$114+ Cheap flights from Puerto Rico to Chicago (CHI)
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 8/2. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Jul 8 — Jul 151
1 adult, Economy
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Find cheap flights from Puerto Rico to Chicago 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 Puerto Rico to Chicago
Keep the following information in mind while searching for Puerto Rico to Chicago flight deals. Data was last updated July 3, 2025.
Round-trip from | $199 (Priceline) |
|---|---|
One-way from | $114 (eDestinos) |
Popular in | March |
Cheapest in | January |
Average price | $296 |
Good round-trip deal | $302 or less |
Good one-way deal | $189 or less |
Find flight deals from Puerto Rico to Chicago
Cheapest flights from Puerto Rico to ChicagoExplore the most affordable flight options available from Puerto Rico to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.
Explore the most affordable flight options available from Puerto Rico to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/253:50 pmSJU - ORD
1 stop16h 14mMultiple Airlines
Fri 8/15:01 amORD - SJU
1 stop8h 17mMultiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$199
This FlightHub deal was found by Cheapflights users on 7/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1812:29 pmSJU - ORD
1 stop11h 19mSpirit Airlines
Wed 9/246:44 pmORD - SJU
1 stop15h 50mSpirit Airlines
Deal found 7/2![Spirit Airlines logo]()
$209
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2412:59 amSJU - ORD
1 stop19h 28mFrontier
Fri 8/15:01 amORD - SJU
1 stop8h 17mFrontier
Deal found 6/30![Frontier logo]()
$217
This Priceline deal was found by Cheapflights users on 7/3. 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 7/1012:59 amSJU - MDW
1 stop23h 52mFrontier
Sun 7/138:35 amMDW - SJU
1 stop23h 29mFrontier
Deal found 7/3![Frontier logo]()
$225
This Priceline deal was found by Cheapflights users on 7/1. 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.
Mon 8/112:59 amBQN - ORD
1 stop8h 15mFrontier
Sat 8/169:08 amORD - BQN
1 stop15h 53mFrontier
Deal found 7/1![Frontier logo]()
$268
This FlightHub deal was found by Cheapflights users on 7/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/162:59 amBQN - MDW
1 stop18h 23mFrontier
Mon 7/218:35 amMDW - BQN
1 stop16h 26mFrontier
Deal found 7/2![Frontier logo]()
$330
This Delta deal was found by Cheapflights users on 7/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/412:58 pmSJU - MDW
1 stop9h 15mDelta
Tue 10/76:00 amMDW - SJU
1 stop9h 18mDelta
Deal found 7/3![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 7/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/225:50 amSJU - MDW
2 stops9h 10mSouthwest
Tue 9/301:00 pmMDW - SJU
2 stops8h 30mSouthwest
Deal found 7/2![Southwest logo]()
$362
This Mytrip deal was found by Cheapflights users on 7/2. 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.
Thu 8/710:14 pmSJU - MDW
2 stops16h 42mMultiple Airlines
Mon 8/111:11 pmMDW - SJU
2 stops11h 24mMultiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$375
This United Airlines deal was found by Cheapflights users on 7/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1512:15 amBQN - ORD
1 stop10h 24mUnited Airlines
Tue 11/412:00 pmORD - BQN
1 stop9h 57mUnited Airlines
Deal found 7/2![United Airlines logo]()
$401
This Mytrip deal was found by Cheapflights users on 7/2. 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.
Fri 7/187:35 amMAZ - ORD
2 stops24h 29mMultiple Airlines
Tue 7/225:05 amORD - MAZ
2 stops12h 37mMultiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$479
This Expedia deal was found by Cheapflights users on 7/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/73:16 pmBQN - ORD
2 stops17h 39mJetBlue
Mon 8/116:15 amORD - BQN
2 stops14h 49mJetBlue
Deal found 7/2![JetBlue logo]()
$481
Cheapflights Fare Finder
Customize your flight search to find flights from Puerto Rico to Chicago 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 July 3, 2025.
Use the filters below to find and compare flights from Puerto Rico to Chicago that are best for you.
Fly from
Puerto Rico
Fly to
Chicago
Route
Depart
Return
Price
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 7/25
3:50 pm-7:04 am
1 stop16h 14m
Chicago O'Hare Intl
Fri 8/1
5:01 am-2:18 pm
1 stop8h 17m
$199
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 9/18
12:29 pm-10:48 pm
1 stop11h 19m
Chicago O'Hare Intl
Wed 9/24
6:44 pm-11:34 am
1 stop15h 50m
$209
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 7/24
12:59 am-7:27 pm
1 stop19h 28m
Chicago O'Hare Intl
Fri 8/1
5:01 am-2:18 pm
1 stop8h 17m
$217
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 12/3
11:05 am-1:10 pm
1 stop28h 05m
Chicago Midway
Mon 12/8
6:00 am-2:54 pm
1 stop6h 54m
$261
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Mon 8/11
2:59 am-10:14 am
1 stop8h 15m
Chicago O'Hare Intl
Sat 8/16
9:08 am-2:01 am
1 stop15h 53m
$268
AguadillaChicago
BQN - MDW
BQNMDW
Aguadilla Borinquen
Wed 7/16
2:59 am-8:22 pm
1 stop18h 23m
Chicago Midway
Mon 7/21
8:35 am-2:01 am
1 stop16h 26m
$330
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 10/4
12:58 pm-9:13 pm
1 stop9h 15m
Chicago Midway
Tue 10/7
6:00 am-4:18 pm
1 stop9h 18m
$337
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Mon 9/22
5:50 am-2:00 pm
2 stops9h 10m
Chicago Midway
Tue 9/30
1:00 pm-10:30 pm
2 stops8h 30m
$362
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 8/7
10:14 pm-1:56 pm
2 stops16h 42m
Chicago Midway
Mon 8/11
1:11 pm-1:35 am
2 stops11h 24m
$375
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Wed 10/15
12:15 am-9:39 am
1 stop10h 24m
Chicago O'Hare Intl
Tue 11/4
12:00 pm-11:57 pm
1 stop9h 57m
$401
Showing 1-10 of 27 results
Best time to book a flight from Puerto Rico to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago 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 Chicago
What is the cheapest month to book a flight from Puerto Rico to Chicago?
Currently, August is the cheapest month in which you can book a flight from Puerto Rico to Chicago (average of $245). Flying from Puerto Rico to Chicago in March is currently the most expensive (average of $321). 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 CHI?
Find hourly flight availability from Puerto Rico to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 3, 2025.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Puerto Rico to Chicago as you normally would.
Weekly flight availability from Puerto Rico to Chicago
Explore weekly flight availability from Puerto Rico to Chicago. 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 July 3, 2025.
The most flights from PR0 to CHI are scheduled on a Thursday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 on average).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated July 3, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Puerto Rico to Chicago. 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.
Boarding
8.2
Entertainment
7.6
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Boarding
8.2
Entertainment
7.6
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Boarding
8.2
Entertainment
7.6
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Boarding
8.2
Entertainment
7.6
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Boarding
8.2
Entertainment
7.6
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Boarding
8.2
Entertainment
7.6
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Related info for your journey
Find useful and relevant information for your journey from Puerto Rico to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Puerto Rico?
Book flights to Puerto Rico if you plan to visit one of these locationsMerrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Puerto Rico to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from Puerto Rico to Chicago
Discover the top 6 airlines that operate flights from Puerto Rico to Chicago. 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 July 3, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$130 | Average$246 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$136 | Average$268 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$160 | Average$469 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$172 | Average$374 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$257 | Average$442 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$329 | Average$480 | FlexibilityNo cancel fee | On-time71% |