$110+ Cheap flights from Illinois to San Juan
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/16. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Jul 6 — Jul 131
1 adult, Economy
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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
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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 Illinois to San Juan
Keep the following information in mind while searching for Illinois to San Juan flight deals. Data was last updated July 1, 2025.
Round-trip from | $207 (Priceline) |
|---|---|
One-way from | $110 (Southwest) |
Popular in | December |
Cheapest in | September |
Average price | $376 |
Find flight deals from Illinois to San Juan
Cheapest flights from Illinois to San JuanExplore the most affordable flight options available from Illinois to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 1, 2025.
Explore the most affordable flight options available from Illinois to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 1, 2025.
This Priceline deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/511:28 amORD - SJU
1 stop29h 34mMultiple Airlines
Wed 8/133:55 pmSJU - ORD
Nonstop5h 04mMultiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$205
This Priceline deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/85:10 amORD - SJU
1 stop8h 01mFrontier
Thu 9/251:11 amSJU - ORD
1 stop11h 52mFrontier
Deal found 6/30![Frontier logo]()
$207
This Priceline deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/216:15 amMDW - SJU
1 stop7h 11mFrontier
Wed 8/2712:59 amSJU - MDW
1 stop13h 11mFrontier
Deal found 6/29![Frontier logo]()
$207
This FlightHub deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/205:05 amORD - SJU
1 stop15h 04mSpirit Airlines
Sat 8/22:28 pmSJU - ORD
Nonstop5h 19mSpirit Airlines
Deal found 6/30![Spirit Airlines logo]()
$213
This Delta deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1211:51 amSTL - SJU
1 stop9h 26mDelta
Thu 11/203:25 pmSJU - STL
1 stop7h 10mDelta
Deal found 6/30![Delta logo]()
$219
This American Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/206:32 pmMLI - SJU
2 stops17h 09mAmerican Airlines
Fri 10/247:05 pmSJU - MLI
2 stops16h 07mAmerican Airlines
Deal found 7/1![American Airlines logo]()
$225
This FlightHub deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/185:40 pmSTL - SJU
1 stop14h 19mMultiple Airlines
Thu 7/241:37 amSJU - STL
1 stop9h 15mMultiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$243
This United Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/110:30 amSTL - SJU
2 stops9h 52mUnited Airlines
Sat 11/84:52 pmSJU - STL
1 stop7h 55mUnited Airlines
Deal found 6/30![United Airlines logo]()
$245
This Expedia deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1810:39 amSTL - SJU
2 stops22h 13mFrontier
Sun 9/217:50 pmSJU - STL
2 stops20h 14mFrontier
Deal found 6/30![Frontier logo]()
$258
This American Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/811:24 amBMI - SJU
2 stops22h 41mAmerican Airlines
Thu 12/114:45 pmSJU - BMI
2 stops23h 45mAmerican Airlines
Deal found 6/29![American Airlines logo]()
$265
This Cheapflightsfares deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1210:45 amSTL - SJU
1 stop13h 50mSpirit Airlines
Tue 7/152:40 amSJU - STL
1 stop8h 49mSpirit Airlines
Deal found 6/29![Spirit Airlines logo]()
$283
This American Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/218:50 amSTL - SJU
2 stops13h 47mAmerican Airlines
Sat 9/274:45 pmSJU - STL
1 stop16h 20mAmerican Airlines
Deal found 6/30![American Airlines logo]()
$295
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois to San Juan that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 1, 2025.
Use the filters below to find and compare flights from Illinois to San Juan that are best for you.
Fly from
Illinois
Fly to
San Juan
Route
Depart
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/5
11:28 am-6:02 pm
1 stop29h 34m
San Juan Luis Munoz Marin Intl
Wed 8/13
3:55 pm-7:59 pm
Nonstop5h 04m
$205
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 9/8
5:10 am-2:11 pm
1 stop8h 01m
San Juan Luis Munoz Marin Intl
Sun 9/14
1:11 am-11:53 am
1 stop11h 42m
$207
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 8/21
6:15 am-2:26 pm
1 stop7h 11m
San Juan Luis Munoz Marin Intl
Wed 8/27
12:59 am-1:10 pm
1 stop13h 11m
$207
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 7/20
5:05 am-9:09 pm
1 stop15h 04m
San Juan Luis Munoz Marin Intl
Sat 8/2
2:28 pm-6:47 pm
Nonstop5h 19m
$213
St. LouisSan Juan
STL - SJU
STLSJU
Lambert-St Louis
Sun 9/21
6:04 am-4:31 pm
1 stop9h 27m
San Juan Luis Munoz Marin Intl
Sat 9/27
2:15 pm-9:50 pm
1 stop8h 35m
$219
MolineSan Juan
MLI - SJU
MLISJU
Moline Quad-City
Mon 10/20
6:32 pm-12:41 pm
2 stops17h 09m
San Juan Luis Munoz Marin Intl
Fri 10/24
7:05 pm-10:12 am
2 stops16h 07m
$225
St. LouisSan Juan
STL - SJU
STLSJU
Lambert-St Louis
Fri 7/18
5:40 pm-8:59 am
1 stop14h 19m
San Juan Luis Munoz Marin Intl
Thu 7/24
1:37 am-9:52 am
1 stop9h 15m
$243
St. LouisSan Juan
STL - SJU
STLSJU
Lambert-St Louis
Thu 9/18
10:39 am-9:52 am
2 stops22h 13m
San Juan Luis Munoz Marin Intl
Sun 9/21
7:50 pm-3:04 pm
2 stops20h 14m
$258
BloomingtonSan Juan
BMI - SJU
BMISJU
Bloomington-Normal
Mon 12/8
11:24 am-12:05 pm
2 stops22h 41m
San Juan Luis Munoz Marin Intl
Thu 12/11
4:45 pm-2:30 pm
2 stops23h 45m
$265
St. LouisSan Juan
STL - SJU
STLSJU
Lambert-St Louis
Sat 7/12
10:45 am-1:35 am
1 stop13h 50m
San Juan Luis Munoz Marin Intl
Tue 7/15
2:40 am-10:29 am
1 stop8h 49m
$283
Showing 1-10 of 34 results
Best time to book a flight from Illinois to San Juan
Have a flexible travel schedule? Discover the best time to fly to San Juan from Illinois with our price prediction graph.
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 Illinois to San Juan
What is the cheapest month to book a flight from Illinois to San Juan?
Currently, September is the cheapest month in which you can book a flight from Illinois to San Juan (average of $254). Flying from Illinois to San Juan in June is currently the most expensive (average of $339). 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 IL to SJU?
Find hourly flight availability from Illinois to San Juan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 1, 2025.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to San Juan as you normally would.
Weekly flight availability from Illinois to San Juan
Explore weekly flight availability from Illinois to San Juan. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 1, 2025.
The most flights from USIL to PR1 are scheduled on a Monday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 on average).
Reviews of airlines servicing San Juan
Get insights into the airlines that provide service to San Juan. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San Juan. Reviews last updated July 1, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from Illinois to San Juan 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.
Crew
8.6
Comfort
8.0
Boarding
8.2
Overall
8.0
Entertainment
7.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Crew
8.6
Comfort
8.0
Boarding
8.2
Overall
8.0
Entertainment
7.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Crew
8.6
Comfort
8.0
Boarding
8.2
Overall
8.0
Entertainment
7.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Crew
8.6
Comfort
8.0
Boarding
8.2
Overall
8.0
Entertainment
7.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Crew
8.6
Comfort
8.0
Boarding
8.2
Overall
8.0
Entertainment
7.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Crew
8.6
Comfort
8.0
Boarding
8.2
Overall
8.0
Entertainment
7.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Related info for your journey
Find useful and relevant information for your journey from Illinois to San Juan. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Illinois to San Juan
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from Illinois to San Juan
Discover the top 7 airlines that operate flights from Illinois to San Juan. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 1, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$106 | Average$264 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$139 | Average$311 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$194 | Average$578 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$212 | Average$413 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$267 | Average$484 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$287 | Average$418 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$354 | Average$488 | FlexibilityNo cancel fee | On-time63% |