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$107+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Dec 7 — Dec 141
Sun 12/7
Sun 12/14
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 November 7, 2025.

Round-trip from

$183
(Mytrip)

One-way from

$107
(Super.com)

Popular in

August

Cheapest in

January

Average price

$285

Good round-trip deal

$339 or less

Good one-way deal

$179 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. 0% potential increase in price ($3 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 November 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 November 7, 2025.

This CheapOair deal was found by Cheapflights users on 11/5. 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.
Sun 11/237:20 amSJU - ORD
1 stop11h 51mSpirit Airlines
Tue 11/254:58 pmORD - SJU
1 stop15h 51mSpirit Airlines
Deal found 11/5$187
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/206:05 amSJU - ORD
1 stop11h 18mMultiple Airlines
Mon 11/2411:40 amORD - SJU
1 stop8h 10mMultiple Airlines
Deal found 11/5$189
This eDestinos deal was found by Cheapflights users on 11/5. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/44:31 pmSJU - ORD
1 stop7h 53mFrontier
Mon 12/86:11 amORD - SJU
1 stop7h 00mFrontier
Deal found 11/5$196
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Sun 11/2311:55 amSJU - ORD
1 stop13h 18mMultiple Airlines
Mon 11/2411:48 amORD - SJU
1 stop26h 07mMultiple Airlines
Deal found 11/6$197
This eDestinos deal was found by Cheapflights users on 11/4. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:30 amSJU - MDW
1 stop16h 42mFrontier
Sat 1/32:24 pmMDW - SJU
1 stop10h 15mFrontier
Deal found 11/4$203
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/44:31 pmSJU - ORD
1 stop7h 53mMultiple Airlines
Mon 12/89:14 pmORD - SJU
1 stop24h 11mMultiple Airlines
Deal found 11/5$203
This Kiwi.com deal was found by Cheapflights users on 11/7. 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 11/247:11 amSJU - ORD
1 stop12h 48mFrontier
Thu 11/276:35 pmORD - SJU
1 stop28h 37mFrontier
Deal found 11/7$205
This Cheapflightsfares deal was found by Cheapflights users on 11/6. 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.
Wed 12/107:31 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Fri 12/125:40 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 11/6$206
This Mytrip deal was found by Cheapflights users on 11/6. 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 12/124:31 pmSJU - ORD
1 stop7h 53mMultiple Airlines
Mon 12/155:40 amORD - SJU
Nonstop4h 41mMultiple Airlines
Deal found 11/6$208
This Cheapflightsfares deal was found by Cheapflights users on 11/6. 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.
Tue 12/96:00 amSJU - ORD
1 stop16h 09mSpirit Airlines
Fri 12/125:40 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 11/6$209
This Frontier deal was found by Cheapflights users on 11/6. 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 12/54:31 pmSJU - MDW
1 stop7h 41mFrontier
Mon 12/86:15 amMDW - SJU
1 stop6h 56mFrontier
Deal found 11/6$211
This eDestinos deal was found by Cheapflights users on 11/6. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/217:15 amSJU - ORD
1 stop30h 15mFrontier
Sun 1/411:34 amORD - SJU
1 stop26h 38mFrontier
Deal found 11/6$211

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 November 7, 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

10:42 am-9:53 pm

1 stop13h 11m

Chicago Midway

Mon 12/8

6:15 am-3:11 pm

1 stop6h 56m

$211

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/26

8:35 am-11:57 am

Nonstop5h 22m

Chicago O'Hare Intl

Mon 3/2

2:20 pm-9:00 pm

Nonstop4h 40m

$218

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/26

2:05 am-9:36 am

1 stop9h 31m

Chicago O'Hare Intl

Mon 3/2

2:20 pm-9:00 pm

Nonstop4h 40m

$223

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/19

7:00 am-12:55 pm

1 stop7h 55m

Chicago Midway

Tue 2/24

3:15 pm-12:35 am

1 stop7h 20m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/23

7:30 am-12:01 pm

1 stop6h 31m

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

Wed 2/18

2:05 am-9:36 am

1 stop9h 31m

Chicago O'Hare Intl

Tue 2/24

2:20 pm-9:00 pm

Nonstop4h 40m

$247

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 2/13

6:30 am-1:20 pm

2 stops8h 50m

Chicago Midway

Tue 2/17

1:35 pm-12:05 am

2 stops8h 30m

$257

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 2/13

6:30 am-1:20 pm

2 stops8h 50m

Chicago Midway

Sun 2/22

7:20 pm-10:30 am

1 stop13h 10m

$287

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/12

4:11 pm-11:25 pm

1 stop9h 14m

Chicago Midway

Sun 2/15

6:00 am-3:06 pm

1 stop7h 06m

$288

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/12

3:55 am-7:50 pm

1 stop17h 55m

Chicago Midway

Sun 2/22

6:30 am-1:42 am

1 stop17h 12m

$288

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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, January is the cheapest month in which you can book a flight from Puerto Rico to Chicago (average of $116). 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 November 7, 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 15% versus a flight in the afternoon.

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.

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 November 7, 2025.

The most flights from PR0 to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 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 November 7, 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
4,240 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

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
9,007 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

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
11,040 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

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
8,123 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

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
3,115 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

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 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?

    $108 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Delta and Southwest, with prices starting from $114 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 (100%), Air Canada (78%) or United Airlines (78%) 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 $625. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $176.

  • 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, January is the cheapest month in which you can book a flight from Puerto Rico to Chicago (average of $116). 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
Lansing
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Porter
Benton Harbor
Merrillville

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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
Oranjestad to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
Santo Domingo to O'Hare Intl flights
Luis Munoz Marin Intl to St. Louis flights
Nassau to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Santo Domingo to Midway flights
Kingston to O'Hare Intl flights
Nassau to Midway flights
Port of Spain to O'Hare Intl flights
Aguadilla to O'Hare Intl flights
Willemstad 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 St. Louis flights
Simpson Bay to O'Hare Intl flights
Montego Bay to Midway flights
Oranjestad to St. Louis flights
Christiansted to O'Hare Intl flights
St. George's to St. Louis flights
Saint Thomas Island to St. Louis flights
Roseau to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Simpson Bay to Midway 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
Vieques to O'Hare Intl flights
Port Au Prince to Midway 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 November 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$137Average$279FlexibilityNo cancel feeOn-time65%
FrontierCheapest$139Average$261FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$487FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$290Average$485FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$334Average$482FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$384Average$516FlexibilityNo cancel feeOn-time63%

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