HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$90+ 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Puerto Rico to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 March 28, 2025.

Round-trip from

$175
(Cheapflightsfares)

One-way from

$90
(eDestinos)

Popular in

March

Cheapest in

January

Average price

$353

Good round-trip deal

$334 or less

Good one-way deal

$177 or less
From Puerto Rico to Chicago (CHI)
Search Deals
One-way flight from Puerto Rico to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2025
Search Deals
Price to beat on a round-trip flight from Puerto Rico to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Puerto Rico to Chicago (CHI).
Search Deals

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 March 28, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/256:35 amSJU - ORD
Nonstop5h 23mSpirit Airlines
Tue 4/297:00 pmORD - SJU
1 stop12h 26mSpirit Airlines
Deal found 3/27$159
This JetBlue deal was found by Cheapflights users on 3/26. 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.
Wed 5/77:01 amSJU - ORD
1 stop9h 03mJetBlue
Mon 5/128:45 amORD - SJU
1 stop8h 20mJetBlue
Deal found 3/26$265
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/166:21 amSJU - ORD
1 stop7h 41mMultiple Airlines
Tue 4/228:04 amORD - SJU
Nonstop4h 41mMultiple Airlines
Deal found 3/27$290
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/22:45 amSJU - MDW
1 stop7h 39mFrontier
Sat 4/55:48 pmMDW - SJU
1 stop7h 02mFrontier
Deal found 3/27$292
This Frontier deal was found by Cheapflights users on 3/26. 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 4/1012:42 pmBQN - ORD
1 stop8h 13mFrontier
Sun 4/1311:25 amORD - BQN
1 stop13h 32mFrontier
Deal found 3/26$296
This Frontier deal was found by Cheapflights users on 3/26. 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.
Tue 4/82:55 amSJU - ORD
1 stop8h 45mFrontier
Mon 4/145:19 pmORD - SJU
1 stop6h 35mFrontier
Deal found 3/26$296
This Delta deal was found by Cheapflights users on 3/26. 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 5/221:55 pmSJU - ORD
1 stop7h 26mDelta
Sat 6/1411:18 amORD - SJU
1 stop10h 33mDelta
Deal found 3/26$341
This Southwest deal was found by Cheapflights users on 3/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/298:00 amSJU - MDW
2 stops10h 35mSouthwest
Sat 5/38:35 amMDW - SJU
Nonstop4h 40mSouthwest
Deal found 3/27$377
This Delta deal was found by Cheapflights users on 3/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/182:40 pmSJU - MDW
1 stop7h 58mDelta
Tue 6/2410:39 amMDW - SJU
1 stop11h 12mDelta
Deal found 3/27$393
This Mytrip deal was found by Cheapflights users on 3/26. 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.
Wed 4/92:40 pmSJU - MDW
2 stops27h 00mMultiple Airlines
Sun 4/132:19 pmMDW - SJU
2 stops32h 33mMultiple Airlines
Deal found 3/26$604
This deal was found by Cheapflights users on 3/26. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1812:15 amBQN - ORD
1 stop9h 24mUnited Airlines
Mon 7/2111:46 amORD - BQN
1 stop10h 23mUnited Airlines
Deal found 3/26$714

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 March 28, 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 4/25

6:35 am-10:58 am

Nonstop5h 23m

Chicago O'Hare Intl

Tue 4/29

7:00 pm-8:26 am

1 stop12h 26m

$159

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 5/7

7:01 am-3:04 pm

1 stop9h 03m

Chicago O'Hare Intl

Mon 5/12

8:45 am-6:05 pm

1 stop8h 20m

$265

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 4/16

6:21 am-1:02 pm

1 stop7h 41m

Chicago O'Hare Intl

Tue 4/22

8:04 am-1:45 pm

Nonstop4h 41m

$290

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 4/2

2:45 am-9:24 am

1 stop7h 39m

Chicago Midway

Sat 4/5

5:48 pm-1:50 am

1 stop7h 02m

$292

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Thu 4/10

12:42 pm-7:55 pm

1 stop8h 13m

Chicago O'Hare Intl

Sun 4/13

11:25 am-1:57 am

1 stop13h 32m

$296

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 4/8

2:55 am-10:40 am

1 stop8h 45m

Chicago O'Hare Intl

Mon 4/14

5:19 pm-12:54 am

1 stop6h 35m

$296

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 5/22

1:55 pm-8:21 pm

1 stop7h 26m

Chicago O'Hare Intl

Sat 6/14

11:18 am-10:51 pm

1 stop10h 33m

$341

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 4/29

8:00 am-5:35 pm

2 stops10h 35m

Chicago Midway

Sat 5/3

8:35 am-2:15 pm

Nonstop4h 40m

$377

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 6/18

2:40 pm-9:38 pm

1 stop7h 58m

Chicago Midway

Tue 6/24

10:39 am-10:51 pm

1 stop11h 12m

$393

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 4/9

2:40 pm-4:40 pm

2 stops27h 00m

Chicago Midway

Sun 4/13

2:19 pm-11:52 pm

2 stops32h 33m

$604

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 29 results
1
2
3

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 $323). 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 March 28, 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 March 28, 2025.

The most flights from PR0 to CHI are scheduled on a Thursday (11 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 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 March 28, 2025.
Read reviews from past customers who have flown Southwest, Delta and Avelo Airlines from Puerto Rico to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,274 reviews

Food

7.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,274 reviews
Southwest
8.1
Very good
4,274 reviews

Food

7.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,897 reviews
Southwest
8.1
Very good
4,274 reviews

Food

7.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Avelo Airlines
7.5
Good
Southwest
8.1
Very good
4,274 reviews

Food

7.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,603 reviews
Southwest
8.1
Very good
4,274 reviews

Food

7.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,923 reviews
Southwest
8.1
Very good
4,274 reviews

Food

7.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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?

    $90 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 $141, 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 (95%), Air Canada (94%) or United Airlines (94%) 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 $99. On average you can expect to pay $480. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $180.

  • 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 $323). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
Montego Bay to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
Santo Domingo to Midway flights
Punta Cana to Midway flights
Nassau to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
Montego Bay to Midway flights
Port of Spain to O'Hare Intl flights
Nassau to Midway flights
Kingston to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
George Town to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Nassau to St. Louis flights
Willemstad to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Saint Thomas Island to St. Louis flights
Aguadilla to Midway flights
Christiansted to O'Hare Intl flights
St. George's to St. Louis flights
Oranjestad to St. Louis flights
Aguadilla to O'Hare Intl flights
Culebra to O'Hare Intl flights
St. John's to O'Hare Intl flights
Simpson Bay to Midway flights
Port Au Prince to Midway flights
Vieques to O'Hare Intl flights
Roseau to O'Hare Intl flights
Road Town to O'Hare Intl flights
Port of Spain to St. Louis flights
Port Au Prince to O'Hare Intl 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$137Average$296FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$257FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$160Average$475FlexibilityNo cancel feeOn-time69%
DeltaCheapest$172Average$424FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$257Average$420FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$308Average$471FlexibilityNo cancel feeOn-time71%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.