What are the cheapest airlines flying from San José, San José Province to Chicago round-trip?

Cheapflights users have booked flights from San José, San José Province to Chicago round-trip from $297. Other airlines that can offer you cheap pricing are Southwest, from $316, and Avianca, from $340. Spirit Airlines is 37% 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 José, San José Province to Chicago one-way?

To fly one-way, consider booking your trip with Viva, which is currently one of the cheapest options available, starting at $155. Spirit Airlines flights start at $163 while deals on Southwest start at $182 one-way.

What is the cheapest day to fly from San José, San José Province to Chicago?

Travelers seeking maximum savings on their San José, San José Province to Chicago flight should consider departing on Tuesday 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.

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.

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).

What are the cheapest flights from San José, San José Province to Chicago?

On average you can expect to pay $403 for a flight from San José, San José Province to Chicago. The cheapest flight overall is $216 while the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl) is currently priced at $289.

What are the most popular airlines that fly from San José, San José Province to Chicago?

Before booking your flight from San José, San José Province to Chicago check out the most popular airlines for this route: American Airlines, Avianca or Copa Airlines.

What is the cheapest day to fly round-trip from San José, San José Province to Chicago?

Leaving on a Tuesday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 58% on the overall cost on flights from San José, San José Province to Chicago.

How far in advance should I book a flight from San José, San José Province to Chicago?

To save on the cost of your flight from San José, San José Province to Chicago, book at least 57 days before your planned departure. Booking around this time can save you about 48% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $429 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $569.

What is the cheapest month to fly from San José, San José Province to Chicago?

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, August can be a great choice for travel to Chicago. Flights to Chicago from San José, San José Province in August are about $472 on average during August, but can be found for as low as $252.

What airport do you fly from for flights from San José to Chicago?

Located just 8.8 mi from the city center, San José Juan Santamaria Intl is the airport most travelers will use when flying to Chicago from San José. Booking flights from Juan Santamaria Intl (SJO) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 7 different airlines.

Can I find deals for flights from San José to Chicago that include hotel bookings?

Yes. In addition to deals on San José to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from San José to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San José to Chicago.

Can I find deals for business class flights from San José to Chicago?

Yes. Cheapflights offers flight deals from San José 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.

$155+ Flights from San José to Chicago

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Cheapflights Tip: The best prices from San José Juan Santamaria Intl to Chicago are usually found in August or July, booked 56 days in advance, depart on a Wednesday or Tuesday and return on a Monday

Cheap flight deals from San José to Chicago

Round-trip from	$297 (Cheapflightsfares)
One-way from	$155 (Booking.com)
Popular in	December
Cheapest in	August
Average price	$433
Good round-trip deal	$442 or less
Good one-way deal	$237 or less

From San José Juan Santamaria Intl to Chicago (CHI)

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One-way flight from San José Juan Santamaria Intl to Chicago (CHI)

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Highest demand for flights based on searches. 3% potential increase in price ($16 potential increase over avg. RT price).

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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).

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Average for round-trip flights in July 2025

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Price to beat on a round-trip flight from San José Juan Santamaria Intl to Chicago (CHI).

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Price to beat on a one-way flight from San José Juan Santamaria Intl to Chicago (CHI).

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Find flight deals from San José to Chicago

Cheapest flights from San José to Chicago
Explore the most affordable flight options available from San José to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

Wed 7/2312:16 pmSJO - ORD

1 stop9h 57mSpirit Airlines

Wed 7/305:05 amORD - SJO

1 stop7h 06mSpirit Airlines

Deal found 7/1

$297

Wed 7/94:45 pmSJO - ORD

1 stop19h 30mAvianca

Sat 7/125:25 pmORD - SJO

2 stops15h 15mAvianca

Deal found 7/2

$302

Sat 7/261:47 pmSJO - ORD

1 stop8h 42mMultiple Airlines

Tue 7/295:05 amORD - SJO

1 stop7h 06mMultiple Airlines

Deal found 7/1

$303

Tue 9/161:40 pmSJO - MDW

1 stop8h 40mSouthwest

Tue 9/306:25 amMDW - SJO

1 stop13h 30mSouthwest

Deal found 6/30

$316

Wed 9/242:55 pmSJO - ORD

1 stop8h 26mCopa Airlines

Thu 10/23:07 pmORD - SJO

3 stops26h 45mCopa Airlines

Deal found 7/3

$351

Thu 9/1111:27 amSJO - MDW

1 stop20h 26mMultiple Airlines

Mon 9/152:39 pmMDW - SJO

2 stops21h 35mMultiple Airlines

Deal found 7/1

$367

Best flights from San José to Chicago
Discover carefully curated flight deals from San José to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 3, 2025.

Wed 7/2312:16 pmSJO - ORD

1 stop9h 57mSpirit Airlines

Wed 7/305:05 amORD - SJO

1 stop7h 06mSpirit Airlines

Deal found 7/1

$297

Sat 7/261:47 pmSJO - ORD

1 stop8h 42mMultiple Airlines

Tue 7/295:05 amORD - SJO

1 stop7h 06mMultiple Airlines

Deal found 7/1

$303

Tue 9/161:40 pmSJO - MDW

1 stop8h 40mSouthwest

Tue 9/306:25 amMDW - SJO

1 stop13h 30mSouthwest

Deal found 6/30

$316

Wed 8/275:45 amSJO - ORD

1 stop7h 40mAvianca

Fri 8/293:45 pmORD - SJO

1 stop7h 05mAvianca

Deal found 7/1

$340

Wed 9/242:29 pmSJO - ORD

1 stop8h 52mCopa Airlines

Thu 10/23:07 pmORD - SJO

3 stops26h 45mCopa Airlines

Deal found 7/3

$351

Sat 8/21:47 pmSJO - ORD

1 stop8h 42mFrontier

Sat 8/95:01 amORD - SJO

1 stop8h 30mFrontier

Deal found 7/2

$353

Wed 8/271:35 pmSJO - MDW

2 stops18h 00mDelta

Wed 9/36:00 amMDW - SJO

1 stop7h 10mDelta

Deal found 7/2

$680

Thu 9/1111:27 amSJO - MDW

1 stop20h 26mMultiple Airlines

Mon 9/152:39 pmMDW - SJO

2 stops21h 35mMultiple Airlines

Deal found 7/1

$367

Last-minute flights from San José to Chicago
Discover last-minute flight deals from San José to Chicago. Data last updated July 3, 2025 and is based on user searches.

Tue 7/85:30 amSJO - ORD

1 stop16h 42mUnited Airlines

Sun 7/137:10 amORD - SJO

1 stop16h 29mUnited Airlines

Deal found 7/1

$470

Wed 7/94:45 pmSJO - ORD

1 stop19h 30mAvianca

Sat 7/125:25 pmORD - SJO

2 stops15h 15mAvianca

Deal found 7/2

$302

Wed 7/97:45 pmSJO - ORD

1 stop19h 20mMultiple Airlines

Wed 7/238:09 amORD - SJO

1 stop15h 31mMultiple Airlines

Deal found 7/2

$372

Wed 7/92:25 pmSJO - ORD

1 stop8h 55mCopa Airlines

Tue 7/221:07 amORD - SJO

1 stop18h 41mCopa Airlines

Deal found 7/2

$554

Thu 7/1012:16 pmSJO - ORD

1 stop10h 37mSpirit Airlines

Mon 7/145:05 amORD - SJO

1 stop7h 06mSpirit Airlines

Deal found 7/2

$427

Thu 7/108:45 amSJO - MDW

1 stop13h 55mSouthwest

Sun 7/135:15 amMDW - SJO

1 stop7h 20mSouthwest

Deal found 7/1

$531

Sat 7/122:30 pmSJO - MDW

1 stop18h 15mDelta

Mon 7/1412:43 pmMDW - SJO

1 stop24h 13mDelta

Deal found 7/1

$2,379

Wed 7/2312:16 pmSJO - ORD

1 stop9h 57mSpirit Airlines

Wed 7/305:05 amORD - SJO

1 stop7h 06mSpirit Airlines

Deal found 7/1

$297

Sat 7/261:47 pmSJO - ORD

1 stop8h 42mMultiple Airlines

Tue 7/295:05 amORD - SJO

1 stop7h 06mMultiple Airlines

Deal found 7/1

$303

Tue 8/125:10 pmSJO - MDW

1 stop25h 26mMultiple Airlines

Fri 8/158:35 amMDW - SJO

2 stops11h 23mMultiple Airlines

Deal found 7/1

$398

Fri 8/221:40 pmSJO - MDW

1 stop9h 25mSouthwest

Sun 8/246:00 amMDW - SJO

1 stop14h 05mSouthwest

Deal found 7/2

$426

Wed 8/271:35 pmSJO - MDW

2 stops18h 00mDelta

Wed 9/36:00 amMDW - SJO

1 stop7h 10mDelta

Deal found 7/2

$680

One-way flights from San José to Chicago
Search for one-way flight options from San José to Chicago. Find affordable one-way fares based on user searches. Data last updated July 3, 2025.

Fri 11/72:20 amSJO - ORD

1 stop12h 40mViva

Deal found 7/2

$155

Wed 9/312:18 pmSJO - ORD

2 stops30h 32mSpirit Airlines

Deal found 7/2

$163

Wed 8/271:40 pmSJO - MDW

1 stop8h 40mSouthwest

Deal found 6/30

$182

Wed 9/312:18 pmSJO - MDW

2 stops22h 52mMultiple Airlines

Deal found 7/2

$185

Wed 8/2712:18 pmSJO - ORD

2 stops29h 59mMultiple Airlines

Deal found 6/30

$185

Thu 8/284:20 pmSJO - ORD

1 stop21h 05mAvianca

Deal found 7/3

$198

Sat 11/82:49 pmSJO - ORD

1 stop8h 32mFrontier

Deal found 7/2

$200

Cheapflights Fare Finder

Use the filters below to find and compare flights from San José to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 7/23

12:16 pm-11:13 pm

1 stop9h 57m

Chicago O'Hare Intl

Wed 7/30

5:05 am-11:11 am

1 stop7h 06m

$297

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 7/26

1:47 pm-11:29 pm

1 stop8h 42m

Chicago O'Hare Intl

Tue 7/29

5:05 am-11:11 am

1 stop7h 06m

$303

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 9/16

1:40 pm-11:20 pm

1 stop8h 40m

Chicago Midway

Tue 9/30

6:25 am-6:55 pm

1 stop13h 30m

$316

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 8/27

5:45 am-2:25 pm

1 stop7h 40m

Chicago O'Hare Intl

Fri 8/29

3:45 pm-9:50 pm

1 stop7h 05m

$340

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 9/24

2:29 pm-12:21 am

1 stop8h 52m

Chicago O'Hare Intl

Thu 10/2

3:07 pm-4:52 pm

3 stops26h 45m

$351

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 8/2

1:47 pm-11:29 pm

1 stop8h 42m

Chicago O'Hare Intl

Sat 8/9

5:01 am-12:31 pm

1 stop8h 30m

$353

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 9/11

11:27 am-8:53 am

1 stop20h 26m

Chicago Midway

Mon 9/15

2:39 pm-11:14 am

2 stops21h 35m

$367

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 8/27

1:35 pm-8:35 am

2 stops18h 00m

Chicago Midway

Wed 9/3

6:00 am-12:10 pm

1 stop7h 10m

$680

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 9/3

12:18 pm-7:50 pm

2 stops30h 32m

$163

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 8/27

1:40 pm-11:20 pm

1 stop8h 40m

$182

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 15 results

Best time to book a flight from San José to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from San José 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 José to Chicago

How far ahead should I book a flight from San José, San José Province to Chicago?

The price you pay for your flight from San José, San José Province to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 56 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from San José, San José Province to Chicago?

Currently, August is the cheapest month in which you can book a flight from San José, San José Province to Chicago (average of $245). Flying from San José, San José Province 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 SJO to CHI?

One of the essential ways to save on airfare from San José, San José Province to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 45% on airfare.

How much does it cost to fly round-trip from San José, San José Province to Chicago?

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from San José to Chicago, such as Southwest, Delta, and Copa Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Southwest

8.0

Very good

4,270 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Southwest

8.0

Very good

4,270 reviews

Southwest

8.0

Very good

4,270 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Delta

8.0

Very good

7,970 reviews

Southwest

8.0

Very good

4,270 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Copa Airlines

7.5

Good

1,467 reviews

Southwest

8.0

Very good

4,270 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Viva

7.0

Good

788 reviews

Southwest

8.0

Very good

4,270 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Avianca

6.7

Okay

2,363 reviews

Southwest

8.0

Very good

4,270 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

What airport do you fly from for flights from San José to Chicago?
Located just 8.8 mi from the city center, San José Juan Santamaria Intl is the airport most travelers will use when flying to Chicago from San José. Booking flights from Juan Santamaria Intl (SJO) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 7 different airlines.
What are the cheapest airlines flying from San José, San José Province to Chicago round-trip?
Cheapflights users have booked flights from San José, San José Province to Chicago round-trip from $297. Other airlines that can offer you cheap pricing are Southwest, from $316, and Avianca, from $340. Spirit Airlines is 37% 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 José, San José Province to Chicago one-way?
To fly one-way, consider booking your trip with Viva, which is currently one of the cheapest options available, starting at $155. Spirit Airlines flights start at $163 while deals on Southwest start at $182 one-way.
What are the cheapest flights from San José, San José Province to Chicago?
On average you can expect to pay $403 for a flight from San José, San José Province to Chicago. The cheapest flight overall is $216 while the most popular route, (San José Juan Santamaria Intl - Chicago O'Hare Intl) is currently priced at $289.
Can I find deals for flights from San José to Chicago that include hotel bookings?
Yes. In addition to deals on San José to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from San José to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San José to Chicago.
Can I find deals for business class flights from San José to Chicago?
Yes. Cheapflights offers flight deals from San José 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 José, San José Province to Chicago?
Currently, August is the cheapest month in which you can book a flight from San José, San José Province to Chicago (average of $245). Flying from San José, San José Province 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

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Top 7 airlines flying from San José to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Avianca	Cheapest$249	Average$462	FlexibilityNo cancel fee	On-time71%
Spirit Airlines	Cheapest$266	Average$413	FlexibilityNo cancel fee	On-time65%
Copa Airlines	Cheapest$314	Average$485	FlexibilityNo cancel fee	On-time70%
Southwest	Cheapest$425	Average$527	FlexibilityNo cancel fee	On-time63%
Delta	Cheapest$434	Average$558	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$437	Average$623	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$446	Average$569	FlexibilityNo cancel fee	On-time71%

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$155+ Cheap flights from San José (SJO) 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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from San José to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from San José Juan Santamaria Intl to Chicago are usually found in August or July, booked 56 days in advance, depart on a Wednesday or Tuesday and return on a Monday

Cheap flight deals from San José to Chicago

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from San José to Chicago

Cheapest flights from San José to ChicagoExplore the most affordable flight options available from San José to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

Explore the most affordable flight options available from San José to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from San José to Chicago that are best for you.

Best time to book a flight from San José to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from San José with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from San José to Chicago

How far ahead should I book a flight from San José, San José Province to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from San José to Chicago. Price data was last updated on June 27, 2025.

What is the cheapest month to book a flight from San José, San José Province to Chicago?

What is the cheapest time of day to fly from SJO to CHI?

Find hourly flight availability from San José 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 3, 2025.

How much does it cost to fly round-trip from San José, San José Province to Chicago?

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from San José to Chicago, such as Southwest, Delta, and Copa Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from San José to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly from for flights from San José to Chicago?

What are the cheapest airlines flying from San José, San José Province to Chicago round-trip?

What are the cheapest airlines to fly from San José, San José Province to Chicago one-way?

What are the cheapest flights from San José, San José Province to Chicago?

Can I find deals for flights from San José to Chicago that include hotel bookings?

How can I find direct flights from San José to Chicago?

Can I find deals for business class flights from San José to Chicago?

What is the cheapest month to book a flight from San José, San José Province to Chicago?

Traveling to a place near San José?

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Alternative routes for San José to Chicago

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Top 7 airlines flying from San José to Chicago

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Cheapest flights from San José to Chicago
Explore the most affordable flight options available from San José to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.