$92+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Mar 13 — Mar 201
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 April or October, booked 57 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 February 11, 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 February 11, 2026.
This Spirit deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2012:18 pm
ORD
- SJU
Nonstop4h 36m
Spirit Airlines
Thu 4/2312:30 pm
SJU
- ORD
Nonstop5h 08m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/28:16 pm
ORD
- SJU
1 stop17h 15m
Spirit Airlines
Fri 3/611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Fri 2/275:45 pm
SJU
- ORD
1 stop8h 55m
Spirit Airlines
Deal found 2/8![Spirit Airlines logo]()
$182
This Cheapflightsfares deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/28:16 pm
ORD
- SJU
1 stop17h 15m
Spirit Airlines
Thu 3/512:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/91:27 pm
ORD
- SJU
1 stop22h 06m
Frontier
Fri 5/156:00 am
SJU
- ORD
1 stop17h 57m
Frontier
Deal found 2/10![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2412:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Mon 3/93:22 pm
SJU
- ORD
1 stop8h 17m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2412:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Tue 3/106:00 am
SJU
- ORD
1 stop12h 03m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Wed 2/254:06 pm
SJU
- ORD
2 stops32h 59m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2512:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Fri 3/612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$188
This CheapOair deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 3/29:22 pm
MDW
- SJU
1 stop25h 21m
Frontier
Wed 3/45:25 pm
SJU
- MDW
1 stop23h 01m
Frontier
Deal found 2/7![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/48:30 am
ORD
- SJU
1 stop16h 23m
Multiple Airlines
Fri 3/611:52 am
SJU
- ORD
1 stop8h 26m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/22:19 pm
MDW
- SJU
2 stops26h 39m
Multiple Airlines
Fri 3/66:50 pm
SJU
- MDW
1 stop20h 51m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$189
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 February 11, 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 February 11, 2026.
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 5/1312:51 pm
MDW
- SJU
1 stop8h 26m
Delta
Mon 5/1812:50 pm
SJU
- MDW
1 stop9h 19m
Delta
Deal found 2/9![Delta logo]()
$246
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/248:25 am
MDW
- SJU
1 stop6h 40m
Southwest
Thu 2/265:30 am
SJU
- MDW
2 stops10h 20m
Southwest
Deal found 2/10![Southwest logo]()
$286
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/152:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Fri 5/227:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 2/10![United Airlines logo]()
$323
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/132:59 pm
ORD
- SJU
1 stop6h 18m
Delta
Sun 5/2412:50 pm
SJU
- ORD
1 stop12h 09m
Delta
Deal found 2/10![Delta logo]()
$256
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/139:44 am
ORD
- SJU
1 stop11h 33m
Delta
Sat 5/237:00 am
SJU
- ORD
1 stop11h 35m
Delta
Deal found 2/10![Delta logo]()
$256
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 5/107:45 am
MDW
- SJU
2 stops7h 45m
Southwest
Sat 5/1610:00 am
SJU
- MDW
1 stop11h 40m
Southwest
Deal found 2/9![Southwest logo]()
$296
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/58:15 am
ORD
- SJU
1 stop7h 08m
Delta
Thu 5/145:15 pm
SJU
- ORD
1 stop7h 44m
Delta
Deal found 2/10![Delta logo]()
$256
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 6/12:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Fri 6/51:00 am
SJU
- ORD
1 stop7h 42m
United Airlines
Deal found 2/9![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/67:14 am
ORD
- SJU
1 stop8h 09m
Delta
Wed 5/132:20 pm
SJU
- ORD
1 stop7h 05m
Delta
Deal found 2/10![Delta logo]()
$256
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/126:41 am
ORD
- SJU
1 stop8h 42m
Delta
Wed 5/135:15 pm
SJU
- ORD
1 stop7h 44m
Delta
Deal found 2/10![Delta logo]()
$256
This Southwest deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 4/257:45 am
MDW
- SJU
Nonstop4h 35m
Southwest
Sat 5/305:15 am
SJU
- MDW
1 stop14h 00m
Southwest
Deal found 2/7![Southwest logo]()
$342
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:55 am
ORD
- SJU
Nonstop4h 45m
United Airlines
Thu 3/58:30 am
SJU
- ORD
Nonstop5h 22m
United Airlines
Deal found 2/10![United Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/109:44 am
ORD
- SJU
1 stop11h 33m
Delta
Wed 5/132:20 pm
SJU
- ORD
1 stop7h 05m
Delta
Deal found 2/10![Delta logo]()
$256
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 5/113:45 pm
ORD
- SJU
2 stops17h 50m
Southwest
Mon 5/188:40 pm
SJU
- ORD
2 stops17h 10m
Southwest
Deal found 2/9![Southwest logo]()
$346
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/912:22 pm
ORD
- SJU
1 stop8h 55m
Delta
Wed 5/132:20 pm
SJU
- ORD
1 stop8h 29m
Delta
Deal found 2/10![Delta logo]()
$256
This Southwest deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/91:55 pm
ORD
- SJU
2 stops18h 10m
Southwest
Mon 5/118:40 pm
SJU
- ORD
2 stops17h 10m
Southwest
Deal found 2/7![Southwest logo]()
$346
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:00 am
MDW
- SJU
1 stop9h 23m
Delta
Sat 4/256:15 am
SJU
- MDW
1 stop11h 14m
Delta
Deal found 2/10![Delta logo]()
$256
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/131:00 pm
MDW
- SJU
1 stop8h 40m
Southwest
Wed 5/205:05 am
SJU
- MDW
2 stops11h 45m
Southwest
Deal found 2/10![Southwest logo]()
$359
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/612:53 pm
MDW
- SJU
1 stop9h 20m
Delta
Sat 5/162:20 pm
SJU
- MDW
1 stop7h 49m
Delta
Deal found 2/10![Delta logo]()
$256
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/181:25 pm
MDW
- SJU
2 stops9h 30m
Southwest
Thu 5/216:50 am
SJU
- MDW
2 stops14h 45m
Southwest
Deal found 2/10![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/257:45 am
MDW
- SJU
Nonstop4h 35m
Southwest
Sat 5/25:15 am
SJU
- MDW
1 stop14h 00m
Southwest
Deal found 2/10![Southwest logo]()
$368
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 6/17:55 am
MDW
- SJU
1 stop6h 40m
Southwest
Sat 6/65:30 am
SJU
- MDW
Nonstop4h 50m
Southwest
Deal found 2/9![Southwest logo]()
$377
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 5/184:35 pm
MDW
- SJU
1 stop6h 20m
Southwest
Sat 5/2310:00 am
SJU
- MDW
1 stop9h 15m
Southwest
Deal found 2/9![Southwest logo]()
$381
Last-minute flights from Chicago to San JuanDiscover last-minute flight deals from Chicago to San Juan. Data last updated February 11, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San Juan. Data last updated February 11, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 2/264:36 pm
SJU
- ORD
1 stop9h 11m
Spirit Airlines
Deal found 2/8![Spirit Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Wed 2/254:06 pm
SJU
- ORD
2 stops32h 59m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:00 am
MDW
- SJU
1 stop30h 22m
Multiple Airlines
Fri 2/276:27 pm
SJU
- MDW
1 stop29h 12m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2412:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Mon 3/93:22 pm
SJU
- ORD
1 stop8h 17m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2412:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Tue 3/106:00 am
SJU
- ORD
1 stop12h 03m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:00 am
ORD
- SJU
1 stop6h 31m
Spirit Airlines
Fri 3/611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2512:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 3/511:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$188
This Cheapflightsfares deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/28:16 pm
ORD
- SJU
1 stop17h 15m
Spirit Airlines
Fri 3/611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/28:16 pm
ORD
- SJU
1 stop17h 15m
Spirit Airlines
Thu 3/512:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$183
This Expedia deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
Mon 3/26:00 am
MDW
- SJU
1 stop7h 02m
Frontier
Wed 3/45:25 pm
SJU
- MDW
1 stop23h 01m
Frontier
Deal found 2/9![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/22:19 pm
MDW
- SJU
2 stops26h 39m
Multiple Airlines
Fri 3/66:50 pm
SJU
- MDW
1 stop20h 51m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/48:30 am
ORD
- SJU
1 stop16h 23m
Multiple Airlines
Fri 3/611:52 am
SJU
- ORD
1 stop8h 26m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$189
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 February 11, 2026.
Search for one-way flight options from Chicago to San Juan. Find affordable one-way fares based on user searches. Data last updated February 11, 2026.
This eDestinos deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/104:18 pm
ORD
- SJU
1 stop8h 45m
Frontier
Deal found 2/8![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:00 am
MDW
- SJU
1 stop31h 06m
Frontier
Deal found 2/10![Frontier logo]()
$92
This Super.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:15 am
ORD
- SJU
1 stop8h 16m
Spirit Airlines
Deal found 2/8![Spirit Airlines logo]()
$93
This Cheapflightsfares deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/245:15 am
ORD
- SJU
1 stop8h 16m
Spirit Airlines
Deal found 2/8![Spirit Airlines logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 5/712:22 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$95
This Trip.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/96:00 am
MDW
- SJU
1 stop18h 21m
Frontier
Deal found 2/11![Frontier logo]()
$95
This Cheapflightsfares deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/99:18 am
ORD
- SJU
1 stop7h 40m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$96
This eDestinos deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 4/177:15 pm
ORD
- SJU
1 stop19h 15m
Frontier
Deal found 2/8![Frontier logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:00 am
MDW
- SJU
2 stops31h 31m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$97
This WAYA deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/244:51 pm
ORD
- SJU
1 stop7h 28m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$98
This Super.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/115:05 am
ORD
- SJU
1 stop12h 50m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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.
Wed 4/110:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$100
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 February 11, 2026.
Round-trip from | $179 (Spirit) |
|---|---|
One-way from | $92 (eDestinos) |
Popular in | December |
Cheapest in | April |
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 February 11, 2026.
Use the filters below to find and compare flights from Chicago to San Juan that are best for you.
Fly from
Chicago
Fly to
San Juan
Route
Depart
Return
Price
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 5/13
12:51 pm-10:17 pm
1 stop8h 26m
San Juan Luis Munoz Marin Intl
Mon 5/18
12:50 pm-9:09 pm
1 stop9h 19m
$246
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 5/13
2:59 pm-10:17 pm
1 stop6h 18m
San Juan Luis Munoz Marin Intl
Sun 5/24
12:50 pm-11:59 pm
1 stop12h 09m
$256
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 5/13
9:44 am-10:17 pm
1 stop11h 33m
San Juan Luis Munoz Marin Intl
Sat 5/23
7:00 am-5:35 pm
1 stop11h 35m
$256
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/5
8:15 am-4:23 pm
1 stop7h 08m
San Juan Luis Munoz Marin Intl
Thu 5/14
5:15 pm-11:59 pm
1 stop7h 44m
$256
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 5/6
7:14 am-4:23 pm
1 stop8h 09m
San Juan Luis Munoz Marin Intl
Wed 5/13
2:20 pm-8:25 pm
1 stop7h 05m
$256
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/12
6:41 am-4:23 pm
1 stop8h 42m
San Juan Luis Munoz Marin Intl
Wed 5/13
5:15 pm-11:59 pm
1 stop7h 44m
$256
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 5/10
9:44 am-10:17 pm
1 stop11h 33m
San Juan Luis Munoz Marin Intl
Wed 5/13
2:20 pm-8:25 pm
1 stop7h 05m
$256
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 5/9
12:22 pm-10:17 pm
1 stop8h 55m
San Juan Luis Munoz Marin Intl
Wed 5/13
2:20 pm-9:49 pm
1 stop8h 29m
$256
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 4/20
6:00 am-4:23 pm
1 stop9h 23m
San Juan Luis Munoz Marin Intl
Sat 4/25
6:15 am-4:29 pm
1 stop11h 14m
$256
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 5/6
12:53 pm-11:13 pm
1 stop9h 20m
San Juan Luis Munoz Marin Intl
Sat 5/16
2:20 pm-9:09 pm
1 stop7h 49m
$256
Showing 1-10 of 43 results
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
ORD-SJU
MDW-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
ORD-SJU
MDW-SJU
How far ahead should I book a flight from Chicago to San Juan?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to San Juan. Price data was last updated on February 6, 2026.
To ensure you get the cheapest price possible for a flight from Chicago to San Juan, you should look to book at least 57 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 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 $91). Flying from Chicago to San Juan in December is currently the most expensive (average of $224). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to 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 February 11, 2026.
It’s typically best to fly out from Chicago to San Juan in the evening. Doing so could potentially save you 32% on the flight price compared to flying at noon, which is usually more expensive.
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 February 10, 2025.
Travelers seeking maximum savings on their Chicago to San Juan flight should consider departing on Tuesday mornings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to 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 February 11, 2026.
The most flights from CHI to PR1 are scheduled on a Monday (11 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (7 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 18% 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 Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to San Juan flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 14% of flights being delayed.
Reviews of airlines servicing 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 February 11, 2026.
Read through reviews of airlines operating flights from Chicago to San Juan, such as United Airlines, American Airlines, and JetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.1
Overall
7.4
Food
6.6
Comfort
7.3
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Crew
8.1
Overall
7.4
Food
6.6
Comfort
7.3
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Crew
8.1
Overall
7.4
Food
6.6
Comfort
7.3
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Crew
8.1
Overall
7.4
Food
6.6
Comfort
7.3
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Crew
8.1
Overall
7.4
Food
6.6
Comfort
7.3
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Crew
8.1
Overall
7.4
Food
6.6
Comfort
7.3
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Related info for your journey
Find useful and relevant information for your journey from Chicago to 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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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 February 11, 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 February 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 7 airlines flying from Chicago to San Juan
Discover the top 7 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 February 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$106 | Average$287 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$237 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$132 | Average$440 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$309 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$251 | Average$507 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$350 | Average$528 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$379 | Average$487 | FlexibilityNo cancel fee | On-time63% |