$119+ Cheap flights from Puerto Rico 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Jul 25 — Aug 11
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
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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 June 25, 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 June 25, 2026.
This Priceline deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/287:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Sun 8/3012:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/22![Frontier logo]()
$235
This United Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 9/53:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Tue 9/88:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 6/21![United Airlines logo]()
$237
This Frontier deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/207:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Mon 8/2412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/21![Frontier logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Tue 9/87:44 pm
ORD
- SJU
1 stop16h 32m
Frontier
Deal found 6/21![Frontier logo]()
$239
This Frontier deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Sun 8/2312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/24![Frontier logo]()
$240
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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
SJU
- MDW
2 stops15h 30m
Southwest
Fri 8/212:55 pm
MDW
- SJU
1 stop6h 15m
Southwest
Deal found 6/24![Southwest logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Mon 8/3112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/21![Frontier logo]()
$241
This American Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:24 pm
SJU
- ORD
1 stop13h 10m
American Airlines
Sun 8/235:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 6/20![American Airlines logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 8/287:14 pm
SJU
- ORD
Nonstop5h 13m
Multiple Airlines
Mon 8/318:05 am
ORD
- SJU
2 stops15h 51m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$243
This eDestinos deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/97:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Sat 7/1112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/24![Frontier logo]()
$244
This Frontier deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Tue 8/1112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/23![Frontier logo]()
$245
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/286:00 am
SJU
- MDW
2 stops9h 30m
Southwest
Mon 8/313:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 6/22![Southwest logo]()
$246
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 June 25, 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 June 25, 2026.
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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
SJU
- MDW
1 stop12h 50m
Southwest
Sun 8/238:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Deal found 6/24![Southwest logo]()
$246
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/284:55 pm
SJU
- ORD
1 stop7h 45m
United Airlines
Mon 8/316:30 am
ORD
- SJU
1 stop8h 12m
United Airlines
Deal found 6/22![United Airlines logo]()
$246
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:56 pm
SJU
- ORD
1 stop8h 59m
Delta
Sun 9/66:40 am
ORD
- SJU
1 stop8h 58m
Delta
Deal found 6/24![Delta logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/183:10 am
BQN
- ORD
1 stop20h 58m
Frontier
Wed 8/265:59 pm
ORD
- BQN
1 stop16h 10m
Frontier
Deal found 6/23![Frontier logo]()
$341
This JetBlue deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 9/234:23 pm
BQN
- ORD
1 stop8h 08m
JetBlue
Sat 9/261:00 pm
ORD
- BQN
1 stop8h 39m
JetBlue
Deal found 6/21![JetBlue logo]()
$393
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 8/206:00 am
SJU
- MDW
1 stop7h 40m
Southwest
Mon 8/243:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 6/24![Southwest logo]()
$246
This United Airlines deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:20 pm
SJU
- ORD
1 stop10h 06m
United Airlines
Mon 8/246:30 am
ORD
- SJU
1 stop8h 12m
United Airlines
Deal found 6/24![United Airlines logo]()
$246
This Priceline deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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.
Thu 7/233:10 am
BQN
- ORD
1 stop7h 01m
Multiple Airlines
Mon 7/278:10 pm
ORD
- BQN
2 stops16h 32m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$512
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Sun 8/308:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Deal found 6/23![Southwest logo]()
$246
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:49 pm
SJU
- ORD
1 stop7h 08m
Delta
Mon 8/315:30 am
ORD
- SJU
1 stop10h 08m
Delta
Deal found 6/23![Delta logo]()
$276
This KAYAK deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:00 am
SJU
- ORD
2 stops12h 42m
American Airlines
Tue 8/188:49 pm
ORD
- SJU
1 stop15h 35m
American Airlines
Deal found 6/22![American Airlines logo]()
$569
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 8/278:55 pm
SJU
- MDW
2 stops15h 30m
Southwest
Sun 8/308:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Deal found 6/24![Southwest logo]()
$246
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/272:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Sat 8/296:05 am
MDW
- SJU
1 stop9h 33m
Delta
Deal found 6/21![Delta logo]()
$346
This Cheapflightsfares deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/215:01 am
BQN
- ORD
1 stop9h 38m
JetBlue
Sat 8/83:20 pm
ORD
- BQN
1 stop8h 13m
JetBlue
Deal found 6/21![JetBlue logo]()
$414
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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.
Sun 8/165:49 pm
SJU
- ORD
1 stop7h 08m
Delta
Sun 8/235:30 am
ORD
- SJU
1 stop7h 12m
Delta
Deal found 6/22![Delta logo]()
$348
This JetBlue deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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.
Thu 8/135:05 am
SJU
- ORD
1 stop9h 34m
JetBlue
Mon 8/177:00 am
ORD
- SJU
1 stop10h 53m
JetBlue
Deal found 6/23![JetBlue logo]()
$416
This Frontier deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/711:52 am
BQN
- ORD
1 stop13h 58m
Frontier
Sun 11/154:44 pm
ORD
- BQN
1 stop8h 09m
Frontier
Deal found 6/20![Frontier logo]()
$486
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/156:25 am
SJU
- MDW
2 stops11h 40m
Southwest
Mon 8/243:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 6/23![Southwest logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/227:35 am
MAZ
- ORD
1 stop16h 52m
Multiple Airlines
Tue 7/2812:44 am
ORD
- MAZ
1 stop7h 58m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$517
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/22:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Mon 9/76:05 am
MDW
- SJU
1 stop9h 33m
Delta
Deal found 6/24![Delta logo]()
$401
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Sun 8/98:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Deal found 6/24![Southwest logo]()
$396
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/74:36 pm
MAZ
- ORD
2 stops20h 39m
Multiple Airlines
Fri 7/1012:44 am
ORD
- MAZ
1 stop11h 00m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$560
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 9/2212:15 am
BQN
- ORD
1 stop8h 26m
United Airlines
Sat 9/267:15 am
ORD
- BQN
2 stops14h 54m
United Airlines
Deal found 6/22![United Airlines logo]()
$561
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/142:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Sun 8/166:05 am
MDW
- SJU
1 stop6h 37m
Delta
Deal found 6/22![Delta logo]()
$426
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:00 am
SJU
- MDW
1 stop6h 45m
Southwest
Tue 7/712:00 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 6/23![Southwest logo]()
$426
This United Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/17:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Sun 7/122:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 6/21![United Airlines logo]()
$582
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 7/57:35 am
MAZ
- ORD
1 stop16h 52m
Multiple Airlines
Wed 7/812:44 am
ORD
- MAZ
1 stop14h 27m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$586
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/1812:15 am
BQN
- ORD
2 stops15h 40m
United Airlines
Wed 8/268:45 am
ORD
- BQN
2 stops13h 24m
United Airlines
Deal found 6/23![United Airlines logo]()
$592
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 9/32:20 pm
SJU
- ORD
1 stop11h 39m
United Airlines
Mon 9/71:00 pm
ORD
- SJU
2 stops9h 50m
United Airlines
Deal found 6/23![United Airlines logo]()
$754
This United deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/117:05 am
MAZ
- ORD
2 stops16h 42m
Multiple Airlines
Wed 12/238:55 am
ORD
- MAZ
1 stop28h 54m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$994
Last-minute flights from Puerto Rico to ChicagoDiscover last-minute flight deals from Puerto Rico to Chicago. Data last updated June 25, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Chicago. Data last updated June 25, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/27:14 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Fri 7/312:44 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/24![Frontier logo]()
$269
This eDestinos deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/27:14 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Sat 7/412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/23![Frontier logo]()
$272
This eDestinos deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/27:14 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Sun 7/512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/24![Frontier logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/37:14 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Fri 7/1012:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/23![Frontier logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/37:14 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Sun 7/1212:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/23![Frontier logo]()
$258
This Frontier deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/37:14 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Sun 7/512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/23![Frontier logo]()
$263
This eDestinos deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/37:14 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Sat 7/412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/22![Frontier logo]()
$281
This eDestinos deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/37:14 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Tue 7/712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/24![Frontier logo]()
$293
This eDestinos deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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.
Sun 7/57:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Sat 7/1112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/24![Frontier logo]()
$267
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1710:20 pm
SJU
- MDW
1 stop11h 30m
Southwest
Fri 8/72:55 pm
MDW
- SJU
1 stop7h 55m
Southwest
Deal found 6/23![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1710:20 pm
SJU
- MDW
1 stop12h 30m
Southwest
Mon 7/208:55 pm
MDW
- SJU
1 stop11h 05m
Southwest
Deal found 6/24![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2310:20 pm
SJU
- MDW
1 stop11h 55m
Southwest
Tue 7/284:40 pm
MDW
- SJU
1 stop6h 40m
Southwest
Deal found 6/24![Southwest logo]()
$326
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 June 25, 2026.
Search for one-way flight options from Puerto Rico to Chicago. Find affordable one-way fares based on user searches. Data last updated June 25, 2026.
This Frontier deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/21![Frontier logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/186:45 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 6/20![Frontier logo]()
$122
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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
SJU
- MDW
1 stop12h 50m
Southwest
Deal found 6/23![Southwest logo]()
$123
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/262:20 pm
SJU
- ORD
1 stop10h 06m
United Airlines
Deal found 6/23![United Airlines logo]()
$123
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/143:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 6/23![United Airlines logo]()
$124
This American Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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.
Fri 8/283:44 pm
SJU
- ORD
1 stop8h 46m
American Airlines
Deal found 6/21![American Airlines logo]()
$127
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 9/139:25 pm
SJU
- MDW
1 stop13h 35m
Southwest
Deal found 6/20![Southwest logo]()
$128
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:59 pm
SJU
- ORD
1 stop7h 00m
Delta
Deal found 6/23![Delta logo]()
$128
This eDestinos deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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.
Wed 7/87:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/22![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/76:00 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 6/21![Frontier logo]()
$130
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/295:55 am
SJU
- MDW
1 stop11h 45m
Southwest
Deal found 6/23![Southwest logo]()
$133
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:49 pm
SJU
- ORD
1 stop7h 08m
Delta
Deal found 6/22![Delta logo]()
$133
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 June 25, 2026.
Round-trip from | $235 (Priceline) |
|---|---|
One-way from | $119 (Frontier) |
Popular in | June |
Cheapest in | February |
Average price | $443 |
Good round-trip deal | $404 or less |
Good one-way deal | $191 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 2,558,603 searches. Data last updated June 25, 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 - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 8/20
8:55 pm-8:45 am
1 stop12h 50m
Chicago Midway
Sun 8/23
8:05 pm-9:10 am
1 stop12h 05m
$246
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 8/28
4:55 pm-11:40 pm
1 stop7h 45m
Chicago O'Hare Intl
Mon 8/31
6:30 am-3:42 pm
1 stop8h 12m
$246
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 9/2
12:56 pm-8:55 pm
1 stop8h 59m
Chicago O'Hare Intl
Sun 9/6
6:40 am-4:38 pm
1 stop8h 58m
$246
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 8/20
6:00 am-12:40 pm
1 stop7h 40m
Chicago Midway
Mon 8/24
3:15 pm-11:05 pm
1 stop6h 50m
$246
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 8/21
2:20 pm-11:26 pm
1 stop10h 06m
Chicago O'Hare Intl
Mon 8/24
6:30 am-3:42 pm
1 stop8h 12m
$246
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 8/26
5:15 am-12:05 pm
2 stops7h 50m
Chicago Midway
Sun 8/30
8:05 pm-9:10 am
1 stop12h 05m
$246
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 8/27
8:55 pm-11:25 am
2 stops15h 30m
Chicago Midway
Sun 8/30
8:05 pm-9:10 am
1 stop12h 05m
$246
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Mon 8/24
5:49 pm-11:57 pm
1 stop7h 08m
Chicago O'Hare Intl
Mon 8/31
5:30 am-4:38 pm
1 stop10h 08m
$276
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Tue 8/18
3:10 am-11:08 pm
1 stop20h 58m
Chicago O'Hare Intl
Wed 8/26
5:59 pm-11:09 am
1 stop16h 10m
$341
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 8/27
2:59 pm-10:36 pm
1 stop8h 37m
Chicago Midway
Sat 8/29
6:05 am-4:38 pm
1 stop9h 33m
$346
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
MAZ-ORD
BQN-MDW
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
MAZ-ORD
What is the cheapest month to book a flight from Puerto Rico to Chicago?
Currently, May is the cheapest month in which you can book a flight from Puerto Rico to Chicago (average of $64). Flying from Puerto Rico to Chicago in June is currently the most expensive (average of $915). 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 June 25, 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 22% 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 June 25, 2026.
The most flights from PR0 to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 on average).
How often are flights from Puerto Rico to Chicago delayed?
About 8% of weekly flights between Puerto Rico and Chicago have experienced delays in the past year, with the average delay time being 184 minutes.
What is the most punctual flight time for Puerto Rico 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 Saturday 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 June 20, 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. Sunday mornings 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 June 25, 2026.
Read reviews from past customers who have flown United Airlines,American 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.
Comfort
7.3
Crew
8.1
Overall
7.4
Food
6.6
Boarding
7.7
Entertainment
7.1
Reviews
1 / 20
6.0
GoodROHIT,Jun 2026
IND - EWR
Comfort
7.3
Crew
8.1
Overall
7.4
Food
6.6
Boarding
7.7
Entertainment
7.1
Reviews
1 / 20
6.0
GoodROHIT,Jun 2026
IND - EWR
Comfort
7.3
Crew
8.1
Overall
7.4
Food
6.6
Boarding
7.7
Entertainment
7.1
Reviews
1 / 20
6.0
GoodROHIT,Jun 2026
IND - EWR
Comfort
7.3
Crew
8.1
Overall
7.4
Food
6.6
Boarding
7.7
Entertainment
7.1
Reviews
1 / 20
6.0
GoodROHIT,Jun 2026
IND - EWR
Comfort
7.3
Crew
8.1
Overall
7.4
Food
6.6
Boarding
7.7
Entertainment
7.1
Reviews
1 / 20
6.0
GoodROHIT,Jun 2026
IND - EWR
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
Hammond
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.
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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 June 25, 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 June 25, 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 2,558,603 searches. Data last updated June 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$254 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$227 | Average$432 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$262 | Average$482 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$292 | Average$508 | FlexibilityNo cancel fee | On-time63% |