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$98+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Apr 20 — Apr 271
Mon 4/20
Mon 4/27
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 March 21, 2026.

This eDestinos deal was found by Cheapflights users on 3/20. 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.
Thu 4/96:07 pm
SJU
-
ORD
1 stop22h 50m
Frontier
Sun 4/124:21 pm
ORD
-
SJU
1 stop26h 39m
Frontier
Deal found 3/20$168
This eDestinos deal was found by Cheapflights users on 3/21. 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.
Thu 4/2311:30 am
SJU
-
ORD
1 stop13h 29m
Frontier
Mon 4/276:00 am
ORD
-
SJU
1 stop19h 01m
Frontier
Deal found 3/21$178
This Frontier deal was found by Cheapflights users on 3/21. 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.
Fri 5/13:23 pm
SJU
-
MDW
1 stop8h 03m
Frontier
Mon 5/48:41 am
MDW
-
SJU
1 stop13h 07m
Frontier
Deal found 3/21$186
This Frontier deal was found by Cheapflights users on 3/20. 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 4/163:31 pm
SJU
-
ORD
1 stop9h 13m
Frontier
Thu 4/232:05 pm
ORD
-
SJU
1 stop10h 56m
Frontier
Deal found 3/20$186
This Priceline deal was found by Cheapflights users on 3/20. 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.
Fri 4/33:16 am
SJU
-
STL
1 stop21h 09m
Frontier
Wed 4/84:59 pm
STL
-
SJU
1 stop8h 02m
Frontier
Deal found 3/20$196
This Priceline deal was found by Cheapflights users on 3/20. 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 4/303:39 pm
SJU
-
MDW
1 stop19h 49m
Frontier
Mon 5/48:41 am
MDW
-
SJU
1 stop13h 07m
Frontier
Deal found 3/20$196
This Frontier deal was found by Cheapflights users on 3/20. 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.
Fri 4/243:23 pm
SJU
-
ORD
1 stop8h 16m
Frontier
Sun 4/2612:38 pm
ORD
-
SJU
1 stop10h 21m
Frontier
Deal found 3/20$196
This eDestinos deal was found by Cheapflights users on 3/20. 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 4/181:59 am
SJU
-
ORD
1 stop12h 33m
Frontier
Sun 4/2612:38 pm
ORD
-
SJU
1 stop10h 21m
Frontier
Deal found 3/20$200
This eDestinos deal was found by Cheapflights users on 3/19. 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.
Tue 4/76:30 am
SJU
-
STL
1 stop17h 55m
Frontier
Fri 4/104:59 pm
STL
-
SJU
1 stop26h 50m
Frontier
Deal found 3/19$201
This eDestinos deal was found by Cheapflights users on 3/17. 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 5/86:09 pm
SJU
-
ORD
1 stop30h 04m
Frontier
Mon 5/117:52 pm
ORD
-
SJU
1 stop7h 09m
Frontier
Deal found 3/17$201
This Cheapflightsfares deal was found by Cheapflights users on 3/18. 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 4/71:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Sun 4/127:17 am
ORD
-
SJU
1 stop10h 38m
Spirit Airlines
Deal found 3/18$202
This CheapOair deal was found by Cheapflights users on 3/18. 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 4/81:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Mon 4/135:05 am
ORD
-
SJU
1 stop12h 50m
Spirit Airlines
Deal found 3/18$203

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 March 21, 2026.

Round-trip from

$168
(eDestinos)

One-way from

$98
(Priceline)

Popular in

December

Cheapest in

February

Average price

$359
From San Juan to Illinois
Search Deals
One-way flight from San Juan to Illinois
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($23 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 March 2026
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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 March 21, 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

Sat 5/16

6:00 am-12:21 am

1 stop19h 21m

Lambert-St Louis

Mon 5/18

4:19 pm-1:15 pm

1 stop19h 56m

$306

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 7/9

2:35 pm-8:24 pm

1 stop6h 49m

Chicago O'Hare Intl

Fri 7/31

11:10 am-11:00 pm

1 stop10h 50m

$316

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 8/12

8:20 am-2:45 pm

1 stop7h 25m

Chicago Midway

Fri 8/21

5:00 am-1:45 pm

1 stop7h 45m

$326

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Wed 4/15

3:56 pm-11:11 pm

1 stop8h 15m

Lambert-St Louis

Wed 4/22

7:45 am-9:24 pm

2 stops12h 39m

$334

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 7/9

6:30 am-2:40 pm

1 stop9h 10m

Chicago Midway

Thu 7/30

11:55 am-9:15 pm

1 stop8h 20m

$336

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 4/21

7:40 am-11:53 am

Nonstop5h 13m

Chicago O'Hare Intl

Tue 5/12

2:38 pm-8:34 pm

Nonstop4h 56m

$336

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 7/15

12:20 pm-7:50 pm

2 stops8h 30m

Chicago Midway

Sun 7/19

5:05 am-3:40 pm

1 stop9h 35m

$356

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 4/15

11:25 am-5:30 pm

1 stop7h 05m

Chicago Midway

Wed 4/22

9:25 am-9:05 pm

1 stop10h 40m

$356

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Thu 4/16

1:31 pm-11:46 pm

2 stops11h 15m

Lambert-St Louis

Sun 4/19

5:24 am-6:10 pm

1 stop11h 46m

$358

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Tue 5/19

1:14 pm-9:29 pm

1 stop9h 15m

Lambert-St Louis

Tue 6/2

1:27 pm-10:17 pm

1 stop7h 50m

$360

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/18

Showing 1-10 of 54 resultsSorted by cheapest first
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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

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 $113). Flying from San Juan to Illinois in December is currently the most expensive (average of $157). 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 March 21, 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 51% 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 March 14, 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 March 21, 2026.

The most flights from PR1 to USIL are scheduled on a Monday (13 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (10 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 March 21, 2026.
See what other customers who have flown with United Airlines,JetBlue, andAmerican Airlines 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
9,454 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Comfort

7.3

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
9,454 reviews
United Airlines
7.4
Good
9,454 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Comfort

7.3

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
7.2
Good
2,909 reviews
United Airlines
7.4
Good
9,454 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Comfort

7.3

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
11,485 reviews
United Airlines
7.4
Good
9,454 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Comfort

7.3

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
8,535 reviews
United Airlines
7.4
Good
9,454 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Comfort

7.3

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
5.7
Fair
3,024 reviews
United Airlines
7.4
Good
9,454 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Comfort

7.3

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 6h 49m. Fly via Frontier, Southwest, or Delta 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 $94 and $103 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 (88%), United Airlines (88%) or Air New Zealand (88%) 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 $679, our data indicates the cheapest price to be $132. The most popular route (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), is priced around $202.

  • 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 $113). Flying from San Juan to Illinois in December is currently the most expensive (average of $157). 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 6 airlines flying from San Juan to Illinois

Discover the top 6 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 March 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$64Average$259FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$123Average$268FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$131Average$201FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$256Average$482FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$257Average$462FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$292Average$499FlexibilityNo cancel feeOn-time63%

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