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$97+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
1 adult, Economy
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Cheapflights Tip: The best prices from San Juan to Chicago are usually found in February or May, booked 72 days in advance, depart on a Friday or Thursday and return on a Monday

Cheap 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 February 4, 2026.

This CheapOair deal was found by Cheapflights users on 2/2. 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.
Thu 2/2611:52 am
SJU
-
ORD
1 stop8h 26m
Spirit Airlines
Tue 3/35:15 am
ORD
-
SJU
1 stop8h 16m
Spirit Airlines
Deal found 2/2$136
This Expedia deal was found by Cheapflights users on 2/2. 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.
Thu 2/2612:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Mon 3/212:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/2$141
This Expedia deal was found by Cheapflights users on 2/1. 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.
Thu 2/51:22 pm
SJU
-
ORD
Nonstop5h 15m
Spirit Airlines
Sat 2/712:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/1$149
This Orbitz deal was found by Cheapflights users on 2/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2711:52 am
SJU
-
ORD
1 stop8h 26m
Spirit Airlines
Mon 3/212:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/2$150
This Expedia deal was found by Cheapflights users on 2/3. 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.
Tue 3/312:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Sat 3/712:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/3$151
This Expedia deal was found by Cheapflights users on 2/2. 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.
Thu 2/1212:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Tue 2/2412:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/2$152
This Flightnetwork deal was found by Cheapflights users on 2/4. 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.
Wed 2/1812:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Sun 2/2212:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/4$166
This Frontier deal was found by Cheapflights users on 2/3. 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.
Fri 2/273:53 am
SJU
-
MDW
1 stop13h 02m
Frontier
Mon 3/29:22 pm
MDW
-
SJU
1 stop10h 32m
Frontier
Deal found 2/3$188
This Frontier deal was found by Cheapflights users on 2/2. 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.
Wed 4/81:11 pm
SJU
-
MDW
1 stop10h 08m
Frontier
Sat 4/112:56 pm
MDW
-
SJU
1 stop8h 18m
Frontier
Deal found 2/2$202
This Expedia deal was found by Cheapflights users on 2/2. 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.
Thu 2/124:11 pm
SJU
-
MDW
1 stop8h 23m
Frontier
Tue 2/246:10 am
MDW
-
SJU
1 stop6h 56m
Frontier
Deal found 2/2$209
This Frontier deal was found by Cheapflights users on 2/3. 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 3/54:11 pm
SJU
-
MDW
1 stop8h 18m
Frontier
Mon 3/96:05 am
MDW
-
SJU
1 stop7h 12m
Frontier
Deal found 2/3$220
This Frontier deal was found by Cheapflights users on 2/2. 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 4/99:01 am
SJU
-
MDW
1 stop8h 08m
Frontier
Sat 4/112:56 pm
MDW
-
SJU
1 stop8h 18m
Frontier
Deal found 2/2$223

Find 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 February 4, 2026.

Round-trip from

$134
(Expedia)

One-way from

$97
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$235
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. 6% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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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 February 4, 2026.
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

Thu 3/5

11:52 am-6:18 pm

1 stop8h 26m

Chicago O'Hare Intl

Sun 3/8

8:16 pm-2:31 pm

1 stop17h 15m

$175

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sat 2/14

11:52 am-7:47 pm

1 stop9h 55m

Chicago O'Hare Intl

Sun 2/22

12:17 pm-6:49 pm

Nonstop4h 32m

$204

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 3/31

1:29 am-5:45 am

Nonstop5h 16m

Chicago O'Hare Intl

Thu 4/9

1:02 pm-12:53 am

1 stop10h 51m

$206

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 3/6

7:00 am-5:03 pm

1 stop12h 03m

Chicago O'Hare Intl

Sun 3/8

7:00 am-2:31 pm

1 stop6h 31m

$206

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 4/22

12:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

Sat 4/25

12:22 pm-5:54 pm

Nonstop4h 32m

$208

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/26

12:32 pm-3:48 pm

Nonstop5h 16m

Chicago O'Hare Intl

Sun 3/1

12:17 pm-6:49 pm

Nonstop4h 32m

$209

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Mon 3/2

2:59 am-11:47 am

3 stops34h 48m

Chicago O'Hare Intl

Sat 3/7

12:17 pm-6:49 pm

Nonstop4h 32m

$210

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 5/7

12:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

Thu 5/14

1:27 pm-12:33 pm

1 stop22h 06m

$212

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sat 5/16

11:59 pm-9:48 am

1 stop10h 49m

Chicago O'Hare Intl

Sat 5/23

10:35 am-8:03 pm

1 stop8h 28m

$231

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 2/25

11:52 am-1:56 pm

1 stop28h 04m

Chicago Midway

Sat 2/28

9:15 am-11:09 pm

2 stops11h 54m

$232

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

Showing 1-10 of 41 results
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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 January 30, 2026.

To ensure you get the cheapest price possible for a flight from San Juan to Chicago, you should look to book at least 72 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, February is the cheapest month in which you can book a flight from San Juan to Chicago (average of $120). Flying from San Juan to Chicago in December is currently the most expensive (average of $157). 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 February 4, 2026.

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 53% versus a flight in the afternoon.

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 February 10, 2025.

Travelers seeking maximum savings on their San Juan to Chicago flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday afternoons 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 February 4, 2026.

The most flights from PR1 to CHI are scheduled on a Monday (12 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (9 on average).

How often are flights from San Juan to Chicago delayed?

About 9% of weekly flights between San Juan and Chicago have experienced delays in the past year, with the average delay time being 183 minutes.

What is the most punctual flight time for San Juan to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Thursday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on San Juan to Chicago flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 5% of flights being delayed.

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 4, 2026.
Read reviews from past customers who have flown United Airlines, American Airlines, and JetBlue 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.
United Airlines
7.4
Good
9,236 reviews

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,236 reviews
United Airlines
7.4
Good
9,236 reviews

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.2
Good
11,224 reviews
United Airlines
7.4
Good
9,236 reviews

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
JetBlue
7.2
Good
2,893 reviews
United Airlines
7.4
Good
9,236 reviews

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Spirit Airlines
6.3
Okay
8,415 reviews
United Airlines
7.4
Good
9,236 reviews

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Frontier
5.7
Fair
3,052 reviews
United Airlines
7.4
Good
9,236 reviews

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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.

  • How long is the flight from San Juan to Chicago?

    For as low as $237, Spirit Airlines can have you in Chicago from San Juan in 8h 01m. The distance from San Juan to Chicago is about 2057 mi. This flight may include one or multiple stops.

  • 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 $116. Other airlines that can offer you cheap pricing are Spirit Airlines, from $120, and JetBlue, from $131. Delta is 62% 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 JetBlue, which is currently one of the cheapest options available, starting at $74. Spirit Airlines flights start at $93 while deals on Frontier start at $102 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 Air Canada (83%), United Airlines (83%) or Air New Zealand (83%) 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 $474, our data shows the cheapest flight currently is $119. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $135 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, February is the cheapest month in which you can book a flight from San Juan to Chicago (average of $120). Flying from San Juan to Chicago in December is currently the most expensive (average of $157). 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
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Top 7 airlines flying from San Juan to Chicago

Discover the top 7 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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$538FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$120Average$266FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$131Average$201FlexibilityNo cancel feeOn-time62%
FrontierCheapest$137Average$258FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$256Average$481FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$258Average$483FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$419Average$559FlexibilityNo cancel feeOn-time63%

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