$87+ Cheap flights from San Juan to Illinois
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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Mar 4 — Mar 111
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from San Juan to Illinois with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from San Juan to Illinois
Cheapest
Best
Last-minute
One-way
Cheapest flights from San Juan to IllinoisExplore the most affordable flight options available from San Juan to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 2, 2026.
Explore the most affordable flight options available from San Juan to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 2, 2026.
This Expedia deal was found by Cheapflights users on 2/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Mon 3/98:16 pm
ORD
- SJU
1 stop17h 15m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$134
This Orbitz deal was found by Cheapflights users on 2/1. 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.
Fri 2/2711:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Mon 3/28:16 pm
ORD
- SJU
1 stop17h 15m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$144
This Orbitz deal was found by Cheapflights users on 2/1. 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.
Thu 3/512:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Sat 3/78:16 pm
ORD
- SJU
1 stop16h 15m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$146
This Orbitz deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1912:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Mon 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$147
This Expedia deal was found by Cheapflights users on 2/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/51:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Sat 2/712:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$149
This Orbitz deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1111:32 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Wed 3/1810:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$156
This Cheapflightsfares deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Tue 3/38:16 pm
ORD
- SJU
1 stop17h 15m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$157
This Orbitz deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
SJU
- MDW
1 stop9h 56m
Frontier
Sat 2/288:00 am
MDW
- SJU
1 stop14h 43m
Frontier
Deal found 1/31![Frontier logo]()
$188
This Frontier deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:25 pm
SJU
- STL
1 stop8h 34m
Frontier
Mon 3/23:49 pm
STL
- SJU
1 stop9h 04m
Frontier
Deal found 1/31![Frontier logo]()
$202
This Frontier deal was found by Cheapflights users on 2/2. 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.
Thu 3/54:11 pm
SJU
- MDW
1 stop8h 18m
Frontier
Mon 3/96:05 am
MDW
- SJU
1 stop7h 12m
Frontier
Deal found 2/2![Frontier logo]()
$220
This Frontier deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/113:22 pm
SJU
- MDW
1 stop7h 57m
Frontier
Mon 3/166:05 am
MDW
- SJU
1 stop7h 12m
Frontier
Deal found 1/31![Frontier logo]()
$221
This Frontier deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/273:53 am
SJU
- MDW
1 stop13h 02m
Frontier
Mon 3/29:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Deal found 1/31![Frontier logo]()
$223
Best flights from San Juan to IllinoisDiscover carefully curated flight deals from San Juan to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 2, 2026.
Discover carefully curated flight deals from San Juan to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/30. 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.
Tue 3/106:39 pm
SJU
- ORD
1 stop16h 00m
Multiple Airlines
Tue 3/1710:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$182
This eDestinos deal was found by Cheapflights users on 2/2. 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.
Thu 2/267:09 pm
SJU
- ORD
1 stop28h 31m
Frontier
Mon 3/25:05 am
ORD
- SJU
1 stop7h 57m
Frontier
Deal found 2/2![Frontier logo]()
$183
This Travelocity deal was found by Cheapflights users on 1/30. 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 3/113:36 pm
SJU
- ORD
1 stop9h 11m
Spirit Airlines
Sat 3/146:10 pm
ORD
- SJU
1 stop16h 39m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$201
This American Airlines deal was found by Cheapflights users on 2/2. 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 4/1611:59 pm
SJU
- STL
1 stop9h 55m
American Airlines
Sun 4/198:03 pm
STL
- SJU
1 stop17h 17m
American Airlines
Deal found 2/2![American Airlines logo]()
$246
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/109:45 pm
SJU
- STL
1 stop11h 05m
Southwest
Sun 5/176:00 am
STL
- SJU
1 stop9h 30m
Southwest
Deal found 1/31![Southwest logo]()
$286
This Frontier deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:25 pm
SJU
- STL
1 stop8h 34m
Frontier
Mon 3/23:49 pm
STL
- SJU
1 stop9h 04m
Frontier
Deal found 1/31![Frontier logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 3/56:00 am
SJU
- MDW
1 stop9h 56m
Multiple Airlines
Mon 3/96:00 am
MDW
- SJU
1 stop10h 58m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$202
This Cheapflightsfares deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/61:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Sun 2/812:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$206
This Cheapflightsfares deal was found by Cheapflights users on 2/1. 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.
Wed 4/222:15 am
SJU
- ORD
1 stop17h 00m
Spirit Airlines
Sun 4/2612:22 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$207
This Frontier deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/54:11 pm
SJU
- MDW
1 stop8h 18m
Frontier
Mon 3/99:51 pm
MDW
- SJU
1 stop11h 21m
Frontier
Deal found 1/31![Frontier logo]()
$220
This American Airlines deal was found by Cheapflights users on 2/1. 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 3/58:40 am
SJU
- STL
1 stop11h 27m
American Airlines
Wed 3/1111:22 am
STL
- SJU
1 stop10h 36m
American Airlines
Deal found 2/1![American Airlines logo]()
$246
This Mytrip deal was found by Cheapflights users on 1/30. 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.
Mon 2/233:53 am
SJU
- ORD
1 stop13h 59m
Multiple Airlines
Sun 3/112:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$226
This Cheapflightsfares deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/311:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Mon 4/68:56 pm
ORD
- SJU
Nonstop4h 33m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$208
This American Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/274:10 pm
SJU
- STL
1 stop9h 25m
American Airlines
Mon 3/26:00 am
STL
- SJU
1 stop15h 40m
American Airlines
Deal found 1/31![American Airlines logo]()
$246
This Mytrip deal was found by Cheapflights users on 2/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1011:07 am
SJU
- MDW
1 stop8h 06m
Frontier
Thu 3/126:00 am
MDW
- SJU
1 stop18h 21m
Frontier
Deal found 2/1![Frontier logo]()
$227
This Cheapflightsfares deal was found by Cheapflights users on 2/1. 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.
Mon 3/301:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Wed 4/812:29 pm
ORD
- SJU
Nonstop4h 31m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
SJU
- MDW
1 stop9h 56m
Multiple Airlines
Sat 2/289:15 am
MDW
- SJU
2 stops11h 54m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$249
This Cheapflightsfares deal was found by Cheapflights users on 2/1. 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.
Wed 4/2212:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Sat 4/2512:22 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$208
This Frontier deal was found by Cheapflights users on 2/1. 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.
Mon 4/203:19 pm
SJU
- STL
1 stop9h 00m
Frontier
Sat 4/254:55 pm
STL
- SJU
1 stop8h 06m
Frontier
Deal found 2/1![Frontier logo]()
$244
This American Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/143:07 pm
SJU
- STL
1 stop9h 41m
American Airlines
Tue 5/196:27 am
STL
- SJU
1 stop14h 38m
American Airlines
Deal found 1/31![American Airlines logo]()
$286
This Cheapflightsfares deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1212:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Sun 2/1512:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:00 am
SJU
- MDW
1 stop9h 56m
Multiple Airlines
Sun 3/87:30 am
MDW
- SJU
1 stop7h 09m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 4/1710:53 am
SJU
- MDW
2 stops33h 38m
Frontier
Fri 4/247:30 am
MDW
- SJU
1 stop25h 56m
Frontier
Deal found 2/1![Frontier logo]()
$260
This Cheapflightsfares deal was found by Cheapflights users on 1/30. 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.
Sat 2/144:36 pm
SJU
- ORD
1 stop9h 11m
Spirit Airlines
Sun 2/225:15 am
ORD
- SJU
1 stop8h 16m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 2/134:16 pm
SJU
- MDW
1 stop30h 52m
Frontier
Mon 2/169:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Deal found 1/30![Frontier logo]()
$278
This CheapOair deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Sun 3/87:23 pm
ORD
- SJU
1 stop21h 35m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$234
This eDestinos deal was found by Cheapflights users on 2/2. 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.
Tue 2/243:53 am
SJU
- MDW
2 stops17h 14m
Frontier
Sat 2/286:25 am
MDW
- SJU
2 stops42h 00m
Frontier
Deal found 2/2![Frontier logo]()
$278
This Frontier deal was found by Cheapflights users on 1/30. 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 2/54:22 pm
SJU
- MDW
1 stop7h 57m
Frontier
Mon 2/91:00 pm
MDW
- SJU
1 stop8h 59m
Frontier
Deal found 1/30![Frontier logo]()
$279
Last-minute flights from San Juan to IllinoisDiscover last-minute flight deals from San Juan to Illinois. Data last updated February 2, 2026 and is based on user searches.
Discover last-minute flight deals from San Juan to Illinois. Data last updated February 2, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 2/1. 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.
Wed 2/114:40 pm
SJU
- ORD
1 stop9h 07m
Spirit Airlines
Wed 3/47:00 am
ORD
- SJU
1 stop6h 31m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$169
This eDestinos deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1212:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Mon 2/1612:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$175
This eDestinos deal was found by Cheapflights users on 1/30. 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.
Thu 2/1212:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Sun 2/1512:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$179
This CheapOair deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1212:32 pm
SJU
- ORD
Nonstop5h 16m
Multiple Airlines
Tue 2/178:30 am
ORD
- SJU
1 stop16h 18m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/147:05 am
SJU
- MDW
1 stop16h 03m
Frontier
Sun 2/156:15 am
MDW
- SJU
1 stop28h 24m
Frontier
Deal found 2/1![Frontier logo]()
$238
This Frontier deal was found by Cheapflights users on 2/1. 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 2/196:00 am
SJU
- MDW
1 stop10h 26m
Frontier
Sun 2/226:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Deal found 2/1![Frontier logo]()
$237
This Frontier deal was found by Cheapflights users on 2/1. 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 2/193:53 am
SJU
- MDW
1 stop12h 33m
Frontier
Mon 2/239:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Deal found 2/1![Frontier logo]()
$246
This Orbitz deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
SJU
- MDW
1 stop9h 56m
Frontier
Sat 2/288:00 am
MDW
- SJU
1 stop14h 43m
Frontier
Deal found 1/31![Frontier logo]()
$188
This Frontier deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:25 pm
SJU
- STL
1 stop8h 34m
Frontier
Mon 3/23:49 pm
STL
- SJU
1 stop9h 04m
Frontier
Deal found 1/31![Frontier logo]()
$202
This Frontier deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/273:53 am
SJU
- MDW
1 stop13h 02m
Frontier
Mon 3/29:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Deal found 1/31![Frontier logo]()
$223
This Priceline deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/273:53 am
SJU
- STL
1 stop22h 06m
Frontier
Sat 3/74:21 pm
STL
- SJU
1 stop9h 37m
Frontier
Deal found 1/30![Frontier logo]()
$232
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/278:40 am
SJU
- STL
1 stop11h 27m
American Airlines
Mon 3/26:20 pm
STL
- SJU
1 stop13h 40m
American Airlines
Deal found 2/1![American Airlines logo]()
$246
One-way flights from San Juan to IllinoisSearch for one-way flight options from San Juan to Illinois. Find affordable one-way fares based on user searches. Data last updated February 2, 2026.
Search for one-way flight options from San Juan to Illinois. Find affordable one-way fares based on user searches. Data last updated February 2, 2026.
This Priceline deal was found by Cheapflights users on 2/1. 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.
Wed 3/411:07 am
SJU
- STL
1 stop13h 20m
Frontier
Deal found 2/1![Frontier logo]()
$87
This Priceline deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/243:53 am
SJU
- STL
1 stop20h 34m
Frontier
Deal found 1/31![Frontier logo]()
$93
This Trip.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/710:53 am
SJU
- ORD
1 stop14h 06m
Frontier
Deal found 1/31![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Thu 2/194:36 pm
SJU
- STL
2 stops16h 15m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/66:50 pm
SJU
- MDW
1 stop20h 51m
Frontier
Deal found 2/1![Frontier logo]()
$97
This Expedia deal was found by Cheapflights users on 2/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/287:00 am
SJU
- ORD
1 stop12h 03m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Wed 3/1110:52 am
SJU
- MDW
1 stop27h 49m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$98
This Super.com deal was found by Cheapflights users on 2/2. 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 2/196:00 am
SJU
- MDW
1 stop10h 26m
Frontier
Deal found 2/2![Frontier logo]()
$100
This Cheapflightsfares deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$100
This Priceline deal was found by Cheapflights users on 2/1. 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.
Wed 2/1811:07 am
SJU
- STL
1 stop13h 20m
Frontier
Deal found 2/1![Frontier logo]()
$101
This Priceline deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/163:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Deal found 2/2![Frontier logo]()
$101
This Frontier deal was found by Cheapflights users on 2/2. 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.
Thu 4/163:18 pm
SJU
- ORD
1 stop8h 21m
Frontier
Deal found 2/2![Frontier logo]()
$101
Find flight deals from San Juan to Illinois
Keep the following information in mind while searching for San Juan to Illinois flight deals. Data was last updated February 2, 2026.
Round-trip from | $134 (Expedia) |
|---|---|
One-way from | $87 (Priceline) |
Popular in | December |
Cheapest in | February |
Average price | $235 |
Cheapflights Fare Finder
Customize your flight search to find flights from San Juan to Illinois 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 2, 2026.
Use the filters below to find and compare flights from San Juan to Illinois that are best for you.
Fly from
San Juan
Fly to
Illinois
Route
Depart
Return
Price
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 3/10
6:39 pm-9:39 am
1 stop16h 00m
Chicago O'Hare Intl
Tue 3/17
10:55 am-11:58 pm
1 stop12h 03m
$182
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 2/26
7:09 pm-9:40 pm
1 stop28h 31m
Chicago O'Hare Intl
Mon 3/2
5:05 am-3:02 pm
1 stop7h 57m
$183
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 3/11
3:36 pm-11:47 pm
1 stop9h 11m
Chicago O'Hare Intl
Sat 3/14
6:10 pm-11:49 am
1 stop16h 39m
$201
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Thu 2/26
5:25 pm-11:59 pm
1 stop8h 34m
Lambert-St Louis
Mon 3/2
3:49 pm-2:53 am
1 stop9h 04m
$202
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 3/5
6:00 am-1:56 pm
1 stop9h 56m
Chicago Midway
Mon 3/9
6:00 am-5:58 pm
1 stop10h 58m
$202
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 2/6
1:22 pm-4:37 pm
Nonstop5h 15m
Chicago O'Hare Intl
Sun 2/8
12:17 pm-6:49 pm
Nonstop4h 32m
$206
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 4/22
2:15 am-6:15 pm
1 stop17h 00m
Chicago O'Hare Intl
Sun 4/26
12:22 pm-5:54 pm
Nonstop4h 32m
$207
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 3/31
1:29 am-5:45 am
Nonstop5h 16m
Chicago O'Hare Intl
Mon 4/6
8:56 pm-2:29 am
Nonstop4h 33m
$208
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Mon 3/30
1:29 am-5:45 am
Nonstop5h 16m
Chicago O'Hare Intl
Wed 4/8
12:29 pm-6:00 pm
Nonstop4h 31m
$208
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 4/22
12:22 pm-4:37 pm
Nonstop5h 15m
Chicago O'Hare Intl
Sat 4/25
12:22 pm-5:54 pm
Nonstop4h 32m
$208
Showing 1-10 of 56 results
Best time to book a flight from San Juan to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from San Juan with our price prediction graph.
SJU-STL
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 Illinois
PR1-USIL
SJU-STL
SJU-ORD
SJU-MDW
What is the cheapest month to book a flight from San Juan to Illinois?
Currently, February is the cheapest month in which you can book a flight from San Juan to Illinois (average of $120). Flying from San Juan to Illinois in December is currently the most expensive (average of $157). 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 IL?
Find hourly flight availability from San Juan to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 2, 2026.
One of the essential ways to save on airfare from San Juan to Illinois is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 53% on airfare.
What is the cheapest day to fly from San Juan to Illinois?
Use this chart to determine the cheapest time to fly round-trip from San Juan to Illinois. Price data was last updated on February 10, 2025.
Travelers seeking maximum savings on their San Juan to Illinois flight should consider departing on Thursday afternoons 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 Illinois
Explore weekly flight availability from San Juan to Illinois. 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 2, 2026.
The most flights from PR1 to USIL are scheduled on a Monday (12 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 on average).
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated February 2, 2026.
See what other customers who have flown with United Airlines, American Airlines, and JetBlue from San Juan to Illinois have to say. 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.
Entertainment
7.1
Food
6.6
Comfort
7.3
Crew
8.1
Boarding
7.7
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Entertainment
7.1
Food
6.6
Comfort
7.3
Crew
8.1
Boarding
7.7
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Entertainment
7.1
Food
6.6
Comfort
7.3
Crew
8.1
Boarding
7.7
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Entertainment
7.1
Food
6.6
Comfort
7.3
Crew
8.1
Boarding
7.7
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Entertainment
7.1
Food
6.6
Comfort
7.3
Crew
8.1
Boarding
7.7
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Entertainment
7.1
Food
6.6
Comfort
7.3
Crew
8.1
Boarding
7.7
Overall
7.4
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 Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for San Juan to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from San Juan to Illinois
Discover the top 7 airlines that operate flights from San Juan to Illinois. 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 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$116 | Average$538 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$120 | Average$266 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$131 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$137 | Average$258 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$256 | Average$481 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$258 | Average$468 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$419 | Average$559 | FlexibilityNo cancel fee | On-time63% |