Question 1

What is the cheapest day to depart on your flight to San José?

Accepted Answer

On average, the least expensive day to fly to San José from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $525. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago to San José on a Saturday will generally be more expensive and average around $724. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

Question 2

What is the cheapest month to fly to San José?

Accepted Answer

In general, September is the cheapest month to fly from Chicago to San José. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $315. If you don’t want to visit San José in September, then you should wait until October to fly from Chicago, when ticket prices are also cheap, with an average price of $381.

Question 3

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

Accepted Answer

You could potentially save up to 34% on your flight if you consider stops on a Chicago to San José flight.

Question 4

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

Accepted Answer

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

Question 5

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

Accepted Answer

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

Question 6

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

Accepted Answer

As of January 2026, prices for Chicago to San José flights are approximately 20% cheaper when compared to flights at the same time last year.

Question 7

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

Accepted Answer

Flights via Fort Lauderdale (FLL) offer the lowest average round-trip price of $316.

Question 8

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

Accepted Answer

Charlotte (CLT) has the shortest average layover time for this route: 1h 19m.

Question 9

How far in advance should I book a flight to San José?

Accepted Answer

You are more likely to see cheaper flights to San José from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San José for around $525 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San José from Chicago for as low as $457 on momondo.

Question 10

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

Accepted Answer

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

Question 11

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

Accepted Answer

Fort Lauderdale (FLL) was the most common stop: 45% of momondo users choosing 1-stop flights on this route connected there.

Question 12

What is the typical price of a round-trip flight between Chicago and San José?

Accepted Answer

Prices are currently low for flights on this route.Typical prices usually range from $413 to $681.
The lowest price recently found on this route was $346.

Question 13

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

Accepted Answer

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

Question 14

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

Accepted Answer

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 10% of their flights experiencing any sort of delay.

Question 15

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

Accepted Answer

13 flights are operational weekly from Chicago to San José as of January 2026. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.

Question 16

What airlines fly to San José?

Accepted Answer

United Airlines, American Airlines and Spirit Airlines are the top three most popular airlines that fly to San José from Chicago according to our data. United Airlines is the first choice among our users, with 38% of people opting to fly with this airline when traveling to San José. Keep in mind that there are 8 different airlines that fly to San José on a routine basis, so you have a few additional options to choose from.

Question 17

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

Accepted Answer

The number of flights available between Chicago and San José is 1 per day as of January 2026. The most frequent departure time is 5:00PM, with 64% of daily flights leaving in the afternoon.

Question 18

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

Accepted Answer

Our data shows that the cheapest Chicago to San José flights are usually those with departure times in the afternoon. Our users have found flights to San José in the afternoon for as low as $510. Flights at noon are often more expensive with an average ticket price of $664.

Question 19

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

Accepted Answer

Flights connecting via Orlando (MCO) have the shortest average one-way travel time: 6h 58m.

Question 20

How often are flights from Chicago to San José delayed?

Accepted Answer

Historically, on average around 10% of flights between Chicago and San José have experienced a delay on any given week. The average delay length over the past 12 months has been 173 minutes.

Question 21

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

Accepted Answer

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

Question 22

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

Accepted Answer

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

Question 23

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

Accepted Answer

As of January 2026, there are 8 operators available to choose from for flights from Chicago to San José Juan Santamaria Intl Airport.

Question 24

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

Accepted Answer

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 Chicago to San José Juan Santamaria Intl Airport.

Question 25

What documentation or ID do you need to fly to San José Juan Santamaria Intl Airport?

Accepted Answer

The travel and health documents required for your trip to San José Juan Santamaria Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at San José Juan Santamaria Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best Price Found	$258
Fastest flight time	5h 00m
Direct flights	Every day
Airports in San José	1 airport

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $221	Free Cancellation	Rating 7.9 8,040 reviews	Search Delta flights
Spirit Airlines	PriceFrom $257	Free Cancellation	Rating 6.3 8,309 reviews	Search Spirit Airlines flights
Avianca	PriceFrom $307	Free Cancellation	Rating 6.6 2,489 reviews	Search Avianca flights
Copa Airlines	PriceFrom $309	Free Cancellation	Rating 7.6 1,559 reviews	Search Copa Airlines flights
American Airlines	PriceFrom $345	Free Cancellation	Rating 7.2 11,119 reviews	Search American Airlines flights
Frontier	PriceFrom $345	Free Cancellation	Rating 5.7 3,056 reviews	Search Frontier flights
Southwest	PriceFrom $394	Free Cancellation	Rating 8.0 4,257 reviews	Search Southwest flights
United Airlines	PriceFrom $410	Free Cancellation	Rating 7.4 9,156 reviews	Search United Airlines flights

Cheap flights from Chicago to San José from $121

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to San José departing on 2/26. 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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