$122+ Cheap flights from San Juan to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Dec 3 — Dec 101
Round-trip
1 adult, Economy
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Find cheap flights from San Juan to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from San Juan to Chicago are usually found in February or September, booked 23 days in advance, depart on a Thursday or Friday and return on a Tuesday
Cheap flight deals from San Juan to Chicago
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Cheapest flights from San Juan to ChicagoExplore the most affordable flight options available from San Juan to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2026.
Explore the most affordable flight options available from San Juan to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/227:17 am -
1 stop14h 30m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 11/1![Frontier logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/2110:26 pm -
Nonstop5h 07m
Wed 12/3012:26 am -
Nonstop4h 53m
Deal found 11/1![Frontier logo]()
$233
This OneTravel deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/85:01 am -
1 stop8h 32m
Sat 12/1212:28 pm -
1 stop10h 39m
Deal found 11/3![Frontier logo]()
$234
This eDestinos deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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.
Mon 11/237:12 pm -
Nonstop5h 09m
Fri 11/276:20 am -
1 stop10h 18m
Deal found 11/1![Frontier logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/2410:26 pm -
Nonstop5h 07m
Sun 1/312:26 am -
Nonstop4h 39m
Deal found 11/1![Frontier logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/207:12 pm -
Nonstop5h 09m
Fri 11/272:52 pm -
1 stop22h 08m
Deal found 11/1![Frontier logo]()
$237
This Trip.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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.
Thu 12/1710:26 pm -
Nonstop5h 07m
Thu 12/318:22 am -
1 stop13h 52m
Deal found 10/31![Frontier logo]()
$238
This Trip.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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.
Thu 12/35:01 am -
1 stop13h 06m
Thu 12/108:37 pm -
1 stop24h 52m
Deal found 11/1![Frontier logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:00 am -
1 stop11h 57m
Fri 11/272:52 pm -
1 stop22h 08m
Deal found 11/1![Frontier logo]()
$239
This CheapOair deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:01 am -
1 stop13h 06m
Sun 12/68:37 pm -
1 stop27h 36m
Deal found 11/2![Frontier logo]()
$240
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:55 pm -
1 stop10h 18m
Thu 11/2611:53 pm -
Nonstop4h 39m
Deal found 11/3![Frontier logo]()
$240
This OneTravel deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:01 am -
1 stop13h 06m
Sun 12/68:37 pm -
1 stop24h 52m
Deal found 11/3![Frontier logo]()
$241
Best flights from San Juan to ChicagoDiscover carefully curated flight deals from San Juan to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 3, 2026.
Discover carefully curated flight deals from San Juan to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 3, 2026.
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/116:05 am -
2 stops10h 20m
Tue 12/1512:45 pm -
2 stops10h 05m
Deal found 10/30![Southwest logo]()
$338
This Mytrip deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/75:01 am -
2 stops14h 15m
Sat 12/1212:28 pm -
2 stops11h 30m
Deal found 10/29![Frontier logo]()
$349
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:25 am -
Nonstop5h 24m
Tue 1/192:16 pm -
Nonstop4h 44m
Deal found 10/31![United Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/213:30 pm -
Nonstop5h 10m
Sun 12/68:40 pm -
1 stop13h 00m
Deal found 11/1![Southwest logo]()
$351
This Sun Country Air deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/263:10 pm -
1 stop30h 00m
Wed 12/3011:40 am -
1 stop24h 22m
Deal found 11/1![Sun Country Air logo]()
$787
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2111:00 am -
2 stops8h 35m
Fri 11/278:40 pm -
1 stop11h 30m
Deal found 11/2![Southwest logo]()
$398
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/252:52 pm -
1 stop10h 47m
Sun 1/38:12 pm -
1 stop8h 03m
Deal found 11/1![United Airlines logo]()
$446
This Cheapflightsfares deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:19 am -
1 stop9h 02m
Sun 11/298:42 pm -
1 stop11h 17m
Deal found 10/29![Frontier logo]()
$477
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/27:40 am -
2 stops9h 15m
Wed 12/91:20 pm -
2 stops9h 30m
Deal found 11/2![Southwest logo]()
$398
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:40 am -
2 stops9h 15m
Sun 12/61:20 pm -
2 stops9h 40m
Deal found 10/31![Southwest logo]()
$398
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/95:50 pm -
1 stop7h 25m
Tue 11/103:00 pm -
1 stop7h 50m
Deal found 10/29![Southwest logo]()
$415
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/148:25 am -
Nonstop5h 22m
Wed 12/22:16 pm -
Nonstop4h 44m
Deal found 10/31![United Airlines logo]()
$566
This Alaska Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/107:20 am -
2 stops33h 01m
Mon 1/46:00 am -
2 stops35h 30m
Deal found 10/30![Alaska Airlines logo]()
$1,254
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1711:20 am -
2 stops9h 00m
Thu 12/311:15 pm -
2 stops8h 10m
Deal found 10/30![Southwest logo]()
$453
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/194:55 pm -
Nonstop5h 31m
Thu 11/262:16 pm -
Nonstop4h 44m
Deal found 11/2![United Airlines logo]()
$615
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/238:25 am -
Nonstop5h 22m
Fri 12/42:16 pm -
Nonstop4h 44m
Deal found 11/2![United Airlines logo]()
$622
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:10 am -
1 stop8h 50m
Mon 11/163:00 pm -
1 stop7h 50m
Deal found 10/29![Southwest logo]()
$472
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/2212:40 pm -
2 stops9h 40m
Tue 11/2412:50 pm -
2 stops9h 25m
Deal found 11/2![Southwest logo]()
$490
This United Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/164:55 pm -
Nonstop5h 31m
Thu 12/32:16 pm -
Nonstop4h 44m
Deal found 10/30![United Airlines logo]()
$733
This Alaska Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:59 pm -
2 stops37h 00m
Wed 12/92:08 pm -
2 stops29h 26m
Deal found 11/2![Alaska Airlines logo]()
$1,259
This Alaska Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2111:28 am -
2 stops28h 53m
Wed 1/272:11 pm -
2 stops30h 29m
Deal found 10/31![Alaska Airlines logo]()
$1,261
This Alaska Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/238:20 pm -
2 stops25h 41m
Mon 1/46:00 am -
2 stops28h 06m
Deal found 10/30![Alaska Airlines logo]()
$1,273
This Alaska Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:00 am -
2 stops33h 10m
Sat 1/166:57 pm -
2 stops25h 43m
Deal found 10/31![Alaska Airlines logo]()
$1,283
Last-minute flights from San Juan to ChicagoDiscover last-minute flight deals from San Juan to Chicago. Data last updated November 3, 2026 and is based on user searches.
Discover last-minute flight deals from San Juan to Chicago. Data last updated November 3, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:55 pm -
1 stop10h 18m
Thu 11/2611:53 pm -
Nonstop4h 39m
Deal found 11/3![Frontier logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/207:12 pm -
Nonstop5h 09m
Fri 11/272:52 pm -
1 stop22h 08m
Deal found 11/1![Frontier logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/227:17 am -
1 stop14h 30m
Thu 11/261:16 pm -
1 stop10h 20m
Deal found 11/1![Frontier logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:00 am -
1 stop11h 57m
Fri 11/272:52 pm -
1 stop22h 08m
Deal found 11/1![Frontier logo]()
$239
This eDestinos deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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.
Mon 11/237:12 pm -
Nonstop5h 09m
Fri 11/276:20 am -
1 stop10h 18m
Deal found 11/1![Frontier logo]()
$235
This Cheapflightsfares deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/267:12 pm -
Nonstop5h 09m
Thu 12/35:24 pm -
1 stop14h 41m
Deal found 10/29![Frontier logo]()
$238
This Trip.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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.
Thu 12/35:01 am -
1 stop13h 06m
Thu 12/108:37 pm -
1 stop24h 52m
Deal found 11/1![Frontier logo]()
$239
This OneTravel deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:01 am -
1 stop13h 06m
Sun 12/68:37 pm -
1 stop24h 52m
Deal found 11/3![Frontier logo]()
$241
This CheapOair deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:01 am -
1 stop13h 06m
Sun 12/68:37 pm -
1 stop27h 36m
Deal found 11/2![Frontier logo]()
$240
This OneTravel deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/85:01 am -
1 stop8h 32m
Sat 12/1212:28 pm -
1 stop10h 39m
Deal found 11/3![Frontier logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/2110:26 pm -
Nonstop5h 07m
Wed 12/3012:26 am -
Nonstop4h 53m
Deal found 11/1![Frontier logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/2410:26 pm -
Nonstop5h 07m
Sun 1/312:26 am -
Nonstop4h 39m
Deal found 11/1![Frontier logo]()
$236
One-way flights from San Juan to ChicagoSearch for one-way flight options from San Juan to Chicago. Find affordable one-way fares based on user searches. Data last updated November 3, 2026.
Search for one-way flight options from San Juan to Chicago. Find affordable one-way fares based on user searches. Data last updated November 3, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:12 pm -
Nonstop5h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/85:01 am -
1 stop18h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$125
This Cheapflightsfares deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:00 am -
1 stop12h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$126
This deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/87:00 am -
1 stop10h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$127
This JetBlue deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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.
Sun 12/206:45 am -
1 stop8h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![JetBlue logo]()
$129
This FlightHub deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/103:09 am -
1 stop23h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/119:52 pm -
2 stops26h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$131
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/2010:30 pm -
1 stop13h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Southwest logo]()
$133
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/23:50 pm -
Nonstop5h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![American Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/82:49 am -
2 stops13h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$135
This Super.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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.
Tue 11/103:55 pm -
1 stop9h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$136
This Super.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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.
Tue 11/107:23 am -
1 stop11h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$136
Find flight deals from San Juan to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from San Juan (PR1) to Chicago (CHI). 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 November 3, 2026.
Round-trip from | $233 (Kiwi.com) |
|---|---|
One-way from | $122 (Cheapflightsfares) |
Popular in | June |
Cheapest in | February |
Average price | $384 |
Cheapflights Fare Finder
Customize your flight search to find flights from San Juan to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 3, 2026.
Use the filters below to find and compare flights from San Juan to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Fri 12/25
6:24 pm-11:33 pm
1 stop7h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$129
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Sun 12/20
6:45 am-1:30 pm
1 stop8h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$129
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Wed 1/20
11:45 am-6:55 pm
1 stop9h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$129
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Sun 12/20
10:30 pm-9:55 am
1 stop13h 25m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$133
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Thu 12/24
2:05 am-10:49 am
1 stop10h 44m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$133
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Sat 2/6
2:05 am-10:02 am
1 stop9h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$133
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 1/21
4:10 pm-11:55 pm
1 stop9h 45m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$145
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Fri 12/25
7:50 am-5:29 pm
1 stop11h 39m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$145
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Tue 11/10
8:25 am-11:47 am
Nonstop5h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$149
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 1/13
7:25 am-2:45 pm
2 stops9h 20m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$153
Showing 1-10 of 41 resultsSorted by cheapest first
Best time to book a flight from San Juan to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from San Juan with our price prediction graph.
PR1-CHI
SJU-MDW
SJU-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from San Juan to Chicago
PR1-CHI
SJU-MDW
SJU-ORD
What is the cheapest month to book a flight from San Juan to Chicago?
Currently, February is the cheapest month in which you can book a flight from San Juan to Chicago (average of $218). Flying from San Juan to Chicago in June is currently the most expensive (average of $448). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from SJU to CHI?
Find hourly flight availability from San Juan to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 3, 2026.
When flying from San Juan to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 30% versus a flight in the afternoon.
Weekly flight availability from San Juan to Chicago
Explore weekly flight availability from San Juan to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 3, 2026.
The most flights from PR1 to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).
How much does it cost to fly round-trip from San Juan to Chicago?
Airfare is below average for this route at the moment.
San Juan to Chicago flights typically cost between $324 and $480 in November.The cheapest round-trip price found within the last 5 days was $233 on Frontier (Nov 22-Nov 26).
How often are flights from San Juan to Chicago delayed?
About 9% of weekly flights between San Juan and Chicago have experienced delays in the past year, with the average delay time being 187 minutes.
What is the most punctual flight time for San Juan to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on San Juan to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 4% of flights being delayed.
How far ahead should I book a flight from San Juan to Chicago?
To ensure you get the cheapest price possible for a flight from San Juan to Chicago, you should look to book at least 81 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 San Juan to Chicago?
Use this chart to determine the cheapest time to fly round-trip from San Juan to Chicago. Price data was last updated on October 31, 2026.
Travelers seeking maximum savings on their San Juan to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated November 3, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andJetBlue from San Juan to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from San Juan to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for San Juan to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on November 3, 2026.
Complete your trip
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San Juan and Chicago flights
Browse other San Juan and Chicago flight options. Last updated on November 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from San Juan to Chicago
Discover the top 5 airlines that operate flights from San Juan to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$116 | Average$274 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$136 | Average$231 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$226 | Average$386 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$253 | Average$447 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$476 | FlexibilityNo cancel fee | On-time63% |