$115+ 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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Apr 22 — Apr 291
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 Monday
Cheap flight deals from San Juan to Chicago
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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 March 23, 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 March 23, 2026.
This eDestinos deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:07 pm
SJU
- ORD
1 stop22h 50m
Frontier
Sun 4/124:21 pm
ORD
- SJU
1 stop26h 39m
Frontier
Deal found 3/20![Frontier logo]()
$168
This Expedia deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/173:23 pm
SJU
- ORD
1 stop8h 16m
Frontier
Mon 4/204:58 pm
ORD
- SJU
1 stop24h 01m
Frontier
Deal found 3/22![Frontier logo]()
$176
This eDestinos deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:31 pm
SJU
- ORD
1 stop27h 43m
Frontier
Sun 4/2612:38 pm
ORD
- SJU
1 stop10h 21m
Frontier
Deal found 3/20![Frontier logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/163:31 pm
SJU
- ORD
1 stop9h 13m
Frontier
Sun 4/193:52 pm
ORD
- SJU
1 stop25h 07m
Frontier
Deal found 3/21![Frontier logo]()
$183
This Priceline deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/283:08 am
SJU
- MDW
1 stop29h 13m
Frontier
Sun 5/38:39 am
MDW
- SJU
1 stop16h 22m
Frontier
Deal found 3/21![Frontier logo]()
$186
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/163:31 pm
SJU
- ORD
1 stop9h 13m
Frontier
Thu 4/232:05 pm
ORD
- SJU
1 stop10h 56m
Frontier
Deal found 3/20![Frontier logo]()
$186
This eDestinos deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/1511:05 am
SJU
- ORD
1 stop27h 48m
Frontier
Sun 4/193:52 pm
ORD
- SJU
1 stop25h 07m
Frontier
Deal found 3/21![Frontier logo]()
$191
This Priceline deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/303:39 pm
SJU
- MDW
1 stop19h 49m
Frontier
Sun 5/38:39 am
MDW
- SJU
1 stop16h 22m
Frontier
Deal found 3/22![Frontier logo]()
$196
This Frontier deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/811:00 am
SJU
- ORD
1 stop13h 59m
Frontier
Mon 5/115:30 pm
ORD
- SJU
1 stop7h 38m
Frontier
Deal found 3/22![Frontier logo]()
$196
This CheapOair deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/13:23 pm
SJU
- MDW
1 stop8h 03m
Frontier
Mon 5/48:41 am
MDW
- SJU
1 stop16h 20m
Frontier
Deal found 3/23![Frontier logo]()
$197
This Gotogate deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:00 am
SJU
- ORD
1 stop17h 54m
Frontier
Sun 4/262:20 pm
ORD
- SJU
1 stop9h 09m
Frontier
Deal found 3/22![Frontier logo]()
$198
This eDestinos deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/181:59 am
SJU
- ORD
1 stop12h 33m
Frontier
Sun 4/2612:38 pm
ORD
- SJU
1 stop10h 21m
Frontier
Deal found 3/20![Frontier logo]()
$200
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 March 23, 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 March 23, 2026.
This Spirit deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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.
Tue 4/2110:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Tue 4/2810:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Deal found 3/22![Spirit Airlines logo]()
$274
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 6/1112:54 pm
SJU
- ORD
1 stop10h 19m
Delta
Sun 6/148:03 am
ORD
- SJU
1 stop11h 40m
Delta
Deal found 3/22![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/176:50 am
SJU
- MDW
1 stop12h 20m
Southwest
Tue 5/512:50 pm
MDW
- SJU
2 stops8h 50m
Southwest
Deal found 3/18![Southwest logo]()
$356
This United Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/247:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Sun 4/262:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 3/19![United Airlines logo]()
$437
This JetBlue deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/141:00 pm
SJU
- ORD
1 stop9h 39m
JetBlue
Tue 4/218:31 am
ORD
- SJU
1 stop8h 59m
JetBlue
Deal found 3/18![JetBlue logo]()
$515
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:00 am
SJU
- MDW
2 stops8h 20m
Southwest
Mon 8/1712:15 pm
MDW
- SJU
2 stops9h 50m
Southwest
Deal found 3/19![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 7/1010:20 pm
SJU
- MDW
1 stop11h 30m
Southwest
Mon 7/208:55 pm
MDW
- SJU
1 stop11h 05m
Southwest
Deal found 3/23![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 6/105:00 am
SJU
- MDW
1 stop10h 00m
Southwest
Tue 6/233:00 pm
MDW
- SJU
2 stops8h 15m
Southwest
Deal found 3/19![Southwest logo]()
$376
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/217:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Tue 4/282:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 3/22![United Airlines logo]()
$477
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 7/85:30 am
SJU
- MDW
1 stop8h 15m
Southwest
Wed 7/2212:05 pm
MDW
- SJU
1 stop6h 40m
Southwest
Deal found 3/21![Southwest logo]()
$376
This Delta deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 6/236:15 am
SJU
- ORD
1 stop11h 29m
Delta
Thu 7/2311:10 am
ORD
- SJU
1 stop7h 57m
Delta
Deal found 3/18![Delta logo]()
$546
This United Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/207:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Wed 4/222:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 3/18![United Airlines logo]()
$513
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 6/115:30 am
SJU
- MDW
2 stops9h 35m
Southwest
Mon 6/1512:45 pm
MDW
- SJU
2 stops10h 30m
Southwest
Deal found 3/19![Southwest logo]()
$396
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/17:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Tue 5/52:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 3/22![United Airlines logo]()
$522
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 6/2311:15 am
SJU
- MDW
2 stops9h 35m
Southwest
Sat 7/253:30 pm
MDW
- SJU
1 stop6h 30m
Southwest
Deal found 3/18![Southwest logo]()
$401
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/212:00 pm
SJU
- MDW
2 stops9h 15m
Southwest
Tue 4/281:00 pm
MDW
- SJU
1 stop8h 40m
Southwest
Deal found 3/22![Southwest logo]()
$421
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 6/125:30 am
SJU
- MDW
2 stops9h 35m
Southwest
Mon 6/1511:35 am
MDW
- SJU
1 stop11h 50m
Southwest
Deal found 3/18![Southwest logo]()
$451
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/205:35 am
SJU
- MDW
1 stop7h 30m
Southwest
Wed 4/229:25 am
MDW
- SJU
1 stop10h 40m
Southwest
Deal found 3/19![Southwest logo]()
$466
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 5/179:45 pm
SJU
- ORD
2 stops16h 05m
Southwest
Sun 5/312:40 pm
ORD
- SJU
2 stops17h 30m
Southwest
Deal found 3/18![Southwest logo]()
$494
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 5/295:35 am
SJU
- ORD
2 stops17h 20m
Southwest
Mon 6/16:00 am
ORD
- SJU
2 stops16h 40m
Southwest
Deal found 3/19![Southwest logo]()
$546
Last-minute flights from San Juan to ChicagoDiscover last-minute flight deals from San Juan to Chicago. Data last updated March 23, 2026 and is based on user searches.
Discover last-minute flight deals from San Juan to Chicago. Data last updated March 23, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:07 pm
SJU
- ORD
1 stop22h 50m
Frontier
Sun 4/124:21 pm
ORD
- SJU
1 stop26h 39m
Frontier
Deal found 3/20![Frontier logo]()
$168
This eDestinos deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/1511:05 am
SJU
- ORD
1 stop27h 48m
Frontier
Sun 4/193:52 pm
ORD
- SJU
1 stop25h 07m
Frontier
Deal found 3/21![Frontier logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/163:31 pm
SJU
- ORD
1 stop9h 13m
Frontier
Sun 4/193:52 pm
ORD
- SJU
1 stop25h 07m
Frontier
Deal found 3/21![Frontier logo]()
$183
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/163:31 pm
SJU
- ORD
1 stop9h 13m
Frontier
Thu 4/232:05 pm
ORD
- SJU
1 stop10h 56m
Frontier
Deal found 3/20![Frontier logo]()
$186
This eDestinos deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
SJU
- ORD
1 stop16h 17m
Frontier
Sat 4/188:00 am
ORD
- SJU
1 stop17h 01m
Frontier
Deal found 3/19![Frontier logo]()
$201
This Expedia deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/173:23 pm
SJU
- ORD
1 stop8h 16m
Frontier
Mon 4/204:58 pm
ORD
- SJU
1 stop24h 01m
Frontier
Deal found 3/22![Frontier logo]()
$176
This Gotogate deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:00 am
SJU
- ORD
1 stop17h 54m
Frontier
Sun 4/262:20 pm
ORD
- SJU
1 stop9h 09m
Frontier
Deal found 3/22![Frontier logo]()
$198
This eDestinos deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/181:59 am
SJU
- ORD
1 stop12h 33m
Frontier
Sun 4/2612:38 pm
ORD
- SJU
1 stop10h 21m
Frontier
Deal found 3/20![Frontier logo]()
$200
This eDestinos deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:31 pm
SJU
- ORD
1 stop27h 43m
Frontier
Sun 4/2612:38 pm
ORD
- SJU
1 stop10h 21m
Frontier
Deal found 3/20![Frontier logo]()
$178
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/243:23 pm
SJU
- ORD
1 stop8h 16m
Frontier
Sun 4/2612:38 pm
ORD
- SJU
1 stop10h 21m
Frontier
Deal found 3/20![Frontier logo]()
$196
This Priceline deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/283:08 am
SJU
- MDW
1 stop29h 13m
Frontier
Sun 5/38:39 am
MDW
- SJU
1 stop16h 22m
Frontier
Deal found 3/21![Frontier logo]()
$186
This Priceline deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/303:39 pm
SJU
- MDW
1 stop19h 49m
Frontier
Mon 5/48:41 am
MDW
- SJU
1 stop13h 07m
Frontier
Deal found 3/20![Frontier logo]()
$196
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 March 23, 2026.
Search for one-way flight options from San Juan to Chicago. Find affordable one-way fares based on user searches. Data last updated March 23, 2026.
This Super.com deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 5/43:03 am
SJU
- ORD
1 stop21h 10m
Frontier
Deal found 3/19![Frontier logo]()
$115
This Priceline deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/294:35 pm
SJU
- ORD
1 stop19h 28m
Frontier
Deal found 3/20![Frontier logo]()
$117
This CheapOair deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 5/146:09 pm
SJU
- ORD
1 stop30h 04m
Frontier
Deal found 3/20![Frontier logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/911:03 am
SJU
- MDW
1 stop27h 58m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/303:03 pm
SJU
- ORD
1 stop8h 36m
Frontier
Deal found 3/18![Frontier logo]()
$119
This OneTravel deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:54 pm
SJU
- ORD
2 stops15h 29m
Spirit Airlines
Deal found 3/18![Spirit Airlines logo]()
$120
This Trip.com deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/912:55 pm
SJU
- ORD
1 stop10h 55m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$121
This Super.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/163:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 3/22![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/181:59 am
SJU
- ORD
1 stop12h 33m
Frontier
Deal found 3/21![Frontier logo]()
$122
This Priceline deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 5/143:03 am
SJU
- MDW
1 stop13h 54m
Frontier
Deal found 3/20![Frontier logo]()
$123
This Super.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2210:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Deal found 3/23![Spirit Airlines logo]()
$123
This FlightHub deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/152:37 pm
SJU
- ORD
Nonstop5h 13m
Spirit Airlines
Deal found 3/21![Spirit Airlines logo]()
$125
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 March 23, 2026.
Round-trip from | $168 (eDestinos) |
|---|---|
One-way from | $115 (Super.com) |
Popular in | December |
Cheapest in | February |
Average price | $359 |
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 March 23, 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
Quickest round-trip
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 4/21
10:59 am-3:08 pm
Nonstop5h 09m
Chicago O'Hare Intl
Tue 4/28
10:00 am-3:39 pm
Nonstop4h 39m
$274
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 6/11
12:54 pm-10:13 pm
1 stop10h 19m
Chicago O'Hare Intl
Sun 6/14
8:03 am-8:43 pm
1 stop11h 40m
$316
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 4/17
6:50 am-6:10 pm
1 stop12h 20m
Chicago Midway
Tue 5/5
12:50 pm-10:40 pm
2 stops8h 50m
$356
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 8/14
5:00 am-12:20 pm
2 stops8h 20m
Chicago Midway
Mon 8/17
12:15 pm-11:05 pm
2 stops9h 50m
$356
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 7/10
10:20 pm-8:50 am
1 stop11h 30m
Chicago Midway
Mon 7/20
8:55 pm-9:00 am
1 stop11h 05m
$356
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 6/10
5:00 am-2:00 pm
1 stop10h 00m
Chicago Midway
Tue 6/23
3:00 pm-12:15 am
2 stops8h 15m
$376
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 7/8
5:30 am-12:45 pm
1 stop8h 15m
Chicago Midway
Wed 7/22
12:05 pm-7:45 pm
1 stop6h 40m
$376
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 6/11
5:30 am-2:05 pm
2 stops9h 35m
Chicago Midway
Mon 6/15
12:45 pm-12:15 am
2 stops10h 30m
$396
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 6/23
11:15 am-7:50 pm
2 stops9h 35m
Chicago Midway
Sat 7/25
3:30 pm-11:00 pm
1 stop6h 30m
$401
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 4/21
2:00 pm-10:15 pm
2 stops9h 15m
Chicago Midway
Tue 4/28
1:00 pm-10:40 pm
1 stop8h 40m
$421
Showing 1-10 of 38 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?
Use this chart to determine the optimal time to book a round-trip flight from San Juan to Chicago. Price data was last updated on March 13, 2026.
To ensure you get the cheapest price possible for a flight from San Juan to Chicago, you should look to book at least 90 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest 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 $113). Flying from San Juan to Chicago 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 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 March 23, 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 51% 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 March 14, 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 March 23, 2026.
The most flights from PR1 to CHI are scheduled on a Saturday (17 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (10 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 185 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 March 23, 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.
Entertainment
7.1
Overall
7.4
Food
6.6
Boarding
7.7
Comfort
7.3
Crew
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Entertainment
7.1
Overall
7.4
Food
6.6
Boarding
7.7
Comfort
7.3
Crew
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Entertainment
7.1
Overall
7.4
Food
6.6
Boarding
7.7
Comfort
7.3
Crew
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Entertainment
7.1
Overall
7.4
Food
6.6
Boarding
7.7
Comfort
7.3
Crew
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Entertainment
7.1
Overall
7.4
Food
6.6
Boarding
7.7
Comfort
7.3
Crew
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Entertainment
7.1
Overall
7.4
Food
6.6
Boarding
7.7
Comfort
7.3
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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Alternative routes for San Juan to Chicago
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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 March 23, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from 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 March 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from San Juan to Chicago
Discover the top 6 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 March 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$64 | Average$259 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$122 | Average$268 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$131 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$256 | Average$483 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$257 | Average$446 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$292 | Average$499 | FlexibilityNo cancel fee | On-time63% |