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$99+ Cheap flights from San Juan to Illinois

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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Jun 5 — Jun 121
Fri 6/5
Fri 6/12
1 adult, Economy
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Cheap flight deals from San Juan to Illinois

Cheapest flights from San Juan to Illinois
Explore the most affordable flight options available from San Juan to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 6, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Sat 5/307:04 pm
SJU
-
ORD
Nonstop5h 22m
Frontier
Sun 5/3112:33 am
ORD
-
SJU
Nonstop4h 51m
Frontier
Deal found 5/1$171
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Sat 8/16:00 am
SJU
-
ORD
1 stop7h 25m
Frontier
Sat 8/1512:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 5/2$172
This Orbitz deal was found by Cheapflights users on 5/4. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Mon 8/2412:29 am
ORD
-
SJU
Nonstop4h 57m
Frontier
Deal found 5/4$173
This Frontier deal was found by Cheapflights users on 5/2. 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.
Sun 8/24:05 pm
SJU
-
ORD
1 stop8h 00m
Frontier
Sat 8/1512:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 5/2$182
This Frontier deal was found by Cheapflights users on 5/2. 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.
Thu 8/67:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Sat 8/1512:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 5/2$183
This deal was found by Cheapflights users on 5/5. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:00 am
SJU
-
ORD
1 stop7h 25m
Frontier
Fri 8/1412:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 5/5$192
This eDestinos deal was found by Cheapflights users on 5/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1511:00 am
SJU
-
ORD
1 stop13h 59m
Frontier
Sun 5/1710:22 am
ORD
-
SJU
1 stop12h 35m
Frontier
Deal found 5/1$196
This eDestinos deal was found by Cheapflights users on 5/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:00 am
SJU
-
ORD
1 stop7h 37m
Frontier
Tue 5/2612:33 am
ORD
-
SJU
Nonstop4h 51m
Frontier
Deal found 5/1$201
This Priceline deal was found by Cheapflights users on 5/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:24 pm
SJU
-
ORD
Nonstop5h 22m
Frontier
Sat 5/3012:33 am
ORD
-
SJU
Nonstop4h 51m
Frontier
Deal found 5/3$204
This eDestinos deal was found by Cheapflights users on 5/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:30 am
SJU
-
ORD
1 stop13h 14m
Frontier
Fri 5/157:30 am
ORD
-
SJU
1 stop14h 58m
Frontier
Deal found 5/1$205
This eDestinos deal was found by Cheapflights users on 5/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:30 am
SJU
-
ORD
1 stop13h 14m
Frontier
Fri 5/2212:33 am
ORD
-
SJU
Nonstop4h 51m
Frontier
Deal found 5/1$206
This eDestinos deal was found by Cheapflights users on 5/5. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/57:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Tue 8/1112:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Deal found 5/5$208

Find flight deals from San Juan to Illinois

Keep the following information in mind while searching for San Juan to Illinois flight deals. Data was last updated May 6, 2026.

Round-trip from

$171
(Kiwi.com)

One-way from

$99
(Cheapflightsfares)

Popular in

December

Cheapest in

February

Average price

$317
From San Juan to Illinois
Search Deals
One-way flight from San Juan to Illinois
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Juan to Illinois 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 May 6, 2026.
Use the filters below to find and compare flights from San Juan to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Fri 8/28

4:05 pm-12:14 am

1 stop9h 09m

Lambert-St Louis

Tue 9/1

3:33 pm-4:55 am

1 stop12h 22m

$276
Quickest round-trip

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sat 8/1

7:40 am-11:53 am

Nonstop5h 13m

Chicago O'Hare Intl

Sun 8/16

8:55 am-2:44 pm

Nonstop4h 49m

$307

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Fri 9/11

2:35 pm-8:00 pm

1 stop6h 25m

Lambert-St Louis

Sun 9/13

3:30 pm-12:30 am

1 stop8h 00m

$336

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Fri 9/11

5:00 am-10:40 am

1 stop6h 40m

Lambert-St Louis

Mon 9/14

6:05 am-2:30 pm

1 stop7h 25m

$336

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 9/2

2:40 pm-9:46 pm

1 stop8h 06m

Chicago Midway

Mon 9/7

6:00 am-4:35 pm

1 stop9h 35m

$346

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mon 7/13

12:56 pm-10:15 pm

1 stop10h 19m

Chicago Midway

Mon 7/20

6:00 am-4:45 pm

1 stop9h 45m

$356

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sun 9/13

6:00 am-12:40 pm

1 stop7h 40m

Chicago Midway

Fri 9/18

7:50 pm-9:25 am

1 stop12h 35m

$366

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/8

9:45 pm-9:45 am

1 stop13h 00m

Chicago Midway

Tue 10/13

7:50 am-2:50 pm

1 stop6h 00m

$396

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sun 5/10

7:40 am-11:53 am

Nonstop5h 13m

Chicago O'Hare Intl

Tue 5/12

2:38 pm-8:34 pm

Nonstop4h 56m

$412

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/8

3:56 pm-8:15 pm

Nonstop5h 19m

Chicago O'Hare Intl

Mon 5/11

8:49 am-2:44 pm

Nonstop4h 55m

$412

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 60 resultsSorted by cheapest first
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6

Best time to book a flight from San Juan to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from San Juan 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 San Juan to Illinois

How far ahead should I book a flight from San Juan to Illinois?

Booking 81 days in advance of your planned departure date is, on average, the best time to get cheap flights from San Juan to Illinois. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from San Juan to Illinois?

Currently, May is the cheapest month in which you can book a flight from San Juan to Illinois (average of $64). Flying from San Juan to Illinois in July is currently the most expensive (average of $575). 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 SJU to IL?

Find hourly flight availability from San Juan to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 6, 2026.

One of the essential ways to save on airfare from San Juan to Illinois is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 46% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from San Juan to Illinois. Price data was last updated on May 2, 2026.

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

Weekly flight availability from San Juan to Illinois

Explore weekly flight availability from San Juan to Illinois. 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 May 6, 2026.

The most flights from PR1 to USIL are scheduled on a Monday (9 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 on average).

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

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated May 6, 2026.
See what other customers who have flown with United Airlines,American Airlines, andJetBlue from San Juan to Illinois have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,684 reviews

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,684 reviews
United Airlines
7.4
Good
9,684 reviews

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.1
Good
11,669 reviews
United Airlines
7.4
Good
9,684 reviews

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
JetBlue
7.1
Good
2,978 reviews
United Airlines
7.4
Good
9,684 reviews

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Spirit Airlines
6.3
Okay
8,638 reviews
United Airlines
7.4
Good
9,684 reviews

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Frontier
5.6
Fair
2,964 reviews
United Airlines
7.4
Good
9,684 reviews

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from San Juan to Illinois. 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 San Juan to Illinois?

    There are many flights that can get you from San Juan to Illinois in 5h 13m. Fly via Frontier, United Airlines, or Southwest to get the fastest option. The distance between San Juan and Illinois is about 2073 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $74. Users have also found prices from $96 and $99 on Spirit Airlines and Frontier, respectively.

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

    While some choose either San Juan Luis Munoz Marin Intl - Chicago Midway or San Juan Luis Munoz Marin Intl - Lambert-St Louis, San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl is the most popular route from San Juan to Illinois.

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

    Consider Air Canada (89%), United Airlines (89%) or Air New Zealand (89%) when booking your flight. These represent the most reliable airlines when flying from San Juan to Illinois.

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

    Looking for the cheapest flight from San Juan to Illinois? While on average our users pay $456, our data indicates the cheapest price to be $103. The most popular route (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), is priced around $226.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from San Juan to Illinois 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 San Juan to Illinois?

    Currently, May is the cheapest month in which you can book a flight from San Juan to Illinois (average of $64). Flying from San Juan to Illinois in July is currently the most expensive (average of $575). 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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Top 7 airlines flying from San Juan to Illinois

Discover the top 7 airlines that operate flights from San Juan to Illinois. 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 May 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$418FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$121Average$265FlexibilityNo cancel feeOn-time65%
FrontierCheapest$128Average$254FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$131Average$201FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$254Average$484FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$257Average$440FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$292Average$512FlexibilityNo cancel feeOn-time63%

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