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.

How often are flights from San José to Chicago delayed?

Historically, on average around 19% 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 183 minutes.

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

Panama City (PTY) was the most common stop: 53% of momondo users choosing 1-stop flights on this route connected there.

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

The number of flights available between San José and Chicago is 9 per week as of December 2025. The most frequent departure day is Wed, with 22% of weekly flights leaving on this day.

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

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 19% of their flights experiencing any sort of delay.

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 35% 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.

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 has the shortest connection time from San José to Chicago?

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

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 offers the lowest fares from San José to Chicago?

Flights via Fort Lauderdale (FLL) offer the lowest average round-trip price of $292.

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

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

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 December 2025. The most frequent departure time is 6:00AM, with 83% of daily flights leaving at noon.

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 December 2025, 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.

$131 Cheap Flights from San José to Chicago in 2025/26

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1:30 pm - 10:36 pm

SJO

ORD

9h 06m1 stop

8:15 am - 12:22 pm

ORD

SJO

28h 07m2 stops

$260Multiple Airlines

Thu, Jan 29 - Fri, Feb 6

1:30 pm - 11:46 pm

SJO

ORD

10h 16m1 stop

5:15 am - 12:22 pm

ORD

SJO

7h 07m1 stop

$262Spirit Airlines

Mon, Jan 26 - Fri, Jan 30

1:30 pm - 11:22 am

SJO

ORD

21h 52m1 stop

8:43 pm - 12:22 pm

ORD

SJO

15h 39m1 stop

$264Spirit Airlines

Wed, Jan 14 - Thu, Jan 22

1:31 pm - 12:18 am

SJO

ORD

10h 47m1 stop

5:15 am - 12:22 pm

ORD

SJO

7h 07m1 stop

$266Spirit Airlines

Sat, Feb 14 - Wed, Feb 18

1:30 pm - 2:17 pm

SJO

ORD

24h 47m2 stops

3:22 pm - 11:37 am

ORD

SJO

20h 15m2 stops

$267Spirit Airlines

Thu, Jan 29 - Sun, Feb 1

10:36 am - 9:04 pm

SJO

MDW

10h 28m1 stop

6:12 am - 1:42 pm

MDW

SJO

7h 30m1 stop

$335Frontier

Sat, Dec 20 - Mon, Jan 5

10:36 am - 9:04 pm

SJO

MDW

10h 28m1 stop

6:12 am - 1:42 pm

MDW

SJO

7h 30m1 stop

$340Frontier

Sat, Dec 20 - Wed, Dec 31

7:00 am - 5:29 pm

SJO

MDW

10h 29m1 stop

12:48 pm - 10:15 pm

MDW

SJO

9h 27m1 stop

$344Delta

Thu, Jan 22 - Wed, Jan 28

1:50 pm - 10:15 pm

SJO

MDW

8h 25m1 stop

6:15 am - 7:30 pm

MDW

SJO

13h 15m1 stop

$352Southwest

Thu, Feb 12 - Mon, Feb 16

2:31 pm - 8:52 am

SJO

MDW

18h 21m2 stops

12:48 pm - 10:15 pm

MDW

SJO

9h 27m1 stop

$358Delta

Thu, Jan 22 - Mon, Jan 26

Spirit Airlines flights from San José to Chicago

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

Spirit Airlines

Jan 26

SJO1:30 pmSan José Juan Santamaria Intl

10h 16m

1 stop

ORD11:46 pmChicago O'Hare Intl

Jan 30

ORD5:15 amChicago O'Hare Intl

7h 07m

1 stop

SJO12:22 pmSan José Juan Santamaria Intl

$262

Find similar

Spirit Airlines

Jan 14

SJO1:30 pmSan José Juan Santamaria Intl

21h 52m

1 stop

ORD11:22 amChicago O'Hare Intl

Jan 22

ORD8:43 pmChicago O'Hare Intl

15h 39m

1 stop

SJO12:22 pmSan José Juan Santamaria Intl

$264

Find similar

Spirit Airlines

Feb 14

SJO1:31 pmSan José Juan Santamaria Intl

10h 47m

1 stop

ORD12:18 amChicago O'Hare Intl

Feb 18

ORD5:32 pmChicago O'Hare Intl

18h 08m

2 stops

SJO11:40 amSan José Juan Santamaria Intl

$266

Find similar

American Airlines flights from San José to Chicago

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

American Airlines

Dec 9

SJO6:00 amSan José Juan Santamaria Intl

5h 31m

ORD11:31 amChicago O'Hare Intl

Jan 8

ORD7:00 amChicago O'Hare Intl

12h 44m

1 stop

SJO7:44 pmSan José Juan Santamaria Intl

$407

Find similar

American Airlines

Dec 9

SJO6:00 amSan José Juan Santamaria Intl

5h 31m

ORD11:31 amChicago O'Hare Intl

Jan 8

ORD5:30 pmChicago O'Hare Intl

5h 00m

SJO10:30 pmSan José Juan Santamaria Intl

$438

Find similar

American Airlines

Dec 9

SJO6:00 amSan José Juan Santamaria Intl

5h 31m

ORD11:31 amChicago O'Hare Intl

Jan 8

ORD10:05 amChicago O'Hare Intl

9h 39m

1 stop

SJO7:44 pmSan José Juan Santamaria Intl

$445

Find similar

Fly from

Fly to

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 1/29

1:30 pm-10:36 pm

1 stop9h 06m

Chicago O'Hare Intl

Fri 2/6

8:15 am-12:22 pm

2 stops28h 07m

$260

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Mon 1/26

1:30 pm-11:46 pm

1 stop10h 16m

Chicago O'Hare Intl

Fri 1/30

5:15 am-12:22 pm

1 stop7h 07m

$262

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 1/14

1:30 pm-11:22 am

1 stop21h 52m

Chicago O'Hare Intl

Thu 1/22

8:43 pm-12:22 pm

1 stop15h 39m

$264

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 2/14

1:31 pm-12:18 am

1 stop10h 47m

Chicago O'Hare Intl

Wed 2/18

5:15 am-12:22 pm

1 stop7h 07m

$266

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 1/29

1:30 pm-2:17 pm

2 stops24h 47m

Chicago O'Hare Intl

Sun 2/1

3:22 pm-11:37 am

2 stops20h 15m

$267

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 12/20

10:36 am-9:04 pm

1 stop10h 28m

Chicago Midway

Mon 1/5

6:12 am-1:42 pm

1 stop7h 30m

$335

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 12/20

10:36 am-9:04 pm

1 stop10h 28m

Chicago Midway

Wed 12/31

6:12 am-1:42 pm

1 stop7h 30m

$340

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 1/22

7:00 am-5:29 pm

1 stop10h 29m

Chicago Midway

Wed 1/28

12:48 pm-10:15 pm

1 stop9h 27m

$344

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 2/12

1:50 pm-10:15 pm

1 stop8h 25m

Chicago Midway

Mon 2/16

6:15 am-7:30 pm

1 stop13h 15m

$352

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 1/22

2:31 pm-8:52 am

2 stops18h 21m

Chicago Midway

Mon 1/26

12:48 pm-10:15 pm

1 stop9h 27m

$358

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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 typical price of a round-trip flight between San José and 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 $418. If you’re not able to fly to Chicago in January, then October is your next best option. Flight prices from San José to Chicago during October average around $424.

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 Friday when prices can be found for as low as $463. 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 $562.

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 afternoon. Flights from San José to Chicago during this time can be as low as $335. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $506.

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 $462 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 $370 on momondo.

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

There are 2 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 December 2025, prices for San José to Chicago flights are approximately 12% 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	$198
Fastest flight time	5h 30m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from San José in the past 72 hours is $198. The best round-trip flight deal from San José to Chicago found on momondo in the last 72 hours is $429.

The fastest flight from San José to Chicago takes 5h 30m

Direct flights go from San José to Chicago every day.

There is 1 airport near Chicago: 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 7h 45m, 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 December 2025, 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 9, making up 44.60% of the total bookings. Other popular models include Boeing 737 MAX 8 with 39.09%, Airbus A320-100/200 with 3.84%, and Airbus A320neo with 3.60%.
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 30% of all bookings. The subsequent popular airlines are Copa Airlines at 20%, Spirit Airlines at 17%, and United Airlines at 15%.

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 $228	Free Cancellation	Rating 6.3 8,157 reviews	Search Spirit Airlines flights
Avianca	PriceFrom $249	Free Cancellation	Rating 6.6 2,479 reviews	Search Avianca flights
Copa Airlines	PriceFrom $314	Free Cancellation	Rating 7.6 1,554 reviews	Search Copa Airlines flights
American Airlines	PriceFrom $324	Free Cancellation	Rating 7.2 11,047 reviews	Search American Airlines flights
Southwest	PriceFrom $425	Free Cancellation	Rating 8.0 4,250 reviews	Search Southwest flights
United Airlines	PriceFrom $434	Free Cancellation	Rating 7.4 9,066 reviews	Search United Airlines flights

American Airlines Flights From San José to Chicago
The lowest priced American Airlines flight from San José to Chicago from the last 72 hours was $324. Generally, American Airlines has 7 flights on this route every week with an average price of $469. American Airlines is rated 7.2/10 by our users.
Avianca Flights From San José to Chicago
The best Avianca deal for San José to Chicago flight tickets found on momondo in the last 72 hours was $249, round-trip. It should be noted that an average Avianca flight deal for this route in this time was higher, at $485 round-trip. Avianca operates 2 flights out of San José into Chicago in an average week, so prices vary by time and availability. 2,479 Avianca reviews by users on momondo have scored the airline at 6.6/10.

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Saint Joseph

Portage

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Schererville

Valparaiso

Crown Point

Munster

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Monticello

Porter

Griffith

Saint John

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 $131

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 1/31. 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

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

What is the typical price of a round-trip flight between San José and 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 $418. If you’re not able to fly to Chicago in January, then October is your next best option. Flight prices from San José to Chicago during October average around $424.

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 afternoon. Flights from San José to Chicago during this time can be as low as $335. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $506.

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 2 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 December 2025, prices for San José to Chicago flights are approximately 12% 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 and Frontier 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 19% 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 183 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, United Airlines have had the least number of delays on this route over the last 12 months; with about 19% 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: 53% 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 $292.

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 December 2025. The most frequent departure time is 6:00AM, with 83% 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 9 per week as of December 2025. The most frequent departure day is Wed, with 22% 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

Fastest flight time

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

American Airlines Flights From San José to Chicago

Avianca Flights From San José to Chicago