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San Juan

$58+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
ene. 11 — ene. 181
dom. 1/11
dom. 1/18
1 adult, Economy
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Cheap 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 diciembre 12, 2025.

This Priceline deal was found by Cheapflights users on 12/10. 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.
mié. 12/177:00 amORD - SJU
1 stop9h 53mMultiple Airlines
mié. 12/248:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Deal found 12/10$201
This Frontier deal was found by Cheapflights users on 12/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/3111:23 amORD - SJU
1 stop7h 04mFrontier
jue. 1/154:35 pmSJU - ORD
1 stop8h 09mFrontier
Deal found 12/11$205
This Trip.com deal was found by Cheapflights users on 12/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/137:00 amORD - SJU
1 stop9h 53mMultiple Airlines
jue. 12/185:09 pmSJU - ORD
1 stop17h 43mMultiple Airlines
Deal found 12/10$206
This WAYA deal was found by Cheapflights users on 12/10. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/312:15 pmORD - SJU
1 stop8h 35mMultiple Airlines
vie. 1/95:18 pmSJU - ORD
1 stop8h 28mMultiple Airlines
Deal found 12/10$208
This Trip.com deal was found by Cheapflights users on 12/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/137:00 amORD - SJU
1 stop9h 53mJetBlue
lun. 12/151:45 pmSJU - ORD
1 stop10h 07mJetBlue
Deal found 12/11$215
This Trip.com deal was found by Cheapflights users on 12/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/127:00 amORD - SJU
1 stop9h 52mJetBlue
lun. 12/151:45 pmSJU - ORD
1 stop10h 07mJetBlue
Deal found 12/10$220
This Trip.com deal was found by Cheapflights users on 12/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/137:00 amORD - SJU
1 stop9h 53mJetBlue
dom. 12/141:45 pmSJU - ORD
1 stop10h 07mJetBlue
Deal found 12/11$221
This Priceline deal was found by Cheapflights users on 12/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/1611:25 amORD - SJU
1 stop10h 29mMultiple Airlines
mar. 12/236:25 amSJU - ORD
1 stop7h 40mMultiple Airlines
Deal found 12/11$223
This CheapOair deal was found by Cheapflights users on 12/10. 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.
mié. 12/315:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
jue. 1/151:22 pmSJU - ORD
Nonstop5h 15mSpirit Airlines
Deal found 12/10$224
This Frontier deal was found by Cheapflights users on 12/9. 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.
mar. 12/301:27 pmORD - SJU
1 stop15h 07mFrontier
vie. 1/97:10 amSJU - ORD
1 stop11h 57mFrontier
Deal found 12/9$227
This Trip.com deal was found by Cheapflights users on 12/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/137:00 amORD - SJU
1 stop9h 53mMultiple Airlines
lun. 12/158:45 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Deal found 12/11$228
This Priceline deal was found by Cheapflights users on 12/10. 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.
lun. 12/153:30 pmSTL - SJU
1 stop9h 20mFrontier
dom. 12/213:55 amSJU - STL
1 stop7h 50mFrontier
Deal found 12/10$243

Find 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 diciembre 12, 2025.

Round-trip from

$116
(Priceline)

One-way from

$58
(Frontier)

Popular in

December

Cheapest in

April

Average price

$592
From Illinois to San Juan
Search Deals
One-way flight from Illinois to San Juan
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($55 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 diciembre 12, 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

MDW - SJU

MDWSJU

Chicago Midway

sáb. 2/28

8:00 am-2:53 am

1 stop16h 53m

San Juan Luis Munoz Marin Intl

sáb. 3/7

12:07 pm-11:32 pm

1 stop13h 25m

$201

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

vie. 2/27

12:41 pm-11:44 pm

1 stop9h 03m

San Juan Luis Munoz Marin Intl

sáb. 3/7

5:10 am-11:58 am

1 stop8h 48m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

dom. 1/18

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

vie. 1/23

11:06 am-7:36 pm

1 stop10h 30m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 6/2

3:15 pm-1:59 am

1 stop9h 44m

San Juan Luis Munoz Marin Intl

mar. 6/9

12:30 pm-7:26 pm

1 stop7h 56m

$214

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

vie. 2/6

1:00 pm-3:26 pm

1 stop24h 26m

San Juan Luis Munoz Marin Intl

sáb. 2/14

8:02 pm-2:26 pm

1 stop20h 24m

$215

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

vie. 3/6

6:00 am-3:59 pm

1 stop7h 59m

San Juan Luis Munoz Marin Intl

lun. 3/9

4:09 pm-10:33 pm

1 stop7h 24m

$215

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

vie. 2/6

11:18 am-11:59 pm

1 stop10h 41m

San Juan Luis Munoz Marin Intl

lun. 2/9

4:36 pm-11:33 pm

1 stop8h 57m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 2/21

6:04 am-4:56 pm

1 stop8h 52m

San Juan Luis Munoz Marin Intl

dom. 3/1

5:10 am-11:48 am

1 stop8h 38m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 1/31

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

lun. 2/2

11:06 am-7:36 pm

1 stop10h 30m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mié. 3/11

12:41 pm-9:31 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

jue. 3/19

1:30 am-10:05 am

1 stop9h 35m

$220

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

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 $221). 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 diciembre 12, 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 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 diciembre 12, 2025.

The most flights from USIL to PR1 are scheduled on a Monday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 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 Frontier, JetBlue, and Southwest fly from Illinois to San Juan in about 7h 25m. The time it takes to get you to your destination can typically vary by up to 9h 28m. The distance from Illinois to San Juan is about 2057 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 Spirit Airlines and JetBlue, with prices starting from $76 and $82, 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 (79%), Air Canada (77%) or United 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 $109. On average you can expect to pay $566. The most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $113.

  • 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 $221). 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 diciembre 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$107Average$288FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$140Average$290FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$147Average$347FlexibilityNo cancel feeOn-time62%
DeltaCheapest$190Average$407FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$225Average$575FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$284Average$537FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$381Average$489FlexibilityNo cancel feeOn-time63%

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