$127+ Cheap flights from San Juan to Chicago (CHI)
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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Sep 4 — Sep 111
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 August 5, 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 August 5, 2026.
This eDestinos deal was found by Cheapflights users on 8/2. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:14 pm -
Nonstop5h 13m
Sun 8/3012:44 am -
Nonstop5h 00m
Deal found 8/2![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:45 am -
1 stop31h 00m
Wed 9/307:11 am -
1 stop29h 23m
Deal found 7/31![Frontier logo]()
$180
This eDestinos deal was found by Cheapflights users on 8/2. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:14 pm -
Nonstop5h 13m
Sat 8/2912:44 am -
Nonstop5h 00m
Deal found 8/2![Frontier logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Wed 9/168:45 am -
1 stop31h 00m
Wed 9/237:11 am -
1 stop29h 23m
Deal found 8/2![Frontier logo]()
$217
This Super.com deal was found by Cheapflights users on 8/1. 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.
Sat 8/297:14 pm -
Nonstop5h 13m
Fri 9/412:44 am -
Nonstop5h 00m
Deal found 8/1![Frontier logo]()
$224
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:14 pm -
Nonstop5h 13m
Sun 9/612:44 am -
Nonstop5h 00m
Deal found 7/31![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:45 am -
1 stop31h 00m
Wed 9/237:11 am -
1 stop29h 23m
Deal found 8/3![Frontier logo]()
$229
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/161:20 pm -
1 stop6h 50m
Tue 9/227:30 am -
1 stop10h 35m
Deal found 8/4![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/510:25 am -
1 stop10h 20m
Tue 9/159:40 am -
1 stop7h 30m
Deal found 8/4![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 8/2. 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.
Tue 11/35:40 am -
1 stop7h 40m
Tue 11/31:20 pm -
1 stop7h 00m
Deal found 8/2![Southwest logo]()
$271
This Southwest deal was found by Cheapflights users on 7/30. 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 9/175:00 am -
1 stop7h 45m
Tue 9/227:30 am -
1 stop10h 35m
Deal found 7/30![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/46:00 am -
2 stops9h 30m
Tue 9/812:45 pm -
2 stops8h 20m
Deal found 8/4![Southwest logo]()
$291
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 August 5, 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 August 5, 2026.
This Southwest deal was found by Cheapflights users on 7/31. 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.
Tue 9/151:20 pm -
1 stop6h 50m
Tue 9/2212:20 pm -
1 stop8h 45m
Deal found 7/31![Southwest logo]()
$276
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Thu 9/173:56 pm -
Nonstop5h 09m
Tue 9/228:55 am -
Nonstop4h 49m
Deal found 7/31![United Airlines logo]()
$377
This Sun Country Air deal was found by Cheapflights users on 7/31. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/245:20 pm -
1 stop19h 03m
Mon 12/287:40 pm -
1 stop18h 39m
Deal found 7/31![Sun Country Air logo]()
$548
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/58:20 am -
2 stops9h 25m
Tue 9/158:30 am -
1 stop6h 55m
Deal found 8/4![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 8/1. 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.
Tue 10/65:05 am -
2 stops10h 35m
Thu 10/82:50 pm -
2 stops8h 15m
Deal found 8/1![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/151:20 pm -
1 stop6h 50m
Sat 9/1911:45 am -
2 stops9h 15m
Deal found 8/4![Southwest logo]()
$320
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/22:20 pm -
1 stop10h 06m
Sun 9/65:00 am -
1 stop7h 45m
Deal found 8/4![United Airlines logo]()
$416
This Southwest deal was found by Cheapflights users on 7/30. 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 8/208:55 pm -
1 stop12h 50m
Mon 8/241:00 pm -
1 stop8h 50m
Deal found 7/30![Southwest logo]()
$320
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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
Mon 11/302:16 pm -
Nonstop4h 44m
Deal found 8/4![United Airlines logo]()
$427
This Southwest deal was found by Cheapflights users on 8/1. 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.
Wed 10/712:40 pm -
2 stops10h 15m
Mon 10/126:40 pm -
1 stop13h 30m
Deal found 8/1![Southwest logo]()
$326
This Delta deal was found by Cheapflights users on 7/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/32:59 pm -
1 stop9h 58m
Mon 9/75:30 am -
1 stop7h 12m
Deal found 7/31![Delta logo]()
$1,092
This United Airlines deal was found by Cheapflights users on 8/1. 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.
Thu 9/173:56 pm -
Nonstop5h 09m
Mon 9/218:55 am -
Nonstop4h 49m
Deal found 8/1![United Airlines logo]()
$457
This Southwest deal was found by Cheapflights users on 7/31. 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.
Wed 9/96:00 am -
2 stops8h 05m
Mon 9/143:10 pm -
2 stops7h 45m
Deal found 7/31![Southwest logo]()
$380
This United Airlines deal was found by Cheapflights users on 7/31. 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 9/252:55 pm -
1 stop10h 28m
Mon 9/288:55 am -
Nonstop4h 49m
Deal found 7/31![United Airlines logo]()
$472
This Southwest deal was found by Cheapflights users on 7/31. 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 8/138:55 pm -
2 stops15h 30m
Sun 8/161:30 pm -
2 stops8h 55m
Deal found 7/31![Southwest logo]()
$396
This Sun Country Air deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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.
Mon 12/215:20 pm -
1 stop19h 03m
Sat 12/268:30 pm -
1 stop15h 37m
Deal found 8/4![Sun Country Air logo]()
$773
This Southwest deal was found by Cheapflights users on 7/31. 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.
Fri 8/146:30 am -
1 stop10h 05m
Sat 8/227:50 am -
2 stops9h 15m
Deal found 7/31![Southwest logo]()
$401
This Southwest deal was found by Cheapflights users on 8/2. 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.
Fri 9/45:00 am -
1 stop7h 45m
Mon 9/75:00 am -
1 stop7h 45m
Deal found 8/2![Southwest logo]()
$445
This United Airlines deal was found by Cheapflights users on 8/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:00 am -
2 stops11h 46m
Mon 8/248:50 am -
1 stop10h 48m
Deal found 8/3![United Airlines logo]()
$700
This United Airlines deal was found by Cheapflights users on 8/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/258:05 am -
2 stops9h 06m
Wed 12/3011:07 am -
1 stop11h 29m
Deal found 8/3![United Airlines logo]()
$908
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Wed 9/93:56 pm -
Nonstop5h 09m
Mon 9/148:55 am -
Nonstop4h 49m
Deal found 7/31![United Airlines logo]()
$1,012
Last-minute flights from San Juan to ChicagoDiscover last-minute flight deals from San Juan to Chicago. Data last updated August 5, 2026 and is based on user searches.
Discover last-minute flight deals from San Juan to Chicago. Data last updated August 5, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:00 am -
1 stop31h 15m
Sun 8/1612:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$283
This Cheapflightsfares deal was found by Cheapflights users on 7/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:05 am -
1 stop9h 34m
Wed 8/192:35 pm -
1 stop7h 45m
Deal found 7/31![JetBlue logo]()
$298
This eDestinos deal was found by Cheapflights users on 8/1. 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.
Thu 8/137:14 pm -
Nonstop5h 13m
Sun 8/3012:44 am -
Nonstop5h 00m
Deal found 8/1![Frontier logo]()
$256
This Frontier deal was found by Cheapflights users on 8/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:14 pm -
Nonstop5h 13m
Mon 8/1712:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$268
This eDestinos deal was found by Cheapflights users on 8/1. 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.
Fri 8/143:10 am -
1 stop21h 00m
Mon 8/1712:44 am -
Nonstop5h 00m
Deal found 8/1![Frontier logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1410:48 pm -
1 stop25h 22m
Sun 8/1612:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$282
This Expedia deal was found by Cheapflights users on 8/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/143:10 am -
1 stop21h 00m
Sun 8/2312:44 am -
Nonstop5h 00m
Deal found 8/1![Frontier logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Fri 8/146:00 am -
1 stop31h 15m
Sat 8/2212:44 am -
Nonstop5h 00m
Deal found 8/2![Frontier logo]()
$299
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/46:00 am -
2 stops9h 30m
Tue 9/812:45 pm -
2 stops8h 20m
Deal found 8/4![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/510:25 am -
1 stop10h 20m
Tue 9/159:40 am -
1 stop7h 30m
Deal found 8/4![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/161:20 pm -
1 stop6h 50m
Tue 9/227:30 am -
1 stop10h 35m
Deal found 8/4![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 7/30. 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 9/175:00 am -
1 stop7h 45m
Tue 9/227:30 am -
1 stop10h 35m
Deal found 7/30![Southwest logo]()
$276
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 August 5, 2026.
Search for one-way flight options from San Juan to Chicago. Find affordable one-way fares based on user searches. Data last updated August 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 11/16:12 pm -
1 stop23h 12m
Deal found 8/1![Frontier logo]()
$127
This Southwest deal was found by Cheapflights users on 8/3. 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.
Thu 8/2710:00 am -
1 stop9h 00m
Deal found 8/3![Southwest logo]()
$128
This Super.com deal was found by Cheapflights users on 8/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:24 pm -
2 stops16h 34m
Deal found 7/30![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:00 am -
1 stop8h 45m
Deal found 8/3![Frontier logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:00 am -
1 stop8h 45m
Deal found 8/3![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/298:45 am -
2 stops34h 06m
Deal found 7/31![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/16:35 am -
1 stop31h 15m
Deal found 8/4![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Thu 10/295:12 pm -
1 stop23h 12m
Deal found 8/2![Frontier logo]()
$137
This Southwest deal was found by Cheapflights users on 7/31. 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.
Wed 9/301:20 pm -
1 stop6h 50m
Deal found 7/31![Southwest logo]()
$138
This Frontier deal was found by Cheapflights users on 8/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 10/57:00 am -
2 stops17h 44m
Deal found 8/1![Frontier logo]()
$140
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 August 5, 2026.
Round-trip from | $179 (eDestinos) |
|---|---|
One-way from | $127 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $287 |
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 2,558,603 searches. Data last updated August 5, 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 - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 9/15
1:20 pm-7:10 pm
1 stop6h 50m
Chicago Midway
Tue 9/22
12:20 pm-10:05 pm
1 stop8h 45m
$276
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 9/5
8:20 am-4:45 pm
2 stops9h 25m
Chicago Midway
Tue 9/15
8:30 am-4:25 pm
1 stop6h 55m
$291
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 10/6
5:05 am-2:40 pm
2 stops10h 35m
Chicago Midway
Thu 10/8
2:50 pm-12:05 am
2 stops8h 15m
$301
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 9/15
1:20 pm-7:10 pm
1 stop6h 50m
Chicago Midway
Sat 9/19
11:45 am-10:00 pm
2 stops9h 15m
$320
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 8/20
8:55 pm-8:45 am
1 stop12h 50m
Chicago Midway
Mon 8/24
1:00 pm-10:50 pm
1 stop8h 50m
$320
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 10/7
12:40 pm-9:55 pm
2 stops10h 15m
Chicago Midway
Mon 10/12
6:40 pm-9:10 am
1 stop13h 30m
$326
Quickest round-trip
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 9/17
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Tue 9/22
8:55 am-2:44 pm
Nonstop4h 49m
$377
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 9/9
6:00 am-1:05 pm
2 stops8h 05m
Chicago Midway
Mon 9/14
3:10 pm-11:55 pm
2 stops7h 45m
$380
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 8/13
8:55 pm-11:25 am
2 stops15h 30m
Chicago Midway
Sun 8/16
1:30 pm-11:25 pm
2 stops8h 55m
$396
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 8/14
6:30 am-3:35 pm
1 stop10h 05m
Chicago Midway
Sat 8/22
7:50 am-6:05 pm
2 stops9h 15m
$401
Showing 1-10 of 45 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 $227). Flying from San Juan to Chicago in June is currently the most expensive (average of $447). 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 August 5, 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 28% 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 August 5, 2026.
The most flights from PR1 to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 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 $249 and $367 in August.The cheapest round-trip price found within the last 5 days was $179 on Frontier (Aug 27-Aug 30).
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 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?
Thursday tends to have the lowest number of delays on this route, whereas Tuesday 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 August 1, 2026.
Travelers seeking maximum savings on their San Juan to Chicago flight should consider departing on Sunday at noon 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 August 5, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines 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.
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from 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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for San Juan to Chicago
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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 August 5, 2026.
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San Juan and Chicago flights
Browse other San Juan and Chicago flight options. Last updated on August 5, 2026.
Popular flight searches
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Top 6 airlines flying from San Juan to Chicago
Discover the top 6 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 2,558,603 searches. Data last updated August 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$128 | Average$284 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$204 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$227 | Average$428 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$266 | Average$490 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$267 | Average$477 | FlexibilityNo cancel fee | On-time69% |