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$87+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Nov 10 — Nov 171
Sun 11/10
Sun 11/17
1 adult, Economy
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The best prices from San Juan to Chicago are usually found in January or November, booked 15 days in advance, depart on a Thursday or Friday 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 November 5, 2024.

Popular in

March

Cheapest in

January

Round-trip from

$126
(eDestinos)

One-way from

$87
(Trip.com)
High demand for flights, 21% potential price rise
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Best time to find cheap flights, 31% potential price drop
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From San Juan to Chicago (CHI)
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One-way flight from San Juan to Chicago (CHI)
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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 November 5, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/52:17 pmSJU - ORD
Nonstop5h 30mSpirit Airlines
Fri 12/67:45 pmORD - SJU
1 stop14h 48mSpirit Airlines
Deal found 11/4$166
This Frontier deal was found by Cheapflights users on 11/5. 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 12/49:15 pmSJU - ORD
1 stop13h 09mFrontier
Mon 12/94:58 pmORD - SJU
1 stop7h 04mFrontier
Deal found 11/5$168
This FlightHub deal was found by Cheapflights users on 11/4. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/511:45 amSJU - MDW
1 stop25h 56mFrontier
Sun 12/87:25 amMDW - SJU
1 stop16h 32mFrontier
Deal found 11/4$172
This Mytrip deal was found by Cheapflights users on 11/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/59:49 pmSJU - ORD
1 stop14h 05mMultiple Airlines
Tue 12/109:58 amORD - SJU
1 stop8h 24mMultiple Airlines
Deal found 11/4$172
This eDestinos deal was found by Cheapflights users on 11/4. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/116:40 pmSJU - MDW
2 stops25h 32mMultiple Airlines
Sun 12/157:25 amMDW - SJU
1 stop16h 32mMultiple Airlines
Deal found 11/4$200
This Southwest deal was found by Cheapflights users on 11/5. 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 12/51:35 pmSJU - MDW
1 stop10h 05mSouthwest
Sat 1/118:35 amMDW - SJU
1 stop6h 35mSouthwest
Deal found 11/5$374
This Delta deal was found by Cheapflights users on 11/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/98:00 amSJU - MDW
1 stop11h 24mDelta
Tue 11/1210:41 amMDW - SJU
1 stop10h 41mDelta
Deal found 11/4$494

Find flights from San Juan to Chicago within your budget

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 2,554,862 searches. Data last updated November 5, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sun 12/15

9:32 pm-1:40 pm

1 stop18h 08m

$87

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 12/11

10:34 am-8:15 pm

1 stop11h 41m

$90

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 12/4

6:20 am-8:15 pm

2 stops15h 55m

$110

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Mon 2/3

6:45 am-3:28 pm

1 stop10h 43m

$146

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 12/5

9:49 pm-9:54 am

1 stop14h 05m

$87

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 1/18

2:55 pm-6:10 pm

Nonstop5h 15m

$183

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/27

2:05 am-10:46 am

1 stop10h 41m

$187

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 12/20

4:00 pm-7:25 pm

Nonstop5h 25m

$221

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/6

3:20 am-11:29 pm

1 stop22h 09m

$120

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sun 2/16

6:15 am-11:59 am

1 stop7h 44m

$242

Flights are sorted by cheapest first

Deals found on 11/5

Showing 1-10 of 19 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.

Travel insights for flights from San Juan to Chicago

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

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 November 1, 2024.

To ensure you get the cheapest price possible for a flight from San Juan to Chicago, you should look to book at least 15 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.

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

Currently, September is the cheapest month in which you can book a flight from San Juan to Chicago (average of $232). Flying from San Juan to Chicago in June is currently the most expensive (average of $308). 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 November 5, 2024.

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 39% 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 November 3, 2024.

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

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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 November 5, 2024.

The most flights from PR1 to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 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 November 5, 2024.
To help decide which airline to fly from San Juan to Chicago, see what other customers have to say about Spirit Airlines, Southwest and Delta. 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
8.1
Very good
5,082 reviews

Food

7.2

Comfort

8.1

Boarding

8.3

Entertainment

7.7

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,082 reviews
Southwest
8.1
Very good
5,082 reviews

Food

7.2

Comfort

8.1

Boarding

8.3

Entertainment

7.7

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,830 reviews
Southwest
8.1
Very good
5,082 reviews

Food

7.2

Comfort

8.1

Boarding

8.3

Entertainment

7.7

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,486 reviews
Southwest
8.1
Very good
5,082 reviews

Food

7.2

Comfort

8.1

Boarding

8.3

Entertainment

7.7

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,215 reviews
Southwest
8.1
Very good
5,082 reviews

Food

7.2

Comfort

8.1

Boarding

8.3

Entertainment

7.7

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
5,082 reviews

Food

7.2

Comfort

8.1

Boarding

8.3

Entertainment

7.7

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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.

  • Can I find flights from San Juan to Chicago for under $200 on Cheapflights?

    Yes, there are multiple flights from San Juan to Chicago for under $200. The cheapest flight booked recently is on Spirit Airlines for just $126, but on average you can expect to pay $239.

  • Are there nonstop flights from San Juan to Chicago for under $200 on Cheapflights?

    Cheapflights has at least 3 direct flights from San Juan to Chicago under $200. A good price for a nonstop flight from San Juan to Chicago is less than $338.

  • Are there last-minute flights available from San Juan to Chicago for under $200?

    There are currently 12+ open flights from San Juan to Chicago within the next 7 days for less than $200.

  • 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 $126. Other airlines that can offer you cheap pricing are Frontier, from $132, and Southwest, from $374. Spirit Airlines is 55% 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 $87. Spirit Airlines flights start at $94 while deals on JetBlue start at $146 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 (86%), Air Canada (85%) or United Airlines (85%) 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 $614, our data shows the cheapest flight currently is $95. When looking at the most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), you can expect to pay $126 for that flight.

  • What does SJU to ORD mean?

    SJU stands for San Juan Luis Munoz Marin Intl Airport, while ORD stands for Chicago O'Hare Intl Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry. While you’re still figuring out your travel plans, it’s not a bad idea to learn the names and codes of other airports around these areas: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from San Juan to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your San Juan to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from San Juan to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter San Juan to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from San Juan to Chicago that allow pets onboard?

    Many airlines flying from San Juan to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from San Juan to Chicago?

    Yes, you can often find last-minute deals on San Juan to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the San Juan to Chicago flight deals updated?

    The San Juan to Chicago flight deals you see on this page were last updated on 11/5.

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

    Currently, September is the cheapest month in which you can book a flight from San Juan to Chicago (average of $232). Flying from San Juan to Chicago in June is currently the most expensive (average of $308). 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

Browse thousands of different options on Cheapflights for your next trip

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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 2,554,862 searches. Data last updated November 5, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$114Average$230FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$142Average$266FlexibilityNo cancel feeOn-time65%
DeltaCheapest$182Average$466FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$202Average$472FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$274Average$351FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$301Average$479FlexibilityNo cancel feeOn-time71%
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