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.

How many flights depart from San José to Chicago O'Hare Intl Airport on average per week?

As of November 2025, there are 7 flights per week flying from San José to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.

Which layover airport offers the lowest fares from San José to Chicago O'Hare Intl Airport?

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

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

Sunday 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 185 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 has the shortest travel time from San José to Chicago O'Hare Intl Airport?

Flights connecting via Houston (IAH) have the shortest average one-way travel time: 8h 09m.

Which airport is the most popular layover for flights between San José and Chicago O'Hare Intl Airport?

Panama City (PTY) was the most common stop: 54% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport has the shortest connection time from San José to Chicago O'Hare Intl Airport?

Panama City (PTY) has the shortest average layover time for this route: 2h 03m.

What airlines fly to Chicago O'Hare Intl Airport?

United Airlines, American Airlines and Copa Airlines are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from San José according to our data. United Airlines is the first choice among our users, with 30% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 6 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

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

Viva and Spirit Airlines are the most popular carriers operating from San José Juan Santamaria Intl to Chicago O'Hare Intl

How many flights depart from San José to Chicago O'Hare Intl Airport on average per day?

As of November 2025, 1 flights take off from San José and land in Chicago O'Hare Intl Airport each day. The most common flight departure time for this route is 1:00PM, with 100% of daily flights taking off in the afternoon.

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

Prices for flights from San José Juan Santamaria Intl Airport to Chicago O'Hare Intl Airport refresh daily.

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

As of November 2025, there are 6 operators available to choose from for flights from San José Juan Santamaria Intl Airport to Chicago O'Hare Intl Airport.

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

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San José Juan Santamaria Intl Airport to Chicago O'Hare Intl Airport.

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$116 Cheap Flights from San José to Chicago O'Hare Intl Airport in 2025/26

Q: What is the typical price of a round-trip flight between San José and Chicago O'Hare Intl Airport?

Prices are currently low for flights on this route. Typical prices usually range from $400 to $562. The lowest price recently found on this route was $267.

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12:39 pm - 12:09 amSJO-ORD

11h 30m2 stops

8:22 pm - 11:37 amORD-SJO

15h 15m2 stops

$267Spirit Airlines

Find Deal

ter, dez 9 - qui, jan 8

1:30 pm - 11:22 amSJO-ORD

21h 52m1 stop

5:15 am - 12:22 pmORD-SJO

7h 07m1 stop

$268Spirit Airlines

Find Deal

qua, jan 21 - qui, jan 29

1:31 pm - 12:30 amSJO-ORD

10h 59m1 stop

3:26 pm - 12:25 pmORD-SJO

20h 59m1 stop

$269Spirit Airlines

Find Deal

dom, dez 21 - qua, dez 31

1:31 pm - 3:02 pmSJO-ORD

25h 31m1 stop

3:26 pm - 12:25 pmORD-SJO

20h 59m1 stop

$270Multiple Airlines

Find Deal

qua, dez 24 - qua, dez 31

1:31 pm - 12:09 amSJO-ORD

10h 38m1 stop

5:32 pm - 11:37 amORD-SJO

18h 05m2 stops

$271Spirit Airlines

Find Deal

sáb, dez 6 - qua, jan 14

1:30 pm - 2:19 pmSJO-ORD

24h 49m2 stops

3:25 pm - 11:37 amORD-SJO

20h 12m2 stops

$273Spirit Airlines

Find Deal

sex, jan 23 - qui, fev 5

1:20 pm - 11:08 amSJO-ORD

21h 48m1 stop

2:00 pm - 12:25 pmORD-SJO

22h 25m2 stops

$274Multiple Airlines

Find Deal

qua, dez 3 - sex, dez 5

1:31 pm - 12:09 amSJO-ORD

10h 38m1 stop

5:15 am - 12:22 pmORD-SJO

7h 07m1 stop

$275Spirit Airlines

Find Deal

seg, dez 15 - qui, jan 8

12:33 pm - 11:46 pmSJO-ORD

11h 13m2 stops

5:15 am - 12:22 pmORD-SJO

7h 07m1 stop

$276Spirit Airlines

Find Deal

qui, jan 15 - ter, jan 20

1:31 pm - 12:30 amSJO-ORD

10h 59m1 stop

3:26 pm - 11:42 amORD-SJO

20h 16m2 stops

$277Spirit Airlines

Find Deal

qua, dez 24 - qua, dez 31

Spirit Airlines flights from San José to Chicago O'Hare Intl Airport

Our best Spirit Airlines deals on San José to Chicago O'Hare Intl Airport flight tickets

Spirit Airlines

Dec 9

SJO12:39 pmSan José Juan Santamaria Intl

11h 30m

2 stops

ORD12:09 amChicago O'Hare Intl

Jan 8

ORD8:22 pmChicago O'Hare Intl

15h 15m

2 stops

SJO11:37 amSan José Juan Santamaria Intl

$267

Find similar

Spirit Airlines

Jan 21

SJO1:30 pmSan José Juan Santamaria Intl

21h 52m

1 stop

ORD11:22 amChicago O'Hare Intl

Jan 29

ORD5:15 amChicago O'Hare Intl

7h 07m

1 stop

SJO12:22 pmSan José Juan Santamaria Intl

$268

Find similar

Spirit Airlines

Dec 21

SJO1:31 pmSan José Juan Santamaria Intl

10h 59m

1 stop

ORD12:30 amChicago O'Hare Intl

Dec 31

ORD3:26 pmChicago O'Hare Intl

20h 59m

1 stop

SJO12:25 pmSan José Juan Santamaria Intl

$269

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from San José to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

ter 12/9

12:39 pm-12:09 am

2 stops11h 30m

Chicago O'Hare Intl

qui 1/8

8:22 pm-11:37 am

2 stops15h 15m

$267

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

qua 1/21

1:30 pm-11:22 am

1 stop21h 52m

Chicago O'Hare Intl

qui 1/29

5:15 am-12:22 pm

1 stop7h 07m

$268

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

dom 12/21

1:31 pm-12:30 am

1 stop10h 59m

Chicago O'Hare Intl

qua 12/31

3:26 pm-12:25 pm

1 stop20h 59m

$269

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

qua 12/24

1:31 pm-3:02 pm

1 stop25h 31m

Chicago O'Hare Intl

qua 12/31

3:26 pm-12:25 pm

1 stop20h 59m

$270

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

sáb 12/6

1:31 pm-12:09 am

1 stop10h 38m

Chicago O'Hare Intl

qua 1/14

5:32 pm-11:37 am

2 stops18h 05m

$271

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

sex 1/23

1:30 pm-2:19 pm

2 stops24h 49m

Chicago O'Hare Intl

qui 2/5

3:25 pm-11:37 am

2 stops20h 12m

$273

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

qua 12/3

1:20 pm-11:08 am

1 stop21h 48m

Chicago O'Hare Intl

sex 12/5

2:00 pm-12:25 pm

2 stops22h 25m

$274

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

seg 12/15

1:31 pm-12:09 am

1 stop10h 38m

Chicago O'Hare Intl

qui 1/8

5:15 am-12:22 pm

1 stop7h 07m

$275

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

qui 1/15

12:33 pm-11:46 pm

2 stops11h 13m

Chicago O'Hare Intl

ter 1/20

5:15 am-12:22 pm

1 stop7h 07m

$276

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

qua 12/24

1:31 pm-12:30 am

1 stop10h 59m

Chicago O'Hare Intl

qua 12/31

3:26 pm-11:42 am

2 stops20h 16m

$277

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from San José to Chicago O'Hare Intl Airport

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

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Other information

What is the typical price of a round-trip flight between San José and Chicago O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from San José averaging around $425.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $448. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from San José because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $588.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from San José in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $371 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $540. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

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

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from San José when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $463 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from San José for as low as $391 on momondo.

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

There are 2 cabin classes available to choose from on San José Juan Santamaria Intl to Chicago O'Hare Intl 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 O'Hare Intl Airport flights?

You could potentially save up to 12% on your flight if you consider stops on a San José to Chicago O'Hare Intl Airport flight.

How have San José to Chicago O'Hare Intl Airport flight prices changed over time?

As of November 2025, prices for San José to Chicago O'Hare Intl Airport flights are approximately 16% cheaper when compared to flights at the same time last year.

When to book flights from San José to Chicago O'Hare Intl Airport

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

Estimated round-trip price

Cheap San José to Chicago O'Hare Intl Airport (SJO to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San José to Chicago O'Hare Intl Airport

Best Price Found	$175
Fastest flight time	5h 29m
Direct flights	Every day

The best one-way flight to Chicago O'Hare Intl Airport from San José in the past 72 hours is $175. The best round-trip flight deal from San José to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $325.

The fastest flight from San José to Chicago O'Hare Intl Airport takes 5h 29m

Direct flights go from San José to Chicago O'Hare Intl Airport every day.

Search flight deals

How far is San José Juan Santamaria Intl to Chicago O'Hare Intl by plane?
A flight from San José Juan Santamaria Intl to Chicago O'Hare Intl will travel around 2224.7 mi. A reasonable flight in good conditions will take 8h 41m.
When did momondo last update prices for flights from San José Juan Santamaria Intl Airport to Chicago O'Hare Intl Airport?
Prices for flights from San José Juan Santamaria Intl Airport to Chicago O'Hare Intl Airport refresh daily.
How many operators does momondo search for flights from San José Juan Santamaria Intl Airport to Chicago O'Hare Intl Airport?
As of November 2025, there are 6 operators available to choose from for flights from San José Juan Santamaria Intl Airport to Chicago O'Hare Intl Airport.
How old do you have to be to fly from San José Juan Santamaria Intl Airport to Chicago O'Hare Intl Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San José Juan Santamaria Intl Airport to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from San José to Chicago O'Hare Intl Airport?
Based on momondo bookings for flights between San José and Chicago O'Hare Intl Airport, the leading plane model is Boeing 737 MAX 8, making up 40.45% of the total bookings. Other popular models include Boeing 737 MAX 9 with 33.66%, Airbus A320neo with 6.80%, and Airbus A330-300 with 4.53%.
What is the most popular airline from San José to Chicago O'Hare Intl Airport?
Based on momondo bookings for flights between San José and Chicago O'Hare Intl Airport, the leading airline is United Airlines, making up 25% of the total bookings. Other popular airlines include American Airlines with 24%, Copa Airlines with 18%, and Spirit Airlines with 17%.

Best airlines flying from San José to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from San José to Chicago O'Hare Intl Airport with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $230	Free Cancellation	Rating 6.3 8,158 reviews	Search Spirit Airlines flights
Avianca	PriceFrom $249	Free Cancellation	Rating 6.6 2,477 reviews	Search Avianca flights
Copa Airlines	PriceFrom $314	Free Cancellation	Rating 7.6 1,566 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 4,251 reviews	Search Southwest flights
United Airlines	PriceFrom $434	Free Cancellation	Rating 7.4 9,029 reviews	Search United Airlines flights

American Airlines Flights From San José to Chicago O'Hare Intl Airport
American Airlines operates around 7 flights from San José to Chicago O'Hare Intl Airport every week. The average price of these flights found in the last 72 hours has been $463, but momondo users have found American Airlines deals from San José to Chicago O'Hare Intl Airport from as low as $324 round-trip. American Airlines has been scored 7.2/10 in 11,047 reviews.

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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 all potential San José to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from San José and alert you when they change.

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Cheap flights from San José to Chicago from $116

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 12/5. 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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Spirit Airlines flights from San José to Chicago O'Hare Intl Airport

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Use the filters below to find and compare flights from San José to Chicago O'Hare Intl Airport that are best for you.

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How to get the cheapest flight ticket from San José to Chicago O'Hare Intl Airport

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 O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from San José averaging around $425.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

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

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

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

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

There are 2 cabin classes available to choose from on San José Juan Santamaria Intl to Chicago O'Hare Intl 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 O'Hare Intl Airport flights?

You could potentially save up to 12% on your flight if you consider stops on a San José to Chicago O'Hare Intl Airport flight.

How have San José to Chicago O'Hare Intl Airport flight prices changed over time?

As of November 2025, prices for San José to Chicago O'Hare Intl Airport flights are approximately 16% cheaper 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 O'Hare Intl?

Viva and Spirit Airlines are the most popular carriers operating from San José Juan Santamaria Intl to Chicago O'Hare Intl

What airlines fly to Chicago O'Hare Intl Airport?

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 185 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?

Sunday 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 O'Hare Intl Airport?

Panama City (PTY) was the most common stop: 54% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from San José to Chicago O'Hare Intl Airport?

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 O'Hare Intl Airport?

Flights connecting via Houston (IAH) have the shortest average one-way travel time: 8h 09m.

Which layover airport has the shortest connection time from San José to Chicago O'Hare Intl Airport?

Panama City (PTY) has the shortest average layover time for this route: 2h 03m.

How many flights depart from San José to Chicago O'Hare Intl Airport on average per day?

As of November 2025, 1 flights take off from San José and land in Chicago O'Hare Intl Airport each day. The most common flight departure time for this route is 1:00PM, with 100% of daily flights taking off in the afternoon.

How many flights depart from San José to Chicago O'Hare Intl Airport on average per week?

As of November 2025, there are 7 flights per week flying from San José to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.

When to book flights from San José to Chicago O'Hare Intl Airport

Cheap San José to Chicago O'Hare Intl Airport (SJO to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San José to Chicago O'Hare Intl Airport

Best Price Found

Fastest flight time

Direct flights

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

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

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

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

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

What is the most popular plane model from San José to Chicago O'Hare Intl Airport?

What is the most popular airline from San José to Chicago O'Hare Intl Airport?

Best airlines flying from San José to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from San José to Chicago O'Hare Intl Airport with momondo

American Airlines Flights From San José to Chicago O'Hare Intl Airport

Traveling to a place near Chicago?

Why use momondo?

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

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

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