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$119+ 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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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 September 17, 2025.

Round-trip from

$178
(Mytrip)

One-way from

$119
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$297

Good round-trip deal

$339 or less

Good one-way deal

$174 or less
From Puerto Rico to Chicago (CHI)
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One-way flight from Puerto Rico to Chicago (CHI)
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Highest demand for flights based on searches. 3% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Puerto Rico to Chicago (CHI).
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Price to beat on a one-way flight from Puerto Rico to Chicago (CHI).
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Find 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 September 17, 2025.

This Mytrip deal was found by Cheapflights users on 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Sat 10/253:00 pmORD - SJU
Nonstop4h 40mSpirit Airlines
Deal found 9/15$178
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Thu 10/211:59 amSJU - ORD
1 stop11h 49mSpirit Airlines
Mon 10/69:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/15$186
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Mon 10/279:06 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 9/15$192
This Frontier deal was found by Cheapflights users on 9/16. 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.
Sun 10/269:19 pmSJU - ORD
1 stop10h 51mFrontier
Wed 10/296:40 amORD - SJU
1 stop10h 14mFrontier
Deal found 9/16$197
This Frontier deal was found by Cheapflights users on 9/16. 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.
Sat 10/256:22 amSJU - MDW
2 stops17h 25mFrontier
Fri 10/319:32 amMDW - SJU
1 stop10h 52mFrontier
Deal found 9/16$203
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Fri 10/311:59 amSJU - ORD
1 stop11h 49mSpirit Airlines
Wed 10/86:00 amORD - SJU
1 stop7h 12mSpirit Airlines
Deal found 9/15$206
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Thu 10/1611:51 amSJU - ORD
1 stop7h 47mSpirit Airlines
Sat 10/183:00 pmORD - SJU
Nonstop4h 40mSpirit Airlines
Deal found 9/15$208
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/315:51 pmSJU - ORD
2 stops18h 39mFrontier
Sun 11/25:40 amORD - SJU
1 stop9h 14mFrontier
Deal found 9/15$209
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Sat 11/12:03 pmORD - SJU
Nonstop4h 39mSpirit Airlines
Deal found 9/15$214
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Thu 11/132:38 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Mon 11/176:55 amORD - SJU
Nonstop4h 38mSpirit Airlines
Deal found 9/15$215
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/247:43 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Wed 10/296:40 amORD - SJU
1 stop10h 14mMultiple Airlines
Deal found 9/15$217
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/243:56 pmSJU - ORD
Nonstop5h 07mUnited Airlines
Sun 10/268:55 amORD - SJU
Nonstop4h 45mUnited Airlines
Deal found 9/16$218

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 September 17, 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 10/24

3:56 pm-8:03 pm

Nonstop5h 07m

Chicago O'Hare Intl

Sun 10/26

8:55 am-2:40 pm

Nonstop4h 45m

$218

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 11/5

4:52 pm-8:20 pm

Nonstop5h 28m

Chicago O'Hare Intl

Sat 11/8

2:20 pm-9:00 pm

Nonstop4h 40m

$218

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 10/23

3:56 pm-8:03 pm

Nonstop5h 07m

Chicago O'Hare Intl

Sun 10/26

8:55 am-2:40 pm

Nonstop4h 45m

$218

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 11/4

8:10 am-11:32 am

Nonstop5h 22m

Chicago O'Hare Intl

Sat 11/8

2:20 pm-9:00 pm

Nonstop4h 40m

$218

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 11/12

2:05 am-9:48 am

1 stop9h 43m

Chicago O'Hare Intl

Mon 11/17

2:20 pm-9:00 pm

Nonstop4h 40m

$223

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 11/13

6:40 am-11:25 am

1 stop6h 45m

Chicago Midway

Mon 11/17

12:55 pm-11:20 pm

1 stop8h 25m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 10/24

5:43 pm-11:58 pm

1 stop7h 15m

Chicago O'Hare Intl

Mon 10/27

7:00 am-4:25 pm

1 stop8h 25m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 11/5

5:45 am-1:05 pm

2 stops9h 20m

Chicago Midway

Sat 11/8

1:00 pm-12:15 am

1 stop9h 15m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 10/22

1:06 pm-9:39 pm

1 stop9h 33m

Chicago O'Hare Intl

Wed 10/29

7:00 am-4:25 pm

1 stop8h 25m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 11/4

5:45 am-2:30 pm

1 stop10h 45m

Chicago Midway

Sat 11/8

1:00 pm-12:15 am

1 stop9h 15m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 60 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 $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 September 17, 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 September 17, 2025.

The most flights from PR0 to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 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 September 17, 2025.
Read reviews from past customers who have flown Southwest, 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.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,173 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 $218, United Airlines can have you in Chicago from Puerto Rico in 5h 07m. 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?

    $124 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on United Airlines and JetBlue, with prices starting from $143 and $154, 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 Aguadilla Borinquen - 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 (82%), Air Canada (81%) or United Airlines (81%) 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 $106. On average you can expect to pay $515. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $177.

  • 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 $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.

See more FAQs

Traveling to a place near Chicago?

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

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

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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$136Average$278FlexibilityNo cancel feeOn-time65%
FrontierCheapest$137Average$246FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$390FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$255Average$499FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$478FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$333Average$481FlexibilityNo cancel feeOn-time71%

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