$128+ Cheap flights from Chicago (CHI) to San Juan
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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Aug 1 — Aug 81
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to San Juan 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.Cheapflights Tip: The best prices from Chicago to San Juan are usually found in January or August, booked 82 days in advance, depart on a Monday or Tuesday and return on a Friday
Cheap flight deals from Chicago to San Juan
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Best
Last-minute
One-way
Cheapest flights from Chicago to San JuanExplore the most affordable flight options available from Chicago to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 2, 2026.
Explore the most affordable flight options available from Chicago to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 2, 2026.
This Super.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 7/107:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/1![Frontier logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Thu 8/208:05 am
ORD
- SJU
2 stops15h 29m
Multiple Airlines
Sun 9/67:14 pm
SJU
- ORD
Nonstop5h 13m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 6/27. 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.
Thu 8/278:05 am
ORD
- SJU
1 stop31h 06m
Frontier
Thu 9/37:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/27![Frontier logo]()
$259
This Frontier deal was found by Cheapflights users on 6/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Wed 9/27:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/30![Frontier logo]()
$261
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am
ORD
- SJU
1 stop11h 30m
American Airlines
Fri 8/2812:55 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 6/30![American Airlines logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 6/30. 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.
Fri 7/312:44 am
ORD
- SJU
Nonstop4h 57m
Frontier
Sat 7/47:14 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 6/30![Frontier logo]()
$263
This Trip.com deal was found by Cheapflights users on 7/1. 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.
Wed 8/1912:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 8/257:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/1![Frontier logo]()
$264
This Super.com deal was found by Cheapflights users on 6/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sun 8/167:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/27![Frontier logo]()
$265
This Delta deal was found by Cheapflights users on 6/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:30 am
ORD
- SJU
1 stop10h 08m
Delta
Sat 8/295:49 pm
SJU
- ORD
1 stop7h 08m
Delta
Deal found 6/29![Delta logo]()
$266
This Southwest deal was found by Cheapflights users on 7/1. 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 8/227:50 am
MDW
- SJU
2 stops7h 50m
Southwest
Wed 8/265:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Deal found 7/1![Southwest logo]()
$266
This American Airlines deal was found by Cheapflights users on 7/2. 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.
Thu 8/275:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Thu 9/31:38 pm
SJU
- ORD
1 stop11h 57m
American Airlines
Deal found 7/2![American Airlines logo]()
$267
This Frontier deal was found by Cheapflights users on 6/28. 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.
Sat 7/412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Wed 7/157:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/28![Frontier logo]()
$268
Best flights from Chicago to San JuanDiscover carefully curated flight deals from Chicago to San Juan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 2, 2026.
Discover carefully curated flight deals from Chicago to San Juan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 2, 2026.
This Southwest deal was found by Cheapflights users on 7/1. 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 9/43:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Sun 9/65:20 am
SJU
- MDW
1 stop6h 55m
Southwest
Deal found 7/1![Southwest logo]()
$266
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Mon 8/248:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Wed 8/263:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 7/1![United Airlines logo]()
$274
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/165:30 am
ORD
- SJU
1 stop7h 12m
Delta
Sat 8/295:49 pm
SJU
- ORD
1 stop7h 08m
Delta
Deal found 6/30![Delta logo]()
$291
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/111:50 pm
ORD
- SJU
1 stop7h 39m
Delta
Tue 9/157:30 am
SJU
- ORD
1 stop10h 29m
Delta
Deal found 7/1![Delta logo]()
$311
This Southwest deal was found by Cheapflights users on 6/28. 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.
Mon 7/278:55 pm
MDW
- SJU
1 stop11h 05m
Southwest
Fri 7/3110:20 pm
SJU
- MDW
1 stop11h 30m
Southwest
Deal found 6/28![Southwest logo]()
$351
This United Airlines deal was found by Cheapflights users on 6/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/48:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Fri 10/93:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 6/28![United Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 7/2. 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.
Fri 8/219:54 am
ORD
- SJU
1 stop11h 35m
Delta
Sun 8/307:00 am
SJU
- ORD
1 stop10h 51m
Delta
Deal found 7/2![Delta logo]()
$371
This Southwest deal was found by Cheapflights users on 6/27. 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.
Sat 9/511:00 am
MDW
- SJU
1 stop6h 15m
Southwest
Sat 9/1211:45 am
SJU
- MDW
1 stop7h 35m
Southwest
Deal found 6/27![Southwest logo]()
$371
This United Airlines deal was found by Cheapflights users on 7/1. 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 11/88:52 am
ORD
- SJU
Nonstop4h 48m
United Airlines
Fri 11/132:05 am
SJU
- ORD
1 stop10h 43m
United Airlines
Deal found 7/1![United Airlines logo]()
$372
This United Airlines deal was found by Cheapflights users on 6/29. 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.
Thu 10/292:16 pm
ORD
- SJU
Nonstop4h 44m
United Airlines
Tue 11/31:00 pm
SJU
- ORD
1 stop9h 14m
United Airlines
Deal found 6/29![United Airlines logo]()
$372
This Southwest deal was found by Cheapflights users on 6/30. 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.
Thu 10/1512:45 pm
MDW
- SJU
2 stops8h 35m
Southwest
Thu 10/229:45 pm
SJU
- MDW
1 stop13h 00m
Southwest
Deal found 6/30![Southwest logo]()
$376
This United Airlines deal was found by Cheapflights users on 6/29. 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.
Sat 11/710:30 am
ORD
- SJU
1 stop8h 54m
United Airlines
Sat 11/148:05 am
SJU
- ORD
1 stop8h 16m
United Airlines
Deal found 6/29![United Airlines logo]()
$376
This Southwest deal was found by Cheapflights users on 6/29. 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.
Tue 10/1312:25 pm
MDW
- SJU
2 stops8h 50m
Southwest
Thu 10/155:00 am
SJU
- MDW
2 stops9h 00m
Southwest
Deal found 6/29![Southwest logo]()
$376
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:11 am
MDW
- SJU
1 stop9h 27m
Delta
Mon 8/247:00 am
SJU
- MDW
1 stop10h 15m
Delta
Deal found 6/30![Delta logo]()
$436
This Southwest deal was found by Cheapflights users on 7/1. 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.
Tue 10/205:45 am
MDW
- SJU
1 stop6h 50m
Southwest
Sun 10/255:40 pm
SJU
- MDW
1 stop6h 55m
Southwest
Deal found 7/1![Southwest logo]()
$376
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Fri 10/28:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Sun 10/113:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 7/1![United Airlines logo]()
$391
This Southwest deal was found by Cheapflights users on 7/1. 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.
Wed 10/77:50 am
MDW
- SJU
1 stop11h 40m
Southwest
Sun 10/185:30 am
SJU
- MDW
1 stop9h 25m
Southwest
Deal found 7/1![Southwest logo]()
$376
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Mon 9/143:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 7/1![United Airlines logo]()
$392
This Southwest deal was found by Cheapflights users on 6/27. 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.
Thu 10/88:50 pm
MDW
- SJU
1 stop11h 30m
Southwest
Mon 10/125:00 am
SJU
- MDW
2 stops8h 10m
Southwest
Deal found 6/27![Southwest logo]()
$421
This United Airlines deal was found by Cheapflights users on 6/29. 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 11/111:00 pm
ORD
- SJU
1 stop9h 36m
United Airlines
Mon 11/165:50 pm
SJU
- ORD
1 stop7h 47m
United Airlines
Deal found 6/29![United Airlines logo]()
$428
This Southwest deal was found by Cheapflights users on 7/1. 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 7/175:10 pm
MDW
- SJU
1 stop7h 15m
Southwest
Tue 7/218:35 pm
SJU
- MDW
1 stop13h 25m
Southwest
Deal found 7/1![Southwest logo]()
$436
This United Airlines deal was found by Cheapflights users on 6/27. 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.
Fri 9/118:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Thu 9/173:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 6/27![United Airlines logo]()
$457
Last-minute flights from Chicago to San JuanDiscover last-minute flight deals from Chicago to San Juan. Data last updated July 2, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San Juan. Data last updated July 2, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/30. 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.
Fri 7/312:44 am
ORD
- SJU
Nonstop4h 57m
Frontier
Sat 7/47:14 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 6/30![Frontier logo]()
$263
This Frontier deal was found by Cheapflights users on 7/1. 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.
Sat 7/412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 7/77:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/1![Frontier logo]()
$268
This Super.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 7/107:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/1![Frontier logo]()
$257
This Super.com deal was found by Cheapflights users on 6/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sun 8/167:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/27![Frontier logo]()
$265
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am
ORD
- SJU
1 stop11h 30m
American Airlines
Fri 8/2812:55 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 6/30![American Airlines logo]()
$262
This Trip.com deal was found by Cheapflights users on 7/1. 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.
Wed 8/1912:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 8/257:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/1![Frontier logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Thu 8/208:05 am
ORD
- SJU
2 stops15h 29m
Multiple Airlines
Sun 9/67:14 pm
SJU
- ORD
Nonstop5h 13m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$258
This Delta deal was found by Cheapflights users on 6/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:30 am
ORD
- SJU
1 stop10h 08m
Delta
Sat 8/295:49 pm
SJU
- ORD
1 stop7h 08m
Delta
Deal found 6/29![Delta logo]()
$266
This Southwest deal was found by Cheapflights users on 7/1. 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 8/227:50 am
MDW
- SJU
2 stops7h 50m
Southwest
Wed 8/265:15 am
SJU
- MDW
2 stops7h 50m
Southwest
Deal found 7/1![Southwest logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 6/27. 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.
Thu 8/278:05 am
ORD
- SJU
1 stop31h 06m
Frontier
Thu 9/37:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/27![Frontier logo]()
$259
This Frontier deal was found by Cheapflights users on 6/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Wed 9/27:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/30![Frontier logo]()
$261
This American Airlines deal was found by Cheapflights users on 7/2. 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.
Thu 8/275:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Thu 9/31:38 pm
SJU
- ORD
1 stop11h 57m
American Airlines
Deal found 7/2![American Airlines logo]()
$267
One-way flights from Chicago to San JuanSearch for one-way flight options from Chicago to San Juan. Find affordable one-way fares based on user searches. Data last updated July 2, 2026.
Search for one-way flight options from Chicago to San Juan. Find affordable one-way fares based on user searches. Data last updated July 2, 2026.
This American Airlines deal was found by Cheapflights users on 7/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/228:30 am
ORD
- SJU
1 stop13h 27m
American Airlines
Deal found 7/1![American Airlines logo]()
$128
This Orbitz deal was found by Cheapflights users on 7/1. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/1![Frontier logo]()
$129
This American Airlines deal was found by Cheapflights users on 6/29. 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 8/154:59 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 6/29![American Airlines logo]()
$131
This Frontier deal was found by Cheapflights users on 7/1. 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.
Thu 7/912:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/1![Frontier logo]()
$132
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2711:23 am
ORD
- SJU
1 stop10h 06m
Delta
Deal found 7/1![Delta logo]()
$133
This Southwest deal was found by Cheapflights users on 7/1. 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 9/43:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 7/1![Southwest logo]()
$133
This American Airlines deal was found by Cheapflights users on 7/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:59 pm
ORD
- SJU
1 stop14h 44m
American Airlines
Deal found 7/1![American Airlines logo]()
$136
This eDestinos deal was found by Cheapflights users on 6/28. 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.
Thu 7/2312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/28![Frontier logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 6/30. 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.
Thu 8/138:05 am
ORD
- SJU
1 stop31h 06m
Frontier
Deal found 6/30![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 9/287:45 am
ORD
- SJU
1 stop14h 53m
Frontier
Deal found 7/1![Frontier logo]()
$141
This Super.com deal was found by Cheapflights users on 7/2. 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.
Thu 8/1312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/2![Frontier logo]()
$142
This United Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/75:45 pm
ORD
- SJU
1 stop10h 44m
United Airlines
Deal found 6/30![United Airlines logo]()
$143
Find flight deals from Chicago to San Juan
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to San Juan (PR1). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 2, 2026.
Round-trip from | $257 (Super.com) |
|---|---|
One-way from | $128 (American Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $387 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to San Juan 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 July 2, 2026.
Use the filters below to find and compare flights from Chicago to San Juan that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 9/4
3:15 pm-11:05 pm
1 stop6h 50m
San Juan Luis Munoz Marin Intl
Sun 9/6
5:20 am-11:15 am
1 stop6h 55m
$266
Quickest round-trip
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 8/24
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Wed 8/26
3:56 pm-8:05 pm
Nonstop5h 09m
$274
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 8/16
5:30 am-1:42 pm
1 stop7h 12m
San Juan Luis Munoz Marin Intl
Sat 8/29
5:49 pm-11:57 pm
1 stop7h 08m
$291
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/11
1:50 pm-10:29 pm
1 stop7h 39m
San Juan Luis Munoz Marin Intl
Tue 9/15
7:30 am-4:59 pm
1 stop10h 29m
$311
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 7/27
8:55 pm-9:00 am
1 stop11h 05m
San Juan Luis Munoz Marin Intl
Fri 7/31
10:20 pm-8:50 am
1 stop11h 30m
$351
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 10/4
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Fri 10/9
3:56 pm-8:05 pm
Nonstop5h 09m
$367
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 8/21
9:54 am-10:29 pm
1 stop11h 35m
San Juan Luis Munoz Marin Intl
Sun 8/30
7:00 am-4:51 pm
1 stop10h 51m
$371
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 9/5
11:00 am-6:15 pm
1 stop6h 15m
San Juan Luis Munoz Marin Intl
Sat 9/12
11:45 am-6:20 pm
1 stop7h 35m
$371
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 11/8
8:52 am-3:40 pm
Nonstop4h 48m
San Juan Luis Munoz Marin Intl
Fri 11/13
2:05 am-10:48 am
1 stop10h 43m
$372
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 10/29
2:16 pm-8:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Tue 11/3
1:00 pm-8:14 pm
1 stop9h 14m
$372
Showing 1-10 of 40 resultsSorted by cheapest first
Best time to book a flight from Chicago to San Juan
Have a flexible travel schedule? Discover the best time to fly to San Juan from Chicago with our price prediction graph.
CHI-PR1
MDW-SJU
ORD-SJU
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 San Juan
CHI-PR1
MDW-SJU
ORD-SJU
What is the cheapest month to book a flight from Chicago to San Juan?
Currently, April is the cheapest month in which you can book a flight from Chicago to San Juan (average of $316). Flying from Chicago to San Juan in December is currently the most expensive (average of $631). 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 SJU?
Find hourly flight availability from Chicago to San Juan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 2, 2026.
It’s typically best to fly out from Chicago to San Juan in the evening. Doing so could potentially save you 35% on the flight price compared to flying in the morning, which is usually more expensive.
Weekly flight availability from Chicago to San Juan
Explore weekly flight availability from Chicago to San Juan. 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 July 2, 2026.
The most flights from CHI to PR1 are scheduled on a Monday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (6 on average).
How much does it cost to fly round-trip from Chicago to San Juan?
How often are flights from Chicago to San Juan delayed?
About 22% of weekly flights between Chicago and San Juan 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 San Juan flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to San Juan flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 19% of flights being delayed.
How far ahead should I book a flight from Chicago to San Juan?
To ensure you get the cheapest price possible for a flight from Chicago to San Juan, you should look to book at least 90 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Chicago to San Juan?
Use this chart to determine the cheapest time to fly round-trip from Chicago to San Juan. Price data was last updated on June 27, 2026.
Travelers seeking maximum savings on their Chicago to San Juan flight should consider departing on Saturday 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 San Juan
Get insights into the airlines that provide service to San Juan. 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 San Juan. Reviews last updated July 2, 2026.
Read through reviews of airlines operating flights from Chicago to San Juan, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
7.9
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
7.9
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
7.9
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
7.9
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
7.9
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
7.9
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to San Juan. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to San Juan
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Complete your trip
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Search flights from Chicago to San Juan by cabin class
Find flights from Chicago to San Juan, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and San Juan flights
Browse other Chicago and San Juan flight options. Last updated on July 2, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on July 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Chicago to San Juan
Discover the top 6 airlines that operate flights from Chicago to San Juan. 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 July 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$314 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$461 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$234 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$262 | Average$508 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$300 | Average$502 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$352 | Average$486 | FlexibilityNo cancel fee | On-time63% |