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San Juan

$86+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Feb 10 — Feb 171
Tue 2/10
Tue 2/17
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 January 11, 2026.

Round-trip from

$192
(JetBlue)

One-way from

$86
(Super.com)

Popular in

December

Cheapest in

April

Average price

$359
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 ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 11, 2026.

This JetBlue deal was found by Cheapflights users on 1/9. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/67:45 amORD - SJU
1 stop8h 20mJetBlue
Tue 2/109:25 amSJU - ORD
1 stop12h 06mJetBlue
Deal found 1/9$192
This Super.com deal was found by Cheapflights users on 1/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/712:17 pmORD - SJU
Nonstop4h 32mSpirit Airlines
Sat 2/1412:32 pmSJU - ORD
Nonstop5h 16mSpirit Airlines
Deal found 1/9$193
This Mytrip deal was found by Cheapflights users on 1/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/188:43 pmORD - SJU
1 stop16h 52mSpirit Airlines
Tue 1/276:00 amSJU - ORD
1 stop9h 13mSpirit Airlines
Deal found 1/10$194
This Priceline deal was found by Cheapflights users on 1/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/310:00 amORD - SJU
1 stop9h 56mMultiple Airlines
Thu 3/512:32 pmSJU - ORD
Nonstop5h 16mMultiple Airlines
Deal found 1/9$195
This CheapOair deal was found by Cheapflights users on 1/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2211:51 amORD - SJU
1 stop10h 08mFrontier
Wed 1/284:36 pmSJU - ORD
1 stop20h 05mFrontier
Deal found 1/9$196
This Super.com deal was found by Cheapflights users on 1/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/1812:17 pmORD - SJU
Nonstop4h 32mSpirit Airlines
Wed 1/211:22 pmSJU - ORD
Nonstop5h 15mSpirit Airlines
Deal found 1/9$197
This Priceline deal was found by Cheapflights users on 1/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/99:51 pmMDW - SJU
1 stop11h 06mFrontier
Wed 3/116:39 pmSJU - MDW
1 stop20h 02mFrontier
Deal found 1/9$198
This Cheapflightsfares deal was found by Cheapflights users on 1/10. 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.
Sun 2/2212:17 pmORD - SJU
Nonstop4h 32mSpirit Airlines
Thu 2/2611:52 amSJU - ORD
1 stop8h 26mSpirit Airlines
Deal found 1/10$199
This Priceline deal was found by Cheapflights users on 1/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:00 amMDW - SJU
1 stop8h 59mFrontier
Wed 2/255:25 pmSJU - MDW
1 stop23h 01mFrontier
Deal found 1/10$199
This CheapOair deal was found by Cheapflights users on 1/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/188:30 amORD - SJU
1 stop16h 23mFrontier
Mon 2/235:25 pmSJU - ORD
1 stop24h 27mFrontier
Deal found 1/11$200
This CheapOair deal was found by Cheapflights users on 1/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/51:00 pmMDW - SJU
1 stop19h 24mFrontier
Wed 2/115:25 pmSJU - MDW
1 stop23h 01mFrontier
Deal found 1/10$200
This Cheapflightsfares deal was found by Cheapflights users on 1/9. 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.
Thu 1/299:23 amORD - SJU
1 stop7h 35mSpirit Airlines
Thu 2/511:52 amSJU - ORD
1 stop8h 24mSpirit Airlines
Deal found 1/9$201

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 January 11, 2026.
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

Sat 2/21

6:04 am-4:56 pm

1 stop8h 52m

San Juan Luis Munoz Marin Intl

Sat 2/28

5:10 am-12:04 pm

1 stop8h 54m

$203

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 2/19

10:00 am-10:53 pm

1 stop10h 53m

San Juan Luis Munoz Marin Intl

Sat 2/28

5:10 am-12:04 pm

1 stop8h 54m

$217

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Wed 3/4

3:49 pm-2:53 am

1 stop9h 04m

San Juan Luis Munoz Marin Intl

Fri 3/6

3:19 pm-11:19 pm

1 stop10h 00m

$226

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Mon 2/2

6:00 am-5:03 pm

2 stops9h 03m

San Juan Luis Munoz Marin Intl

Sat 2/7

4:38 pm-10:44 pm

1 stop8h 06m

$226

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Mon 2/2

6:00 am-4:36 pm

1 stop8h 36m

San Juan Luis Munoz Marin Intl

Fri 2/6

2:05 am-10:41 am

1 stop10h 36m

$226

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 3/2

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Fri 3/6

8:30 am-11:52 am

Nonstop5h 22m

$232

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 1/29

7:40 am-6:05 pm

1 stop8h 25m

San Juan Luis Munoz Marin Intl

Sat 2/7

9:25 am-7:31 pm

1 stop12h 06m

$232

MolineSan Juan

MLI - SJU

MLISJU

Moline Quad-City

Thu 2/26

8:04 pm-5:24 am

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Tue 3/3

5:25 pm-11:37 pm

1 stop8h 12m

$236

PeoriaSan Juan

PIA - SJU

PIASJU

Greater Peoria

Mon 2/23

10:01 am-9:34 pm

2 stops9h 33m

San Juan Luis Munoz Marin Intl

Wed 3/4

8:00 am-4:52 pm

2 stops10h 52m

$236

BloomingtonSan Juan

BMI - SJU

BMISJU

Bloomington-Normal

Sat 2/28

11:31 am-11:34 pm

2 stops10h 03m

San Juan Luis Munoz Marin Intl

Wed 3/4

7:00 am-9:41 pm

2 stops16h 41m

$236

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/9

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 $127). Flying from Illinois to San Juan in December is currently the most expensive (average of $224). 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 January 11, 2026.

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 32% 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 February 10, 2025.

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. Saturday at noon 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 January 11, 2026.

The most flights from USIL to PR1 are scheduled on a Monday (11 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (9 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 JetBlue, Frontier, and American Airlines fly from Illinois to San Juan in about 8h 52m. The time it takes to get you to your destination can typically vary by up to 12m. 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?

    $65 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on JetBlue and Spirit Airlines, with prices starting from $67 and $92, 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 United Airlines (79%), Air New Zealand (79%) or Alaska Airlines (75%) 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 $108. On average you can expect to pay $595. The most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $51.

  • 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 $127). Flying from Illinois to San Juan in December is currently the most expensive (average of $224). 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 January 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$113Average$289FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$120Average$267FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$152Average$316FlexibilityNo cancel feeOn-time65%
DeltaCheapest$190Average$400FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$225Average$614FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$267Average$531FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$381Average$487FlexibilityNo cancel feeOn-time63%

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