Question 1

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

Accepted Answer

You are more likely to see cheaper flights to Chicago from San Jose when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago 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 from San Jose for as low as $262 on momondo.

Question 2

What is the cheapest airline that flies from San Jose to Chicago?

Accepted Answer

Spirit Airlines, Frontier, and American Airlines are the most popular carriers operating from San Jose to Chicago

Question 3

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

Accepted Answer

As of August 2025, prices for San Jose to Chicago flights are approximately 17% more expensive when compared to flights at the same time last year.

Question 4

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

Accepted Answer

Flights connecting via Denver (DEN) have the shortest average one-way travel time: 6h 41m.

Question 5

What is the cheapest month to fly to Chicago?

Accepted Answer

The month of January is, on average, the cheapest month to fly to Chicago from San Jose, with most prices found around $305. If you’re not able to fly to Chicago in January, then December is your next best option. Flight prices from San Jose to Chicago during December average around $369.

Question 6

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

Accepted Answer

Flights via Las Vegas (LAS) offer the lowest average round-trip price of $116.

Question 7

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

Accepted Answer

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from San Jose to Chicago during this time can be as low as $433. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $644.

Question 8

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

Accepted Answer

You could potentially save up to 18% on your flight if you consider stops on a San Jose to Chicago flight.

Question 9

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

Accepted Answer

Seattle (SEA) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Question 10

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

Accepted Answer

Seattle (SEA) has the shortest average layover time for this route: 1h 20m.

Question 11

What is the cheapest San Jose to Chicago flight route?

Accepted Answer

Fly from San Jose to Chicago Midway for the best San Jose - Chicago flight prices

Question 12

What cabin class options are available on San Jose to Chicago flights?

Accepted Answer

There are 4 cabin classes available to choose from on San Jose to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Question 13

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

Accepted Answer

As of August 2025, 4 flights take off from San Jose and land in Chicago each day. The most common flight departure time for this route is 8:00AM, with 100% of daily flights taking off at noon.

Question 14

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

Accepted Answer

28 flights are operational weekly from San Jose to Chicago as of August 2025. The most popular departure day for this route is Thu, with 29% of flights per week taking off on this day.

Question 15

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

Accepted Answer

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $446. 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 Jose to Chicago for around $572.

Question 16

What airlines fly to Chicago?

Accepted Answer

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from San Jose according to our data. United Airlines is the first choice among our users, with 49% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 8 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Question 17

What are the benefits of the different airports in San Jose and Chicago?

Accepted Answer

SJC is the main airport in San Jose, serving most flights in and out of the city. The airport is well-connected to downtown and has many transport options, including a train to downtown. You can get domestic and international flights from SJC, including direct flights to Chicago offered by Alaska Airlines and Southwest. Its compact size makes it easy to clear security, with wait times of less than 20min. Moreover, you’ll have plenty of amenities to enjoy, including free Wi-Fi. The two airports serving flights from San Jose to Chicago are ORD and MDW, and each has its benefits. If you want easier access to downtown, MDW is the better option as it is closer, and transportation fares are much cheaper. Moreover, you’ll have an easier time getting through security at MDW. However, ORD is a much larger airport, offering many domestic and international flights, and offers travelers more flexibility. ORD also has more amenities than MDW, including premium lounges like Polaris.

Question 18

Which airlines fly direct from San Jose to Chicago?

Accepted Answer

Southwest Airlines and Alaska Airlines are the only airlines offering direct flights from San Jose to Chicago. These San Jose to Chicago flights are available from San Jose International Airport (SJC) to both Chicago Midway International Airport (MDW) and Chicago O’Hare International Airport (ORD). One-way direct flights from San Jose to Chicago take around 4h and 10min to MDW and about 4h and 30min to ORD. You can also book cheap flights from San Jose to Chicago with a single- or double-layover en route. These connecting flights from San Jose to Chicago are offered by American Airlines, Delta, United Airlines, Frontier Airlines, and Alaska Airlines. The most common layover options for flights from San Jose to Chicago are Los Angeles, Seattle, Dallas, Charlotte, Phoenix, and Atlanta. Connecting flights from San Jose to Chicago are cheaper than direct flights but can take up to 10h longer.

Question 19

What is the best way to get in and out of airports in San Jose and Chicago?

Accepted Answer

SJC is well-connected to downtown San Jose, and there are many transport options to and from downtown. The first option is car rentals, and many rental agencies, including Hertz, Avis, Budget, Thrifty, Enterprise, and Alamo, have rental counters at SJC. Taxis are another option, available outside Terminals A and B. All are metered, and prior reservations aren’t required. Shared-ride shuttles are also available, and they provide door-to-door services to and from the airport. You can get these shuttles at the Terminal A parking garage. The final option is the train; the Airport Flyer has frequent trips from Santa Clara Caltrain Station. Similarly, you’ll have many options from Chicago airports to downtown. The first is bus transportation; CTA buses offer regular trips downtown, while the PACE buses serve the Chicago suburbs. Another cheap option is the CTA Blue Line, or the "L" train, operating 24h between Chicago airports and downtown. Taxis are also available curbside, and car rentals are available at Chicago airports, with companies like Avis, Thrifty, Hertz, National, Alamo, Avis, Budget, and SIXT at both ORD and MDW.

Which cities can you get to from Chicago Airports?

Several cities are within driving distance of both Chicago airports, and a rental car will be the best way of getting to these cities. You can rent cars at Midway and O’Hare and drive to many cities from Chicago in less than 3h, including Michigan City, Milwaukee, Grand Rapids, South Bend, Indianapolis, and Ann Arbor. You also can take regional buses available at ORD, which offer regional service to Iowa, Illinois, Wisconsin, and Indiana.

Question 20

When did momondo last update prices for flights from San Jose Airport to Chicago?

Accepted Answer

Prices for flights from San Jose Airport to Chicago are updated daily.

Question 21

How many operators does momondo search for flights from San Jose Airport to Chicago?

Accepted Answer

As of August 2025, there are 7 operators available to choose from for flights from San Jose Airport to Chicago.

Question 22

How old do you have to be to fly from San Jose Airport to Chicago?

Accepted Answer

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San Jose Airport to Chicago.

Question 23

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

Accepted Answer

The travel and health documents required for your trip to Chicago 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 Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best Price Found	$55
Fastest flight time	4h 05m
Direct flights	Every day
Airports in Chicago	3 airports

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $98	Free Cancellation	Rating 5.8 3,219 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $108	Free Cancellation	Rating 6.3 8,045 reviews	Search Spirit Airlines flights
Alaska Airlines	PriceFrom $170	Free Cancellation	Rating 8.0 10,000 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $200	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Delta	PriceFrom $236	Free Cancellation	Rating 8.0 7,980 reviews	Search Delta flights
United Airlines	PriceFrom $332	Free Cancellation	Rating 7.4 8,916 reviews	Search United Airlines flights
Southwest	PriceFrom $358	Free Cancellation	Rating 8.0 4,244 reviews	Search Southwest flights

Cheap flights from San Jose to Chicago from $55

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 Jose to Chicago departing on 9/6. 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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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 Jose, with most prices found around $305. If you’re not able to fly to Chicago in January, then December is your next best option. Flight prices from San Jose to Chicago during December average around $369.

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 Jose to Chicago during this time can be as low as $433. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $644.

What is the cheapest San Jose to Chicago flight route?

Fly from San Jose to Chicago Midway for the best San Jose - Chicago flight prices

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

What cabin class options are available on San Jose to Chicago flights?

There are 4 cabin classes available to choose from on San Jose 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 Jose to Chicago flights?

You could potentially save up to 18% on your flight if you consider stops on a San Jose to Chicago flight.

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

As of August 2025, prices for San Jose to Chicago flights are approximately 17% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from San Jose to Chicago?

Spirit Airlines, Frontier, and American Airlines are the most popular carriers operating from San Jose to Chicago

What airlines fly to Chicago?

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

Seattle (SEA) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

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

Flights via Las Vegas (LAS) offer the lowest average round-trip price of $116.

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

Flights connecting via Denver (DEN) have the shortest average one-way travel time: 6h 41m.

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

Seattle (SEA) has the shortest average layover time for this route: 1h 20m.

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

As of August 2025, 4 flights take off from San Jose and land in Chicago each day. The most common flight departure time for this route is 8:00AM, with 100% of daily flights taking off at noon.

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

28 flights are operational weekly from San Jose to Chicago as of August 2025. The most popular departure day for this route is Thu, with 29% of flights per week taking off on this day.

When to book flights from San Jose to Chicago

Cheap San Jose to Chicago (SJC to CHI) flight deals and tips

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When did momondo last update prices for flights from San Jose Airport to Chicago?

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How old do you have to be to fly from San Jose Airport to Chicago?

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

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

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