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San Juan

$108+ 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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$209
(Cheapflightsfares)

One-way from

$108
(Cheapflightsfares)

Popular in

December

Cheapest in

October

Average price

$317
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. 10% potential increase in price ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 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 September 11, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 10/183:00 pmORD - SJU
Nonstop4h 40mSpirit Airlines
Sat 10/255:18 pmSJU - ORD
1 stop19h 15mSpirit Airlines
Deal found 9/11$208
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 9/236:30 amORD - SJU
1 stop6h 41mSpirit Airlines
Tue 9/306:44 amSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 9/11$209
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 9/256:44 pmORD - SJU
1 stop15h 20mSpirit Airlines
Thu 10/27:40 pmSJU - ORD
Nonstop5h 16mSpirit Airlines
Deal found 9/10$211
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 10/35:17 pmORD - SJU
1 stop6h 37mSpirit Airlines
Wed 10/83:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/10$212
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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 10/76:00 amORD - SJU
1 stop7h 12mSpirit Airlines
Wed 10/83:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/9$213
This Frontier deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:40 amORD - SJU
1 stop7h 44mFrontier
Fri 10/315:51 pmSJU - ORD
2 stops18h 39mFrontier
Deal found 9/9$214
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 10/35:17 pmORD - SJU
1 stop6h 37mSpirit Airlines
Tue 10/73:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/10$215
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 12/610:15 amORD - SJU
1 stop8h 29mSpirit Airlines
Wed 12/172:38 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 9/10$216
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 10/117:43 pmORD - SJU
1 stop14h 13mSpirit Airlines
Sat 10/189:48 amSJU - ORD
Nonstop5h 08mSpirit Airlines
Deal found 9/11$217
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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 10/76:00 amORD - SJU
1 stop7h 12mSpirit Airlines
Tue 10/143:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 9/9$218
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Mon 10/69:06 pmORD - SJU
Nonstop4h 45mMultiple Airlines
Tue 10/216:22 amSJU - ORD
1 stop31h 23mMultiple Airlines
Deal found 9/10$219
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 10/16:44 pmORD - SJU
1 stop15h 20mSpirit Airlines
Mon 10/67:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 9/10$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 September 11, 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

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Wed 10/1

9:20 am-11:57 pm

2 stops13h 37m

San Juan Luis Munoz Marin Intl

Sat 10/4

3:56 pm-10:35 pm

1 stop7h 39m

$225

PeoriaSan Juan

PIA - SJU

PIASJU

Greater Peoria

Sun 11/16

10:51 am-9:00 pm

1 stop8h 09m

San Juan Luis Munoz Marin Intl

Wed 11/19

8:30 am-4:40 pm

2 stops10h 10m

$235

PeoriaSan Juan

PIA - SJU

PIASJU

Greater Peoria

Tue 1/27

1:24 pm-12:36 am

2 stops9h 12m

San Juan Luis Munoz Marin Intl

Fri 2/6

2:05 am-12:38 pm

2 stops12h 33m

$235

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 3/3

6:00 am-2:15 pm

1 stop6h 15m

San Juan Luis Munoz Marin Intl

Wed 3/4

6:17 pm-11:40 pm

1 stop7h 23m

$260

BloomingtonSan Juan

BMI - SJU

BMISJU

Bloomington-Normal

Mon 11/17

5:00 am-2:53 pm

1 stop7h 53m

San Juan Luis Munoz Marin Intl

Thu 11/20

3:53 pm-11:59 pm

1 stop10h 06m

$275

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 9/22

5:15 pm-9:56 am

2 stops15h 41m

San Juan Luis Munoz Marin Intl

Fri 9/26

3:39 am-9:51 am

1 stop7h 12m

$280

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Mon 1/12

6:00 am-4:36 pm

1 stop8h 36m

San Juan Luis Munoz Marin Intl

Fri 1/16

2:05 am-12:29 pm

2 stops12h 24m

$291

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sat 1/31

4:49 pm-6:11 am

2 stops11h 22m

San Juan Luis Munoz Marin Intl

Wed 2/4

8:35 am-2:30 pm

1 stop7h 55m

$293

ChampaignSan Juan

CMI - SJU

CMISJU

Champaign University-Willard

Tue 3/3

1:20 pm-9:55 pm

1 stop6h 35m

San Juan Luis Munoz Marin Intl

Wed 3/4

9:30 am-10:38 am

2 stops27h 08m

$295

BloomingtonSan Juan

BMI - SJU

BMISJU

Bloomington-Normal

Mon 12/8

11:21 am-11:59 am

2 stops22h 38m

San Juan Luis Munoz Marin Intl

Thu 12/11

6:42 pm-10:50 am

2 stops18h 08m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

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 September 11, 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 September 11, 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 American Airlines fly from Illinois to San Juan in about 6h 15m. The time it takes to get you to your destination can typically vary by up to 7h 22m. The distance from Illinois to San Juan is about 2024 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?

    $113 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on United Airlines and Spirit Airlines, with prices starting from $113 and $126, 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 Spirit Airlines (79%), American Airlines (77%) or Alaska Airlines (77%) 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 $463. 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$280FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$335FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$194Average$575FlexibilityNo cancel feeOn-time71%
DeltaCheapest$212Average$410FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$271Average$422FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$274Average$511FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$360Average$487FlexibilityNo cancel feeOn-time63%

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