$99+ 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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
May 30 — Jun 61
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Puerto Rico to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Puerto Rico to Chicago
Cheapest
Best
Last-minute
One-way
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 April 30, 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 April 30, 2026.
This Expedia deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2211:39 am
SJU
- ORD
Nonstop5h 10m
Multiple Airlines
Sun 5/2412:33 am
ORD
- SJU
Nonstop4h 51m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/286:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sat 5/3012:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/26![Frontier logo]()
$147
This CheapOair deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
Fri 5/2211:39 am
SJU
- ORD
Nonstop5h 10m
Multiple Airlines
Mon 5/2512:33 am
ORD
- SJU
Nonstop4h 51m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$149
This Mytrip deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Sat 5/237:04 pm
SJU
- ORD
Nonstop5h 22m
Multiple Airlines
Sat 5/3012:59 pm
ORD
- SJU
Nonstop4h 36m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$154
This Mytrip deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Fri 5/297:52 pm
ORD
- SJU
1 stop7h 09m
Frontier
Deal found 4/26![Frontier logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/237:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sat 5/3012:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/26![Frontier logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/246:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Mon 5/2512:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/28![Frontier logo]()
$162
This Priceline deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/237:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sat 5/307:52 pm
ORD
- SJU
1 stop7h 09m
Frontier
Deal found 4/29![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/237:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Tue 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/25![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/227:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sat 5/2312:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/27![Frontier logo]()
$172
This CheapOair deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Fri 5/227:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sun 5/2412:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/27![Frontier logo]()
$173
This Priceline deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/712:26 pm
BQN
- ORD
1 stop11h 47m
Frontier
Tue 5/123:55 pm
ORD
- BQN
1 stop9h 07m
Frontier
Deal found 4/28![Frontier logo]()
$226
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 April 30, 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 April 30, 2026.
This Booking.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
Tue 5/123:03 am
SJU
- ORD
1 stop21h 10m
Frontier
Fri 5/2912:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/29![Frontier logo]()
$214
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/63:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Mon 5/112:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 4/27![United Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:00 am
SJU
- MDW
2 stops9h 30m
Southwest
Mon 9/75:00 am
MDW
- SJU
1 stop7h 45m
Southwest
Deal found 4/25![Southwest logo]()
$276
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 7/285:56 pm
SJU
- ORD
1 stop6h 57m
Delta
Sat 8/19:00 am
ORD
- SJU
1 stop6h 45m
Delta
Deal found 4/25![Delta logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/134:36 pm
MAZ
- ORD
2 stops32h 02m
Multiple Airlines
Sun 5/174:44 pm
ORD
- MAZ
1 stop15h 58m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$401
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/77:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Tue 5/122:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 4/26![United Airlines logo]()
$283
This Priceline deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Mon 5/112:59 am
BQN
- ORD
1 stop21h 14m
Frontier
Sat 5/165:30 pm
ORD
- BQN
1 stop7h 32m
Frontier
Deal found 4/27![Frontier logo]()
$305
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 8/1710:00 am
SJU
- MDW
1 stop9h 00m
Southwest
Wed 8/1912:20 pm
MDW
- SJU
1 stop7h 45m
Southwest
Deal found 4/29![Southwest logo]()
$326
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/43:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Thu 5/711:00 am
ORD
- SJU
1 stop9h 24m
United Airlines
Deal found 4/27![United Airlines logo]()
$332
This Frontier deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 7/93:00 am
BQN
- ORD
1 stop7h 11m
Frontier
Thu 8/65:13 pm
ORD
- BQN
1 stop7h 52m
Frontier
Deal found 4/29![Frontier logo]()
$361
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 8/75:00 am
SJU
- MDW
2 stops8h 20m
Southwest
Mon 8/1012:15 pm
MDW
- SJU
2 stops9h 50m
Southwest
Deal found 4/29![Southwest logo]()
$381
This Frontier deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 8/2512:28 pm
BQN
- ORD
1 stop11h 46m
Frontier
Sat 8/295:30 pm
ORD
- BQN
1 stop7h 34m
Frontier
Deal found 4/29![Frontier logo]()
$366
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/87:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Mon 5/112:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 4/26![United Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:06 pm
SJU
- MDW
1 stop9h 40m
Delta
Mon 9/76:00 am
MDW
- SJU
1 stop6h 30m
Delta
Deal found 4/27![Delta logo]()
$446
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/102:59 am
BQN
- MDW
2 stops33h 10m
Multiple Airlines
Fri 5/154:52 pm
MDW
- BQN
1 stop8h 10m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$448
This United Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/67:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Wed 5/62:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 4/29![United Airlines logo]()
$373
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 6/272:04 pm
SJU
- ORD
1 stop7h 27m
Delta
Mon 7/66:35 am
ORD
- SJU
1 stop9h 11m
Delta
Deal found 4/25![Delta logo]()
$461
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 7/95:00 am
SJU
- MDW
1 stop6h 55m
Southwest
Thu 7/165:10 pm
MDW
- SJU
1 stop7h 10m
Southwest
Deal found 4/26![Southwest logo]()
$426
This Priceline deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 8/133:00 am
BQN
- ORD
1 stop21h 05m
Frontier
Sat 8/225:30 pm
ORD
- BQN
1 stop7h 34m
Frontier
Deal found 4/26![Frontier logo]()
$406
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/114:36 pm
MAZ
- ORD
2 stops31h 37m
Multiple Airlines
Fri 5/154:44 pm
ORD
- MAZ
1 stop15h 58m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$506
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/93:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Sat 5/162:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 4/26![United Airlines logo]()
$387
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 7/202:42 pm
SJU
- MDW
1 stop8h 33m
Delta
Sat 7/2510:55 am
MDW
- SJU
1 stop8h 50m
Delta
Deal found 4/25![Delta logo]()
$471
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 6/2510:20 pm
SJU
- MDW
2 stops12h 40m
Southwest
Mon 6/291:00 pm
MDW
- SJU
2 stops10h 15m
Southwest
Deal found 4/29![Southwest logo]()
$431
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/67:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Sun 5/108:49 am
ORD
- SJU
Nonstop4h 55m
United Airlines
Deal found 4/27![United Airlines logo]()
$392
This Priceline deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/1412:16 pm
BQN
- MDW
1 stop28h 41m
Frontier
Mon 5/184:52 pm
MDW
- BQN
1 stop8h 10m
Frontier
Deal found 4/29![Frontier logo]()
$433
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/312:59 am
BQN
- ORD
2 stops34h 38m
Multiple Airlines
Thu 6/410:54 am
ORD
- BQN
1 stop14h 08m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$534
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 6/810:20 pm
SJU
- MDW
1 stop11h 40m
Southwest
Thu 6/1112:45 pm
MDW
- SJU
2 stops10h 30m
Southwest
Deal found 4/25![Southwest logo]()
$461
This Priceline deal was found by Cheapflights users on 4/30. 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.
Thu 5/142:59 am
BQN
- ORD
1 stop21h 14m
Frontier
Mon 5/185:30 pm
ORD
- BQN
1 stop7h 32m
Frontier
Deal found 4/30![Frontier logo]()
$434
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:30 am
SJU
- MDW
2 stops8h 40m
Southwest
Mon 10/128:40 pm
MDW
- SJU
1 stop11h 25m
Southwest
Deal found 4/28![Southwest logo]()
$466
This deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1612:19 pm
BQN
- ORD
1 stop12h 00m
Frontier
Thu 6/185:25 pm
ORD
- BQN
1 stop7h 40m
Frontier
Deal found 4/28![Frontier logo]()
$446
Last-minute flights from Puerto Rico to ChicagoDiscover last-minute flight deals from Puerto Rico to Chicago. Data last updated April 30, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Chicago. Data last updated April 30, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 4/304:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Mon 5/44:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/25![Spirit Airlines logo]()
$152
This Priceline deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/712:26 pm
BQN
- ORD
1 stop11h 47m
Frontier
Tue 5/123:55 pm
ORD
- BQN
1 stop9h 07m
Frontier
Deal found 4/28![Frontier logo]()
$226
This Expedia deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2211:39 am
SJU
- ORD
Nonstop5h 10m
Multiple Airlines
Sun 5/2412:33 am
ORD
- SJU
Nonstop4h 51m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$144
This CheapOair deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
Fri 5/2211:39 am
SJU
- ORD
Nonstop5h 10m
Multiple Airlines
Mon 5/2512:33 am
ORD
- SJU
Nonstop4h 51m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$149
This Mytrip deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Sat 5/237:04 pm
SJU
- ORD
Nonstop5h 22m
Multiple Airlines
Sat 5/3012:59 pm
ORD
- SJU
Nonstop4h 36m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/237:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sat 5/3012:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/26![Frontier logo]()
$157
This Priceline deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/237:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sat 5/307:52 pm
ORD
- SJU
1 stop7h 09m
Frontier
Deal found 4/29![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/237:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Tue 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/25![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/246:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Mon 5/2512:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/28![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/286:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sat 5/3012:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/26![Frontier logo]()
$147
This Mytrip deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Fri 5/297:52 pm
ORD
- SJU
1 stop7h 09m
Frontier
Deal found 4/26![Frontier logo]()
$155
This Frontier deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/297:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sat 5/3012:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/25![Frontier logo]()
$142
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 April 30, 2026.
Search for one-way flight options from Puerto Rico to Chicago. Find affordable one-way fares based on user searches. Data last updated April 30, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/94:59 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 4/28![Spirit Airlines logo]()
$99
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:25 am
SJU
- MDW
1 stop8h 47m
Frontier
Deal found 4/30![Frontier logo]()
$102
This Super.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/233:03 am
SJU
- ORD
1 stop21h 10m
Frontier
Deal found 4/29![Frontier logo]()
$103
This eDestinos deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/1511:00 am
SJU
- ORD
1 stop13h 59m
Frontier
Deal found 4/28![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/711:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/28![Spirit Airlines logo]()
$105
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/1411:00 am
SJU
- ORD
1 stop13h 38m
Frontier
Deal found 4/28![Frontier logo]()
$108
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
Sat 5/2312:59 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 4/29![American Airlines logo]()
$109
This Super.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
Fri 5/296:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Deal found 4/26![Frontier logo]()
$110
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 8/236:00 am
SJU
- MDW
2 stops9h 20m
Southwest
Deal found 4/27![Southwest logo]()
$113
This Super.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Wed 5/136:41 pm
SJU
- ORD
1 stop23h 13m
Frontier
Deal found 4/25![Frontier logo]()
$113
This Trip.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Wed 5/135:15 pm
SJU
- MDW
1 stop18h 54m
Frontier
Deal found 4/25![Frontier logo]()
$118
This Trip.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Tue 5/55:15 pm
SJU
- MDW
1 stop29h 47m
Frontier
Deal found 4/27![Frontier logo]()
$119
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 April 30, 2026.
Round-trip from | $142 (Frontier) |
|---|---|
One-way from | $99 (Cheapflightsfares) |
Popular in | December |
Cheapest in | February |
Average price | $321 |
Good round-trip deal | $297 or less |
Good one-way deal | $183 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 April 30, 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 - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 5/12
3:03 am-11:13 pm
1 stop21h 10m
Chicago O'Hare Intl
Fri 5/29
12:33 am-6:24 am
Nonstop4h 51m
$214
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 5/6
3:56 pm-8:15 pm
Nonstop5h 19m
Chicago O'Hare Intl
Mon 5/11
2:38 pm-8:34 pm
Nonstop4h 56m
$257
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 9/4
6:00 am-2:30 pm
2 stops9h 30m
Chicago Midway
Mon 9/7
5:00 am-1:45 pm
1 stop7h 45m
$276
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 5/7
7:40 am-11:53 am
Nonstop5h 13m
Chicago O'Hare Intl
Tue 5/12
2:38 pm-8:34 pm
Nonstop4h 56m
$283
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 7/28
5:56 pm-11:53 pm
1 stop6h 57m
Chicago O'Hare Intl
Sat 8/1
9:00 am-4:45 pm
1 stop6h 45m
$296
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Mon 5/11
2:59 am-11:13 pm
1 stop21h 14m
Chicago O'Hare Intl
Sat 5/16
5:30 pm-2:02 am
1 stop7h 32m
$305
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mon 8/17
10:00 am-6:00 pm
1 stop9h 00m
Chicago Midway
Wed 8/19
12:20 pm-9:05 pm
1 stop7h 45m
$326
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Mon 5/4
3:56 pm-8:15 pm
Nonstop5h 19m
Chicago O'Hare Intl
Thu 5/7
11:00 am-9:24 pm
1 stop9h 24m
$332
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Thu 7/9
3:00 am-9:11 am
1 stop7h 11m
Chicago O'Hare Intl
Thu 8/6
5:13 pm-2:05 am
1 stop7h 52m
$361
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Tue 8/25
12:28 pm-11:14 pm
1 stop11h 46m
Chicago O'Hare Intl
Sat 8/29
5:30 pm-2:04 am
1 stop7h 34m
$366
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-MDW
SJU-ORD
BQN-ORD
BQN-MDW
MAZ-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Puerto Rico to Chicago
PR0-CHI
SJU-MDW
SJU-ORD
BQN-ORD
BQN-MDW
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 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 July is currently the most expensive (average of $575). 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 April 30, 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 47% versus a flight in the afternoon.
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 April 25, 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 afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 April 30, 2026.
The most flights from PR0 to CHI are scheduled on a Thursday (9 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 188 minutes.
What is the most punctual flight time for Puerto Rico to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas 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.
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 April 30, 2026.
Read reviews from past customers who have flown United Airlines,JetBlue, andAmerican Airlines 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.
Crew
8.1
Food
6.6
Boarding
7.7
Comfort
7.3
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Food
6.6
Boarding
7.7
Comfort
7.3
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Food
6.6
Boarding
7.7
Comfort
7.3
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Food
6.6
Boarding
7.7
Comfort
7.3
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Food
6.6
Boarding
7.7
Comfort
7.3
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Food
6.6
Boarding
7.7
Comfort
7.3
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - 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.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
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 April 30, 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 April 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 7 airlines flying from Puerto Rico to Chicago
Discover the top 7 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 April 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$116 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$122 | Average$264 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$128 | Average$254 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$246 | Average$441 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$256 | Average$482 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$292 | Average$508 | FlexibilityNo cancel fee | On-time63% |