$69+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from San Juan to Illinois with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap 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 November 2, 2025.
Round-trip from | $153 (Frontier) |
|---|---|
One-way from | $69 (Priceline) |
Popular in | August |
Cheapest in | January |
Average price | $285 |
Find flight deals from San Juan to Illinois
Cheapest flights from San Juan to IllinoisExplore 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 November 2, 2025.
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 November 2, 2025.
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
This Mytrip deal was found by Cheapflights users on 10/31. 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.
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 10/31. 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.
This Priceline deal was found by Cheapflights users on 11/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
This Frontier deal was found by Cheapflights users on 10/31. 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.
This Mytrip deal was found by Cheapflights users on 10/31. 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.
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
This Frontier deal was found by Cheapflights users on 11/2. 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.
This Frontier deal was found by Cheapflights users on 10/30. 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.
Cheapflights Fare Finder
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
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 12/5
4:31 pm-10:12 pm
1 stop7h 41m
Chicago Midway
Mon 12/8
6:15 am-3:11 pm
1 stop6h 56m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 11/15
2:11 am-7:30 am
1 stop7h 19m
Chicago Midway
Thu 11/20
5:30 pm-2:54 am
1 stop7h 24m
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Thu 12/4
12:49 pm-9:28 pm
2 stops10h 39m
Lambert-St Louis
Mon 12/8
4:36 pm-10:09 am
1 stop15h 33m
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Thu 2/12
4:52 pm-10:59 pm
1 stop8h 07m
Lambert-St Louis
Sun 2/15
6:00 am-4:36 pm
1 stop8h 36m
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Thu 12/4
3:10 pm-8:47 pm
1 stop7h 37m
Lambert-St Louis
Mon 12/8
11:40 am-11:20 pm
1 stop9h 40m
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Thu 12/4
2:05 pm-7:30 pm
1 stop7h 25m
Lambert-St Louis
Mon 12/8
8:15 am-9:30 pm
1 stop11h 15m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 1/30
6:10 am-1:55 pm
2 stops9h 45m
Chicago Midway
Sun 2/1
1:25 pm-12:05 am
2 stops8h 40m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 2/18
6:10 am-1:55 pm
2 stops9h 45m
Chicago Midway
Tue 2/24
1:15 pm-11:10 pm
1 stop7h 55m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 11/26
1:10 pm-10:50 pm
1 stop11h 40m
Chicago O'Hare Intl
Sun 11/30
1:25 pm-1:56 am
1 stop10h 31m
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 4/7
5:40 am-12:50 pm
1 stop8h 10m
Chicago O'Hare Intl
Tue 4/14
1:45 pm-1:47 am
1 stop11h 02m
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.
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, January is the cheapest month in which you can book a flight from San Juan to Illinois (average of $116). Flying from San Juan to Illinois in June is currently the most expensive (average of $193). 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 November 2, 2025.
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 morning tend to be the most expensive. A flight in the evening could potentially save you up to 57% 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 December 8, 2024.
Travelers seeking maximum savings on their San Juan to Illinois flight should consider departing on Thursday afternoons when fares are most often at their lowest. Monday 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 November 2, 2025.
The most flights from PR1 to USIL 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 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 November 2, 2025.
See what other customers who have flown with Southwest, United Airlines, and American 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.
Food
Crew
Overall
Comfort
Entertainment
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Food
Crew
Overall
Comfort
Entertainment
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Food
Crew
Overall
Comfort
Entertainment
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Food
Crew
Overall
Comfort
Entertainment
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Food
Crew
Overall
Comfort
Entertainment
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Food
Crew
Overall
Comfort
Entertainment
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
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.
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Alternative routes for San Juan to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
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 November 2, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$279 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$139 | Average$261 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$162 | Average$487 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$290 | Average$485 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$334 | Average$482 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$384 | Average$516 | FlexibilityNo cancel fee | On-time63% |