$93+ Cheap flights from Chicago (CHI) to Puerto Rico
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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Mar 5 — Mar 121
1 adult, Economy
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Find cheap flights from Chicago to Puerto Rico 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 Chicago to Puerto Rico
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Cheapest flights from Chicago to Puerto RicoExplore the most affordable flight options available from Chicago to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.
Explore the most affordable flight options available from Chicago to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.
This CheapOair deal was found by Cheapflights users on 2/2. 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.
Sun 3/17:23 pm
ORD
- SJU
1 stop21h 35m
Spirit Airlines
Fri 3/611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1710:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Wed 3/1812:55 pm
SJU
- ORD
1 stop7h 56m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$185
This Orbitz deal was found by Cheapflights users on 2/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/195:05 am
ORD
- SJU
1 stop7h 56m
Multiple Airlines
Tue 2/2412:32 pm
SJU
- ORD
Nonstop5h 16m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$186
This Booking.com deal was found by Cheapflights users on 2/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/233:50 pm
ORD
- SJU
1 stop6h 53m
Frontier
Tue 3/33:53 am
SJU
- ORD
1 stop13h 59m
Frontier
Deal found 2/2![Frontier logo]()
$187
This Frontier deal was found by Cheapflights users on 2/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:00 am
MDW
- SJU
1 stop8h 21m
Frontier
Fri 2/273:53 am
SJU
- MDW
1 stop13h 02m
Frontier
Deal found 2/2![Frontier logo]()
$187
This Orbitz deal was found by Cheapflights users on 2/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:15 am
ORD
- SJU
1 stop16h 38m
Frontier
Wed 2/255:25 pm
SJU
- ORD
1 stop19h 21m
Frontier
Deal found 2/2![Frontier logo]()
$188
This Priceline deal was found by Cheapflights users on 2/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:30 am
ORD
- BQN
1 stop16h 27m
Frontier
Mon 3/162:42 am
BQN
- ORD
1 stop21h 56m
Frontier
Deal found 2/2![Frontier logo]()
$188
This Orbitz deal was found by Cheapflights users on 2/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:00 am
MDW
- SJU
1 stop16h 53m
Frontier
Wed 2/255:25 pm
SJU
- MDW
1 stop23h 01m
Frontier
Deal found 2/2![Frontier logo]()
$188
This CheapOair deal was found by Cheapflights users on 2/1. 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.
Wed 4/156:34 pm
ORD
- SJU
1 stop22h 24m
Spirit Airlines
Wed 4/2211:07 am
SJU
- ORD
1 stop8h 08m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$189
This Mytrip deal was found by Cheapflights users on 2/2. 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.
Mon 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Tue 3/33:53 am
SJU
- ORD
1 stop13h 59m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Mon 2/236:51 pm
ORD
- SJU
2 stops18h 40m
Spirit Airlines
Tue 3/1010:52 am
SJU
- ORD
1 stop23h 47m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$191
This Booking.com deal was found by Cheapflights users on 2/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 2/2612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$192
Best flights from Chicago to Puerto RicoDiscover carefully curated flight deals from Chicago to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
Discover carefully curated flight deals from Chicago to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
This Priceline deal was found by Cheapflights users on 2/1. 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.
Tue 3/38:30 am
ORD
- BQN
1 stop16h 27m
Frontier
Mon 3/162:42 am
BQN
- ORD
1 stop21h 56m
Frontier
Deal found 2/1![Frontier logo]()
$188
This United Airlines deal was found by Cheapflights users on 2/2. 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 3/22:20 pm
ORD
- SJU
Nonstop4h 40m
United Airlines
Fri 3/68:30 am
SJU
- ORD
Nonstop5h 22m
United Airlines
Deal found 2/2![United Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/258:16 pm
ORD
- PSE
2 stops35h 54m
Multiple Airlines
Sat 3/712:25 pm
PSE
- ORD
1 stop13h 13m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$238
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/212:25 pm
ORD
- SJU
1 stop7h 47m
Delta
Wed 4/296:15 am
SJU
- ORD
1 stop11h 27m
Delta
Deal found 2/2![Delta logo]()
$246
This Spirit deal was found by Cheapflights users on 2/2. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/268:56 pm
ORD
- SJU
Nonstop4h 33m
Spirit Airlines
Tue 3/3111:03 am
SJU
- ORD
1 stop8h 28m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$276
This Cheapflightsfares deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2412:50 pm
ORD
- BQN
1 stop10h 00m
JetBlue
Mon 3/22:30 am
BQN
- ORD
1 stop11h 19m
JetBlue
Deal found 2/2![JetBlue logo]()
$316
This Southwest deal was found by Cheapflights users on 2/2. 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 3/33:15 pm
MDW
- SJU
1 stop7h 20m
Southwest
Tue 3/106:40 am
SJU
- MDW
1 stop9h 25m
Southwest
Deal found 2/2![Southwest logo]()
$331
This CheapOair deal was found by Cheapflights users on 2/2. 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.
Sat 3/74:23 pm
ORD
- PSE
1 stop16h 52m
Frontier
Thu 3/1211:35 am
PSE
- ORD
1 stop13h 03m
Frontier
Deal found 2/2![Frontier logo]()
$230
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Sun 4/262:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Thu 4/303:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Deal found 2/1![United Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Sat 2/288:16 pm
ORD
- PSE
2 stops36h 29m
Multiple Airlines
Sat 3/712:25 pm
PSE
- ORD
1 stop13h 13m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$238
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2112:53 pm
MDW
- SJU
1 stop9h 19m
Delta
Wed 4/292:34 pm
SJU
- MDW
1 stop8h 54m
Delta
Deal found 2/2![Delta logo]()
$246
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Sat 5/22:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Wed 5/67:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 2/1![United Airlines logo]()
$237
This Priceline deal was found by Cheapflights users on 2/1. 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.
Tue 2/178:30 am
ORD
- BQN
1 stop16h 27m
Frontier
Mon 3/302:42 am
BQN
- ORD
1 stop21h 56m
Frontier
Deal found 2/1![Frontier logo]()
$244
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2010:43 am
MDW
- SJU
1 stop8h 41m
Delta
Wed 4/296:15 am
SJU
- MDW
1 stop11h 10m
Delta
Deal found 2/2![Delta logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/273:40 pm
ORD
- PSE
2 stops20h 06m
Multiple Airlines
Sat 3/712:25 pm
PSE
- ORD
1 stop13h 13m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$247
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Sat 5/22:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Tue 5/53:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Deal found 2/1![United Airlines logo]()
$237
This Expedia deal was found by Cheapflights users on 2/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/48:30 am
ORD
- SJU
1 stop14h 13m
Frontier
Sun 3/83:19 pm
SJU
- ORD
1 stop9h 19m
Frontier
Deal found 2/2![Frontier logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Sun 2/2210:44 am
ORD
- PSE
1 stop21h 51m
Multiple Airlines
Sat 3/712:25 pm
PSE
- ORD
1 stop13h 13m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$255
This CheapOair deal was found by Cheapflights users on 2/2. 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 3/198:56 pm
ORD
- SJU
Nonstop4h 33m
Spirit Airlines
Mon 3/2311:03 am
SJU
- ORD
1 stop22h 22m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/189:52 am
ORD
- SJU
1 stop9h 20m
Delta
Sat 2/286:15 am
SJU
- ORD
1 stop9h 55m
Delta
Deal found 2/2![Delta logo]()
$266
This Frontier deal was found by Cheapflights users on 2/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/233:50 pm
ORD
- BQN
1 stop9h 07m
Frontier
Wed 2/253:58 am
BQN
- ORD
1 stop8h 48m
Frontier
Deal found 2/2![Frontier logo]()
$258
This Southwest deal was found by Cheapflights users on 2/2. 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 4/712:50 pm
MDW
- SJU
2 stops8h 50m
Southwest
Tue 4/142:00 pm
SJU
- MDW
2 stops9h 15m
Southwest
Deal found 2/2![Southwest logo]()
$346
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/143:21 pm
ORD
- SJU
1 stop6h 37m
Delta
Wed 2/256:37 pm
SJU
- ORD
1 stop7h 19m
Delta
Deal found 2/2![Delta logo]()
$266
This CheapOair deal was found by Cheapflights users on 2/1. 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 2/218:15 am
ORD
- BQN
1 stop16h 42m
Multiple Airlines
Fri 2/272:30 am
BQN
- ORD
1 stop11h 34m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$281
This Frontier deal was found by Cheapflights users on 2/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/239:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Sat 4/253:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Deal found 2/2![Frontier logo]()
$258
This United Airlines deal was found by Cheapflights users on 2/2. 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 3/38:55 am
ORD
- SJU
Nonstop4h 45m
United Airlines
Tue 3/107:30 am
SJU
- ORD
Nonstop5h 22m
United Airlines
Deal found 2/2![United Airlines logo]()
$304
This CheapOair deal was found by Cheapflights users on 2/2. 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.
Tue 3/310:00 am
ORD
- BQN
2 stops14h 52m
Multiple Airlines
Mon 3/162:42 am
BQN
- ORD
1 stop13h 46m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$281
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2210:43 am
MDW
- SJU
1 stop8h 41m
Delta
Sat 4/251:00 pm
SJU
- MDW
1 stop10h 28m
Delta
Deal found 2/2![Delta logo]()
$284
This Southwest deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:50 am
MDW
- SJU
2 stops8h 45m
Southwest
Wed 5/68:10 am
SJU
- MDW
2 stops9h 35m
Southwest
Deal found 2/1![Southwest logo]()
$390
This CheapOair deal was found by Cheapflights users on 2/1. 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 3/74:23 pm
ORD
- PSE
1 stop16h 52m
Frontier
Sat 3/1411:35 am
PSE
- ORD
1 stop13h 03m
Frontier
Deal found 2/1![Frontier logo]()
$270
Last-minute flights from Chicago to Puerto RicoDiscover last-minute flight deals from Chicago to Puerto Rico. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Puerto Rico. Data last updated February 3, 2026 and is based on user searches.
This Orbitz deal was found by Cheapflights users on 2/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/195:05 am
ORD
- SJU
1 stop7h 56m
Multiple Airlines
Tue 2/2412:32 pm
SJU
- ORD
Nonstop5h 16m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$186
This Frontier deal was found by Cheapflights users on 2/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:00 am
MDW
- SJU
1 stop8h 21m
Frontier
Fri 2/273:53 am
SJU
- MDW
1 stop13h 02m
Frontier
Deal found 2/2![Frontier logo]()
$187
This Orbitz deal was found by Cheapflights users on 2/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:15 am
ORD
- SJU
1 stop16h 38m
Frontier
Wed 2/255:25 pm
SJU
- ORD
1 stop19h 21m
Frontier
Deal found 2/2![Frontier logo]()
$188
This Orbitz deal was found by Cheapflights users on 2/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:00 am
MDW
- SJU
1 stop16h 53m
Frontier
Wed 2/255:25 pm
SJU
- MDW
1 stop23h 01m
Frontier
Deal found 2/2![Frontier logo]()
$188
This Booking.com deal was found by Cheapflights users on 2/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 2/2612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$192
This Gotogate deal was found by Cheapflights users on 2/2. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/233:50 pm
ORD
- SJU
1 stop16h 04m
Frontier
Tue 3/33:53 am
SJU
- ORD
1 stop13h 59m
Frontier
Deal found 2/2![Frontier logo]()
$187
This Mytrip deal was found by Cheapflights users on 2/2. 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.
Mon 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Tue 3/33:53 am
SJU
- ORD
1 stop13h 59m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Mon 2/236:51 pm
ORD
- SJU
2 stops18h 40m
Spirit Airlines
Tue 3/1010:52 am
SJU
- ORD
1 stop23h 47m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Tue 2/2412:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 3/512:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$189
This CheapOair deal was found by Cheapflights users on 2/2. 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.
Sun 3/17:23 pm
ORD
- SJU
1 stop21h 35m
Spirit Airlines
Fri 3/611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$184
This Priceline deal was found by Cheapflights users on 2/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:30 am
ORD
- BQN
1 stop16h 27m
Frontier
Mon 3/162:42 am
BQN
- ORD
1 stop21h 56m
Frontier
Deal found 2/2![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Mon 3/1610:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Wed 3/1812:55 pm
SJU
- ORD
1 stop7h 56m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$185
One-way flights from Chicago to Puerto RicoSearch for one-way flight options from Chicago to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
Search for one-way flight options from Chicago to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
This CheapOair deal was found by Cheapflights users on 2/1. 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.
Tue 3/38:30 am
ORD
- SJU
1 stop16h 23m
Frontier
Deal found 2/1![Frontier logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Sun 5/33:52 pm
ORD
- SJU
1 stop24h 38m
Frontier
Deal found 2/2![Frontier logo]()
$94
This Trip.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/86:00 am
MDW
- SJU
1 stop10h 58m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$94
This Cheapflightsfares deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
ORD
- SJU
1 stop12h 50m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/226:15 am
MDW
- SJU
1 stop28h 24m
Frontier
Deal found 2/1![Frontier logo]()
$96
This Mytrip deal was found by Cheapflights users on 2/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/239:18 am
ORD
- SJU
1 stop7h 40m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$97
This Expedia deal was found by Cheapflights users on 2/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1012:44 pm
ORD
- SJU
1 stop8h 49m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$98
This Expedia deal was found by Cheapflights users on 2/1. 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.
Tue 2/2412:44 pm
ORD
- SJU
1 stop8h 25m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$99
This Super.com deal was found by Cheapflights users on 2/1. 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.
Mon 2/239:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Deal found 2/1![Frontier logo]()
$99
This Super.com deal was found by Cheapflights users on 2/2. 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.
Sat 2/218:15 am
ORD
- SJU
1 stop16h 38m
Frontier
Deal found 2/2![Frontier logo]()
$100
This Frontier deal was found by Cheapflights users on 2/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:20 pm
ORD
- SJU
1 stop9h 09m
Frontier
Deal found 2/2![Frontier logo]()
$101
This CheapOair deal was found by Cheapflights users on 2/2. 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.
Sat 2/218:00 am
MDW
- SJU
1 stop8h 59m
Frontier
Deal found 2/2![Frontier logo]()
$101
Find flight deals from Chicago to Puerto Rico
Keep the following information in mind while searching for Chicago to Puerto Rico flight deals. Data was last updated February 3, 2026.
Round-trip from | $184 (CheapOair) |
|---|---|
One-way from | $93 (CheapOair) |
Popular in | December |
Cheapest in | April |
Average price | $376 |
Good round-trip deal | $296 or less |
Good one-way deal | $128 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Puerto Rico 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 February 3, 2026.
Use the filters below to find and compare flights from Chicago to Puerto Rico that are best for you.
Fly from
Chicago
Fly to
Puerto Rico
Route
Depart
Return
Price
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Tue 3/3
8:30 am-2:57 am
1 stop16h 27m
Aguadilla Borinquen
Mon 3/16
2:42 am-11:38 pm
1 stop21h 56m
$188
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Sat 3/7
4:23 pm-11:15 am
1 stop16h 52m
Ponce Mercedita
Thu 3/12
11:35 am-11:38 pm
1 stop13h 03m
$230
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 3/2
2:20 pm-9:00 pm
Nonstop4h 40m
San Juan Luis Munoz Marin Intl
Fri 3/6
8:30 am-11:52 am
Nonstop5h 22m
$237
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 4/26
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Thu 4/30
3:56 pm-8:15 pm
Nonstop5h 19m
$237
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 5/2
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Wed 5/6
7:40 am-11:53 am
Nonstop5h 13m
$237
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 5/2
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Tue 5/5
3:56 pm-8:15 pm
Nonstop5h 19m
$237
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Wed 2/25
8:16 pm-10:10 am
2 stops35h 54m
Ponce Mercedita
Sat 3/7
12:25 pm-11:38 pm
1 stop13h 13m
$238
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Sat 2/28
8:16 pm-10:45 am
2 stops36h 29m
Ponce Mercedita
Sat 3/7
12:25 pm-11:38 pm
1 stop13h 13m
$238
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Tue 2/17
8:30 am-2:57 am
1 stop16h 27m
Aguadilla Borinquen
Mon 3/30
2:42 am-11:38 pm
1 stop21h 56m
$244
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 4/21
2:25 pm-11:12 pm
1 stop7h 47m
San Juan Luis Munoz Marin Intl
Wed 4/29
6:15 am-4:42 pm
1 stop11h 27m
$246
Showing 1-10 of 60 results
Best time to book a flight from Chicago to Puerto Rico
Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Chicago with our price prediction graph.
ORD-SJU
MDW-SJU
ORD-BQN
ORD-PSE
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Puerto Rico
CHI-PR0
ORD-SJU
MDW-SJU
ORD-BQN
ORD-PSE
What is the cheapest month to book a flight from Chicago to Puerto Rico?
Currently, April is the cheapest month in which you can book a flight from Chicago to Puerto Rico (average of $91). Flying from Chicago to Puerto Rico in December is currently the most expensive (average of $224). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to PR?
Find hourly flight availability from Chicago to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 3, 2026.
When flying from Chicago to Puerto Rico, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 30% versus a flight in the morning.
What is the cheapest day to fly from Chicago to Puerto Rico?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Puerto Rico. Price data was last updated on February 10, 2025.
Travelers seeking maximum savings on their Chicago to Puerto Rico flight should consider departing on Tuesday mornings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Puerto Rico
Explore weekly flight availability from Chicago to Puerto Rico. 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 February 3, 2026.
The most flights from CHI to PR0 are scheduled on a Saturday (12 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 on average).
How often are flights from Chicago to Puerto Rico delayed?
About 18% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 138 minutes.
What is the most punctual flight time for Chicago to Puerto Rico flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Puerto Rico flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 14% of flights being delayed.
Reviews of airlines servicing Puerto Rico
Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated February 3, 2026.
Peruse reviews from past customers who have flown with United Airlines, American Airlines, and JetBlue from Chicago to Puerto Rico to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.3
Food
6.6
Boarding
7.7
Entertainment
7.1
Overall
7.4
Crew
8.1
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Comfort
7.3
Food
6.6
Boarding
7.7
Entertainment
7.1
Overall
7.4
Crew
8.1
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Comfort
7.3
Food
6.6
Boarding
7.7
Entertainment
7.1
Overall
7.4
Crew
8.1
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Comfort
7.3
Food
6.6
Boarding
7.7
Entertainment
7.1
Overall
7.4
Crew
8.1
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Comfort
7.3
Food
6.6
Boarding
7.7
Entertainment
7.1
Overall
7.4
Crew
8.1
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Comfort
7.3
Food
6.6
Boarding
7.7
Entertainment
7.1
Overall
7.4
Crew
8.1
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Related info for your journey
Find useful and relevant information for your journey from Chicago to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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 for Chicago to Puerto Rico
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from Chicago to Puerto Rico
Discover the top 7 airlines that operate flights from Chicago to Puerto Rico. 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 February 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$106 | Average$291 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$238 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$136 | Average$400 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$137 | Average$271 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$250 | Average$523 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$354 | Average$530 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$379 | Average$488 | FlexibilityNo cancel fee | On-time63% |