$97+ Cheap flights from Chicago (CHI) to San Juan
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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Sep 16 — Sep 231
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to San Juan 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.Cheapflights Tip: The best prices from Chicago to San Juan are usually found in August or January, booked 82 days in advance, depart on a Tuesday or Monday and return on a Thursday
Cheap flight deals from Chicago to San Juan
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Best
Last-minute
One-way
Cheapest flights from Chicago to San JuanExplore the most affordable flight options available from Chicago to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 17, 2026.
Explore the most affordable flight options available from Chicago to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 17, 2026.
This Super.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am -
Nonstop5h 00m
Fri 9/47:14 pm -
Nonstop5h 13m
Deal found 8/14![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 10/17:11 am -
1 stop29h 23m
Mon 10/57:00 am -
1 stop8h 45m
Deal found 8/12![Frontier logo]()
$212
This Super.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:44 am -
Nonstop5h 00m
Fri 9/47:14 pm -
Nonstop5h 13m
Deal found 8/16![Frontier logo]()
$213
This CheapOair deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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 9/512:44 am -
Nonstop5h 00m
Wed 9/162:32 pm -
1 stop9h 36m
Deal found 8/14![Multiple Airlines logo]()
$214
This Super.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:44 am -
Nonstop5h 00m
Sun 8/307:14 pm -
Nonstop5h 13m
Deal found 8/13![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:44 am -
Nonstop5h 00m
Wed 9/168:45 am -
2 stops25h 35m
Deal found 8/14![Frontier logo]()
$217
This CheapOair deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2312:44 am -
Nonstop5h 00m
Thu 8/277:14 pm -
Nonstop5h 13m
Deal found 8/16![Frontier logo]()
$218
This deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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.
Sun 8/307:44 pm -
1 stop11h 27m
Wed 9/92:57 am -
1 stop8h 23m
Deal found 8/14![Frontier logo]()
$219
This CheapOair deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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 8/2612:44 am -
Nonstop5h 00m
Sat 8/297:14 pm -
Nonstop5h 13m
Deal found 8/14![Frontier logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:44 am -
Nonstop5h 00m
Sun 9/67:14 pm -
Nonstop5h 13m
Deal found 8/14![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am -
Nonstop5h 00m
Mon 8/316:35 am -
1 stop31h 15m
Deal found 8/13![Frontier logo]()
$223
This Southwest deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:45 pm -
2 stops8h 15m
Wed 9/305:15 am -
2 stops7h 50m
Deal found 8/15![Southwest logo]()
$241
Best flights from Chicago to San JuanDiscover carefully curated flight deals from Chicago to San Juan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 17, 2026.
Discover carefully curated flight deals from Chicago to San Juan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 17, 2026.
This Southwest deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 9/297:30 am -
1 stop10h 35m
Tue 10/65:05 am -
2 stops10h 35m
Deal found 8/15![Southwest logo]()
$246
This United Airlines deal was found by Cheapflights users on 8/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/62:16 pm -
Nonstop4h 44m
Mon 11/94:55 pm -
Nonstop5h 31m
Deal found 8/11![United Airlines logo]()
$301
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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 9/113:15 pm -
1 stop6h 55m
Fri 9/186:00 am -
2 stops9h 30m
Deal found 8/14![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 9/3012:20 pm -
1 stop7h 50m
Wed 10/78:15 am -
2 stops12h 05m
Deal found 8/16![Southwest logo]()
$281
This United Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 10/288:52 am -
Nonstop4h 48m
Tue 11/34:55 pm -
Nonstop5h 31m
Deal found 8/12![United Airlines logo]()
$321
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2811:15 am -
1 stop10h 00m
Mon 10/51:05 pm -
1 stop8h 25m
Deal found 8/14![Southwest logo]()
$295
This United Airlines deal was found by Cheapflights users on 8/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/48:52 am -
Nonstop4h 48m
Sat 11/72:05 am -
1 stop8h 57m
Deal found 8/11![United Airlines logo]()
$338
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/294:15 pm -
2 stops8h 05m
Tue 11/36:10 am -
1 stop10h 50m
Deal found 8/16![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/2611:00 am -
1 stop6h 20m
Sat 10/35:40 am -
2 stops12h 40m
Deal found 8/12![Southwest logo]()
$320
This United Airlines deal was found by Cheapflights users on 8/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:16 pm -
Nonstop4h 44m
Mon 11/94:55 pm -
Nonstop5h 31m
Deal found 8/11![United Airlines logo]()
$421
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:45 pm -
2 stops8h 15m
Sun 9/66:30 am -
2 stops8h 30m
Deal found 8/16![Southwest logo]()
$326
This United Airlines deal was found by Cheapflights users on 8/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/218:55 am -
Nonstop4h 49m
Wed 9/301:00 am -
1 stop9h 42m
Deal found 8/11![United Airlines logo]()
$426
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 11/1512:50 pm -
1 stop8h 40m
Thu 11/196:10 am -
2 stops8h 45m
Deal found 8/16![Southwest logo]()
$336
This United Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/68:55 am -
Nonstop4h 49m
Wed 9/93:56 pm -
Nonstop5h 09m
Deal found 8/12![United Airlines logo]()
$428
This Southwest deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 11/179:55 am -
2 stops9h 55m
Sun 11/229:35 pm -
1 stop13h 45m
Deal found 8/15![Southwest logo]()
$350
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 10/208:55 am -
Nonstop4h 49m
Sat 10/243:56 pm -
Nonstop5h 09m
Deal found 8/13![United Airlines logo]()
$441
This United Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 11/78:52 am -
Nonstop4h 48m
Sat 11/148:25 am -
Nonstop5h 24m
Deal found 8/12![United Airlines logo]()
$441
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 11/62:16 pm -
Nonstop4h 44m
Sat 11/148:25 am -
Nonstop5h 24m
Deal found 8/13![United Airlines logo]()
$441
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 10/238:55 am -
Nonstop4h 49m
Wed 10/287:05 am -
1 stop8h 33m
Deal found 8/13![United Airlines logo]()
$446
This United Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 10/108:55 am -
Nonstop4h 49m
Sat 10/171:25 pm -
1 stop10h 04m
Deal found 8/12![United Airlines logo]()
$446
Last-minute flights from Chicago to San JuanDiscover last-minute flight deals from Chicago to San Juan. Data last updated August 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San Juan. Data last updated August 17, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2312:44 am -
Nonstop5h 00m
Thu 8/277:14 pm -
Nonstop5h 13m
Deal found 8/16![Frontier logo]()
$218
This Super.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:44 am -
Nonstop5h 00m
Fri 8/287:14 pm -
Nonstop5h 13m
Deal found 8/14![Frontier logo]()
$215
This CheapOair deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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 8/2612:44 am -
Nonstop5h 00m
Thu 9/37:14 pm -
Nonstop5h 13m
Deal found 8/14![Frontier logo]()
$220
This Super.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am -
Nonstop5h 00m
Fri 9/47:14 pm -
Nonstop5h 13m
Deal found 8/14![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am -
Nonstop5h 00m
Mon 8/316:35 am -
1 stop31h 15m
Deal found 8/13![Frontier logo]()
$223
This deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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.
Sun 8/307:44 pm -
1 stop11h 27m
Wed 9/92:57 am -
1 stop8h 23m
Deal found 8/14![Frontier logo]()
$219
This Super.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:44 am -
Nonstop5h 00m
Fri 9/47:14 pm -
Nonstop5h 13m
Deal found 8/16![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:44 am -
Nonstop5h 00m
Sun 9/67:14 pm -
Nonstop5h 13m
Deal found 8/14![Frontier logo]()
$221
This Southwest deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:45 pm -
2 stops8h 15m
Wed 9/305:15 am -
2 stops7h 50m
Deal found 8/15![Southwest logo]()
$241
This CheapOair deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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 9/512:44 am -
Nonstop5h 00m
Wed 9/162:32 pm -
1 stop9h 36m
Deal found 8/14![Multiple Airlines logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:44 am -
Nonstop5h 00m
Wed 9/168:45 am -
2 stops25h 35m
Deal found 8/14![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/88:05 am -
1 stop30h 12m
Wed 9/168:45 am -
1 stop31h 00m
Deal found 8/12![Frontier logo]()
$224
One-way flights from Chicago to San JuanSearch for one-way flight options from Chicago to San Juan. Find affordable one-way fares based on user searches. Data last updated August 17, 2026.
Search for one-way flight options from Chicago to San Juan. Find affordable one-way fares based on user searches. Data last updated August 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Sat 9/127:11 am -
1 stop29h 23m
Deal found 8/11![Frontier logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 10/128:04 am -
1 stop30h 14m
Deal found 8/13![Frontier logo]()
$99
This CheapOair deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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.
Tue 9/112:44 am -
Nonstop5h 00m
Deal found 8/13![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” 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 10/148:04 am -
1 stop28h 27m
Deal found 8/13![Frontier logo]()
$101
This Super.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” 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 9/712:44 am -
Nonstop5h 00m
Deal found 8/12![Frontier logo]()
$103
This Super.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:44 am -
Nonstop5h 00m
Deal found 8/12![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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 10/17:11 am -
1 stop29h 23m
Deal found 8/14![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/158:04 am -
1 stop28h 27m
Deal found 8/16![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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 10/138:04 am -
1 stop30h 14m
Deal found 8/14![Frontier logo]()
$111
This eDestinos deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:44 am -
Nonstop5h 00m
Deal found 8/13![Frontier logo]()
$112
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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 9/158:30 am -
1 stop8h 40m
Deal found 8/14![Southwest logo]()
$113
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:45 pm -
2 stops8h 15m
Deal found 8/12![Southwest logo]()
$128
Find flight deals from Chicago to San Juan
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to San Juan (PR1). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 17, 2026.
Round-trip from | $211 (Super.com) |
|---|---|
One-way from | $97 (Kiwi.com) |
Popular in | December |
Cheapest in | August |
Average price | $320 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to San Juan that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 17, 2026.
Use the filters below to find and compare flights from Chicago to San Juan that are best for you.
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Cheapest round-trip
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 9/29
7:30 am-7:05 pm
1 stop10h 35m
San Juan Luis Munoz Marin Intl
Tue 10/6
5:05 am-2:40 pm
2 stops10h 35m
$246
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Fri 9/11
3:15 pm-11:10 pm
1 stop6h 55m
San Juan Luis Munoz Marin Intl
Fri 9/18
6:00 am-2:30 pm
2 stops9h 30m
$246
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Wed 9/30
12:20 pm-9:10 pm
1 stop7h 50m
San Juan Luis Munoz Marin Intl
Wed 10/7
8:15 am-7:20 pm
2 stops12h 05m
$281
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 9/28
11:15 am-10:15 pm
1 stop10h 00m
San Juan Luis Munoz Marin Intl
Mon 10/5
1:05 pm-8:30 pm
1 stop8h 25m
$295
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Fri 11/6
2:16 pm-9:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Mon 11/9
4:55 pm-8:26 pm
Nonstop5h 31m
$301
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Thu 10/29
4:15 pm-1:20 am
2 stops8h 05m
San Juan Luis Munoz Marin Intl
Tue 11/3
6:10 am-3:00 pm
1 stop10h 50m
$301
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Sat 9/26
11:00 am-6:20 pm
1 stop6h 20m
San Juan Luis Munoz Marin Intl
Sat 10/3
5:40 am-5:20 pm
2 stops12h 40m
$320
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Wed 10/28
8:52 am-2:40 pm
Nonstop4h 48m
San Juan Luis Munoz Marin Intl
Tue 11/3
4:55 pm-8:26 pm
Nonstop5h 31m
$321
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 9/1
12:45 pm-10:00 pm
2 stops8h 15m
San Juan Luis Munoz Marin Intl
Sun 9/6
6:30 am-2:00 pm
2 stops8h 30m
$326
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Sun 11/15
12:50 pm-11:30 pm
1 stop8h 40m
San Juan Luis Munoz Marin Intl
Thu 11/19
6:10 am-12:55 pm
2 stops8h 45m
$336
Showing 1-10 of 40 resultsSorted by cheapest first
Best time to book a flight from Chicago to San Juan
Have a flexible travel schedule? Discover the best time to fly to San Juan from Chicago with our price prediction graph.
CHI-PR1
MDW-SJU
ORD-SJU
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 San Juan
CHI-PR1
MDW-SJU
ORD-SJU
What is the cheapest month to book a flight from Chicago to San Juan?
Currently, August is the cheapest month in which you can book a flight from Chicago to San Juan (average of $339). Flying from Chicago to San Juan in December is currently the most expensive (average of $540). 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 SJU?
Find hourly flight availability from Chicago to San Juan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 17, 2026.
It’s typically best to fly out from Chicago to San Juan in the evening. Doing so could potentially save you 39% on the flight price compared to flying in the morning, which is usually more expensive.
Weekly flight availability from Chicago to San Juan
Explore weekly flight availability from Chicago to San Juan. 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 17, 2026.
The most flights from CHI to PR1 are scheduled on a Monday (7 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (3 on average).
How much does it cost to fly round-trip from Chicago to San Juan?
Airfare is below average for this route at the moment.
Chicago to San Juan flights typically cost between $244 and $401 in August.The cheapest round-trip price found within the last 5 days was $211 on Frontier (Aug 27-Sep 4).
How often are flights from Chicago to San Juan delayed?
About 23% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 140 minutes.
What is the most punctual flight time for Chicago to San Juan 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?
Wednesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to San Juan 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 San Juan?
To ensure you get the cheapest price possible for a flight from Chicago to San Juan, you should look to book at least 56 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Chicago to San Juan?
Use this chart to determine the cheapest time to fly round-trip from Chicago to San Juan. Price data was last updated on August 15, 2026.
Travelers seeking maximum savings on their Chicago to San Juan flight should consider departing on Sunday evenings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing San Juan
Get insights into the airlines that provide service to San Juan. 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 San Juan. Reviews last updated August 17, 2026.
Read through reviews of airlines operating flights from Chicago to San Juan, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
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 San Juan. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to San Juan
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Complete your trip
Complete your trip to San Juan by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to San Juan by cabin class
Find flights from Chicago to San Juan, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and San Juan flights
Browse other Chicago and San Juan flight options. Last updated on August 17, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on August 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Chicago to San Juan
Discover the top 6 airlines that operate flights from Chicago to San Juan. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$322 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$486 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$233 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$263 | Average$509 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$296 | Average$490 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$302 | Average$492 | FlexibilityNo cancel fee | On-time71% |