$114+ Cheap flights from Chicago (CHI) to Puerto Rico
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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Dec 4 — Dec 111
Round-trip
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 November 4, 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 November 4, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/105:24 pm -
1 stop7h 28m
Mon 12/143:47 am -
1 stop23h 21m
Deal found 11/1![Frontier logo]()
$230
This Frontier deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/85:24 pm -
1 stop7h 28m
Fri 12/113:47 am -
1 stop13h 43m
Deal found 11/1![Frontier logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/232:52 pm -
1 stop22h 08m
Mon 11/303:43 am -
1 stop23h 16m
Deal found 10/30![Frontier logo]()
$245
This CheapOair deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/68:37 pm -
1 stop27h 36m
Wed 12/95:01 am -
1 stop8h 32m
Deal found 11/2![Frontier logo]()
$245
This Priceline deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/812:28 pm -
1 stop10h 39m
Mon 1/112:41 am -
1 stop23h 05m
Deal found 10/30![Frontier logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/105:24 pm -
1 stop6h 49m
Sat 12/197:28 am -
1 stop13h 40m
Deal found 10/31![Frontier logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/610:29 pm -
1 stop13h 00m
Sun 12/202:29 am -
1 stop11h 31m
Deal found 10/31![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/135:24 pm -
1 stop6h 49m
Fri 12/186:00 am -
1 stop12h 59m
Deal found 11/3![Frontier logo]()
$249
This Cheapflightsfares deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1310:19 am -
1 stop12h 40m
Fri 11/207:12 pm -
Nonstop5h 09m
Deal found 11/1![Frontier logo]()
$250
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:55 am -
1 stop29h 24m
Mon 11/237:58 pm -
1 stop13h 49m
Deal found 11/2![Frontier logo]()
$251
This CheapOair deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:28 pm -
1 stop10h 39m
Sun 12/68:44 pm -
1 stop22h 32m
Deal found 11/3![Frontier logo]()
$251
This Cheapflightsfares deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:42 pm -
1 stop21h 35m
Sun 11/226:00 am -
1 stop11h 57m
Deal found 11/1![Frontier logo]()
$252
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 November 4, 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 November 4, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/165:16 pm -
1 stop7h 48m
Mon 1/183:59 am -
1 stop22h 56m
Deal found 11/3![Frontier logo]()
$230
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/112:16 pm -
Nonstop4h 44m
Thu 1/148:05 am -
1 stop8h 19m
Deal found 11/2![United Airlines logo]()
$262
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/313:40 pm -
1 stop6h 00m
Sat 2/66:05 am -
2 stops13h 10m
Deal found 11/3![Southwest logo]()
$266
This JetBlue deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:00 am -
1 stop7h 09m
Fri 12/46:38 am -
1 stop8h 52m
Deal found 11/2![JetBlue logo]()
$284
This CheapOair deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/185:01 am -
1 stop6h 59m
Sun 1/244:53 pm -
2 stops52h 02m
Deal found 10/30![Multiple Airlines logo]()
$397
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/276:00 am -
1 stop9h 25m
Wed 2/107:45 am -
1 stop11h 09m
Deal found 11/3![Delta logo]()
$535
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/82:30 pm -
1 stop7h 27m
Fri 12/111:09 am -
1 stop8h 36m
Deal found 11/1![United Airlines logo]()
$290
This Trip.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:36 pm -
1 stop9h 09m
Sun 12/62:54 pm -
1 stop28h 22m
Deal found 11/3![Frontier logo]()
$302
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/98:40 pm -
1 stop13h 00m
Wed 11/116:10 am -
1 stop10h 50m
Deal found 10/31![Southwest logo]()
$306
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/811:55 am -
1 stop10h 02m
Sun 12/131:09 am -
1 stop9h 39m
Deal found 10/31![United Airlines logo]()
$290
This United Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/92:16 pm -
Nonstop4h 44m
Tue 12/154:55 pm -
Nonstop5h 31m
Deal found 10/30![United Airlines logo]()
$294
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/158:40 pm -
1 stop11h 15m
Tue 11/176:10 am -
1 stop8h 50m
Deal found 11/3![Southwest logo]()
$340
This CheapOair deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:00 am -
2 stops36h 25m
Fri 12/113:47 am -
1 stop13h 43m
Deal found 10/30![Multiple Airlines logo]()
$397
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/119:21 am -
1 stop10h 03m
Fri 11/138:25 am -
Nonstop5h 22m
Deal found 11/2![United Airlines logo]()
$302
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/43:36 pm -
1 stop9h 09m
Sun 12/62:54 pm -
1 stop28h 22m
Deal found 11/2![Frontier logo]()
$378
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/111:40 pm -
1 stop7h 50m
Thu 1/142:30 pm -
1 stop10h 20m
Deal found 11/3![Southwest logo]()
$348
This CheapOair deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/22:59 pm -
1 stop17h 26m
Wed 12/911:15 am -
1 stop14h 18m
Deal found 11/3![JetBlue logo]()
$436
This Priceline deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/165:16 pm -
1 stop7h 48m
Tue 1/194:53 pm -
2 stops32h 54m
Deal found 11/3![Multiple Airlines logo]()
$412
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1410:34 am -
1 stop8h 50m
Tue 11/174:55 pm -
Nonstop5h 31m
Deal found 11/3![United Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/318:47 pm -
1 stop28h 17m
Fri 2/53:59 am -
2 stops21h 47m
Deal found 11/3![Frontier logo]()
$410
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/2310:10 am -
2 stops9h 55m
Tue 1/267:25 am -
2 stops9h 20m
Deal found 10/30![Southwest logo]()
$375
This FlightHub deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/87:50 pm -
1 stop15h 54m
Sat 1/165:15 pm -
1 stop9h 40m
Deal found 10/31![Multiple Airlines logo]()
$444
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/262:16 pm -
Nonstop4h 44m
Thu 1/288:05 am -
1 stop9h 44m
Deal found 11/3![United Airlines logo]()
$362
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1312:50 pm -
1 stop8h 45m
Wed 11/187:40 am -
1 stop9h 15m
Deal found 11/1![Southwest logo]()
$409
This Frontier deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/285:01 am -
1 stop9h 09m
Sun 1/315:15 pm -
1 stop9h 40m
Deal found 11/3![Frontier logo]()
$450
This FlightHub deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/132:59 pm -
2 stops40h 23m
Tue 11/175:01 am -
1 stop10h 41m
Deal found 10/30![JetBlue logo]()
$559
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/302:16 pm -
Nonstop4h 44m
Mon 12/74:55 pm -
Nonstop5h 31m
Deal found 10/31![United Airlines logo]()
$368
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/198:35 pm -
1 stop27h 08m
Thu 12/243:13 am -
1 stop17h 57m
Deal found 11/2![Frontier logo]()
$454
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/78:15 am -
Nonstop4h 45m
Sat 11/146:45 am -
1 stop11h 45m
Deal found 10/31![Southwest logo]()
$422
This Orbitz deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/165:01 am -
1 stop9h 09m
Tue 1/192:40 pm -
1 stop11h 07m
Deal found 11/3![Multiple Airlines logo]()
$517
Last-minute flights from Chicago to Puerto RicoDiscover last-minute flight deals from Chicago to Puerto Rico. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Puerto Rico. Data last updated November 4, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1310:19 am -
1 stop12h 40m
Fri 11/207:12 pm -
Nonstop5h 09m
Deal found 11/1![Frontier logo]()
$250
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:55 am -
1 stop29h 24m
Mon 11/237:58 pm -
1 stop13h 49m
Deal found 11/2![Frontier logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/232:52 pm -
1 stop22h 08m
Mon 11/303:43 am -
1 stop23h 16m
Deal found 11/1![Frontier logo]()
$246
This CheapOair deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:28 pm -
1 stop10h 39m
Sun 12/68:44 pm -
1 stop22h 32m
Deal found 11/3![Frontier logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/69:34 pm -
1 stop11h 51m
Fri 12/186:00 am -
1 stop12h 59m
Deal found 10/31![Frontier logo]()
$245
This CheapOair deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/68:37 pm -
1 stop27h 36m
Wed 12/95:01 am -
1 stop8h 32m
Deal found 11/2![Frontier logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/610:29 pm -
1 stop13h 00m
Sun 12/202:29 am -
1 stop11h 31m
Deal found 10/31![Frontier logo]()
$248
This Frontier deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/85:24 pm -
1 stop7h 28m
Fri 12/113:47 am -
1 stop13h 43m
Deal found 11/1![Frontier logo]()
$232
This Priceline deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/812:28 pm -
1 stop10h 39m
Mon 1/112:41 am -
1 stop23h 05m
Deal found 10/30![Frontier logo]()
$246
This Cheapflightsfares deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/105:24 pm -
1 stop7h 28m
Mon 12/143:47 am -
1 stop23h 21m
Deal found 11/1![Frontier logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/105:24 pm -
1 stop6h 49m
Sat 12/197:28 am -
1 stop13h 40m
Deal found 10/31![Frontier logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/135:24 pm -
1 stop6h 49m
Fri 12/186:00 am -
1 stop12h 59m
Deal found 11/3![Frontier logo]()
$249
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 November 4, 2026.
Search for one-way flight options from Chicago to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:11 pm -
1 stop6h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$114
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/75:35 am -
1 stop19h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$120
This Trip.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/68:37 pm -
1 stop28h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$124
This CheapOair deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/138:37 pm -
1 stop27h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$124
This Trip.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:42 pm -
1 stop27h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Frontier logo]()
$125
This Mytrip deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/157:55 am -
1 stop27h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$128
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/175:01 pm -
Nonstop4h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![American Airlines logo]()
$129
This eDestinos deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/179:51 am -
1 stop22h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/43:17 pm -
1 stop16h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$131
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/1010:31 pm -
Nonstop4h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$132
This JetBlue deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/142:59 pm -
1 stop9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![JetBlue logo]()
$133
This Priceline deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/231:18 pm -
1 stop23h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$133
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 November 4, 2026.
Round-trip from | $230 (Cheapflightsfares) |
|---|---|
One-way from | $114 (Cheapflightsfares) |
Popular in | December |
Cheapest in | August |
Average price | $492 |
Good round-trip deal | $406 or less |
Good one-way deal | $200 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 7,457,451 searches. Data last updated November 4, 2026.
Use the filters below to find and compare flights from Chicago to Puerto Rico that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoAguadilla
MDW Chicago Midway - BQN Aguadilla Borinquen
MDWBQN
Chicago Midway
Sun 12/6
8:37 pm-2:52 am
1 stop28h 15m
Aguadilla Borinquen
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$124
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Mon 12/14
2:59 pm-1:59 am
1 stop9h 00m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$133
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 1/26
3:35 pm-12:35 am
1 stop7h 00m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$133
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Sun 1/31
3:40 pm-1:40 am
1 stop8h 00m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$133
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 11/23
8:42 pm-9:59 am
1 stop11h 17m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$140
ChicagoAguadilla
ORD Chicago O'Hare Intl - BQN Aguadilla Borinquen
ORDBQN
Chicago O'Hare Intl
Sat 1/23
2:26 pm-11:57 pm
1 stop7h 31m
Aguadilla Borinquen
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$145
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 1/11
6:00 am-5:25 pm
1 stop9h 25m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$145
Quickest round-trip
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Mon 11/9
2:16 pm-9:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$149
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Fri 11/13
2:16 pm-9:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$149
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 11/16
3:00 pm-12:50 am
1 stop7h 50m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$153
Showing 1-10 of 60 resultsSorted by cheapest first
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.
MDW-BQN
ORD-BQN
MDW-SJU
ORD-SJU
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
MDW-BQN
ORD-BQN
MDW-SJU
ORD-SJU
What is the cheapest month to book a flight from Chicago to Puerto Rico?
Currently, August is the cheapest month in which you can book a flight from Chicago to Puerto Rico (average of $332). Flying from Chicago to Puerto Rico in December is currently the most expensive (average of $528). 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 November 4, 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 32% versus a flight in the morning.
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 November 4, 2026.
The most flights from CHI to PR0 are scheduled on a Monday (8 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (6 on average).
How often are flights from Chicago to Puerto Rico delayed?
About 22% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 147 minutes.
What is the most punctual flight time for Chicago to Puerto Rico 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?
Wednesday 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 Chicago to Puerto Rico flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 18% of flights being delayed.
How far ahead should I book a flight from Chicago to Puerto Rico?
The best time to book flights from Chicago to Puerto Rico is 59 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
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 October 31, 2026.
Travelers seeking maximum savings on their Chicago to Puerto Rico flight should consider departing on Sunday evenings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
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 November 4, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andJetBlue 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.
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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.
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Alternative routes for Chicago to Puerto Rico
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Puerto Rico by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Puerto Rico by cabin class
Find flights from Chicago to Puerto Rico, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Puerto Rico flights
Browse other Chicago and Puerto Rico flight options. Last updated on November 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Chicago to Puerto Rico
Discover the top 6 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 7,457,451 searches. Data last updated November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$363 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$483 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$491 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$262 | Average$532 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$276 | Average$488 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$285 | Average$486 | FlexibilityNo cancel fee | On-time71% |