$58+ Cheap flights from Puerto Rico 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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Jan 17 — Jan 241
1 adult, Economy
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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 Puerto Rico to Illinois
Cheapest flights from Puerto Rico to IllinoisExplore the most affordable flight options available from Puerto Rico to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.
Explore the most affordable flight options available from Puerto Rico to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.
This Mytrip deal was found by Cheapflights users on 12/16. 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.
Tue 12/238:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Mon 1/51:44 pmORD - SJU
1 stop9h 22mMultiple Airlines
Deal found 12/16![Multiple Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Thu 12/256:28 pmSJU - ORD
1 stop8h 02mMultiple Airlines
Sat 1/108:27 pmORD - SJU
1 stop10h 27mMultiple Airlines
Deal found 12/16![Multiple Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/248:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Thu 1/88:27 pmORD - SJU
1 stop10h 27mMultiple Airlines
Deal found 12/16![Multiple Airlines logo]()
$186
This Cheapflightsfares deal was found by Cheapflights users on 12/15. 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.
Mon 12/228:08 pmSJU - ORD
Nonstop5h 17mSpirit Airlines
Mon 1/55:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 12/15![Spirit Airlines logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Thu 12/256:28 pmSJU - ORD
1 stop8h 02mMultiple Airlines
Tue 1/65:00 amORD - SJU
1 stop16h 44mMultiple Airlines
Deal found 12/16![Multiple Airlines logo]()
$188
This Frontier deal was found by Cheapflights users on 12/16. 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.
Tue 12/234:19 pmSJU - MDW
1 stop7h 53mFrontier
Mon 1/58:15 amMDW - SJU
1 stop12h 00mFrontier
Deal found 12/16![Frontier logo]()
$192
This Frontier deal was found by Cheapflights users on 12/16. 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.
Tue 12/234:19 pmSJU - ORD
1 stop8h 05mFrontier
Thu 1/83:32 pmORD - SJU
1 stop7h 27mFrontier
Deal found 12/16![Frontier logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
Mon 12/228:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Thu 1/16:00 amORD - SJU
1 stop7h 01mMultiple Airlines
Deal found 12/15![Multiple Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Thu 1/112:39 pmORD - SJU
1 stop9h 58mMultiple Airlines
Deal found 12/17![Multiple Airlines logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Tue 12/236:25 amSJU - ORD
1 stop7h 40mMultiple Airlines
Fri 1/912:17 pmORD - SJU
Nonstop4h 32mMultiple Airlines
Deal found 12/16![Multiple Airlines logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/248:08 pmSJU - ORD
Nonstop5h 17mSpirit Airlines
Fri 1/912:17 pmORD - SJU
Nonstop4h 32mSpirit Airlines
Deal found 12/16![Spirit Airlines logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/2411:57 amSJU - ORD
1 stop10h 09mMultiple Airlines
Wed 1/79:34 amORD - SJU
1 stop7h 21mMultiple Airlines
Deal found 12/16![Multiple Airlines logo]()
$200
Find flight deals from Puerto Rico to Illinois
Keep the following information in mind while searching for Puerto Rico to Illinois flight deals. Data was last updated December 18, 2025.
Round-trip from | $169 (CheapOair) |
|---|---|
One-way from | $58 (Mytrip) |
Popular in | December |
Cheapest in | February |
Average price | $428 |
Good round-trip deal | $271 or less |
Good one-way deal | $159 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Puerto Rico 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 December 18, 2025.
Use the filters below to find and compare flights from Puerto Rico to Illinois that are best for you.
Fly from
Puerto Rico
Fly to
Illinois
Route
Depart
Return
Price
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 2/5
11:06 am-7:31 pm
1 stop10h 25m
Chicago O'Hare Intl
Sun 2/8
7:45 am-6:02 pm
1 stop8h 17m
$179
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Thu 2/5
4:36 pm-11:33 pm
1 stop8h 57m
Lambert-St Louis
Mon 2/9
10:16 am-11:59 pm
1 stop11h 43m
$180
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Thu 1/15
9:04 pm-7:54 am
1 stop12h 50m
Lambert-St Louis
Mon 1/19
12:47 pm-2:30 am
1 stop11h 43m
$199
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 4/7
1:00 pm-9:33 pm
1 stop9h 33m
Chicago O'Hare Intl
Tue 4/14
1:45 pm-1:47 am
1 stop11h 02m
$211
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Mon 2/2
8:00 am-11:33 pm
1 stop17h 33m
Lambert-St Louis
Fri 2/6
5:42 pm-3:26 pm
1 stop19h 44m
$215
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 2/19
4:25 pm-2:26 pm
1 stop24h 01m
Chicago Midway
Sun 2/22
7:30 am-12:54 am
1 stop15h 24m
$215
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 2/25
8:35 am-11:57 am
Nonstop5h 22m
Chicago O'Hare Intl
Mon 3/9
2:20 pm-8:00 pm
Nonstop4h 40m
$216
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Thu 1/15
6:00 am-10:34 pm
1 stop18h 34m
Lambert-St Louis
Mon 1/19
8:32 pm-3:35 pm
2 stops17h 03m
$218
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 3/4
3:53 am-2:26 pm
1 stop12h 33m
Chicago Midway
Mon 3/9
6:00 am-3:06 pm
1 stop8h 06m
$218
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 3/24
1:30 am-10:05 am
1 stop9h 35m
Chicago O'Hare Intl
Sun 3/29
10:56 am-11:23 pm
1 stop11h 27m
$220
Showing 1-10 of 60 results
Best time to book a flight from Puerto Rico to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Puerto Rico 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 Puerto Rico to Illinois
What is the cheapest month to book a flight from Puerto Rico to Illinois?
Currently, August is the cheapest month in which you can book a flight from Puerto Rico to Illinois (average of $121). Flying from Puerto Rico to Illinois in June is currently the most expensive (average of $175). 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 PR to IL?
Find hourly flight availability from Puerto Rico 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 December 18, 2025.
When flying from Puerto Rico to Illinois, 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 35% versus a flight in the morning.
What is the cheapest day to fly from Puerto Rico to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Puerto Rico to Illinois. Price data was last updated on December 16, 2024.
Travelers seeking maximum savings on their Puerto Rico to Illinois flight should consider departing on Thursday afternoons 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 Puerto Rico to Illinois
Explore weekly flight availability from Puerto Rico 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 December 18, 2025.
The most flights from PR0 to USIL are scheduled on a Monday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 on average).
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 December 18, 2025.
Read through reviews of airlines operating flights from Puerto Rico to Illinois, such as Southwest, United Airlines, and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Puerto Rico to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Puerto Rico to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from Puerto Rico to Illinois
Discover the top 7 airlines that operate flights from Puerto Rico 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 December 18, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$120 | Average$236 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$138 | Average$280 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$138 | Average$259 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$162 | Average$538 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$259 | Average$482 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$271 | Average$484 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$341 | Average$519 | FlexibilityNo cancel fee | On-time63% |