HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$116+ Cheap flights from San Juan 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Apr 27 — May 41
Sun 4/27
Sun 5/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from San Juan 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.

Cheapflights Tip: The best prices from San Juan to Chicago are usually found in January or May, booked 51 days in advance, depart on a Friday or Thursday and return on a Tuesday

Cheap flight deals from San Juan to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from San Juan (PR1) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 22, 2025.

Round-trip from

$187
(eDestinos)

One-way from

$116
(Cheapflightsfares)

Popular in

March

Cheapest in

January

Average price

$339
From San Juan to Chicago (CHI)
Search Deals
One-way flight from San Juan to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($31 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 April 2025
Search Deals

Find flight deals from San Juan to Chicago

Cheapest flights from San Juan to Chicago
Explore the most affordable flight options available from San Juan to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2025.

This eDestinos deal was found by Cheapflights users on 4/22. 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.
Fri 5/96:09 amSJU - ORD
Nonstop5h 16mSpirit Airlines
Sun 5/114:35 pmORD - SJU
1 stop7h 19mSpirit Airlines
Deal found 4/22$187
This CheapOair deal was found by Cheapflights users on 4/22. 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.
Fri 5/210:46 amSJU - ORD
1 stop13h 25mMultiple Airlines
Sat 5/104:35 pmORD - SJU
1 stop17h 10mMultiple Airlines
Deal found 4/22$243
This eDestinos deal was found by Cheapflights users on 4/22. 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 4/303:56 amSJU - ORD
1 stop20h 36mFrontier
Sun 5/49:48 amORD - SJU
1 stop15h 02mFrontier
Deal found 4/22$270
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 5/26:00 amSJU - MDW
1 stop7h 24mFrontier
Mon 5/56:15 amMDW - SJU
1 stop7h 32mFrontier
Deal found 4/21$294
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Thu 9/188:30 amSJU - ORD
1 stop15h 04mAmerican Airlines
Sun 9/215:00 amORD - SJU
2 stops8h 45mAmerican Airlines
Deal found 4/21$307
This Delta deal was found by Cheapflights users on 4/21. 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 10/27:30 amSJU - MDW
1 stop8h 24mDelta
Mon 10/66:00 amMDW - SJU
1 stop6h 23mDelta
Deal found 4/21$344
This Southwest deal was found by Cheapflights users on 4/21. 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 10/95:50 amSJU - MDW
2 stops8h 30mSouthwest
Tue 10/147:40 amMDW - SJU
2 stops8h 35mSouthwest
Deal found 4/21$381
This Mytrip deal was found by Cheapflights users on 4/21. 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.
Tue 6/172:36 amSJU - MDW
3 stops15h 18mMultiple Airlines
Tue 6/249:40 amMDW - SJU
3 stops24h 08mMultiple Airlines
Deal found 4/21$709

Cheapflights Fare Finder

Customize your flight search to find flights from San Juan 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 April 22, 2025.
Use the filters below to find and compare flights from San Juan to Chicago that are best for you.

Fly from

San Juan

Fly to

Chicago

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/9

6:09 am-10:25 am

Nonstop5h 16m

Chicago O'Hare Intl

Sun 5/11

4:35 pm-12:54 am

1 stop7h 19m

$187

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/2

10:46 am-11:11 pm

1 stop13h 25m

Chicago O'Hare Intl

Sat 5/10

4:35 pm-10:45 am

1 stop17h 10m

$243

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 4/30

3:56 am-11:32 pm

1 stop20h 36m

Chicago O'Hare Intl

Sun 5/4

9:48 am-1:50 am

1 stop15h 02m

$270

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/2

6:00 am-12:24 pm

1 stop7h 24m

Chicago Midway

Mon 5/5

6:15 am-2:47 pm

1 stop7h 32m

$294

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/2

7:30 am-2:54 pm

1 stop8h 24m

Chicago Midway

Mon 10/6

6:00 am-1:23 pm

1 stop6h 23m

$344

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/9

1:05 pm-9:55 pm

1 stop9h 50m

Chicago Midway

Tue 10/14

6:55 am-5:15 pm

1 stop9h 20m

$381

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 6/17

2:36 am-4:54 pm

3 stops15h 18m

Chicago Midway

Tue 6/24

9:40 am-10:48 am

3 stops24h 08m

$709

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 4/25

9:30 pm-8:04 am

1 stop11h 34m

$116

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/2

10:46 am-11:11 pm

1 stop13h 25m

$135

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/16

12:36 pm-11:11 pm

1 stop11h 35m

$142

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 18 results
1
2

Best time to book a flight from San Juan to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from San Juan 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 San Juan to Chicago

How far ahead should I book a flight from San Juan to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from San Juan to Chicago. Price data was last updated on April 18, 2025.

To ensure you get the cheapest price possible for a flight from San Juan to Chicago, you should look to book at least 51 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from San Juan to Chicago?

Currently, August is the cheapest month in which you can book a flight from San Juan to Chicago (average of $245). Flying from San Juan 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 SJU to CHI?

Find hourly flight availability from San Juan 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 April 22, 2025.

When flying from San Juan 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 50% versus a flight at noon.

What is the cheapest day to fly from San Juan to Chicago?

Use this chart to determine the cheapest time to fly round-trip from San Juan to Chicago. Price data was last updated on December 8, 2024.

Travelers seeking maximum savings on their San Juan to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from San Juan to Chicago

Explore weekly flight availability from San Juan 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 April 22, 2025.

The most flights from PR1 to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 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 April 22, 2025.
To help decide which airline to fly from San Juan to Chicago, see what other customers have to say about Southwest, Delta and United Airlines. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

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
7,920 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

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
8,683 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

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
2,923 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

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!
Spirit Airlines
6.3
Okay
7,940 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

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 San Juan 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 flying from San Juan to Chicago round-trip?

    Cheapflights users have booked flights from San Juan to Chicago round-trip from $187. Other airlines that can offer you cheap pricing are Frontier, from $270, and Southwest, from $401. Spirit Airlines is 37% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from San Juan to Chicago one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $116. Frontier flights start at $135 while deals on JetBlue start at $162 one-way.

  • What are the most reliable airlines from San Juan to Chicago?

    No one likes to see their flight delayed. When booking a flight from San Juan 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 San Juan to Chicago?

    While on average a flight from San Juan to Chicago is generally $500, our data shows the cheapest flight currently is $138. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $187 for that flight.

  • Can I find deals for flights from San Juan to Chicago that include hotel bookings?

    Yes. In addition to deals on San Juan to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Juan to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Juan to Chicago.

  • Can I find deals for business class flights from San Juan to Chicago?

    Yes. Cheapflights offers flight deals from San Juan 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 San Juan to Chicago?

    Currently, August is the cheapest month in which you can book a flight from San Juan to Chicago (average of $245). Flying from San Juan 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 San Juan?

Book flights to San Juan 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

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

Top 6 airlines flying from San Juan to Chicago

Discover the top 6 airlines that operate flights from San Juan 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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$137Average$248FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$258FlexibilityNo cancel feeOn-time65%
DeltaCheapest$172Average$424FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$457FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$419FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$309Average$474FlexibilityNo 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.