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$84+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Round-trip from

$178
(Priceline)

One-way from

$84
(Frontier)

Popular in

August

Cheapest in

January

Average price

$339

Good round-trip deal

$351 or less

Good one-way deal

$171 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. 1% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 30, 2025.

This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/88:45 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Fri 12/1212:15 pmORD - SJU
1 stop9h 41mMultiple Airlines
Deal found 10/30$178
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:45 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Mon 12/83:23 pmORD - SJU
1 stop7h 26mMultiple Airlines
Deal found 10/30$193
This Frontier deal was found by Cheapflights users on 10/28. 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.
Thu 12/410:42 amSJU - MDW
1 stop13h 11mFrontier
Mon 12/86:15 amMDW - SJU
1 stop6h 56mFrontier
Deal found 10/28$196
This CheapOair deal was found by Cheapflights users on 10/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/133:37 pmSJU - ORD
1 stop10h 50mSpirit Airlines
Sun 11/165:10 amORD - SJU
1 stop10h 09mSpirit Airlines
Deal found 10/27$203
This Booking.com deal was found by Cheapflights users on 10/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/44:31 pmSJU - MDW
1 stop7h 41mFrontier
Sun 12/72:59 pmMDW - SJU
1 stop16h 38mFrontier
Deal found 10/28$215
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:10 amSJU - ORD
1 stop8h 58mMultiple Airlines
Sun 12/76:00 amORD - SJU
1 stop12h 08mMultiple Airlines
Deal found 10/30$215
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.
Fri 12/57:00 amSJU - ORD
2 stops15h 42mFrontier
Mon 12/83:23 pmORD - SJU
1 stop7h 26mFrontier
Deal found 10/30$216
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sat 11/223:59 amSJU - MDW
1 stop14h 31mFrontier
Thu 11/275:30 pmMDW - SJU
1 stop7h 24mFrontier
Deal found 10/29$217
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 12/49:00 amSJU - ORD
Nonstop5h 23mSpirit Airlines
Mon 12/85:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 10/28$217
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Sun 12/75:40 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 10/30$218
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/217:11 amSJU - ORD
1 stop12h 48mFrontier
Sun 11/237:09 pmORD - SJU
1 stop29h 45mFrontier
Deal found 10/29$219
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/103:41 pmSJU - ORD
Nonstop5h 10mMultiple Airlines
Mon 11/175:05 amORD - SJU
1 stop8h 14mMultiple Airlines
Deal found 10/30$220

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 October 30, 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 - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 12/4

4:31 pm-10:12 pm

1 stop7h 41m

Chicago Midway

Sun 12/7

2:59 pm-9:37 am

1 stop16h 38m

$216

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/5

7:00 am-11:55 am

1 stop6h 55m

Chicago Midway

Mon 12/8

6:00 am-2:14 pm

1 stop6h 14m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/23

6:15 am-12:01 pm

1 stop7h 46m

Chicago Midway

Tue 2/3

12:48 pm-8:57 pm

1 stop6h 09m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 1/23

6:27 pm-11:57 pm

1 stop7h 30m

Chicago O'Hare Intl

Tue 2/3

7:01 am-4:52 pm

1 stop7h 51m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 12/5

6:38 pm-12:01 am

1 stop7h 23m

Chicago O'Hare Intl

Mon 12/8

5:30 am-2:14 pm

1 stop6h 44m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sun 12/7

6:00 am-8:09 pm

1 stop16h 09m

Chicago O'Hare Intl

Mon 12/8

5:40 am-12:21 pm

Nonstop4h 41m

$251

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Mon 1/26

8:40 am-11:35 pm

2 stops16h 55m

Chicago O'Hare Intl

Sun 2/1

5:20 am-3:06 pm

1 stop7h 46m

$292

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 11/19

6:17 pm-11:42 am

1 stop19h 25m

Chicago Midway

Sun 11/23

5:30 pm-11:44 pm

2 stops28h 14m

$298

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 11/21

9:30 pm-2:40 pm

2 stops19h 10m

Chicago Midway

Sun 11/23

5:30 pm-2:54 am

1 stop7h 24m

$311

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 12/3

2:05 am-8:47 am

1 stop8h 42m

Chicago O'Hare Intl

Mon 12/8

2:20 pm-9:00 pm

Nonstop4h 40m

$313

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 56 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, December is the cheapest month in which you can book a flight from Puerto Rico to Chicago (average of $113). Flying from Puerto Rico to Chicago 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 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 October 30, 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 14% 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. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 30, 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
4,243 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

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
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

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
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

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
8,116 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

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
3,122 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

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 $227, Frontier can have you in Chicago from Puerto Rico in 6h 55m. Airlines will cover a distance of 2057 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?

    $84 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 Southwest, with prices starting from $109 and $114, 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 (88%), Air Canada (68%) or United Airlines (68%) 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 $109. On average you can expect to pay $894. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $217.

  • 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, December is the cheapest month in which you can book a flight from Puerto Rico to Chicago (average of $113). Flying from Puerto Rico to Chicago 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.

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
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
Santo Domingo to O'Hare Intl flights
Luis Munoz Marin Intl to St. Louis flights
Oranjestad to O'Hare Intl flights
Nassau to O'Hare Intl flights
Santo Domingo to Midway flights
Montego Bay to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Nassau to Midway flights
Kingston to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
George Town to O'Hare Intl flights
Port of Spain to O'Hare Intl flights
Christiansted to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Simpson Bay to Midway flights
Montego Bay to Midway flights
Roseau to O'Hare Intl flights
Aguadilla to O'Hare Intl flights
St. George's to St. Louis flights
Oranjestad to St. Louis flights
Vieques to O'Hare Intl flights
Nassau to St. Louis flights
Port of Spain to St. Louis flights
Saint Thomas Island to St. Louis flights
Port Au Prince to O'Hare Intl flights
Road Town to O'Hare Intl flights
Culebra to O'Hare Intl flights
St. John's to O'Hare Intl flights
Port Au Prince to Midway 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$137Average$280FlexibilityNo cancel feeOn-time65%
FrontierCheapest$139Average$261FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$538FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$288Average$487FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$334Average$482FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$384Average$516FlexibilityNo cancel feeOn-time63%

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