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$113+ 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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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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 Monday

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 July 31, 2025.

Round-trip from

$221
(FlightHub)

One-way from

$113
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$301
From San Juan to Chicago (CHI)
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One-way flight from San Juan to Chicago (CHI)
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Highest demand for flights based on searches. 1% potential increase in price ($4 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 July 2025
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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 July 31, 2025.

This FlightHub deal was found by Cheapflights users on 7/31. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1510:16 pmSJU - ORD
1 stop12h 06mSpirit Airlines
Mon 8/1812:55 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 7/31$221
This KAYAK deal was found by Cheapflights users on 7/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/73:00 pmSJU - ORD
Nonstop5h 20mAmerican Airlines
Wed 10/87:11 amORD - SJU
2 stops15h 48mAmerican Airlines
Deal found 7/29$230
This SmartFares deal was found by Cheapflights users on 7/29. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/13:21 pmSJU - MDW
1 stop8h 48mFrontier
Sat 11/156:10 amMDW - SJU
1 stop7h 05mFrontier
Deal found 7/29$234
This Expedia deal was found by Cheapflights users on 7/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/133:29 amSJU - ORD
1 stop12h 58mMultiple Airlines
Sun 8/176:56 amORD - SJU
1 stop7h 14mMultiple Airlines
Deal found 7/30$242
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/123:40 amSJU - ORD
1 stop7h 34mFrontier
Sat 9/138:00 amORD - SJU
1 stop14h 59mFrontier
Deal found 7/30$248
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/113:19 pmSJU - MDW
3 stops26h 24mMultiple Airlines
Mon 9/1512:50 pmMDW - SJU
3 stops24h 21mMultiple Airlines
Deal found 7/29$321
This Southwest deal was found by Cheapflights users on 7/31. 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 9/111:20 pmSJU - MDW
1 stop10h 10mSouthwest
Tue 9/167:40 amMDW - SJU
1 stop8h 45mSouthwest
Deal found 7/31$351
This Delta deal was found by Cheapflights users on 7/31. 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.
Sat 10/412:58 pmSJU - MDW
1 stop9h 12mDelta
Tue 10/76:00 amMDW - SJU
1 stop6h 19mDelta
Deal found 7/31$361

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 July 31, 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 8/15

10:16 pm-9:22 am

1 stop12h 06m

Chicago O'Hare Intl

Mon 8/18

12:55 pm-6:40 pm

Nonstop4h 45m

$221

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 10/7

3:00 pm-7:20 pm

Nonstop5h 20m

Chicago O'Hare Intl

Wed 10/8

7:11 am-11:59 pm

2 stops15h 48m

$230

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 11/1

3:21 pm-11:09 pm

1 stop8h 48m

Chicago Midway

Sat 11/15

6:10 am-3:15 pm

1 stop7h 05m

$234

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 8/13

3:29 am-3:27 pm

1 stop12h 58m

Chicago O'Hare Intl

Sun 8/17

6:56 am-3:10 pm

1 stop7h 14m

$242

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 8/12

3:40 am-10:14 am

1 stop7h 34m

Chicago O'Hare Intl

Sat 9/13

8:00 am-8:02 am

1 stop23h 02m

$248

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/11

3:19 pm-4:43 pm

3 stops26h 24m

Chicago Midway

Mon 9/15

12:50 pm-2:11 pm

3 stops24h 21m

$321

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/11

1:20 pm-10:30 pm

1 stop10h 10m

Chicago Midway

Tue 9/16

9:00 am-7:45 pm

2 stops9h 45m

$351

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 10/4

12:58 pm-9:10 pm

1 stop9h 12m

Chicago Midway

Tue 10/7

6:00 am-1:19 pm

1 stop6h 19m

$361

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 9/12

3:39 am-9:51 am

1 stop7h 12m

$113

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 10/23

12:06 pm-6:06 pm

1 stop7h 00m

$113

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 13 results
1
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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 July 25, 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 July 31, 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. Monday 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 July 31, 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 (8 on average).

How much does it cost to fly round-trip from San Juan to Chicago?

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 July 31, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Spirit Airlines from San Juan to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Spirit Airlines
6.3
Okay
8,049 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,239 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $221. Other airlines that can offer you cheap pricing are Frontier, from $234, and Southwest, from $351. Spirit Airlines is 27% 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 Frontier, which is currently one of the cheapest options available, starting at $113. Spirit Airlines flights start at $113 while deals on Southwest start at $171 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 (99%), Air Canada (92%) or United Airlines (92%) 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 $1,810, our data shows the cheapest flight currently is $127. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $190 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$130Average$246FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$137Average$272FlexibilityNo cancel feeOn-time65%
DeltaCheapest$162Average$374FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$219Average$469FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$445FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$329Average$479FlexibilityNo cancel feeOn-time71%

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