Chicago

$69+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Dec 14 — Dec 211
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The best prices from San Juan to Chicago are usually found in January or August, booked 51 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 December 9, 2024.

Round-trip from

$149
(Kiwi.com)

One-way from

$69
(Booking.com)

Popular in

April

Cheapest in

January

Average price

$278
From San Juan to Chicago (CHI)
One-way flight from San Juan to Chicago (CHI)
High demand for flights, 8% potential price rise
Best time to find cheap flights, 1% potential price drop
Average for round-trip flights in December 2024

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 December 9, 2024.

This FlightHub deal was found by Cheapflights users on 12/9. 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.
Sun 12/223:54 amSJU - ORD
1 stop8h 00mFrontier
Thu 1/210:15 pmORD - SJU
1 stop19h 40mFrontier
Deal found 12/9$154
This Priceline deal was found by Cheapflights users on 12/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/269:59 pmSJU - ORD
1 stop13h 55mMultiple Airlines
Wed 1/81:00 pmORD - SJU
Nonstop4h 36mMultiple Airlines
Deal found 12/8$160
This eDestinos deal was found by Cheapflights users on 12/8. 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.
Mon 12/238:31 pmSJU - ORD
Nonstop5h 27mSpirit Airlines
Tue 12/313:31 pmORD - SJU
1 stop7h 54mSpirit Airlines
Deal found 12/8$181
This Trip.com deal was found by Cheapflights users on 12/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/203:54 amSJU - MDW
1 stop16h 00mFrontier
Mon 1/69:59 pmMDW - SJU
1 stop10h 51mFrontier
Deal found 12/8$214
This American Airlines deal was found by Cheapflights users on 12/8. 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.
Tue 12/247:05 amSJU - ORD
2 stops9h 07mAmerican Airlines
Fri 1/39:55 amORD - SJU
1 stop12h 00mAmerican Airlines
Deal found 12/8$399
This eDestinos deal was found by Cheapflights users on 12/8. 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.
Sun 12/299:40 pmSJU - MDW
1 stop27h 34mMultiple Airlines
Wed 1/18:25 amMDW - SJU
1 stop15h 10mMultiple Airlines
Deal found 12/8$403
This Southwest deal was found by Cheapflights users on 12/9. 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 12/126:10 amSJU - MDW
1 stop10h 05mSouthwest
Fri 12/133:55 pmMDW - SJU
1 stop6h 50mSouthwest
Deal found 12/9$504
This Delta deal was found by Cheapflights users on 12/8. 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.
Wed 12/111:49 pmSJU - MDW
1 stop10h 17mDelta
Wed 12/186:00 amMDW - SJU
1 stop9h 15mDelta
Deal found 12/8$631

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 2,857,848 searches. Data last updated December 9, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/16

9:26 pm-12:51 am

Nonstop5h 25m

Chicago O'Hare Intl

Sun 1/19

1:44 pm-8:21 pm

Nonstop4h 37m

$149

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/16

6:55 pm-8:57 pm

1 stop28h 02m

Chicago O'Hare Intl

Sun 1/19

4:18 pm-10:37 am

1 stop16h 19m

$152

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/17

6:00 am-5:53 pm

1 stop13h 53m

Chicago Midway

Mon 1/20

11:33 am-2:19 am

1 stop12h 46m

$154

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/16

9:26 pm-12:51 am

Nonstop5h 25m

Chicago O'Hare Intl

Sun 1/19

4:18 pm-2:19 am

1 stop8h 01m

$156

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/16

2:05 am-10:44 am

1 stop10h 39m

Chicago O'Hare Intl

Mon 1/20

11:15 am-10:22 pm

1 stop9h 07m

$222

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/23

11:45 am-5:53 pm

2 stops32h 08m

Chicago Midway

Mon 1/27

6:15 am-2:30 pm

2 stops30h 15m

$239

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/30

6:00 am-11:45 am

1 stop7h 45m

Chicago Midway

Sun 2/2

1:20 pm-12:50 am

2 stops9h 30m

$296

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/24

6:15 am-11:59 am

1 stop7h 44m

Chicago Midway

Tue 1/28

6:00 am-5:14 pm

1 stop9h 14m

$324

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/27

6:35 am-10:46 pm

1 stop18h 11m

$69

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/23

9:26 pm-12:51 am

Nonstop5h 25m

$69

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/9

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 December 6, 2024.

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, 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 December 9, 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 41% 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 Monday evenings 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 December 9, 2024.

The most flights from PR1 to CHI are scheduled on a Saturday (10 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (9 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 December 9, 2024.
To help decide which airline to fly from San Juan to Chicago, see what other customers have to say about American Airlines, Delta 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
4,916 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.1
Very good
4,916 reviews
8.1
Very good
4,916 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
8,665 reviews
8.1
Very good
4,916 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Avelo Airlines
7.5
Good
74 reviews
8.1
Very good
4,916 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
3,318 reviews
8.1
Very good
4,916 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
9,120 reviews
8.1
Very good
4,916 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10