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$69+ 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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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 November 6, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/3. 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 11/2010:12 amORD - SJU
1 stop8h 15mMultiple Airlines
Sun 11/232:25 amSJU - ORD
1 stop10h 46mMultiple Airlines
Deal found 11/3$212
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/28:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
Tue 12/96:00 amSJU - ORD
1 stop16h 09mSpirit Airlines
Deal found 11/4$213
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 11/244:58 pmORD - SJU
1 stop15h 51mSpirit Airlines
Thu 12/48:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 11/4$215
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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 11/205:00 amORD - SJU
1 stop13h 27mSpirit Airlines
Thu 12/49:00 amSJU - ORD
Nonstop5h 23mSpirit Airlines
Deal found 11/4$216
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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 12/38:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
Sat 12/67:31 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 11/4$217
This Trip.com deal was found by Cheapflights users on 11/3. 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.
Tue 11/2511:48 amORD - SJU
1 stop9h 56mMultiple Airlines
Thu 11/274:12 pmSJU - ORD
Nonstop5h 11mMultiple Airlines
Deal found 11/3$218
This Priceline deal was found by Cheapflights users on 11/4. 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.
Sun 12/76:00 amORD - SJU
1 stop12h 08mMultiple Airlines
Mon 12/84:10 amSJU - ORD
2 stops11h 48mMultiple Airlines
Deal found 11/4$219
This Mytrip deal was found by Cheapflights users on 11/3. 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 12/28:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
Fri 12/124:10 amSJU - ORD
2 stops19h 38mSpirit Airlines
Deal found 11/3$220
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 11/178:00 amORD - SJU
Nonstop4h 36mSpirit Airlines
Fri 12/54:10 amSJU - ORD
1 stop8h 58mSpirit Airlines
Deal found 11/4$221
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/42:16 pmMDW - SJU
1 stop18h 16mMultiple Airlines
Tue 12/95:00 pmSJU - MDW
2 stops17h 46mMultiple Airlines
Deal found 11/4$221
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/197:34 pmORD - SJU
2 stops22h 53mMultiple Airlines
Sun 11/232:25 amSJU - ORD
1 stop10h 46mMultiple Airlines
Deal found 11/5$222
This Orbitz deal was found by Cheapflights users on 11/3. 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.
Mon 11/175:05 amORD - SJU
1 stop8h 14mMultiple Airlines
Thu 11/2011:55 amSJU - ORD
2 stops21h 48mMultiple Airlines
Deal found 11/3$223

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 November 6, 2025.

Round-trip from

$133
(Frontier)

One-way from

$69
(Priceline)

Popular in

December

Cheapest in

April

Average price

$381
From Illinois to San Juan
Search Deals
One-way flight from Illinois to San Juan
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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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 November 6, 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

Sat 1/24

8:06 pm-9:56 am

1 stop11h 50m

San Juan Luis Munoz Marin Intl

Thu 1/29

11:05 am-10:33 pm

1 stop13h 28m

$138

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/26

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Fri 1/30

8:35 am-11:57 am

Nonstop5h 22m

$216

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sat 1/24

11:20 am-12:36 am

2 stops11h 16m

San Juan Luis Munoz Marin Intl

Thu 1/29

7:45 am-3:52 pm

1 stop10h 07m

$225

MolineSan Juan

MLI - SJU

MLISJU

Moline Quad-City

Tue 12/9

5:27 pm-11:59 am

2 stops16h 32m

San Juan Luis Munoz Marin Intl

Thu 12/11

3:45 pm-10:43 pm

1 stop8h 58m

$235

MolineSan Juan

MLI - SJU

MLISJU

Moline Quad-City

Mon 1/12

11:28 am-9:39 pm

1 stop8h 11m

San Juan Luis Munoz Marin Intl

Sat 1/17

6:00 am-9:58 pm

2 stops17h 58m

$235

MolineSan Juan

MLI - SJU

MLISJU

Moline Quad-City

Sun 12/7

5:36 pm-11:59 am

2 stops16h 23m

San Juan Luis Munoz Marin Intl

Wed 12/10

8:20 am-10:47 pm

1 stop16h 27m

$235

BloomingtonSan Juan

BMI - SJU

BMISJU

Bloomington-Normal

Mon 1/26

8:50 am-9:39 pm

1 stop10h 49m

San Juan Luis Munoz Marin Intl

Sat 1/31

6:00 am-10:16 pm

2 stops18h 16m

$235

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/24

3:35 pm-12:36 am

1 stop7h 01m

San Juan Luis Munoz Marin Intl

Fri 1/30

2:05 am-9:40 am

1 stop9h 35m

$262

BloomingtonSan Juan

BMI - SJU

BMISJU

Bloomington-Normal

Sun 1/11

8:50 am-9:39 pm

1 stop10h 49m

San Juan Luis Munoz Marin Intl

Thu 1/15

8:20 am-8:41 pm

2 stops14h 21m

$268

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/26

2:20 pm-12:35 am

2 stops8h 15m

San Juan Luis Munoz Marin Intl

Fri 1/30

9:05 am-2:45 pm

1 stop7h 40m

$287

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

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, February is the cheapest month in which you can book a flight from Illinois to San Juan (average of $127). Flying from Illinois to San Juan in December is currently the most expensive (average of $188). 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 November 6, 2025.

When flying from Illinois to San Juan, 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 40% versus a flight in the morning.

What is the cheapest day to fly from Illinois to San Juan?

Use this chart to determine the cheapest time to fly round-trip from Illinois to San Juan. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Illinois to San Juan flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 6, 2025.

The most flights from USIL to PR1 are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).

How much does it cost to fly round-trip from Illinois to San Juan?

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 Frontier, United Airlines, and American Airlines 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 11h 52m. 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?

    $69 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on American Airlines and United Airlines, 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 (94%), Alaska Airlines (89%) or Spirit Airlines (72%) 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 $113. On average you can expect to pay $680. The most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $138.

  • 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, February is the cheapest month in which you can book a flight from Illinois to San Juan (average of $127). Flying from Illinois to San Juan in December is currently the most expensive (average of $188). 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.

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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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$288FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$318FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$406FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$225Average$583FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$271Average$406FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$276Average$510FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$380Average$490FlexibilityNo cancel feeOn-time63%

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