$113+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Jun 16 — Jun 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 January or October, booked 28 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 May 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 May 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Thu 8/137:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 5/15![Frontier logo]()
$226
This Southwest deal was found by Cheapflights users on 5/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:10 am
MDW
- SJU
1 stop9h 55m
Southwest
Mon 8/315:00 am
SJU
- MDW
2 stops8h 20m
Southwest
Deal found 5/13![Southwest logo]()
$226
This American Airlines deal was found by Cheapflights users on 5/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:14 pm
ORD
- SJU
Nonstop4h 53m
American Airlines
Wed 9/26:51 am
SJU
- ORD
1 stop8h 24m
American Airlines
Deal found 5/12![American Airlines logo]()
$227
This Frontier deal was found by Cheapflights users on 5/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sat 8/226:00 am
SJU
- ORD
1 stop7h 25m
Frontier
Deal found 5/12![Frontier logo]()
$228
This Frontier deal was found by Cheapflights users on 5/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 8/186:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 5/16![Frontier logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 5/16. 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.
Sat 8/812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Mon 8/177:00 am
SJU
- ORD
2 stops26h 03m
Frontier
Deal found 5/16![Frontier logo]()
$230
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:14 pm
ORD
- SJU
Nonstop4h 53m
American Airlines
Tue 8/117:14 pm
SJU
- ORD
1 stop14h 46m
American Airlines
Deal found 5/13![American Airlines logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 5/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 8/117:00 am
SJU
- ORD
2 stops25h 53m
Frontier
Deal found 5/15![Frontier logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 9/712:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Wed 9/235:12 pm
SJU
- ORD
1 stop23h 14m
Frontier
Deal found 5/13![Frontier logo]()
$234
This Delta deal was found by Cheapflights users on 5/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:02 am
ORD
- SJU
1 stop7h 35m
Delta
Thu 8/275:49 pm
SJU
- ORD
1 stop7h 09m
Delta
Deal found 5/15![Delta logo]()
$236
This Southwest deal was found by Cheapflights users on 5/15. 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.
Wed 8/1912:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Wed 8/261:45 pm
SJU
- MDW
1 stop8h 15m
Southwest
Deal found 5/15![Southwest logo]()
$236
This Southwest deal was found by Cheapflights users on 5/12. 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.
Thu 8/201:00 pm
MDW
- SJU
2 stops8h 50m
Southwest
Mon 8/245:00 am
SJU
- MDW
2 stops8h 20m
Southwest
Deal found 5/12![Southwest logo]()
$246
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 May 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 May 17, 2026.
This Southwest deal was found by Cheapflights users on 5/14. 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.
Thu 8/137:15 am
MDW
- SJU
1 stop8h 40m
Southwest
Mon 8/1710:00 am
SJU
- MDW
1 stop9h 00m
Southwest
Deal found 5/14![Southwest logo]()
$406
This United Airlines deal was found by Cheapflights users on 5/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/32:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Mon 8/103:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Deal found 5/15![United Airlines logo]()
$415
This Delta deal was found by Cheapflights users on 5/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/136:35 am
ORD
- SJU
1 stop9h 10m
Delta
Sat 7/186:05 am
SJU
- ORD
1 stop9h 20m
Delta
Deal found 5/15![Delta logo]()
$441
This Southwest deal was found by Cheapflights users on 5/15. 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.
Wed 7/18:10 pm
MDW
- SJU
1 stop11h 50m
Southwest
Wed 7/88:35 pm
SJU
- MDW
1 stop13h 40m
Southwest
Deal found 5/15![Southwest logo]()
$426
This United Airlines deal was found by Cheapflights users on 5/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/32:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Mon 7/61:00 am
SJU
- ORD
1 stop9h 00m
United Airlines
Deal found 5/16![United Airlines logo]()
$465
This Southwest deal was found by Cheapflights users on 5/14. 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.
Thu 7/302:30 pm
MDW
- SJU
1 stop8h 45m
Southwest
Mon 8/310:20 pm
SJU
- MDW
1 stop12h 00m
Southwest
Deal found 5/14![Southwest logo]()
$466
This United Airlines deal was found by Cheapflights users on 5/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/292:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Tue 7/77:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 5/15![United Airlines logo]()
$468
This Southwest deal was found by Cheapflights users on 5/14. 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.
Thu 6/182:25 pm
MDW
- SJU
1 stop8h 10m
Southwest
Wed 7/88:35 pm
SJU
- MDW
1 stop13h 40m
Southwest
Deal found 5/14![Southwest logo]()
$516
This Delta deal was found by Cheapflights users on 5/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1711:05 am
MDW
- SJU
1 stop8h 40m
Delta
Tue 7/212:42 pm
SJU
- MDW
1 stop8h 33m
Delta
Deal found 5/13![Delta logo]()
$631
This Southwest deal was found by Cheapflights users on 5/12. 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.
Wed 6/177:25 am
MDW
- SJU
2 stops15h 20m
Southwest
Sat 6/209:25 pm
SJU
- MDW
1 stop12h 05m
Southwest
Deal found 5/12![Southwest logo]()
$550
This United Airlines deal was found by Cheapflights users on 5/12. 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 6/132:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Wed 6/171:00 am
SJU
- ORD
1 stop7h 42m
United Airlines
Deal found 5/12![United Airlines logo]()
$632
This Southwest deal was found by Cheapflights users on 5/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/242:00 pm
ORD
- SJU
2 stops18h 10m
Southwest
Thu 5/285:35 am
SJU
- ORD
2 stops17h 20m
Southwest
Deal found 5/13![Southwest logo]()
$581
This United Airlines deal was found by Cheapflights users on 5/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/32:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Fri 7/33:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Deal found 5/14![United Airlines logo]()
$670
This Southwest deal was found by Cheapflights users on 5/16. 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 7/91:30 pm
MDW
- SJU
2 stops9h 35m
Southwest
Mon 7/1310:20 pm
SJU
- MDW
1 stop11h 40m
Southwest
Deal found 5/16![Southwest logo]()
$591
This United Airlines deal was found by Cheapflights users on 5/13. 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 8/75:45 pm
ORD
- SJU
1 stop10h 44m
United Airlines
Mon 8/101:00 am
SJU
- ORD
2 stops11h 37m
United Airlines
Deal found 5/13![United Airlines logo]()
$681
This Southwest deal was found by Cheapflights users on 5/16. 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 6/284:05 pm
MDW
- SJU
1 stop7h 20m
Southwest
Sat 7/46:00 am
SJU
- MDW
1 stop12h 30m
Southwest
Deal found 5/16![Southwest logo]()
$591
This Southwest deal was found by Cheapflights users on 5/12. 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.
Wed 5/208:00 am
MDW
- SJU
2 stops9h 10m
Southwest
Tue 6/308:35 pm
SJU
- MDW
1 stop13h 25m
Southwest
Deal found 5/12![Southwest logo]()
$594
This United Airlines deal was found by Cheapflights users on 5/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/202:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Fri 5/227:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 5/14![United Airlines logo]()
$734
This Southwest deal was found by Cheapflights users on 5/16. 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.
Sat 5/236:00 am
ORD
- SJU
1 stop7h 40m
Southwest
Thu 5/285:35 am
SJU
- ORD
2 stops17h 20m
Southwest
Deal found 5/16![Southwest logo]()
$606
This Southwest deal was found by Cheapflights users on 5/16. 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 6/255:10 pm
MDW
- SJU
1 stop7h 10m
Southwest
Mon 6/297:00 am
SJU
- MDW
1 stop6h 25m
Southwest
Deal found 5/16![Southwest logo]()
$606
This Southwest deal was found by Cheapflights users on 5/14. 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 6/212:50 pm
MDW
- SJU
2 stops8h 50m
Southwest
Sat 6/65:00 am
SJU
- MDW
2 stops9h 10m
Southwest
Deal found 5/14![Southwest logo]()
$616
This Southwest deal was found by Cheapflights users on 5/14. 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 7/241:00 pm
MDW
- SJU
2 stops10h 15m
Southwest
Sun 7/266:05 am
SJU
- MDW
2 stops8h 55m
Southwest
Deal found 5/14![Southwest logo]()
$616
This Southwest deal was found by Cheapflights users on 5/14. 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.
Sat 5/306:00 am
ORD
- SJU
2 stops16h 15m
Southwest
Wed 6/35:05 am
SJU
- ORD
2 stops14h 20m
Southwest
Deal found 5/14![Southwest logo]()
$696
Last-minute flights from Chicago to San JuanDiscover last-minute flight deals from Chicago to San Juan. Data last updated May 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San Juan. Data last updated May 17, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Fri 5/155:30 pm
ORD
- SJU
1 stop7h 38m
Frontier
Sat 5/237:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 5/12![Frontier logo]()
$309
This Priceline deal was found by Cheapflights users on 5/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:30 pm
ORD
- SJU
1 stop7h 38m
Frontier
Mon 8/314:05 pm
SJU
- ORD
1 stop8h 09m
Frontier
Deal found 5/12![Frontier logo]()
$311
This American Airlines deal was found by Cheapflights users on 5/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:40 am
ORD
- SJU
1 stop14h 25m
American Airlines
Sat 5/236:20 am
SJU
- ORD
1 stop14h 18m
American Airlines
Deal found 5/14![American Airlines logo]()
$316
This Frontier deal was found by Cheapflights users on 5/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/2512:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Fri 5/297:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 5/14![Frontier logo]()
$321
This Frontier deal was found by Cheapflights users on 5/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Thu 5/286:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 5/16![Frontier logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 5/14. 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 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Fri 5/297:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 5/14![Frontier logo]()
$285
This eDestinos deal was found by Cheapflights users on 5/16. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Sun 8/167:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 5/16![Frontier logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 5/14. 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.
Wed 5/2712:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Fri 5/297:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 5/14![Frontier logo]()
$323
This Frontier deal was found by Cheapflights users on 5/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Thu 5/286:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 5/16![Frontier logo]()
$329
This Delta deal was found by Cheapflights users on 5/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:35 am
ORD
- SJU
1 stop9h 11m
Delta
Sun 7/126:00 am
SJU
- ORD
1 stop9h 27m
Delta
Deal found 5/12![Delta logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 5/12. 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 6/304:59 pm
ORD
- SJU
1 stop19h 17m
Frontier
Fri 7/176:00 am
SJU
- ORD
1 stop7h 25m
Frontier
Deal found 5/12![Frontier logo]()
$328
This Delta deal was found by Cheapflights users on 5/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:00 am
MDW
- SJU
1 stop9h 46m
Delta
Sun 7/126:00 am
SJU
- MDW
1 stop11h 15m
Delta
Deal found 5/12![Delta logo]()
$356
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 May 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 May 17, 2026.
This Delta deal was found by Cheapflights users on 5/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/109:52 am
ORD
- SJU
1 stop11h 37m
Delta
Deal found 5/13![Delta logo]()
$113
This Delta deal was found by Cheapflights users on 5/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1110:54 am
MDW
- SJU
1 stop10h 35m
Delta
Deal found 5/13![Delta logo]()
$113
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:14 pm
ORD
- SJU
Nonstop4h 53m
American Airlines
Deal found 5/13![American Airlines logo]()
$114
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:00 pm
ORD
- SJU
Nonstop4h 58m
American Airlines
Deal found 5/13![American Airlines logo]()
$119
This Delta deal was found by Cheapflights users on 5/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/88:02 am
ORD
- SJU
1 stop7h 35m
Delta
Deal found 5/13![Delta logo]()
$123
This Delta deal was found by Cheapflights users on 5/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3011:05 am
MDW
- SJU
1 stop10h 24m
Delta
Deal found 5/12![Delta logo]()
$123
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/84:59 pm
ORD
- SJU
Nonstop4h 53m
American Airlines
Deal found 5/13![American Airlines logo]()
$124
This Delta deal was found by Cheapflights users on 5/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:30 am
ORD
- SJU
1 stop10h 16m
Delta
Deal found 5/14![Delta logo]()
$128
This Delta deal was found by Cheapflights users on 5/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:00 am
MDW
- SJU
1 stop9h 46m
Delta
Deal found 5/14![Delta logo]()
$128
This Frontier deal was found by Cheapflights users on 5/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 5/13![Frontier logo]()
$129
This Super.com deal was found by Cheapflights users on 5/12. 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.
Fri 7/175:13 pm
ORD
- SJU
1 stop7h 58m
Frontier
Deal found 5/12![Frontier logo]()
$132
This American Airlines deal was found by Cheapflights users on 5/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/268:05 am
ORD
- SJU
1 stop13h 56m
American Airlines
Deal found 5/12![American Airlines logo]()
$133
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 May 17, 2026.
Round-trip from | $226 (Delta) |
|---|---|
One-way from | $113 (Delta) |
Popular in | December |
Cheapest in | January |
Average price | $363 |
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 May 17, 2026.
Use the filters below to find and compare flights from Chicago to San Juan that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 8/13
7:15 am-4:55 pm
1 stop8h 40m
San Juan Luis Munoz Marin Intl
Mon 8/17
10:00 am-6:00 pm
1 stop9h 00m
$406
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 8/3
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Mon 8/10
3:56 pm-8:15 pm
Nonstop5h 19m
$415
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 7/1
8:10 pm-9:00 am
1 stop11h 50m
San Juan Luis Munoz Marin Intl
Wed 7/8
8:35 pm-9:15 am
1 stop13h 40m
$426
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 7/13
6:35 am-4:45 pm
1 stop9h 10m
San Juan Luis Munoz Marin Intl
Sat 7/18
6:05 am-2:25 pm
1 stop9h 20m
$441
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 7/3
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Mon 7/6
1:00 am-9:00 am
1 stop9h 00m
$465
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 7/30
2:30 pm-12:15 am
1 stop8h 45m
San Juan Luis Munoz Marin Intl
Mon 8/3
10:20 pm-9:20 am
1 stop12h 00m
$466
Quickest round-trip
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 6/29
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Tue 7/7
7:40 am-11:53 am
Nonstop5h 13m
$468
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 6/18
2:25 pm-11:35 pm
1 stop8h 10m
San Juan Luis Munoz Marin Intl
Wed 7/8
8:35 pm-9:15 am
1 stop13h 40m
$516
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 6/17
7:25 am-11:45 pm
2 stops15h 20m
San Juan Luis Munoz Marin Intl
Sat 6/20
9:25 pm-8:30 am
1 stop12h 05m
$550
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 5/24
2:00 pm-9:10 am
2 stops18h 10m
San Juan Luis Munoz Marin Intl
Thu 5/28
5:35 am-9:55 pm
2 stops17h 20m
$581
Showing 1-10 of 46 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
ORD-SJU
MDW-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
ORD-SJU
MDW-SJU
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 month to book a flight from Chicago to San Juan?
Currently, April is the cheapest month in which you can book a flight from Chicago to San Juan (average of $317). Flying from Chicago to San Juan in December is currently the most expensive (average of $647). 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 May 17, 2026.
It’s typically best to fly out from Chicago to San Juan in the evening. Doing so could potentially save you 23% on the flight price compared to flying at noon, which is usually more expensive.
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 May 16, 2026.
Travelers seeking maximum savings on their Chicago to San Juan flight should consider departing on Monday afternoons when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 May 17, 2026.
The most flights from CHI to PR1 are scheduled on a Saturday (9 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (6 on average).
How much does it cost to fly round-trip from Chicago to San Juan?
How often are flights from Chicago to San Juan delayed?
About 22% 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 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 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 19% of flights being delayed.
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 May 17, 2026.
Read through reviews of airlines operating flights from Chicago to San Juan, such as United Airlines,JetBlue, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.1
Entertainment
7.1
Boarding
7.7
Comfort
7.3
Food
6.6
Overall
7.4
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Crew
8.1
Entertainment
7.1
Boarding
7.7
Comfort
7.3
Food
6.6
Overall
7.4
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Crew
8.1
Entertainment
7.1
Boarding
7.7
Comfort
7.3
Food
6.6
Overall
7.4
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Crew
8.1
Entertainment
7.1
Boarding
7.7
Comfort
7.3
Food
6.6
Overall
7.4
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Crew
8.1
Entertainment
7.1
Boarding
7.7
Comfort
7.3
Food
6.6
Overall
7.4
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Crew
8.1
Entertainment
7.1
Boarding
7.7
Comfort
7.3
Food
6.6
Overall
7.4
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
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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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 May 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 May 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 7 airlines flying from Chicago to San Juan
Discover the top 7 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 May 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$119 | Average$235 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$122 | Average$289 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$132 | Average$387 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$140 | Average$314 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$256 | Average$504 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$309 | Average$509 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$352 | Average$489 | FlexibilityNo cancel fee | On-time63% |