Chicago

$121+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
abr. 30 — may. 71
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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 abril 25, 2025.

Round-trip from

$177
(Mytrip)

One-way from

$121
(Mytrip)

Popular in

March

Cheapest in

January

Average price

$339

Good round-trip deal

$336 or less

Good one-way deal

$186 or less
From Puerto Rico to Chicago (CHI)
One-way flight from Puerto Rico to Chicago (CHI)
Highest demand for flights based on searches. 9% potential increase in price ($31 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Average for round-trip flights in April 2025
Price to beat on a round-trip flight from Puerto Rico to Chicago (CHI).
Price to beat on a one-way flight from Puerto Rico to Chicago (CHI).

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 abril 25, 2025.

This Mytrip deal was found by Cheapflights users on 4/24. 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.
vie. 5/98:12 pmSJU - ORD
1 stop13h 38mSpirit Airlines
sáb. 5/104:35 pmORD - SJU
1 stop7h 19mSpirit Airlines
Deal found 4/24$177
This CheapOair deal was found by Cheapflights users on 4/24. 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.
vie. 5/210:46 amSJU - ORD
1 stop13h 25mMultiple Airlines
sáb. 5/104:35 pmORD - SJU
1 stop17h 10mMultiple Airlines
Deal found 4/24$238
This eDestinos deal was found by Cheapflights users on 4/24. 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.
mié. 5/73:56 amSJU - ORD
1 stop20h 36mFrontier
dom. 5/114:15 pmORD - SJU
1 stop20h 14mFrontier
Deal found 4/24$270
This Cheapflightsfares deal was found by Cheapflights users on 4/24. 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.
jue. 5/86:00 amSJU - MDW
1 stop7h 24mFrontier
lun. 5/126:15 amMDW - SJU
1 stop7h 32mFrontier
Deal found 4/24$292
This Frontier deal was found by Cheapflights users on 4/24. 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.
mié. 5/72:47 amBQN - MDW
1 stop10h 37mFrontier
vie. 5/161:19 pmMDW - BQN
1 stop11h 38mFrontier
Deal found 4/24$298
This Booking.com deal was found by Cheapflights users on 4/24. 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.
vie. 5/22:47 amBQN - ORD
1 stop21h 45mFrontier
dom. 5/44:15 pmORD - BQN
1 stop8h 42mFrontier
Deal found 4/24$308
This Delta deal was found by Cheapflights users on 4/24. 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.
jue. 10/27:30 amSJU - MDW
1 stop8h 24mDelta
lun. 10/66:00 amMDW - SJU
1 stop6h 23mDelta
Deal found 4/24$344
This American Airlines deal was found by Cheapflights users on 4/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/2211:55 amSJU - ORD
2 stops10h 30mAmerican Airlines
vie. 9/264:48 pmORD - SJU
1 stop17h 27mAmerican Airlines
Deal found 4/24$353
This Trip.com deal was found by Cheapflights users on 4/23. 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.
jue. 5/152:47 amBQN - ORD
1 stop21h 42mMultiple Airlines
mié. 5/217:47 amORD - BQN
1 stop17h 10mMultiple Airlines
Deal found 4/23$378
This Southwest deal was found by Cheapflights users on 4/25. 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.
jue. 10/231:05 pmSJU - MDW
1 stop9h 50mSouthwest
jue. 10/308:45 pmMDW - SJU
1 stop11h 20mSouthwest
Deal found 4/25$381
This JetBlue deal was found by Cheapflights users on 4/24. 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.
mar. 5/65:05 amBQN - ORD
1 stop10h 59mJetBlue
sáb. 5/104:03 pmORD - BQN
1 stop8h 58mJetBlue
Deal found 4/24$444
This United Airlines deal was found by Cheapflights users on 4/24. 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.
vie. 5/912:15 amBQN - ORD
1 stop10h 20mUnited Airlines
sáb. 5/101:07 pmORD - BQN
1 stop9h 02mUnited Airlines
Deal found 4/24$570

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 abril 25, 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

vie. 5/9

8:12 pm-8:50 am

1 stop13h 38m

Chicago O'Hare Intl

sáb. 5/10

4:35 pm-12:54 am

1 stop7h 19m

$177

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 5/8

4:39 pm-11:32 pm

1 stop7h 53m

Chicago O'Hare Intl

mar. 5/13

11:30 am-5:16 pm

Nonstop4h 46m

$253

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mié. 5/7

3:56 am-11:32 pm

1 stop20h 36m

Chicago O'Hare Intl

dom. 5/11

4:15 pm-1:29 pm

1 stop20h 14m

$270

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 5/8

6:00 am-12:24 pm

1 stop7h 24m

Chicago Midway

lun. 5/12

6:15 am-2:47 pm

1 stop7h 32m

$292

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

mié. 5/7

2:47 am-12:24 pm

1 stop10h 37m

Chicago Midway

lun. 5/12

1:19 pm-1:57 am

1 stop11h 38m

$298

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 10/2

7:30 am-2:54 pm

1 stop8h 24m

Chicago Midway

lun. 10/6

6:00 am-1:23 pm

1 stop6h 23m

$344

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

dom. 5/11

2:47 am-11:32 pm

1 stop21h 45m

Chicago O'Hare Intl

jue. 5/15

4:15 pm-1:57 am

1 stop8h 42m

$348

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

lun. 9/22

11:55 am-9:25 pm

2 stops10h 30m

Chicago O'Hare Intl

vie. 9/26

4:48 pm-11:15 am

1 stop17h 27m

$353

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

jue. 5/15

2:47 am-11:29 pm

1 stop21h 42m

Chicago O'Hare Intl

mié. 5/21

7:47 am-1:57 am

1 stop17h 10m

$378

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 9/11

5:50 am-1:10 pm

2 stops8h 20m

Chicago Midway

mar. 9/16

7:30 am-2:55 pm

1 stop6h 25m

$390

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/24

Showing 1-10 of 32 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 abril 25, 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 abril 25, 2025.

The most flights from PR0 to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (9 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 abril 25, 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.

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.0

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!

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.0

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!
8.0
Very good

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.0

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!

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.0

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!

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.0

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!

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.0

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?

    $121 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 JetBlue, with prices starting from $135 and $152, respectively.

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

  • 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 $138. On average you can expect to pay $500. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $189.

  • 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

Browse thousands of different options on Cheapflights for your next trip

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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 abril 25, 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$419FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$309Average$474FlexibilityNo cancel feeOn-time71%

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