Which layover airport has the shortest connection time from San José to Chicago?

Houston (IAH) has the shortest average layover time for this route: 1h 12m.

How many flights depart from San José to Chicago on average per day?

The number of flights available between San José and Chicago is 1 per day as of February 2026. The most frequent departure time is 7:00AM, with 54% of daily flights leaving at noon.

How often are flights from San José to Chicago delayed?

Historically, on average around 12% of flights between San José and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 224 minutes.

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

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

Which layover airport offers the lowest fares from San José to Chicago?

Flights via Fort Lauderdale (FLL) offer the lowest average round-trip price of $291.

How many flights depart from San José to Chicago on average per week?

The number of flights available between San José and Chicago is 11 per week as of February 2026. The most frequent departure day is Mon, with 18% of weekly flights leaving on this day.

What is the cheapest airline that flies from San José Juan Santamaria Intl to Chicago?

Spirit Airlines, Southwest, and Delta are the most popular carriers operating from San José Juan Santamaria Intl to Chicago

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

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Saturday has historically seen more delays on average compared to the rest of the week.

What airlines fly to Chicago?

American Airlines, United Airlines and Copa Airlines are the top three most popular airlines that fly to Chicago from San José according to our data. American Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Which airport is the most popular layover for flights between San José and Chicago?

Panama City (PTY) was the most common stop: 57% of momondo users choosing 1-stop flights on this route connected there.

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

According to our data, American Airlines have had the least number of delays on this route over the last 12 months; with about 5% of their flights experiencing any sort of delay.

Which layover airport has the shortest travel time from San José to Chicago?

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 7h 51m.

When did momondo last update prices for flights from San José Juan Santamaria Intl Airport to Chicago?

Prices for flights from San José Juan Santamaria Intl Airport to Chicago are refreshed on a daily basis.

How many operators does momondo search for flights from San José Juan Santamaria Intl Airport to Chicago?

As of February 2026, there are 6 operators available to choose from for flights from San José Juan Santamaria Intl Airport to Chicago.

How old do you have to be to fly from San José Juan Santamaria Intl Airport to Chicago?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from San José Juan Santamaria Intl Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$139 Cheap Flights from San José to Chicago in 2026

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One-way

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Enter your travel dates to find the best prices.

1:31 pm - 9:13 pm

SJO

ORD

7h 42m

1 stop

5:05 am - 11:14 am

ORD

SJO

7h 09m

1 stop

$296Spirit Airlines

Thu, Feb 19 - Wed, Apr 8

12:31 pm - 11:41 pm

SJO

ORD

10h 10m

1 stop

8:25 am - 11:22 am

ORD

SJO

27h 57m

2 stops

$297Multiple Airlines

Wed, May 6 - Tue, May 12

12:31 pm - 11:27 am

SJO

ORD

21h 56m

1 stop

5:15 am - 11:22 am

ORD

SJO

7h 07m

1 stop

$298Spirit Airlines

Mon, Apr 20 - Sat, Apr 25

12:31 pm - 11:41 pm

SJO

ORD

10h 10m

1 stop

5:15 am - 11:22 am

ORD

SJO

7h 07m

1 stop

$299Spirit Airlines

Fri, May 1 - Sat, May 9

12:35 pm - 7:46 am

SJO

ORD

19h 11m

1 stop

7:39 am - 12:56 pm

ORD

SJO

5h 17mnonstop

$300United Airlines

Thu, Feb 19 - Sun, Feb 22

12:31 pm - 11:27 am

SJO

ORD

21h 56m

1 stop

5:15 am - 11:22 am

ORD

SJO

7h 07m

1 stop

$301Spirit Airlines

Mon, Apr 20 - Sat, Apr 25

11:01 am - 12:04 am

SJO

ORD

13h 03m

1 stop

2:22 pm - 4:46 pm

ORD

SJO

26h 24m

3 stops

$302Copa Airlines

Thu, Feb 19 - Sun, Feb 22

8:00 am - 4:14 pm

SJO

ORD

8h 14m

1 stop

3:10 pm - 8:12 pm

ORD

SJO

5h 02mnonstop

$305American Airlines

Thu, Feb 19 - Tue, Feb 24

1:10 pm - 11:05 pm

SJO

MDW

8h 55m

1 stop

12:15 pm - 7:00 pm

MDW

SJO

7h 45m

1 stop

$344Southwest

Tue, Apr 21 - Tue, Apr 28

1:10 pm - 11:05 pm

SJO

MDW

8h 55m

1 stop

5:40 am - 7:00 pm

MDW

SJO

14h 20m

2 stops

$348Southwest

Tue, Apr 21 - Tue, Apr 28

Spirit Airlines flights from San José to Chicago

Our best Spirit Airlines deals on San José to Chicago flight tickets

Spirit Airlines

Feb 19

SJO1:31 pmSan José Juan Santamaria Intl

7h 42m

1 stop

ORD9:13 pmChicago O'Hare Intl

Apr 8

ORD5:05 amChicago O'Hare Intl

7h 09m

1 stop

SJO11:14 amSan José Juan Santamaria Intl

$296

Spirit Airlines

Apr 20

SJO12:31 pmSan José Juan Santamaria Intl

21h 56m

1 stop

ORD11:27 amChicago O'Hare Intl

Apr 25

ORD5:15 amChicago O'Hare Intl

7h 07m

1 stop

SJO11:22 amSan José Juan Santamaria Intl

$298

Spirit Airlines

Mar 4

SJO1:31 pmSan José Juan Santamaria Intl

7h 42m

1 stop

ORD9:13 pmChicago O'Hare Intl

Mar 8

ORD4:43 pmChicago O'Hare Intl

18h 57m

2 stops

SJO10:40 amSan José Juan Santamaria Intl

$301

United Airlines flights from San José to Chicago

Our best United Airlines deals on San José to Chicago flight tickets

United Airlines

Feb 19

SJO12:35 pmSan José Juan Santamaria Intl

19h 11m

1 stop

ORD7:46 amChicago O'Hare Intl

Feb 22

ORD7:39 amChicago O'Hare Intl

5h 17m

SJO12:56 pmSan José Juan Santamaria Intl

$300

United Airlines

Mar 10

SJO1:05 pmSan José Juan Santamaria Intl

5h 30m

ORD7:35 pmChicago O'Hare Intl

Mar 17

ORD7:35 amChicago O'Hare Intl

14h 57m

1 stop

SJO9:32 pmSan José Juan Santamaria Intl

$318

United Airlines

Mar 11

SJO1:05 pmSan José Juan Santamaria Intl

5h 30m

ORD7:35 pmChicago O'Hare Intl

Mar 18

ORD9:15 pmChicago O'Hare Intl

25h 17m

1 stop

SJO9:32 pmSan José Juan Santamaria Intl

$323

Fly from

Fly to

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 2/19

1:31 pm-9:13 pm

1 stop7h 42m

Chicago O'Hare Intl

Wed 4/8

5:05 am-11:14 am

1 stop7h 09m

$296

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 5/6

12:31 pm-11:41 pm

1 stop10h 10m

Chicago O'Hare Intl

Tue 5/12

8:25 am-11:22 am

2 stops27h 57m

$297

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Mon 4/20

12:31 pm-11:27 am

1 stop21h 56m

Chicago O'Hare Intl

Sat 4/25

5:15 am-11:22 am

1 stop7h 07m

$298

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 5/1

12:31 pm-11:41 pm

1 stop10h 10m

Chicago O'Hare Intl

Sat 5/9

5:15 am-11:22 am

1 stop7h 07m

$299

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 2/19

12:35 pm-7:46 am

1 stop19h 11m

Chicago O'Hare Intl

Sun 2/22

7:39 am-12:56 pm

Nonstop5h 17m

$300

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Mon 4/20

12:31 pm-11:27 am

1 stop21h 56m

Chicago O'Hare Intl

Sat 4/25

5:15 am-11:22 am

1 stop7h 07m

$301

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 2/19

11:01 am-12:04 am

1 stop13h 03m

Chicago O'Hare Intl

Sun 2/22

2:22 pm-4:46 pm

3 stops26h 24m

$302

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 2/19

8:00 am-4:14 pm

1 stop8h 14m

Chicago O'Hare Intl

Tue 2/24

3:10 pm-8:12 pm

Nonstop5h 02m

$305

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 4/21

1:10 pm-11:05 pm

1 stop8h 55m

Chicago Midway

Tue 4/28

12:15 pm-7:00 pm

1 stop7h 45m

$344

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 4/21

1:10 pm-11:05 pm

1 stop8h 55m

Chicago Midway

Tue 4/28

5:40 am-7:00 pm

2 stops14h 20m

$348

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How to get the cheapest flight ticket from San José to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Delays

Layovers

Other information

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from San José, with most prices found around $369. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from San José to Chicago during February average around $382.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $429. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from San José to Chicago for around $584.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from San José to Chicago during this time can be as low as $459. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $466.

What is the cheapest San José Juan Santamaria Intl to Chicago flight route?

Fly from San José Juan Santamaria Intl to Chicago O'Hare Intl for the best San José Juan Santamaria Intl - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from San José when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $449 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from San José for as low as $395 on momondo.

What cabin class options are available on San José Juan Santamaria Intl to Chicago flights?

There are 3 cabin classes available to choose from on San José Juan Santamaria Intl to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on San José to Chicago flights?

No. A direct flight is the cheapest option for a flight between San José to Chicago.

How have San José to Chicago flight prices changed over time?

As of February 2026, prices for San José to Chicago flights are approximately 43% more expensive when compared to flights at the same time last year.

When to book flights from San José to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from San José to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap San José to Chicago (SJO to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San José to Chicago

Best Price Found	$186
Fastest flight time	5h 24m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from San José in the past 72 hours is $186. The best round-trip flight deal from San José to Chicago found on momondo in the last 72 hours is $299.

The fastest flight from San José to Chicago takes 5h 24m

Direct flights go from San José to Chicago every day.

There are 3 airports in Chicago. From San José there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

How far is San José Juan Santamaria Intl to Chicago by plane?
A flight from San José Juan Santamaria Intl to Chicago will travel around 2215.9 mi. Flights usually cover this in 5h 24m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from San José Juan Santamaria Intl Airport to Chicago?
Prices for flights from San José Juan Santamaria Intl Airport to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from San José Juan Santamaria Intl Airport to Chicago?
As of February 2026, there are 6 operators available to choose from for flights from San José Juan Santamaria Intl Airport to Chicago.
How old do you have to be to fly from San José Juan Santamaria Intl Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from San José Juan Santamaria Intl Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from San José to Chicago?
Based on momondo bookings for flights between San José and Chicago, the leading plane model is Boeing 737 MAX 8, making up 40.23% of the total bookings. Other popular models include Boeing 737 MAX 9 with 30.17%, Airbus A320neo with 7.40%, and Airbus A321-100/200 with 5.55%.
What is the most popular airline from San José to Chicago?
momondo data reveals that the most frequently booked airline on the route from San José to Chicago is American Airlines, representing 34% of all bookings. The subsequent popular airlines are Copa Airlines at 20%, United Airlines at 16%, and Spirit Airlines at 14%.

Best airlines flying from San José to Chicago

Compare and see reviews for airlines that fly from San José to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $206	Free Cancellation	Rating 6.3 8,430 reviews	Search Spirit Airlines flights
Avianca	PriceFrom $249	Free Cancellation	Rating 6.5 2,498 reviews	Search Avianca flights
Copa Airlines	PriceFrom $313	Free Cancellation	Rating 7.5 1,556 reviews	Search Copa Airlines flights
American Airlines	PriceFrom $332	Free Cancellation	Rating 7.2 11,249 reviews	Search American Airlines flights
United Airlines	PriceFrom $400	Free Cancellation	Rating 7.4 9,255 reviews	Search United Airlines flights
Southwest	PriceFrom $463	Free Cancellation	Rating 8.0 4,281 reviews	Search Southwest flights

United Airlines Flights From San José to Chicago
The lowest priced United Airlines flight from San José to Chicago from the last 72 hours was $400. Generally, United Airlines has 5 flights on this route every week with an average price of $500. United Airlines is rated 7.4/10 by our users.
American Airlines Flights From San José to Chicago
The best American Airlines deal for San José to Chicago flight tickets found on momondo in the last 72 hours was $332, round-trip. It should be noted that an average American Airlines flight deal for this route in this time was higher, at $461 round-trip. American Airlines operates 6 flights out of San José into Chicago in an average week, so prices vary by time and availability. 11,249 American Airlines reviews by users on momondo have scored the airline at 7.2/10.

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Why use momondo?

Why should I use momondo to find a flight deal from San José to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from San José to Chicago for you.

Can I find flights from San José to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for San José to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from San José to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from San José.

I’m not ready to book a flight from San José to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from San José are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Cheap flights from San José to Chicago from $139

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San José to Chicago departing on 3/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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How to get the cheapest flight ticket from San José to Chicago

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from San José, with most prices found around $369. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from San José to Chicago during February average around $382.

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from San José to Chicago during this time can be as low as $459. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $466.

What is the cheapest San José Juan Santamaria Intl to Chicago flight route?

Fly from San José Juan Santamaria Intl to Chicago O'Hare Intl for the best San José Juan Santamaria Intl - Chicago flight prices

How far in advance should I book a flight to Chicago?

What cabin class options are available on San José Juan Santamaria Intl to Chicago flights?

There are 3 cabin classes available to choose from on San José Juan Santamaria Intl to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on San José to Chicago flights?

No. A direct flight is the cheapest option for a flight between San José to Chicago.

How have San José to Chicago flight prices changed over time?

As of February 2026, prices for San José to Chicago flights are approximately 43% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from San José Juan Santamaria Intl to Chicago?

Spirit Airlines, Southwest, and Delta are the most popular carriers operating from San José Juan Santamaria Intl to Chicago

What airlines fly to Chicago?

How often are flights from San José to Chicago delayed?

Historically, on average around 12% of flights between San José and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 224 minutes.

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

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

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

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Saturday has historically seen more delays on average compared to the rest of the week.

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

According to our data, American Airlines have had the least number of delays on this route over the last 12 months; with about 5% of their flights experiencing any sort of delay.

Which airport is the most popular layover for flights between San José and Chicago?

Panama City (PTY) was the most common stop: 57% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from San José to Chicago?

Flights via Fort Lauderdale (FLL) offer the lowest average round-trip price of $291.

Which layover airport has the shortest travel time from San José to Chicago?

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 7h 51m.

Which layover airport has the shortest connection time from San José to Chicago?

Houston (IAH) has the shortest average layover time for this route: 1h 12m.

How many flights depart from San José to Chicago on average per day?

The number of flights available between San José and Chicago is 1 per day as of February 2026. The most frequent departure time is 7:00AM, with 54% of daily flights leaving at noon.

How many flights depart from San José to Chicago on average per week?

The number of flights available between San José and Chicago is 11 per week as of February 2026. The most frequent departure day is Mon, with 18% of weekly flights leaving on this day.

When to book flights from San José to Chicago

Cheap San José to Chicago (SJO to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San José to Chicago

Best Price Found

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Direct flights

Airports in Chicago

How far is San José Juan Santamaria Intl to Chicago by plane?

When did momondo last update prices for flights from San José Juan Santamaria Intl Airport to Chicago?

How many operators does momondo search for flights from San José Juan Santamaria Intl Airport to Chicago?

How old do you have to be to fly from San José Juan Santamaria Intl Airport to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from San José to Chicago?

What is the most popular airline from San José to Chicago?

Best airlines flying from San José to Chicago

Compare and see reviews for airlines that fly from San José to Chicago with momondo

United Airlines Flights From San José to Chicago

American Airlines Flights From San José to Chicago

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