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$76+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Round-trip from

$137
(Kiwi.com)

One-way from

$76
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$302

Good round-trip deal

$257 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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High demand for flights, 2% potential price rise
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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 February 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 February 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/20. 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 4/246:35 amSJU - ORD
Nonstop5h 23mMultiple Airlines
Mon 4/284:30 pmORD - SJU
1 stop9h 19mMultiple Airlines
Deal found 2/20$137
This eDestinos deal was found by Cheapflights users on 2/20. 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.
Tue 3/113:38 amSJU - ORD
1 stop7h 01mSpirit Airlines
Mon 3/178:46 pmORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 2/20$138
This Flightnetwork deal was found by Cheapflights users on 2/20. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/111:20 amSJU - MDW
1 stop12h 20mFrontier
Mon 5/51:19 pmMDW - SJU
1 stop12h 32mFrontier
Deal found 2/20$143
This Flightnetwork deal was found by Cheapflights users on 2/20. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/111:20 amSJU - ORD
1 stop20h 46mFrontier
Mon 5/54:15 pmORD - SJU
1 stop9h 36mFrontier
Deal found 2/20$148
This Gotogate deal was found by Cheapflights users on 2/18. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/53:56 amBQN - ORD
1 stop16h 58mFrontier
Sun 3/169:25 amORD - BQN
1 stop15h 31mFrontier
Deal found 2/18$248
This Delta deal was found by Cheapflights users on 2/18. 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.
Thu 3/66:15 amSJU - MDW
1 stop7h 44mDelta
Mon 3/109:54 amMDW - SJU
1 stop9h 16mDelta
Deal found 2/18$271
This Delta deal was found by Cheapflights users on 2/20. 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.
Wed 2/264:15 pmSJU - ORD
1 stop9h 34mDelta
Sun 3/211:15 amORD - SJU
1 stop10h 31mDelta
Deal found 2/20$271
This Southwest deal was found by Cheapflights users on 2/20. 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.
Thu 5/85:35 amSJU - MDW
1 stop9h 45mSouthwest
Tue 5/136:35 amMDW - SJU
1 stop8h 00mSouthwest
Deal found 2/20$378
This United Airlines deal was found by Cheapflights users on 2/19. 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 3/1912:09 amBQN - ORD
1 stop8h 37mUnited Airlines
Wed 3/262:16 pmORD - BQN
1 stop7h 41mUnited Airlines
Deal found 2/19$385
This Gotogate deal was found by Cheapflights users on 2/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/232:47 amBQN - MDW
1 stop10h 44mFrontier
Sun 4/278:00 amMDW - BQN
1 stop24h 06mFrontier
Deal found 2/20$479

Find flights from Puerto Rico to Chicago within your budget

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 February 20, 2025.

Fly from

Puerto Rico

Fly to

Chicago

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 4/24

6:35 am-10:58 am

Nonstop5h 23m

Chicago O'Hare Intl

Mon 4/28

4:30 pm-2:49 am

1 stop9h 19m

$137

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 3/11

3:38 am-9:39 am

1 stop7h 01m

Chicago O'Hare Intl

Mon 3/17

8:46 pm-2:27 am

Nonstop4h 41m

$138

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/1

11:20 am-10:40 pm

1 stop12h 20m

Chicago Midway

Mon 5/5

1:19 pm-2:51 am

1 stop12h 32m

$143

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 5/1

11:20 am-7:06 am

1 stop20h 46m

Chicago O'Hare Intl

Mon 5/5

4:15 pm-2:51 am

1 stop9h 36m

$148

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Wed 3/5

3:56 am-6:54 pm

1 stop16h 58m

Chicago O'Hare Intl

Sun 3/16

9:25 am-1:56 am

1 stop15h 31m

$248

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 3/6

6:15 am-11:59 am

1 stop7h 44m

Chicago Midway

Mon 3/10

9:54 am-8:10 pm

1 stop9h 16m

$271

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/8

5:35 am-2:20 pm

1 stop9h 45m

Chicago Midway

Tue 5/13

6:35 am-3:35 pm

1 stop8h 00m

$378

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Wed 3/19

12:09 am-7:46 am

1 stop8h 37m

Chicago O'Hare Intl

Wed 3/26

2:16 pm-10:57 pm

1 stop7h 41m

$385

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Wed 4/23

2:47 am-12:31 pm

1 stop10h 44m

Chicago Midway

Sun 4/27

8:00 am-9:06 am

1 stop24h 06m

$479

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 5/7

1:10 am-10:28 pm

1 stop22h 18m

$76

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 24 results
1
2
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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.

Travel insights for flights from Puerto Rico to Chicago

Get recent, data-driven insights about flights from Puerto Rico to Chicago including ideal travel times, pricing trends, and more.

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 February 20, 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 February 20, 2025.

The most flights from PR0 to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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 February 20, 2025.
Read reviews from past customers who have flown Southwest, Delta and JetBlue from Puerto Rico to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,765 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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?

    $76 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 American Airlines, with prices starting from $79 and $131, 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 Air Canada (84%), United Airlines (84%) or Air New Zealand (84%) 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 $87. On average you can expect to pay $498. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $122.

  • 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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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
Punta Cana to O'Hare Intl flights
Santo Domingo to O'Hare Intl flights
Luis Munoz Marin Intl to St. Louis flights
Nassau to Midway flights
Santo Domingo to Midway flights
Punta Cana to Midway flights
Port of Spain to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
Nassau to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
George Town to O'Hare Intl flights
Montego Bay to Midway flights
Simpson Bay to O'Hare Intl flights
Kingston to O'Hare Intl flights
Saint Thomas Island to St. Louis flights
Nassau to St. Louis flights
Saint Thomas Island to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Port of Spain to St. Louis flights
Aguadilla to O'Hare Intl flights
Simpson Bay to Midway flights
Christiansted to O'Hare Intl flights
Road Town to O'Hare Intl flights
Roseau to O'Hare Intl flights
Port Au Prince to Midway flights
St. John's to O'Hare Intl flights
Port Au Prince to O'Hare Intl flights
Vieques to O'Hare Intl flights
Oranjestad to St. Louis flights
St. George's to St. Louis flights
Culebra to O'Hare Intl 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$137Average$376FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$257FlexibilityNo cancel feeOn-time65%
DeltaCheapest$182Average$384FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$213Average$478FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$220Average$386FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$314Average$463FlexibilityNo cancel feeOn-time71%
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