$99+ Cheap flights from San Juan 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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Jun 3 — Jun 101
Round-trip
1 adult, Economy
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Find cheap flights from San Juan 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.Cheapflights Tip: The best prices from San Juan to Chicago are usually found in February or September, booked 90 days in advance, depart on a Friday or Thursday and return on a Tuesday
Cheap flight deals from San Juan to Chicago
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Best
Last-minute
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Cheapest flights from San Juan to ChicagoExplore the most affordable flight options available from San Juan to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 4, 2026.
Explore the most affordable flight options available from San Juan to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Sat 5/307:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sun 5/3112:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 5/1![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:00 am
SJU
- ORD
1 stop7h 25m
Frontier
Sat 8/1512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 5/2![Frontier logo]()
$172
This eDestinos 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 eDestinos 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 4/30![Frontier logo]()
$179
This Frontier deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/24:05 pm
SJU
- ORD
1 stop8h 00m
Frontier
Sat 8/1512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 5/2![Frontier logo]()
$182
This Frontier 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 Frontier 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
Sun 5/2412:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/30![Frontier logo]()
$183
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:30 am
SJU
- ORD
1 stop13h 14m
Frontier
Sat 5/307:52 pm
ORD
- SJU
1 stop7h 09m
Frontier
Deal found 4/30![Frontier logo]()
$189
This eDestinos deal was found by Cheapflights users on 5/1. 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 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
Sun 5/1710:22 am
ORD
- SJU
1 stop12h 35m
Frontier
Deal found 5/1![Frontier logo]()
$196
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2111:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Sun 5/244:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$198
This eDestinos deal was found by Cheapflights users on 5/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Tue 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 5/1![Frontier logo]()
$201
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2011:01 am
SJU
- ORD
Nonstop5h 10m
Multiple Airlines
Tue 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$202
This Priceline deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sat 5/3012:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 5/3![Frontier logo]()
$204
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:30 am
SJU
- MDW
2 stops10h 25m
Southwest
Mon 8/242:55 pm
MDW
- SJU
1 stop7h 55m
Southwest
Deal found 4/30![Southwest logo]()
$226
Best flights from San Juan to ChicagoDiscover carefully curated flight deals from San Juan to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 4, 2026.
Discover carefully curated flight deals from San Juan to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 4, 2026.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/131:06 pm
SJU
- ORD
1 stop9h 14m
Delta
Tue 8/186:00 am
ORD
- SJU
1 stop9h 31m
Delta
Deal found 4/30![Delta logo]()
$226
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/17:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Sun 8/168:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 5/1![United Airlines logo]()
$307
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/297:00 am
SJU
- MDW
1 stop6h 45m
Southwest
Tue 8/47:30 am
MDW
- SJU
1 stop10h 30m
Southwest
Deal found 4/30![Southwest logo]()
$331
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/131:06 pm
SJU
- ORD
1 stop8h 11m
Delta
Thu 8/205:30 am
ORD
- SJU
1 stop7h 00m
Delta
Deal found 4/30![Delta logo]()
$266
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Wed 6/35:00 am
ORD
- SJU
1 stop7h 45m
United Airlines
Deal found 5/2![United Airlines logo]()
$312
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/116:00 am
SJU
- MDW
1 stop9h 40m
Southwest
Mon 6/1511:35 am
MDW
- SJU
1 stop11h 50m
Southwest
Deal found 5/2![Southwest logo]()
$391
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.
Sat 5/95:45 am
SJU
- MDW
2 stops9h 10m
Southwest
Tue 5/1212:50 pm
MDW
- SJU
2 stops8h 50m
Southwest
Deal found 4/29![Southwest logo]()
$396
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/21:00 am
SJU
- ORD
1 stop9h 00m
United Airlines
Wed 6/242:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 5/4![United Airlines logo]()
$432
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 7/1610:20 pm
SJU
- MDW
1 stop11h 55m
Southwest
Mon 8/32:45 pm
MDW
- SJU
2 stops8h 20m
Southwest
Deal found 5/4![Southwest logo]()
$411
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 9/13:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Wed 9/308:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 5/4![United Airlines logo]()
$432
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/315:00 am
SJU
- MDW
1 stop6h 55m
Southwest
Thu 8/61:00 pm
MDW
- SJU
2 stops8h 50m
Southwest
Deal found 4/30![Southwest logo]()
$426
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 6/410:20 pm
SJU
- MDW
1 stop12h 40m
Southwest
Mon 6/225:10 pm
MDW
- SJU
1 stop7h 10m
Southwest
Deal found 4/29![Southwest logo]()
$431
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/197:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Tue 5/192:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 5/1![United Airlines logo]()
$507
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 7/1610:20 pm
SJU
- MDW
1 stop12h 40m
Southwest
Sat 8/12:10 pm
MDW
- SJU
2 stops8h 30m
Southwest
Deal found 5/4![Southwest logo]()
$446
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 9/53:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Mon 9/148:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 5/4![United Airlines logo]()
$517
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 6/46:00 am
SJU
- MDW
1 stop11h 20m
Southwest
Sat 6/68:25 am
MDW
- SJU
1 stop9h 40m
Southwest
Deal found 4/29![Southwest logo]()
$461
This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/203:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Wed 6/32:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 5/3![United Airlines logo]()
$522
This Southwest deal was found by Cheapflights users on 5/1. 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.
Mon 5/111:00 pm
SJU
- MDW
1 stop8h 50m
Southwest
Tue 5/121:25 pm
MDW
- SJU
1 stop6h 40m
Southwest
Deal found 5/1![Southwest logo]()
$462
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 10/83:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Tue 10/138:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 5/4![United Airlines logo]()
$547
Last-minute flights from San Juan to ChicagoDiscover last-minute flight deals from San Juan to Chicago. Data last updated May 4, 2026 and is based on user searches.
Discover last-minute flight deals from San Juan to Chicago. Data last updated May 4, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 5/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:30 am
SJU
- ORD
1 stop13h 14m
Frontier
Fri 5/157:30 am
ORD
- SJU
1 stop14h 58m
Frontier
Deal found 5/1![Frontier logo]()
$205
This eDestinos deal was found by Cheapflights users on 5/1. 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 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
Sun 5/1710:22 am
ORD
- SJU
1 stop12h 35m
Frontier
Deal found 5/1![Frontier logo]()
$196
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:30 am
SJU
- ORD
1 stop13h 14m
Frontier
Sat 5/307:52 pm
ORD
- SJU
1 stop7h 09m
Frontier
Deal found 4/30![Frontier logo]()
$189
This eDestinos deal was found by Cheapflights users on 5/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:30 am
SJU
- ORD
1 stop13h 14m
Frontier
Fri 5/2212:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 5/1![Frontier logo]()
$206
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2011:01 am
SJU
- ORD
Nonstop5h 10m
Multiple Airlines
Tue 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$202
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2111:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Sun 5/244:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$198
This eDestinos 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 eDestinos 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 4/30![Frontier logo]()
$179
This Frontier 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 Frontier 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
Sun 5/2412:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/30![Frontier logo]()
$183
This eDestinos deal was found by Cheapflights users on 5/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Tue 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 5/1![Frontier logo]()
$201
This Priceline deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:25 am
SJU
- MDW
1 stop8h 47m
Frontier
Tue 5/263:07 pm
MDW
- SJU
1 stop12h 42m
Frontier
Deal found 5/1![Frontier logo]()
$281
This Priceline deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sat 5/3012:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 5/3![Frontier logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Sat 5/307:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sun 5/3112:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 5/1![Frontier logo]()
$171
One-way flights from San Juan to ChicagoSearch for one-way flight options from San Juan to Chicago. Find affordable one-way fares based on user searches. Data last updated May 4, 2026.
Search for one-way flight options from San Juan to Chicago. Find affordable one-way fares based on user searches. Data last updated May 4, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/234:59 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 5/1![Spirit Airlines logo]()
$99
This Spirit 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 Spirit 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
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$100
This Trip.com deal was found by Cheapflights users on 5/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 5/2![Frontier logo]()
$101
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 Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Fri 5/2911:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 5/1![Spirit Airlines logo]()
$105
This Mytrip deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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
Deal found 5/4![Frontier logo]()
$108
This American Airlines 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 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 4/30![American Airlines logo]()
$109
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:00 am
SJU
- ORD
1 stop7h 24m
Frontier
Deal found 4/30![Frontier logo]()
$110
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Thu 5/2812:59 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 5/1![American Airlines logo]()
$111
This eDestinos deal was found by Cheapflights users on 5/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Deal found 5/1![Frontier logo]()
$112
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/912:56 pm
SJU
- ORD
1 stop10h 12m
Delta
Deal found 5/3![Delta logo]()
$113
This eDestinos deal was found by Cheapflights users on 5/2. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:30 am
SJU
- ORD
1 stop13h 14m
Frontier
Deal found 5/2![Frontier logo]()
$116
Find flight deals from San Juan to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from San Juan (PR1) to Chicago (CHI). 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 May 4, 2026.
Round-trip from | $171 (Kiwi.com) |
|---|---|
One-way from | $99 (Cheapflightsfares) |
Popular in | December |
Cheapest in | February |
Average price | $317 |
Cheapflights Fare Finder
Customize your flight search to find flights from San Juan 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 May 4, 2026.
Use the filters below to find and compare flights from San Juan 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
Thu 8/13
1:06 pm-9:20 pm
1 stop9h 14m
Chicago O'Hare Intl
Tue 8/18
6:00 am-4:31 pm
1 stop9h 31m
$226
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 8/13
1:06 pm-8:17 pm
1 stop8h 11m
Chicago O'Hare Intl
Thu 8/20
5:30 am-1:30 pm
1 stop7h 00m
$266
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Sat 8/1
7:40 am-11:53 am
Nonstop5h 13m
Chicago O'Hare Intl
Sun 8/16
8:55 am-2:44 pm
Nonstop4h 49m
$307
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 5/28
7:40 am-11:53 am
Nonstop5h 13m
Chicago O'Hare Intl
Wed 6/3
5:00 am-1:45 pm
1 stop7h 45m
$312
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 7/29
7:00 am-12:45 pm
1 stop6h 45m
Chicago Midway
Tue 8/4
7:30 am-7:00 pm
1 stop10h 30m
$331
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 6/11
6:00 am-2:40 pm
1 stop9h 40m
Chicago Midway
Mon 6/15
11:35 am-12:25 am
1 stop11h 50m
$391
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 5/9
5:45 am-1:55 pm
2 stops9h 10m
Chicago Midway
Tue 5/12
12:50 pm-10:40 pm
2 stops8h 50m
$396
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 7/16
10:20 pm-9:15 am
1 stop11h 55m
Chicago Midway
Mon 8/3
2:45 pm-12:05 am
2 stops8h 20m
$411
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 7/31
5:00 am-10:55 am
1 stop6h 55m
Chicago Midway
Thu 8/6
1:00 pm-10:50 pm
2 stops8h 50m
$426
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 6/4
10:20 pm-10:00 am
1 stop12h 40m
Chicago Midway
Mon 6/22
5:10 pm-1:20 am
1 stop7h 10m
$431
Showing 1-10 of 41 resultsSorted by cheapest first
Best time to book a flight from San Juan to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from San Juan with our price prediction graph.
PR1-CHI
SJU-ORD
SJU-MDW
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 San Juan to Chicago
PR1-CHI
SJU-ORD
SJU-MDW
How far ahead should I book a flight from San Juan to Chicago?
To ensure you get the cheapest price possible for a flight from San Juan to Chicago, you should look to book at least 81 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 San Juan to Chicago?
Currently, May is the cheapest month in which you can book a flight from San Juan to Chicago (average of $64). Flying from San Juan 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 SJU to CHI?
Find hourly flight availability from San Juan 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 May 4, 2026.
When flying from San Juan 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 46% versus a flight in the afternoon.
What is the cheapest day to fly from San Juan to Chicago?
Use this chart to determine the cheapest time to fly round-trip from San Juan to Chicago. Price data was last updated on May 2, 2026.
Travelers seeking maximum savings on their San Juan 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 San Juan to Chicago
Explore weekly flight availability from San Juan 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 May 4, 2026.
The most flights from PR1 to CHI are scheduled on a Monday (9 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 San Juan to Chicago?
How often are flights from San Juan to Chicago delayed?
About 8% of weekly flights between San Juan 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 San Juan 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 San Juan 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 May 4, 2026.
Read reviews from past customers who have flown United Airlines,JetBlue, andAmerican Airlines from San Juan 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.
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Overall
7.4
Food
6.6
Crew
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Overall
7.4
Food
6.6
Crew
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Overall
7.4
Food
6.6
Crew
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Overall
7.4
Food
6.6
Crew
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Overall
7.4
Food
6.6
Crew
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Overall
7.4
Food
6.6
Crew
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Related info for your journey
Find useful and relevant information for your journey from San Juan 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
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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 May 4, 2026.
Complete your trip
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Search flights from San Juan to Chicago by cabin class
Find flights from San Juan to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
San Juan and Chicago flights
Browse other San Juan and Chicago flight options. Last updated on May 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 7 airlines flying from San Juan to Chicago
Discover the top 7 airlines that operate flights from San Juan 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 May 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$116 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$121 | Average$265 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$128 | Average$254 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$254 | Average$484 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$257 | Average$440 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$292 | Average$512 | FlexibilityNo cancel fee | On-time63% |