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$90+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Puerto Rico to Chicago

Cheapest flights from Puerto Rico to Chicago
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 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$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$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$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$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$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$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$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$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$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$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$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$200

Find 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 December 18, 2025.

Round-trip from

$169
(CheapOair)

One-way from

$90
(Expedia)

Popular in

December

Cheapest in

February

Average price

$428

Good round-trip deal

$271 or less

Good one-way deal

$159 or less
From Puerto Rico to Chicago (CHI)
Search Deals
One-way flight from Puerto Rico to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Puerto Rico to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Puerto Rico to Chicago (CHI).
Search Deals

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 December 18, 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

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 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 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 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

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/22

1:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

Thu 1/29

12:17 pm-6:49 pm

Nonstop4h 32m

$222

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 2/18

5:25 pm-2:26 pm

1 stop23h 01m

Chicago Midway

Wed 2/25

6:10 am-3:06 pm

1 stop6h 56m

$248

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 5/13

12:30 pm-7:26 pm

1 stop7h 56m

Chicago O'Hare Intl

Tue 5/26

3:15 pm-1:59 am

1 stop9h 44m

$248

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 1/21

4:52 pm-8:20 pm

Nonstop5h 28m

Chicago O'Hare Intl

Sat 1/24

2:20 pm-9:00 pm

Nonstop4h 40m

$256

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 55 results
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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 $121). Flying from Puerto Rico to Chicago 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 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 December 18, 2025.

When flying from Puerto Rico to Chicago, 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 19% versus a flight in the morning.

What is the cheapest day to fly from Puerto Rico to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Puerto Rico to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Puerto Rico to Chicago 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 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 December 18, 2025.

The most flights from PR0 to CHI 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).

How often are flights from Puerto Rico to Chicago delayed?

About 9% of weekly flights between Puerto Rico and Chicago have experienced delays in the past year, with the average delay time being 169 minutes.

What is the most punctual flight time for Puerto Rico to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Thursday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Puerto Rico to Chicago flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 6% of flights being delayed.

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 December 18, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American 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.
Delta
7.9
Good
8,005 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,005 reviews
Delta
7.9
Good
8,005 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,091 reviews
Delta
7.9
Good
8,005 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,054 reviews
Delta
7.9
Good
8,005 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,190 reviews
Delta
7.9
Good
8,005 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Frontier
5.8
Fair
3,081 reviews
Delta
7.9
Good
8,005 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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.

  • How long is the flight from Puerto Rico to Chicago?

    For as low as $216, JetBlue can have you in Chicago from Puerto Rico in 5h 22m. Airlines will cover a distance of 2073 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Puerto Rico to Chicago one-way?

    $71 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on Frontier and Spirit Airlines, with prices starting from $91 and $94, respectively.

  • What are the most popular routes from Puerto Rico to Chicago?

    The most popular route from Puerto Rico to Chicago is San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl. You may also consider San Juan Luis Munoz Marin Intl - Chicago Midway or Mayagüez Eugenio M De Hostos - Chicago O'Hare Intl.

  • What are the most reliable airlines from Puerto Rico to Chicago?

    No one likes to see their flight delayed. When booking a flight from Puerto Rico to Chicago consider choosing Spirit Airlines (87%), Air Canada (82%) or United Airlines (82%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Puerto Rico to Chicago?

    The cheapest flight price from Puerto Rico to Chicago is $108. On average you can expect to pay $821. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $159.

  • Can I find deals for flights from Puerto Rico to Chicago that include hotel bookings?

    Yes. In addition to deals on Puerto Rico to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Puerto Rico to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Puerto Rico to Chicago.

  • Can I find deals for business class flights from Puerto Rico to Chicago?

    Yes. Cheapflights offers flight deals from Puerto Rico to Chicago 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 Puerto Rico to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Puerto Rico to Chicago (average of $121). Flying from Puerto Rico to Chicago 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
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Hammond
Porter
Benton Harbor

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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.
Punta Cana to O'Hare Intl flights
Punta Cana to Midway flights
Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Midway flights
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Luis Munoz Marin Intl to St. Louis flights
Santo Domingo to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Santo Domingo to Midway flights
Kingston to O'Hare Intl flights
Nassau to Midway flights
Christiansted to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
Port of Spain to O'Hare Intl flights
Saint Thomas Island to St. Louis flights
George Town to O'Hare Intl flights
Nassau to St. Louis flights
Port of Spain to St. Louis flights
Aguadilla to O'Hare Intl flights
Montego Bay to Midway flights
Road Town to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Oranjestad to St. Louis flights
Aguadilla to Midway flights
St. George's to St. Louis flights
Vieques to O'Hare Intl flights
Port Au Prince to Midway flights
Simpson Bay to Midway flights
St. John's to O'Hare Intl flights
Culebra to O'Hare Intl flights
Port Au Prince to O'Hare Intl flights
Roseau to O'Hare Intl flights

Top 7 airlines flying from Puerto Rico to Chicago

Discover the top 7 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$120Average$236FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$138Average$280FlexibilityNo cancel feeOn-time65%
FrontierCheapest$138Average$259FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$538FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$259Average$482FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$271Average$484FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$341Average$519FlexibilityNo cancel feeOn-time63%

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