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$126+ 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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Round-trip from

$190
(eDestinos)

One-way from

$126
(eDestinos)

Popular in

March

Cheapest in

January

Average price

$262

Good round-trip deal

$319 or less

Good one-way deal

$186 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. 9% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This eDestinos deal was found by Cheapflights users on 4/29. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/298:12 pmSJU - ORD
1 stop13h 38mSpirit Airlines
Thu 6/511:30 amORD - SJU
Nonstop4h 46mSpirit Airlines
Deal found 4/29$188
This Booking.com deal was found by Cheapflights users on 4/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/83:56 amSJU - ORD
1 stop20h 36mMultiple Airlines
Sat 5/177:47 amORD - SJU
1 stop16h 07mMultiple Airlines
Deal found 4/30$244
This eDestinos deal was found by Cheapflights users on 4/29. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/73:56 amSJU - ORD
1 stop20h 36mFrontier
Sun 5/114:15 pmORD - SJU
1 stop6h 50mFrontier
Deal found 4/29$270
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/86:00 amSJU - MDW
1 stop7h 24mFrontier
Mon 5/126:15 amMDW - SJU
1 stop7h 32mFrontier
Deal found 4/30$292
This JetBlue deal was found by Cheapflights users on 4/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/106:30 amSJU - ORD
1 stop9h 34mJetBlue
Tue 5/136:15 amORD - SJU
1 stop9h 00mJetBlue
Deal found 4/29$344
This Southwest deal was found by Cheapflights users on 4/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/243:35 pmSJU - MDW
1 stop7h 15mSouthwest
Mon 10/279:35 amMDW - SJU
2 stops11h 20mSouthwest
Deal found 4/30$391
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2912:56 pmSJU - MDW
1 stop9h 51mDelta
Tue 9/26:00 amMDW - SJU
1 stop9h 50mDelta
Deal found 4/30$429
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2712:15 amBQN - ORD
1 stop9h 23mUnited Airlines
Wed 9/32:20 pmORD - BQN
1 stop7h 49mUnited Airlines
Deal found 4/29$475
This Trip.com deal was found by Cheapflights users on 4/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/196:00 amSJU - MDW
1 stop12h 28mMultiple Airlines
Fri 6/66:30 amMDW - SJU
2 stops15h 08mMultiple Airlines
Deal found 4/30$500

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 May 1, 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 5/30

8:12 pm-8:50 am

1 stop13h 38m

Chicago O'Hare Intl

Fri 6/20

5:05 am-7:19 pm

1 stop13h 14m

$190

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 5/29

8:12 pm-8:50 am

1 stop13h 38m

Chicago O'Hare Intl

Sun 6/1

5:10 am-3:26 pm

1 stop9h 16m

$230

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sun 5/11

3:56 am-12:24 pm

1 stop9h 28m

Chicago Midway

Mon 5/19

1:19 pm-10:01 pm

1 stop7h 42m

$298

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 5/15

4:39 pm-11:32 pm

1 stop7h 53m

Chicago O'Hare Intl

Sun 5/18

4:15 pm-12:05 am

1 stop6h 50m

$314

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 10/24

3:35 pm-9:50 pm

1 stop7h 15m

Chicago Midway

Mon 10/27

9:35 am-9:55 pm

2 stops11h 20m

$391

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 8/29

12:56 pm-9:47 pm

1 stop9h 51m

Chicago Midway

Tue 9/2

6:00 am-4:50 pm

1 stop9h 50m

$429

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Wed 8/27

12:15 am-8:38 am

1 stop9h 23m

Chicago O'Hare Intl

Wed 9/3

2:20 pm-11:09 pm

1 stop7h 49m

$475

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mon 5/19

6:00 am-5:28 pm

1 stop12h 28m

Chicago Midway

Fri 6/6

6:30 am-10:38 pm

2 stops15h 08m

$500

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/9

6:09 am-10:25 am

Nonstop5h 16m

$126

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 6/3

2:54 pm-10:44 pm

1 stop8h 50m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 24 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 May 1, 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 May 1, 2025.

The most flights from PR0 to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (4 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 1, 2025.
Read reviews from past customers who have flown Southwest, Delta and United Airlines from Puerto Rico to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

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

    $126 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and United Airlines, with prices starting from $140 and $176, 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 Midway.

  • 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 (81%), American Airlines (78%) or Alaska Airlines (76%) 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 $134. On average you can expect to pay $487. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $167.

  • 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 Puerto Rico?

Book flights to Puerto Rico if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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
Punta Cana to O'Hare Intl flights
Luis Munoz Marin Intl to St. Louis flights
Santo Domingo to Midway flights
Bridgetown to O'Hare Intl flights
Nassau to O'Hare Intl flights
Kingston to O'Hare Intl flights
Punta Cana to Midway flights
Port of Spain to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
George Town to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
Nassau to Midway flights
Montego Bay to Midway flights
Santiago de los Caballeros to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
St. George's to St. Louis flights
Nassau to St. Louis flights
Aguadilla to O'Hare Intl flights
Saint Thomas Island to St. Louis flights
Oranjestad to St. Louis flights
Port of Spain to St. Louis flights
Simpson Bay to Midway flights
Culebra to O'Hare Intl flights
Christiansted to O'Hare Intl flights
St. John's to O'Hare Intl flights
Aguadilla to Midway flights
Port Au Prince to O'Hare Intl flights
Road Town to O'Hare Intl flights
Roseau to O'Hare Intl flights
Vieques to O'Hare Intl flights
Port Au Prince 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$137Average$301FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$258FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$160Average$477FlexibilityNo cancel feeOn-time69%
DeltaCheapest$172Average$424FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$257Average$428FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$326Average$473FlexibilityNo cancel feeOn-time71%

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