$116+ Cheap flights from Puerto Rico 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Nov 4 — Nov 111
Round-trip
1 adult, Economy
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Find cheap flights from Puerto Rico 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.Cheap flight deals from Puerto Rico to Chicago
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Cheapest flights from Puerto Rico to ChicagoExplore the most affordable flight options available from Puerto Rico to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 5, 2026.
Explore the most affordable flight options available from Puerto Rico to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 5, 2026.
This CheapOair deal was found by Cheapflights users on 9/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:56 pm -
1 stop22h 27m
Mon 11/24:42 pm -
1 stop21h 35m
Deal found 9/30![Frontier logo]()
$224
This Cheapflightsfares deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/165:11 pm -
1 stop7h 32m
Mon 10/196:15 am -
1 stop8h 51m
Deal found 10/5![Frontier logo]()
$226
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:42 pm -
1 stop14h 09m
Sat 10/174:41 pm -
1 stop21h 38m
Deal found 9/30![Frontier logo]()
$226
This OneTravel deal was found by Cheapflights users on 10/4. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:15 am -
1 stop17h 24m
Sun 10/256:00 am -
1 stop18h 17m
Deal found 10/4![Frontier logo]()
$227
This Expedia deal was found by Cheapflights users on 10/1. 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 10/165:11 pm -
1 stop7h 32m
Tue 10/206:21 am -
1 stop8h 45m
Deal found 10/1![Frontier logo]()
$228
This Expedia deal was found by Cheapflights users on 10/1. 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.
Thu 10/1512:59 am -
1 stop22h 40m
Tue 10/208:46 am -
1 stop16h 07m
Deal found 10/1![Frontier logo]()
$228
This CheapOair deal was found by Cheapflights users on 10/2. 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.
Thu 10/2210:52 am -
1 stop21h 39m
Wed 10/289:51 am -
1 stop23h 01m
Deal found 10/2![Frontier logo]()
$230
This Cheapflightsfares deal was found by Cheapflights users on 10/1. 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.
Tue 10/62:57 am -
1 stop29h 34m
Tue 11/179:51 am -
1 stop22h 24m
Deal found 10/1![Frontier logo]()
$231
This CheapOair deal was found by Cheapflights users on 10/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:11 pm -
1 stop7h 32m
Tue 10/136:21 am -
1 stop8h 45m
Deal found 10/1![Frontier logo]()
$233
This Cheapflightsfares deal was found by Cheapflights users on 10/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:15 am -
1 stop10h 22m
Mon 11/27:55 am -
1 stop29h 24m
Deal found 10/4![Frontier logo]()
$233
This OneTravel deal was found by Cheapflights users on 10/2. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/145:11 pm -
1 stop7h 32m
Mon 10/196:15 am -
1 stop8h 51m
Deal found 10/2![Frontier logo]()
$234
This Cheapflightsfares deal was found by Cheapflights users on 10/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:31 am -
1 stop18h 03m
Sun 11/2911:53 pm -
Nonstop4h 39m
Deal found 10/4![Frontier logo]()
$234
Best flights from Puerto Rico to ChicagoDiscover carefully curated flight deals from Puerto Rico to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 5, 2026.
Discover carefully curated flight deals from Puerto Rico to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 5, 2026.
This JetBlue deal was found by Cheapflights users on 9/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:25 am -
1 stop8h 19m
Tue 11/31:00 pm -
1 stop10h 13m
Deal found 9/30![JetBlue logo]()
$241
This Southwest deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:50 pm -
1 stop10h 55m
Mon 11/28:40 pm -
1 stop11h 15m
Deal found 10/5![Southwest logo]()
$246
This United Airlines deal was found by Cheapflights users on 10/2. 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.
Tue 11/108:25 am -
Nonstop5h 22m
Sun 11/155:55 am -
1 stop6h 45m
Deal found 10/2![United Airlines logo]()
$266
This CheapOair deal was found by Cheapflights users on 10/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:57 am -
1 stop22h 49m
Mon 11/169:51 am -
1 stop23h 01m
Deal found 10/1![Frontier logo]()
$304
This Priceline deal was found by Cheapflights users on 10/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:43 am -
1 stop10h 19m
Tue 10/207:00 am -
1 stop16h 29m
Deal found 10/1![Multiple Airlines logo]()
$432
This Southwest deal was found by Cheapflights users on 9/30. 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 11/135:50 pm -
1 stop7h 25m
Mon 11/163:00 pm -
1 stop7h 50m
Deal found 9/30![Southwest logo]()
$246
This United Airlines deal was found by Cheapflights users on 10/2. 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.
Tue 10/203:56 pm -
Nonstop5h 09m
Tue 10/272:16 pm -
Nonstop4h 44m
Deal found 10/2![United Airlines logo]()
$281
This Southwest deal was found by Cheapflights users on 10/3. 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 10/155:30 am -
2 stops8h 55m
Mon 10/192:15 pm -
1 stop9h 10m
Deal found 10/3![Southwest logo]()
$286
This United Airlines deal was found by Cheapflights users on 10/1. 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 10/223:56 pm -
Nonstop5h 09m
Sun 10/252:16 pm -
Nonstop4h 44m
Deal found 10/1![United Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 10/3. 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.
Fri 11/136:05 am -
2 stops10h 20m
Sun 11/1512:50 pm -
1 stop8h 45m
Deal found 10/3![Southwest logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 10/1. 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 10/169:43 am -
1 stop23h 08m
Tue 10/206:00 am -
2 stops49h 52m
Deal found 10/1![Frontier logo]()
$378
This Southwest deal was found by Cheapflights users on 10/3. 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 12/36:10 am -
2 stops8h 45m
Tue 12/81:20 pm -
2 stops9h 25m
Deal found 10/3![Southwest logo]()
$286
This United Airlines deal was found by Cheapflights users on 9/30. 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.
Thu 10/2912:09 am -
1 stop10h 36m
Mon 11/22:30 pm -
1 stop7h 27m
Deal found 9/30![United Airlines logo]()
$350
This Southwest deal was found by Cheapflights users on 9/30. 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.
Sun 11/15:35 am -
1 stop6h 50m
Sun 11/88:40 pm -
1 stop13h 10m
Deal found 9/30![Southwest logo]()
$301
This Mytrip deal was found by Cheapflights users on 10/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:52 am -
2 stops14h 32m
Wed 10/287:15 am -
2 stops25h 37m
Deal found 10/2![Frontier logo]()
$432
This United Airlines deal was found by Cheapflights users on 10/2. 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 10/193:56 pm -
Nonstop5h 09m
Mon 10/262:16 pm -
Nonstop4h 44m
Deal found 10/2![United Airlines logo]()
$361
This Southwest deal was found by Cheapflights users on 10/2. 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 11/65:50 pm -
1 stop7h 25m
Fri 11/1312:50 pm -
1 stop8h 45m
Deal found 10/2![Southwest logo]()
$301
This CheapOair deal was found by Cheapflights users on 10/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/183:20 am -
1 stop21h 10m
Mon 10/267:00 am -
1 stop16h 11m
Deal found 10/4![JetBlue logo]()
$489
This Orbitz deal was found by Cheapflights users on 10/4. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:54 am -
1 stop22h 52m
Mon 11/22:50 pm -
1 stop9h 00m
Deal found 10/4![Multiple Airlines logo]()
$493
This Kiwi.com deal was found by Cheapflights users on 10/4. 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.
Fri 10/3011:37 am -
1 stop22h 09m
Mon 11/27:50 pm -
2 stops37h 27m
Deal found 10/4![Frontier logo]()
$455
This United Airlines deal was found by Cheapflights users on 9/30. 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.
Tue 10/273:55 pm -
Nonstop5h 31m
Tue 11/32:16 pm -
Nonstop4h 44m
Deal found 9/30![United Airlines logo]()
$377
This Southwest deal was found by Cheapflights users on 10/2. 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.
Thu 10/155:30 am -
2 stops8h 55m
Tue 10/201:40 pm -
2 stops8h 30m
Deal found 10/2![Southwest logo]()
$321
This Priceline deal was found by Cheapflights users on 10/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:01 am -
1 stop9h 43m
Sat 11/77:05 am -
2 stops48h 42m
Deal found 10/3![Multiple Airlines logo]()
$526
This United Airlines deal was found by Cheapflights users on 10/4. 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 10/153:56 pm -
Nonstop5h 09m
Mon 10/195:00 am -
1 stop7h 45m
Deal found 10/4![United Airlines logo]()
$382
This Mytrip deal was found by Cheapflights users on 10/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:52 am -
3 stops25h 29m
Wed 10/2812:30 pm -
3 stops20h 22m
Deal found 10/2![Multiple Airlines logo]()
$529
This Southwest deal was found by Cheapflights users on 10/2. 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 10/208:15 am -
2 stops12h 05m
Thu 11/1212:45 pm -
2 stops10h 25m
Deal found 10/2![Southwest logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 10/4. 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.
Fri 12/253:47 am -
1 stop23h 22m
Wed 12/304:10 pm -
2 stops32h 42m
Deal found 10/4![Frontier logo]()
$518
This Southwest deal was found by Cheapflights users on 10/4. 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.
Mon 10/1910:50 pm -
1 stop12h 00m
Fri 10/2312:50 pm -
1 stop6h 10m
Deal found 10/4![Southwest logo]()
$345
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Wed 10/287:25 am -
Nonstop5h 22m
Wed 11/42:16 pm -
Nonstop4h 44m
Deal found 10/1![United Airlines logo]()
$419
This United Airlines deal was found by Cheapflights users on 10/3. 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.
Tue 11/178:25 am -
Nonstop5h 22m
Mon 11/302:16 pm -
Nonstop4h 44m
Deal found 10/3![United Airlines logo]()
$449
Last-minute flights from Puerto Rico to ChicagoDiscover last-minute flight deals from Puerto Rico to Chicago. Data last updated October 5, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Chicago. Data last updated October 5, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 10/1. 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.
Tue 10/62:57 am -
1 stop29h 34m
Tue 11/179:51 am -
1 stop22h 24m
Deal found 10/1![Frontier logo]()
$231
This CheapOair deal was found by Cheapflights users on 10/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:11 pm -
1 stop7h 32m
Tue 10/136:21 am -
1 stop8h 45m
Deal found 10/1![Frontier logo]()
$233
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:39 am -
1 stop22h 12m
Sun 10/186:00 am -
1 stop18h 17m
Deal found 9/30![Frontier logo]()
$226
This OneTravel deal was found by Cheapflights users on 10/2. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/145:11 pm -
1 stop7h 32m
Mon 10/196:15 am -
1 stop8h 51m
Deal found 10/2![Frontier logo]()
$234
This Expedia deal was found by Cheapflights users on 10/1. 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.
Thu 10/1512:59 am -
1 stop22h 40m
Tue 10/208:46 am -
1 stop16h 07m
Deal found 10/1![Frontier logo]()
$228
This Cheapflightsfares deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/165:11 pm -
1 stop7h 32m
Mon 10/196:15 am -
1 stop8h 51m
Deal found 10/5![Frontier logo]()
$226
This Expedia deal was found by Cheapflights users on 10/1. 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 10/165:11 pm -
1 stop7h 32m
Tue 10/206:21 am -
1 stop8h 45m
Deal found 10/1![Frontier logo]()
$228
This CheapOair deal was found by Cheapflights users on 10/2. 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.
Thu 10/2210:52 am -
1 stop21h 39m
Wed 10/289:51 am -
1 stop23h 01m
Deal found 10/2![Frontier logo]()
$230
This OneTravel deal was found by Cheapflights users on 10/4. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:15 am -
1 stop17h 24m
Sun 10/256:00 am -
1 stop18h 17m
Deal found 10/4![Frontier logo]()
$227
This CheapOair deal was found by Cheapflights users on 9/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:56 pm -
1 stop22h 27m
Mon 11/24:42 pm -
1 stop21h 35m
Deal found 9/30![Frontier logo]()
$224
This Cheapflightsfares deal was found by Cheapflights users on 10/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:15 am -
1 stop10h 22m
Mon 11/27:55 am -
1 stop29h 24m
Deal found 10/4![Frontier logo]()
$233
This Cheapflightsfares deal was found by Cheapflights users on 10/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:31 am -
1 stop18h 03m
Sun 11/2911:53 pm -
Nonstop4h 39m
Deal found 10/4![Frontier logo]()
$234
One-way flights from Puerto Rico to ChicagoSearch for one-way flight options from Puerto Rico to Chicago. Find affordable one-way fares based on user searches. Data last updated October 5, 2026.
Search for one-way flight options from Puerto Rico to Chicago. Find affordable one-way fares based on user searches. Data last updated October 5, 2026.
This Super.com deal was found by Cheapflights users on 10/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/114:24 pm -
1 stop19h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 10/4. 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.
Sat 12/55:01 am -
1 stop8h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 10/1. 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.
Wed 10/284:52 pm -
2 stops17h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Frontier logo]()
$117
This JetBlue deal was found by Cheapflights users on 10/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:25 am -
1 stop9h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![JetBlue logo]()
$119
This Super.com deal was found by Cheapflights users on 10/1. 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.
Sun 12/208:46 pm -
1 stop23h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Frontier logo]()
$121
This Super.com deal was found by Cheapflights users on 9/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:25 am -
1 stop9h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![JetBlue logo]()
$122
This Southwest deal was found by Cheapflights users on 10/4. 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 11/36:10 am -
1 stop8h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Southwest logo]()
$123
This JetBlue deal was found by Cheapflights users on 10/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:25 am -
1 stop9h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![JetBlue logo]()
$123
This JetBlue deal was found by Cheapflights users on 10/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:25 am -
1 stop9h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![JetBlue logo]()
$124
This United Airlines deal was found by Cheapflights users on 10/4. 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.
Sat 1/231:09 am -
1 stop10h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![United Airlines logo]()
$125
This Delta deal was found by Cheapflights users on 10/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:45 am -
1 stop11h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Delta logo]()
$125
This Cheapflightsfares deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/87:20 am -
1 stop11h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Frontier logo]()
$127
Find flight deals from Puerto Rico to Chicago
Keep the following information in mind while searching for Puerto Rico to Chicago flight deals. Data was last updated October 5, 2026.
Round-trip from | $224 (CheapOair) |
|---|---|
One-way from | $116 (Super.com) |
Popular in | June |
Cheapest in | February |
Average price | $467 |
Good round-trip deal | $312 or less |
Good one-way deal | $189 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Puerto Rico 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 October 5, 2026.
Use the filters below to find and compare flights from Puerto Rico 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
Tue 11/3
5:30 pm-11:57 pm
1 stop8h 27m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$119
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Thu 12/3
8:25 am-11:49 am
Nonstop5h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$119
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Wed 11/4
4:55 pm-8:26 pm
Nonstop5h 31m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$119
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Thu 11/12
5:30 pm-11:36 pm
1 stop8h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$119
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-12:00 pm
2 stops15h 30m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$123
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Sun 12/20
6:24 pm-11:33 pm
1 stop7h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$123
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Sat 11/14
6:25 am-1:42 pm
1 stop9h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$123
AguadillaChicago
BQN Aguadilla Borinquen - ORD Chicago O'Hare Intl
BQNORD
Aguadilla Borinquen
Sat 1/23
1:09 am-10:02 am
1 stop10h 53m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$125
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 12/3
10:45 am-7:05 pm
2 stops10h 20m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$143
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 10/20
8:15 am-7:20 pm
2 stops12h 05m
Chicago Midway
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$143
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Puerto Rico to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Puerto Rico with our price prediction graph.
SJU-ORD
SJU-MDW
BQN-ORD
PSE-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 Puerto Rico to Chicago
PR0-CHI
SJU-ORD
SJU-MDW
BQN-ORD
PSE-ORD
What is the cheapest month to book a flight from Puerto Rico to Chicago?
Currently, February is the cheapest month in which you can book a flight from Puerto Rico to Chicago (average of $218). Flying from Puerto Rico 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 PR to CHI?
Find hourly flight availability from Puerto Rico 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 October 5, 2026.
When flying from Puerto Rico 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 29% versus a flight in the afternoon.
Weekly flight availability from Puerto Rico to Chicago
Explore weekly flight availability from Puerto Rico 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 October 5, 2026.
The most flights from PR0 to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).
How often are flights from Puerto Rico to Chicago delayed?
About 9% of weekly flights between Puerto Rico 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 Puerto Rico 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 Puerto Rico 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 Puerto Rico to Chicago?
Booking 81 days in advance of your planned departure date is, on average, the best time to get cheap flights from Puerto Rico to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Puerto Rico to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Puerto Rico to Chicago. Price data was last updated on October 3, 2026.
Travelers seeking maximum savings on their Puerto Rico 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 October 5, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andJetBlue from Puerto Rico 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.
Entertainment
7.5
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
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 Puerto Rico 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
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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Alternative routes for Puerto Rico 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 October 5, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Puerto Rico to Chicago by cabin class
Find flights from Puerto Rico to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Puerto Rico and Chicago flights
Browse other Puerto Rico and Chicago flight options. Last updated on October 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Puerto Rico to Chicago
Discover the top 6 airlines that operate flights from Puerto Rico 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 October 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$538 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$266 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$228 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$226 | Average$409 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$257 | Average$458 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$476 | FlexibilityNo cancel fee | On-time63% |