stop7h 50m
Deal found 10/29![Southwest logo]()
$340
This Mytrip deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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.
Tue 11/1011:57 am -
2 stops14h 24m
Tue 11/176:30 am -
2 stops26h 47m
Deal found 10/27![Frontier logo]()
$412
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 1/207:25 am -
2 stops9h 20m
Sun 1/242:25 pm -
2 stops8h 10m
Deal found 10/28![Southwest logo]()
$343
This Priceline deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/1112:22 pm -
1 stop22h 24m
Wed 11/187:00 am -
2 stops28h 07m
Deal found 10/28![Multiple Airlines logo]()
$457
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/94:55 pm -
Nonstop5h 31m
Mon 11/162:16 pm -
Nonstop4h 44m
Deal found 10/25![United Airlines logo]()
$472
This Cheapflightsfares deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Wed 11/1112:22 pm -
1 stop22h 24m
Sun 11/159:51 am -
1 stop23h 41m
Deal found 10/28![Frontier logo]()
$415
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:30 pm -
2 stops8h 35m
Mon 12/71:15 pm -
2 stops8h 10m
Deal found 10/25![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/1311:20 am -
2 stops9h 00m
Mon 11/161:20 pm -
2 stops9h 30m
Deal found 10/27![Southwest logo]()
$346
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/261:09 am -
1 stop8h 39m
Sun 12/612:40 pm -
1 stop9h 17m
Deal found 10/28![United Airlines logo]()
$527
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/312:30 pm -
2 stops8h 35m
Tue 12/81:15 pm -
2 stops8h 10m
Deal found 10/26![Southwest logo]()
$346
This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/251:09 am -
1 stop9h 51m
Wed 12/308:30 pm -
1 stop25h 27m
Deal found 10/27![United Airlines logo]()
$540
This Mytrip deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/912:37 pm -
2 stops13h 44m
Fri 11/135:15 pm -
2 stops16h 02m
Deal found 10/25![Frontier logo]()
$533
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/64:00 pm -
2 stops9h 15m
Mon 11/98:40 pm -
1 stop11h 15m
Deal found 10/28![Southwest logo]()
$375
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/94:55 pm -
Nonstop5h 31m
Sun 11/298:52 am -
Nonstop4h 48m
Deal found 10/25![United Airlines logo]()
$550
This Cheapflightsfares deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Mon 12/213:13 am -
1 stop23h 43m
Sun 1/35:01 am -
1 stop18h 42m
Deal found 10/28![Frontier logo]()
$541
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/148:25 am -
Nonstop5h 22m
Tue 12/12:16 pm -
Nonstop4h 44m
Deal found 10/26![United Airlines logo]()
$566
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/410:45 am -
2 stops10h 20m
Wed 11/119:55 am -
2 stops10h 00m
Deal found 10/26![Southwest logo]()
$401
This Cheapflightsfares deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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.
Thu 12/243:13 am -
1 stop15h 20m
Sat 1/25:53 pm -
1 stop18h 33m
Deal found 10/26![Frontier logo]()
$566
This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/132:05 am -
1 stop10h 43m
Thu 12/32:16 pm -
Nonstop4h 44m
Deal found 10/27![United Airlines logo]()
$567
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/78:45 am -
2 stops9h 45m
Wed 11/1111:45 am -
2 stops8h 40m
Deal found 10/27![Southwest logo]()
$411
This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/155:50 pm -
1 stop8h 11m
Tue 11/172:16 pm -
Nonstop4h 44m
Deal found 10/27![United Airlines logo]()
$587
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/254:55 pm -
Nonstop5h 31m
Tue 12/12:16 pm -
Nonstop4h 44m
Deal found 10/26![United Airlines logo]()
$615
This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/148:25 am -
Nonstop5h 22m
Wed 12/28:52 am -
Nonstop4h 48m
Deal found 10/27![United Airlines logo]()
$622
Last-minute flights from Puerto Rico to ChicagoDiscover last-minute flight deals from Puerto Rico to Chicago. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Chicago. Data last updated October 30, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:23 am -
1 stop27h 23m
Thu 11/1210:19 am -
1 stop12h 40m
Deal found 10/25![Frontier logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:26 pm -
1 stop23h 41m
Fri 11/134:42 pm -
1 stop16h 13m
Deal found 10/25![Frontier logo]()
$227
This Cheapflightsfares deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1812:59 am -
1 stop23h 44m
Mon 11/232:52 pm -
1 stop22h 08m
Deal found 10/25![Frontier logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:55 pm -
1 stop9h 52m
Mon 11/231:16 pm -
1 stop10h 20m
Deal found 10/25![Frontier logo]()
$229
This Cheapflightsfares deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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.
Thu 11/193:55 pm -
1 stop9h 52m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 10/27![Frontier logo]()
$230
This Cheapflightsfares deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Thu 11/197:00 am -
1 stop10h 37m
Mon 11/304:00 pm -
1 stop26h 37m
Deal found 10/28![Frontier logo]()
$234
This Trip.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/205:19 am -
1 stop8h 36m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 10/28![Frontier logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/215:19 am -
1 stop10h 26m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 10/27![Frontier logo]()
$231
This Frontier deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/226:00 am -
1 stop11h 57m
Fri 11/275:26 pm -
1 stop7h 07m
Deal found 10/27![Frontier logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/227:17 am -
1 stop14h 30m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 10/27![Frontier logo]()
$233
This FlightHub deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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.
Sun 11/223:55 am -
1 stop17h 52m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 10/27![Frontier logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/235:19 am -
1 stop10h 25m
Fri 12/45:24 pm -
1 stop6h 47m
Deal found 10/26![Frontier logo]()
$231
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 October 30, 2026.
Search for one-way flight options from Puerto Rico to Chicago. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Wed 12/23:47 am -
1 stop7h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$114
This Cheapflightsfares deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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.
Wed 1/1310:53 pm -
1 stop22h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$120
This Cheapflightsfares deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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.
Wed 1/1310:53 pm -
1 stop28h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$120
This eDestinos deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/132:51 pm -
1 stop9h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$122
This Trip.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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.
Sun 12/134:04 pm -
1 stop27h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$124
This Mytrip deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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.
Wed 12/162:29 am -
2 stops16h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$124
This Trip.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/2010:21 pm -
1 stop23h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/207:12 pm -
Nonstop5h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$126
This eDestinos deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/67:26 pm -
1 stop30h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$127
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/43:50 pm -
Nonstop5h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![American Airlines logo]()
$129
This Cheapflightsfares deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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.
Mon 1/115:33 pm -
Nonstop5h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/119:52 pm -
2 stops26h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$131
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 October 30, 2026.
Round-trip from | $227 (Cheapflightsfares) |
|---|---|
One-way from | $114 (Cheapflightsfares) |
Popular in | June |
Cheapest in | February |
Average price | $405 |
Good round-trip deal | $318 or less |
Good one-way deal | $189 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 October 30, 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 - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Sun 12/20
6:45 am-1:30 pm
1 stop8h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$129
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Fri 12/18
3:04 pm-8:15 pm
1 stop7h 11m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$133
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Fri 1/15
2:05 am-10:02 am
1 stop9h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$133
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Sat 2/13
8:05 am-2:27 pm
1 stop8h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$133
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 1/13
7:25 am-2:45 pm
2 stops9h 20m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$145
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 1/23
7:45 am-4:22 pm
1 stop10h 37m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$145
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 1/20
7:25 am-2:45 pm
2 stops9h 20m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$145
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 1/14
4:10 pm-10:17 pm
1 stop8h 07m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$145
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Tue 4/20
1:00 am-7:31 am
1 stop7h 31m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$145
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 1/16
7:45 am-4:22 pm
1 stop10h 37m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$145
Showing 1-10 of 60 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-ORD
SJU-MDW
BQN-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Puerto Rico to Chicago
PR0-CHI
SJU-ORD
SJU-MDW
BQN-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 $225). Flying from Puerto Rico to Chicago in June is currently the most expensive (average of $448). 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 October 30, 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 29% versus a flight in the afternoon.
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 187 minutes.
What is the most punctual flight time for Puerto Rico to Chicago 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 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 October 24, 2026.
Travelers seeking maximum savings on their Puerto Rico to Chicago flight should consider departing on Thursday evenings 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 October 30, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andJetBlue 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.
Entertainment
7.4
Food
7.0
Boarding
8.1
Crew
8.6
Overall
7.9
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.4
Food
7.0
Boarding
8.1
Crew
8.6
Overall
7.9
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.4
Food
7.0
Boarding
8.1
Crew
8.6
Overall
7.9
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.4
Food
7.0
Boarding
8.1
Crew
8.6
Overall
7.9
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.4
Food
7.0
Boarding
8.1
Crew
8.6
Overall
7.9
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.4
Food
7.0
Boarding
8.1
Crew
8.6
Overall
7.9
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 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
Merrillville
Lansing
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 October 30, 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 October 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Puerto Rico to Chicago
Discover the top 5 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 October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$116 | Average$265 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$136 | Average$231 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$226 | Average$390 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$253 | Average$453 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$425 | FlexibilityNo cancel fee | On-time63% |