Chicago

$85+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
nov. 25 — dic. 21
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.

The best prices from San Juan to Chicago are usually found in January or August, 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 noviembre 20, 2024.

Popular in

March

Cheapest in

January

Round-trip from

$158
(FlightHub)

One-way from

$85
(Frontier)
High demand for flights, 19% potential price rise
Best time to find cheap flights, 32% potential price drop
From San Juan to Chicago (CHI)
One-way flight from San Juan to Chicago (CHI)

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 noviembre 20, 2024.

This FlightHub deal was found by Cheapflights users on 11/20. 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.
vie. 12/131:55 pmSJU - MDW
1 stop12h 25mFrontier
lun. 12/167:25 amMDW - SJU
1 stop16h 32mFrontier
Deal found 11/20$158
This Cheapflightsfares deal was found by Cheapflights users on 11/19. 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.
mié. 12/188:31 pmSJU - ORD
Nonstop5h 27mSpirit Airlines
jue. 1/21:00 pmORD - SJU
Nonstop4h 36mSpirit Airlines
Deal found 11/19$158
This Kiwi.com deal was found by Cheapflights users on 11/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/62:17 pmSJU - ORD
Nonstop5h 30mMultiple Airlines
lun. 12/94:58 pmORD - SJU
1 stop7h 04mMultiple Airlines
Deal found 11/20$161
This Gotogate deal was found by Cheapflights users on 11/19. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/203:54 amSJU - ORD
1 stop8h 00mFrontier
mar. 12/3111:24 amORD - SJU
1 stop7h 32mFrontier
Deal found 11/19$163
This eDestinos deal was found by Cheapflights users on 11/20. 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.
sáb. 12/76:20 amSJU - MDW
2 stops37h 52mMultiple Airlines
mar. 12/1012:57 pmMDW - SJU
2 stops34h 43mMultiple Airlines
Deal found 11/20$241
This United Airlines deal was found by Cheapflights users on 11/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/62:05 amSJU - ORD
1 stop9h 38mUnited Airlines
mar. 12/1012:53 pmORD - SJU
1 stop9h 43mUnited Airlines
Deal found 11/19$290
This Southwest deal was found by Cheapflights users on 11/18. 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.
jue. 12/126:10 amSJU - MDW
2 stops12h 55mSouthwest
lun. 12/169:45 amMDW - SJU
2 stops13h 00mSouthwest
Deal found 11/18$325
This Delta deal was found by Cheapflights users on 11/19. 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.
lun. 12/233:30 pmSJU - MDW
1 stop8h 36mDelta
mar. 1/146:00 amMDW - SJU
1 stop6h 20mDelta
Deal found 11/19$359

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 2,629,791 searches. Data last updated noviembre 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

vie. 12/13

1:55 pm-12:20 am

1 stop12h 25m

Chicago Midway

lun. 12/16

7:25 am-1:57 am

1 stop16h 32m

$158

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

lun. 2/3

6:00 am-10:16 pm

1 stop18h 16m

Chicago O'Hare Intl

lun. 2/10

3:16 pm-12:39 am

1 stop7h 23m

$158

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 12/20

4:43 pm-8:13 pm

Nonstop5h 30m

Chicago O'Hare Intl

mar. 1/7

9:32 am-4:15 pm

Nonstop4h 43m

$159

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 12/6

2:17 pm-5:47 pm

Nonstop5h 30m

Chicago O'Hare Intl

lun. 12/9

4:58 pm-2:02 am

1 stop7h 04m

$161

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 1/23

4:50 pm-6:01 pm

1 stop27h 11m

Chicago Midway

lun. 1/27

6:15 am-12:39 am

2 stops16h 24m

$194

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 1/23

2:55 pm-7:45 pm

1 stop6h 50m

Chicago Midway

lun. 1/27

10:05 am-12:25 am

2 stops12h 20m

$210

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 12/6

8:35 am-11:54 am

Nonstop5h 19m

Chicago O'Hare Intl

lun. 12/9

2:20 pm-8:55 pm

Nonstop4h 35m

$221

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 2/20

6:15 am-11:59 am

1 stop7h 44m

Chicago Midway

lun. 2/24

12:44 pm-11:46 pm

1 stop9h 02m

$334

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

mié. 12/4

6:20 am-11:42 am

1 stop7h 22m

$85

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 12/20

4:43 pm-8:13 pm

Nonstop5h 30m

$85

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 20 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.

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 15, 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.

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 noviembre 20, 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 18, 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 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 noviembre 20, 2024.

The most flights from PR1 to CHI are scheduled on a Wednesday (7 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 noviembre 20, 2024.
To help decide which airline to fly from San Juan to Chicago, see what other customers have to say about United Airlines, Frontier and Spirit 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.
8.1
Very good
5,014 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

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

8.1
Very good
5,014 reviews
8.1
Very good
5,014 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

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

8.0
Very good
8,756 reviews
8.1
Very good
5,014 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

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

Avelo Airlines
7.5
Good
74 reviews
8.1
Very good
5,014 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

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

7.4
Good
9,171 reviews
8.1
Very good
5,014 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

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

7.2
Good
10,000 reviews
8.1
Very good
5,014 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

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.
  • 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 $158. Other airlines that can offer you cheap pricing are Spirit Airlines, from $159, and Southwest, from $210. Frontier is 44% 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 $85. Spirit Airlines flights start at $85 while deals on United Airlines start at $100 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 (84%), United Airlines (84%) or Air New Zealand (84%) 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 $736, 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 $122 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, 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

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 2,629,791 searches. Data last updated noviembre 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$120Average$372FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$148Average$287FlexibilityNo cancel feeOn-time65%
DeltaCheapest$182Average$453FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$202Average$469FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$220Average$379FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$303Average$473FlexibilityNo 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.