$106+ Cheap flights from Chicago (CHI) to Puerto Rico
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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Oct 11 — Oct 181
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
One-way
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 September 11, 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 September 11, 2026.
This United Airlines deal was found by Cheapflights users on 9/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:55 am -
Nonstop4h 49m
Sat 10/103:56 pm -
Nonstop5h 09m
Deal found 9/7![United Airlines logo]()
$217
This JetBlue deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/107:00 am -
1 stop7h 23m
Wed 10/146:10 am -
1 stop8h 40m
Deal found 9/11![JetBlue logo]()
$218
This Orbitz deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/104:41 pm -
1 stop16h 38m
Sat 10/177:15 am -
1 stop16h 24m
Deal found 9/10![Frontier logo]()
$219
This JetBlue deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/101:00 pm -
1 stop10h 13m
Tue 11/176:25 am -
1 stop9h 17m
Deal found 9/10![JetBlue logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/277:50 pm -
2 stops19h 26m
Mon 11/23:59 pm -
1 stop22h 52m
Deal found 9/10![Frontier logo]()
$221
This Trip.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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.
Wed 9/306:25 am -
1 stop7h 57m
Mon 10/56:30 am -
1 stop12h 21m
Deal found 9/8![Frontier logo]()
$221
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/248:45 am -
1 stop10h 53m
Sat 10/317:25 am -
Nonstop5h 22m
Deal found 9/9![United Airlines logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/56:50 am -
1 stop7h 29m
Wed 10/147:15 am -
2 stops17h 28m
Deal found 9/11![Frontier logo]()
$223
This deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:50 pm -
1 stop9h 02m
Wed 9/232:57 am -
1 stop8h 23m
Deal found 9/10![Frontier logo]()
$224
This deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:50 pm -
1 stop9h 02m
Wed 9/232:57 am -
1 stop8h 23m
Deal found 9/10![Frontier logo]()
$225
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/243:00 pm -
1 stop7h 50m
Mon 10/261:05 am -
1 stop8h 57m
Deal found 9/9![United Airlines logo]()
$226
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 12/26:05 pm -
1 stop13h 37m
Wed 12/93:49 pm -
Nonstop5h 38m
Deal found 9/10![American Airlines logo]()
$227
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 September 11, 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 September 11, 2026.
This United Airlines deal was found by Cheapflights users on 9/6. 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.
Sun 11/158:52 am -
Nonstop4h 48m
Mon 11/162:05 am -
1 stop10h 43m
Deal found 9/6![United Airlines logo]()
$222
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 9/2312:20 pm -
1 stop8h 45m
Tue 9/291:45 pm -
1 stop8h 40m
Deal found 9/8![Southwest logo]()
$266
This Trip.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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.
Wed 9/233:50 pm -
1 stop17h 23m
Wed 9/3011:12 am -
1 stop12h 47m
Deal found 9/9![Frontier logo]()
$340
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/248:55 am -
Nonstop4h 49m
Tue 10/2712:00 pm -
1 stop10h 30m
Deal found 9/9![United Airlines logo]()
$222
This Priceline deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/73:50 pm -
1 stop16h 02m
Tue 10/133:20 am -
1 stop11h 30m
Deal found 9/8![Multiple Airlines logo]()
$450
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Thu 11/57:00 am -
1 stop16h 50m
Thu 11/195:01 am -
1 stop20h 37m
Deal found 9/10![JetBlue logo]()
$475
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 11/172:16 pm -
Nonstop4h 44m
Tue 11/245:50 pm -
1 stop8h 11m
Deal found 9/8![United Airlines logo]()
$222
This Southwest deal was found by Cheapflights users on 9/6. 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.
Tue 10/201:40 pm -
2 stops8h 30m
Tue 10/275:05 am -
2 stops8h 20m
Deal found 9/6![Southwest logo]()
$281
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/258:52 am -
Nonstop4h 48m
Fri 10/303:55 pm -
Nonstop5h 31m
Deal found 9/10![United Airlines logo]()
$237
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 9/2310:30 am -
1 stop8h 10m
Deal found 9/11![Southwest logo]()
$299
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/215:00 am -
1 stop7h 45m
Sat 9/262:55 pm -
1 stop9h 32m
Deal found 9/9![United Airlines logo]()
$266
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/242:40 pm -
1 stop6h 35m
Sat 10/317:45 am -
2 stops10h 00m
Deal found 9/9![Southwest logo]()
$318
This Priceline deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:11 pm -
1 stop13h 11m
Sun 10/1810:52 am -
1 stop21h 39m
Deal found 9/9![Frontier logo]()
$396
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 11/174:25 pm -
1 stop6h 20m
Tue 11/2410:30 pm -
1 stop13h 25m
Deal found 9/8![Southwest logo]()
$330
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/92:16 pm -
Nonstop4h 44m
Fri 11/134:55 pm -
Nonstop5h 31m
Deal found 9/10![United Airlines logo]()
$307
This Frontier deal was found by Cheapflights users on 9/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:12 pm -
1 stop7h 35m
Mon 11/302:54 pm -
1 stop11h 48m
Deal found 9/6![Frontier logo]()
$436
This CheapOair deal was found by Cheapflights users on 9/7. 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.
Wed 10/76:20 am -
2 stops26h 37m
Fri 10/302:25 pm -
1 stop10h 32m
Deal found 9/7![Multiple Airlines logo]()
$486
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 11/88:40 pm -
1 stop11h 50m
Fri 11/134:00 pm -
2 stops9h 05m
Deal found 9/8![Southwest logo]()
$336
This JetBlue deal was found by Cheapflights users on 9/6. 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.
Wed 11/42:42 pm -
1 stop9h 08m
Tue 11/105:01 am -
1 stop10h 41m
Deal found 9/6![JetBlue logo]()
$499
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/238:45 am -
1 stop10h 53m
Sat 10/317:25 am -
Nonstop5h 22m
Deal found 9/8![United Airlines logo]()
$315
This Travelocity deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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.
Sat 10/178:46 am -
1 stop24h 11m
Sat 11/712:22 pm -
1 stop22h 24m
Deal found 9/11![Frontier logo]()
$439
This FlightHub deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/72:42 pm -
1 stop21h 37m
Sat 11/1412:22 pm -
1 stop22h 24m
Deal found 9/10![Multiple Airlines logo]()
$492
This JetBlue deal was found by Cheapflights users on 9/6. 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 10/192:55 pm -
1 stop10h 11m
Wed 10/212:25 pm -
1 stop10h 05m
Deal found 9/6![JetBlue logo]()
$507
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/101:30 pm -
1 stop6h 52m
Mon 11/165:50 pm -
1 stop8h 12m
Deal found 9/9![United Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/233:45 pm -
1 stop7h 40m
Sat 10/316:50 am -
1 stop9h 25m
Deal found 9/8![Southwest logo]()
$353
This Southwest deal was found by Cheapflights users on 9/6. 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.
Thu 10/83:45 pm -
1 stop7h 40m
Thu 10/1510:50 pm -
1 stop10h 55m
Deal found 9/6![Southwest logo]()
$353
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/22:16 pm -
Nonstop4h 44m
Mon 11/98:25 am -
Nonstop5h 22m
Deal found 9/10![United Airlines logo]()
$321
This JetBlue deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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.
Wed 10/212:55 pm -
1 stop8h 34m
Fri 10/305:01 am -
1 stop9h 43m
Deal found 9/8![JetBlue logo]()
$518
This FlightHub deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Thu 11/56:30 am -
2 stops25h 29m
Thu 11/195:01 am -
1 stop20h 37m
Deal found 9/10![Multiple Airlines logo]()
$563
This Southwest deal was found by Cheapflights users on 9/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:20 pm -
2 stops8h 50m
Fri 10/305:30 am -
2 stops8h 55m
Deal found 9/7![Southwest logo]()
$353
Last-minute flights from Chicago to Puerto RicoDiscover last-minute flight deals from Chicago to Puerto Rico. Data last updated September 11, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Puerto Rico. Data last updated September 11, 2026 and is based on user searches.
This deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:50 pm -
1 stop9h 02m
Wed 9/232:57 am -
1 stop8h 23m
Deal found 9/10![Frontier logo]()
$225
This deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:50 pm -
1 stop9h 02m
Wed 9/232:57 am -
1 stop8h 23m
Deal found 9/10![Frontier logo]()
$224
This Trip.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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.
Wed 9/306:25 am -
1 stop7h 57m
Mon 10/56:30 am -
1 stop12h 21m
Deal found 9/8![Frontier logo]()
$221
This United Airlines deal was found by Cheapflights users on 9/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:55 am -
Nonstop4h 49m
Sat 10/103:56 pm -
Nonstop5h 09m
Deal found 9/7![United Airlines logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/56:50 am -
1 stop7h 29m
Wed 10/147:15 am -
2 stops17h 28m
Deal found 9/11![Frontier logo]()
$223
This JetBlue deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/107:00 am -
1 stop7h 23m
Wed 10/146:10 am -
1 stop8h 40m
Deal found 9/11![JetBlue logo]()
$218
This Orbitz deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/104:41 pm -
1 stop16h 38m
Sat 10/177:15 am -
1 stop16h 24m
Deal found 9/10![Frontier logo]()
$219
This deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:15 am -
1 stop8h 51m
Thu 11/53:59 pm -
1 stop9h 48m
Deal found 9/8![Frontier logo]()
$227
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/248:45 am -
1 stop10h 53m
Sat 10/317:25 am -
Nonstop5h 22m
Deal found 9/9![United Airlines logo]()
$222
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/243:00 pm -
1 stop7h 50m
Mon 10/261:05 am -
1 stop8h 57m
Deal found 9/9![United Airlines logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/277:50 pm -
2 stops19h 26m
Mon 11/23:59 pm -
1 stop22h 52m
Deal found 9/10![Frontier logo]()
$221
This American Airlines deal was found by Cheapflights users on 9/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/288:13 am -
Nonstop4h 50m
Sat 10/317:30 am -
1 stop16h 00m
Deal found 9/7![American Airlines logo]()
$227
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 September 11, 2026.
Search for one-way flight options from Chicago to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
This Frontier deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/46:25 am -
1 stop8h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$106
This CheapOair deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/186:24 am -
1 stop8h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$108
This JetBlue deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/82:50 pm -
1 stop6h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![JetBlue logo]()
$109
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/24:42 pm -
1 stop21h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$110
This Super.com deal was found by Cheapflights users on 9/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:00 am -
1 stop8h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![JetBlue logo]()
$112
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/95:29 pm -
1 stop15h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$113
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/273:25 pm -
1 stop7h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Southwest logo]()
$113
This American Airlines deal was found by Cheapflights users on 9/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/288:13 am -
Nonstop4h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![American Airlines logo]()
$114
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:00 am -
1 stop8h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Delta logo]()
$115
This Super.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/16:25 am -
1 stop8h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$115
This American Airlines deal was found by Cheapflights users on 9/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/288:50 am -
2 stops10h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![American Airlines logo]()
$116
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/129:00 pm -
1 stop15h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![American Airlines logo]()
$117
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 September 11, 2026.
Round-trip from | $217 (United Airlines) |
|---|---|
One-way from | $106 (Frontier) |
Popular in | December |
Cheapest in | August |
Average price | $376 |
Good round-trip deal | $319 or less |
Good one-way deal | $156 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 7,457,451 searches. Data last updated September 11, 2026.
Use the filters below to find and compare flights from Chicago to Puerto Rico that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Mon 10/5
5:00 am-1:45 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$113
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Wed 11/18
1:00 pm-1:13 am
1 stop10h 13m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$113
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Fri 12/4
8:07 pm-6:32 pm
1 stop20h 25m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$125
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Wed 9/16
9:40 am-6:10 pm
1 stop7h 30m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$133
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Mon 11/23
2:30 pm-12:36 am
1 stop8h 06m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$136
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 9/28
6:05 am-4:49 pm
1 stop9h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$143
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Wed 9/30
5:00 am-1:45 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$143
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 9/15
8:30 am-6:10 pm
1 stop8h 40m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$146
Quickest round-trip
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Mon 11/2
2:16 pm-9:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$154
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Fri 10/9
4:15 pm-1:25 am
2 stops8h 10m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$168
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Puerto Rico
Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Chicago with our price prediction graph.
ORD-SJU
MDW-SJU
ORD-MAZ
ORD-BQN
ORD-PSE
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Puerto Rico
CHI-PR0
ORD-SJU
MDW-SJU
ORD-MAZ
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 $332). Flying from Chicago to Puerto Rico in December is currently the most expensive (average of $544). 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 September 11, 2026.
When flying from Chicago to Puerto Rico, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 34% versus a flight in the morning.
Weekly flight availability from Chicago to Puerto Rico
Explore weekly flight availability from Chicago to Puerto Rico. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 11, 2026.
The most flights from CHI to PR0 are scheduled on a Monday (3 on average). You will have fewer flight options on Saturday, 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 142 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 Monday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Puerto Rico flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 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 79 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 September 5, 2026.
Travelers seeking maximum savings on their Chicago to Puerto Rico flight should consider departing on Saturday evenings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Puerto Rico
Get insights into the airlines that provide service to Puerto Rico. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Puerto Rico. Reviews last updated September 11, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to Puerto Rico to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
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
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
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 September 11, 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 7,457,451 searches. Data last updated September 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$376 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$491 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$326 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$264 | Average$523 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$276 | Average$486 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$292 | Average$494 | FlexibilityNo cancel fee | On-time71% |