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$107+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
oct. 17 — oct. 241
vie. 10/17
vie. 10/24
1 adult, Economy
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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 septiembre 17, 2025.

Round-trip from

$208
(Cheapflightsfares)

One-way from

$107
(Mytrip)

Popular in

December

Cheapest in

October

Average price

$380
From Illinois to San Juan
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One-way flight from Illinois to San Juan
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Highest demand for flights based on searches. 8% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Illinois to San Juan

Cheapest flights from Illinois to San Juan
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 septiembre 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
vie. 10/249:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
mar. 10/283:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/15$208
This Booking.com deal was found by Cheapflights users on 9/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/56:30 amMDW - SJU
1 stop16h 27mFrontier
mié. 12/103:59 pmSJU - MDW
1 stop7h 33mFrontier
Deal found 9/16$208
This Frontier deal was found by Cheapflights users on 9/17. 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.
jue. 10/166:07 pmORD - SJU
1 stop7h 23mFrontier
mar. 10/216:22 amSJU - ORD
2 stops18h 37mFrontier
Deal found 9/17$209
This Frontier deal was found by Cheapflights users on 9/16. 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.
mar. 10/78:05 amMDW - SJU
2 stops15h 24mFrontier
sáb. 10/116:22 amSJU - MDW
2 stops17h 58mFrontier
Deal found 9/16$209
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
lun. 10/279:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
lun. 11/38:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 9/16$210
This Frontier deal was found by Cheapflights users on 9/16. 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.
vie. 10/35:50 pmORD - SJU
2 stops15h 06mFrontier
mié. 10/81:26 pmSJU - ORD
2 stops19h 48mFrontier
Deal found 9/16$214
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
sáb. 11/12:03 pmORD - SJU
Nonstop4h 39mSpirit Airlines
jue. 11/62:38 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 9/15$215
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
sáb. 12/610:15 amORD - SJU
1 stop8h 29mSpirit Airlines
mar. 12/162:10 amSJU - ORD
Nonstop5h 15mSpirit Airlines
Deal found 9/15$216
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
sáb. 10/187:43 pmORD - SJU
1 stop14h 13mSpirit Airlines
sáb. 10/253:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/15$217
This United Airlines deal was found by Cheapflights users on 9/16. 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.
mar. 10/288:55 amORD - SJU
Nonstop4h 45mUnited Airlines
lun. 11/38:10 amSJU - ORD
Nonstop5h 22mUnited Airlines
Deal found 9/16$218
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
mié. 10/226:40 amORD - SJU
1 stop18h 22mMultiple Airlines
vie. 10/317:43 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Deal found 9/16$219
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
vie. 10/249:06 pmORD - SJU
Nonstop4h 45mMultiple Airlines
sáb. 11/19:00 amSJU - ORD
1 stop29h 45mMultiple Airlines
Deal found 9/15$220

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 septiembre 17, 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

mar. 10/28

2:20 pm-8:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

lun. 11/3

4:52 pm-8:20 pm

Nonstop5h 28m

$218

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

lun. 10/27

7:00 am-4:25 pm

1 stop8h 25m

San Juan Luis Munoz Marin Intl

mié. 11/5

6:43 pm-11:58 pm

1 stop7h 15m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 10/25

12:40 pm-11:45 pm

2 stops10h 05m

San Juan Luis Munoz Marin Intl

jue. 10/30

5:50 am-12:45 pm

1 stop7h 55m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 11/1

1:30 pm-11:45 pm

1 stop9h 15m

San Juan Luis Munoz Marin Intl

jue. 11/6

6:40 am-2:45 pm

1 stop10h 05m

$227

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 10/21

11:23 am-9:59 pm

1 stop9h 36m

San Juan Luis Munoz Marin Intl

sáb. 10/25

7:00 am-5:22 pm

1 stop11h 22m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

vie. 10/17

5:50 pm-9:50 am

2 stops15h 00m

San Juan Luis Munoz Marin Intl

mar. 10/21

2:45 pm-10:45 pm

1 stop9h 00m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

mar. 10/21

10:35 am-9:59 pm

1 stop10h 24m

San Juan Luis Munoz Marin Intl

sáb. 10/25

7:15 am-3:26 pm

1 stop9h 11m

$227

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

sáb. 10/25

5:30 am-11:54 pm

1 stop17h 24m

San Juan Luis Munoz Marin Intl

mié. 10/29

5:30 am-8:59 pm

2 stops16h 29m

$235

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

lun. 1/26

10:35 am-11:49 pm

1 stop11h 14m

San Juan Luis Munoz Marin Intl

mié. 2/4

7:30 am-4:25 pm

1 stop10h 55m

$267

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

lun. 2/2

6:00 am-2:15 pm

1 stop6h 15m

San Juan Luis Munoz Marin Intl

jue. 2/12

6:15 am-12:01 pm

1 stop7h 46m

$267

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 60 results
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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 septiembre 17, 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 septiembre 17, 2025.

The most flights from USIL to PR1 are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).

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.

  • How long is the flight from Illinois to San Juan?

    Airlines like United Airlines, Delta, and Southwest fly from Illinois to San Juan in about 4h 40m. The time it takes to get you to your destination can typically vary by up to 5h 25m. The distance from Illinois to San Juan is about 2073 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Illinois to San Juan one-way?

    $109 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Delta and Southwest, with prices starting from $113 and $114, respectively.

  • What are the most popular routes from Illinois to San Juan?

    When deciding which route to take from Illinois to San Juan consider Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago Midway - San Juan Luis Munoz Marin Intl or Lambert-St Louis - San Juan Luis Munoz Marin Intl as they are the most popular.

  • What are the most reliable airlines from Illinois to San Juan?

    No one likes to see their flight delayed. When booking a flight from Illinois to San Juan consider choosing American Airlines (77%), Alaska Airlines (77%) or Spirit Airlines (76%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Illinois to San Juan?

    The cheapest flight price from Illinois to San Juan is $127. On average you can expect to pay $791. The most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $177.

  • Can I find deals for flights from Illinois to San Juan that include hotel bookings?

    Yes. In addition to deals on Illinois to San Juan flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to San Juan?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to San Juan.

  • Can I find deals for business class flights from Illinois to San Juan?

    Yes. Cheapflights offers flight deals from Illinois to San Juan by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • 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.

See more FAQs

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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.
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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 septiembre 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$280FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$335FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$194Average$576FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$410FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$271Average$418FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$277Average$511FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$364Average$488FlexibilityNo cancel feeOn-time63%

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