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

Alaska Airlines, Frontier, and Hawaiian Airlines are the most popular carriers operating from San Jose to Chicago

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

Seattle (SEA) was the most common stop: 44% of momondo users choosing 1-stop flights on this route connected there.

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

6 flights are operational weekly from San Jose to Chicago as of October 2025. The most popular departure day for this route is Wed, with 50% of flights per week taking off on this day.

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 $210.

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.

What airlines fly to Chicago?

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.

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 airlines fly direct from San Jose to Chicago?

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.

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

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.

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

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.

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

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

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

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

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

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.

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

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.

$98 Cheap Flights from San Jose to Chicago in 2025/26

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3:00 pm - 11:59 pmSJC-ORD

6h 59m1 stop

6:00 am - 11:32 amORD-SJC

7h 32m1 stop

$194Multiple Airlines

Find Deal

Tue, Nov 4 - Fri, Nov 7

12:27 pm - 12:15 amSJC-ORD

9h 48m1 stop

6:00 am - 5:34 pmORD-SJC

13h 34m2 stops

$196Frontier

Find Deal

Fri, Nov 14 - Mon, Nov 17

8:05 pm - 7:55 pmSJC-ORD

21h 50m1 stop

9:20 am - 2:23 pmORD-SJC

7h 03m1 stop

$207Hawaiian Airlines

Find Deal

Mon, Nov 10 - Tue, Nov 18

3:00 pm - 11:59 pmSJC-ORD

6h 59m1 stop

8:59 pm - 9:48 amORD-SJC

14h 49m1 stop

$208Hawaiian Airlines

Find Deal

Tue, Nov 4 - Wed, Nov 5

10:25 am - 7:55 pmSJC-ORD

7h 30m1 stop

8:59 pm - 9:48 amORD-SJC

14h 49m1 stop

$218Alaska Airlines

Find Deal

Tue, Nov 18 - Tue, Nov 18

12:45 pm - 11:10 pmSJC-ORD

8h 25m1 stop

9:00 am - 4:43 pmORD-SJC

9h 43m1 stop

$225Alaska Airlines

Find Deal

Sat, Feb 21 - Sat, Feb 28

6:30 am - 12:40 pmSJC-MDW

4h 10mnonstop

8:45 am - 11:30 amMDW-SJC

4h 45mnonstop

$283Southwest

Find Deal

Wed, Nov 12 - Wed, Nov 19

7:15 am - 3:55 pmSJC-MDW

6h 40m1 stop

8:45 am - 11:30 amMDW-SJC

4h 45mnonstop

$293Southwest

Find Deal

Wed, Oct 29 - Wed, Nov 5

12:40 pm - 10:14 pmSJC-MDW

7h 34m1 stop

9:20 am - 4:56 pmMDW-SJC

9h 36m2 stops

$308Delta

Find Deal

Wed, Oct 29 - Wed, Nov 5

7:35 pm - 8:55 amSJC-MDW

11h 20m2 stops

9:35 am - 4:56 pmMDW-SJC

9h 21m2 stops

$313Delta

Find Deal

Wed, Oct 29 - Tue, Nov 4

Frontier flights from San Jose to Chicago

Our best Frontier deals on San Jose to Chicago flight tickets

Frontier

Nov 14

SJC12:27 pmSan Jose

9h 48m

1 stop

ORD12:15 amChicago O'Hare Intl

Nov 17

ORD6:00 amChicago O'Hare Intl

13h 34m

2 stops

SJC5:34 pmSan Jose

$196

Find similar

Frontier

Nov 7

SJC12:27 pmSan Jose

9h 48m

1 stop

ORD12:15 amChicago O'Hare Intl

Nov 9

ORD10:43 pmChicago O'Hare Intl

20h 51m

1 stop

SJC5:34 pmSan Jose

$206

Find similar

Frontier

Oct 17

SJC12:27 pmSan Jose

10h 32m

1 stop

ORD12:59 amChicago O'Hare Intl

Oct 20

ORD6:50 amChicago O'Hare Intl

6h 42m

1 stop

SJC11:32 amSan Jose

$240

Find similar

Alaska Airlines flights from San Jose to Chicago

Our best Alaska Airlines deals on San Jose to Chicago flight tickets

Alaska Airlines

Nov 18

SJC10:25 amSan Jose

7h 30m

1 stop

ORD7:55 pmChicago O'Hare Intl

Nov 18

ORD8:59 pmChicago O'Hare Intl

14h 49m

1 stop

SJC9:48 amSan Jose

$218

Find similar

Alaska Airlines

Feb 21

SJC12:45 pmSan Jose

8h 25m

1 stop

ORD11:10 pmChicago O'Hare Intl

Feb 28

ORD9:00 amChicago O'Hare Intl

9h 43m

1 stop

SJC4:43 pmSan Jose

$225

Find similar

Alaska Airlines

Nov 11

SJC10:25 amSan Jose

7h 30m

1 stop

ORD7:55 pmChicago O'Hare Intl

Nov 15

ORD2:54 pmChicago O'Hare Intl

9h 43m

1 stop

SJC10:37 pmSan Jose

$227

Find similar

Fly from

Fly to

Route

Depart

Return

Price

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 11/4

3:00 pm-11:59 pm

1 stop6h 59m

Chicago O'Hare Intl

Fri 11/7

6:00 am-11:32 am

1 stop7h 32m

$194

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 11/14

12:27 pm-12:15 am

1 stop9h 48m

Chicago O'Hare Intl

Mon 11/17

6:00 am-5:34 pm

2 stops13h 34m

$196

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 11/10

8:05 pm-7:55 pm

1 stop21h 50m

Chicago O'Hare Intl

Tue 11/18

9:20 am-2:23 pm

1 stop7h 03m

$207

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 11/4

3:00 pm-11:59 pm

1 stop6h 59m

Chicago O'Hare Intl

Wed 11/5

8:59 pm-9:48 am

1 stop14h 49m

$208

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 11/18

10:25 am-7:55 pm

1 stop7h 30m

Chicago O'Hare Intl

Tue 11/18

8:59 pm-9:48 am

1 stop14h 49m

$218

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sat 2/21

12:45 pm-11:10 pm

1 stop8h 25m

Chicago O'Hare Intl

Sat 2/28

9:00 am-4:43 pm

1 stop9h 43m

$225

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 11/12

6:30 am-12:40 pm

Nonstop4h 10m

Chicago Midway

Wed 11/19

8:45 am-11:30 am

Nonstop4h 45m

$283

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 10/29

7:15 am-3:55 pm

1 stop6h 40m

Chicago Midway

Wed 11/5

8:45 am-11:30 am

Nonstop4h 45m

$293

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 10/29

12:40 pm-10:14 pm

1 stop7h 34m

Chicago Midway

Wed 11/5

9:20 am-4:56 pm

2 stops9h 36m

$308

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 10/29

7:35 pm-8:55 am

2 stops11h 20m

Chicago Midway

Tue 11/4

9:35 am-4:56 pm

2 stops9h 21m

$313

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How to get the cheapest flight ticket from San Jose 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

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 Jose, with most prices found around $298. 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?

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 $566.

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 $658.

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?

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 $471 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.

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 23% 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 October 2025, prices for San Jose to Chicago flights are approximately 43% cheaper when compared to flights at the same time last year.

When to book flights from San Jose to Chicago

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

Estimated round-trip price

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

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

Best Price Found	$193
Fastest flight time	4h 05m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from San Jose in the past 72 hours is $193. The best round-trip flight deal from San Jose to Chicago found on momondo in the last 72 hours is $382.

The fastest flight from San Jose to Chicago takes 4h 05m

Direct flights go from San Jose to Chicago every day.

There is 1 airport near Chicago: Chicago Midway (MDW)

Search flight deals

How far is San Jose to Chicago by plane?
The straight-line distance from San Jose to Chicago is 1836.7 mi. By plane, this route typically takes 4h 05m.
When did momondo last update prices for flights from San Jose Airport to Chicago?
Prices for flights from San Jose Airport to Chicago are updated daily.
How many operators does momondo search for flights from San Jose Airport to Chicago?
As of October 2025, there are 7 operators available to choose from for flights from San Jose Airport to Chicago.
How old do you have to be to fly from San Jose Airport to Chicago?
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.
What documentation or ID do you need to fly to Chicago?
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.
What is the most popular plane model from San Jose to Chicago?
Based on momondo bookings for flights between San Jose and Chicago, the leading plane model is Boeing 737 MAX 8, making up 25.83% of the total bookings. Other popular models include Boeing 737-800 Passenger/BBJ2 (winglets) with 7.96%, Boeing 737 MAX 9 with 6.16%, and Airbus A321neo with 6.01%.
What is the most popular airline from San Jose to Chicago?
momondo data reveals that the most frequently booked airline on the route from San Jose to Chicago is Southwest, representing 44% of all bookings. The subsequent popular airlines are United Airlines at 29%, Frontier at 10%, and Spirit Airlines at 9%.

Best airlines flying from San Jose to Chicago

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

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $98	Free Cancellation	Rating 5.8 3,154 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $140	Free Cancellation	Rating 6.3 8,065 reviews	Search Spirit Airlines flights
Alaska Airlines	PriceFrom $170	Free Cancellation	Rating 8.0 10,000 reviews	Search Alaska Airlines flights
Delta	PriceFrom $236	Free Cancellation	Rating 7.9 7,961 reviews	Search Delta flights
American Airlines	PriceFrom $253	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $308	Free Cancellation	Rating 7.4 8,929 reviews	Search United Airlines flights
Southwest	PriceFrom $331	Free Cancellation	Rating 8.0 4,248 reviews	Search Southwest flights

Southwest Flights From San Jose to Chicago
Southwest operates around 4 flights from San Jose to Chicago every week. The average price of these flights found in the last 72 hours has been $505, but momondo users have found Southwest deals from San Jose to Chicago from as low as $331 round-trip. Southwest has been scored 8.0/10 in 4,248 reviews.
United Airlines Flights From San Jose to Chicago
The best United Airlines deal for San Jose to Chicago flight tickets found on momondo in the last 72 hours was $308, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $526 round-trip. United Airlines operates 2 flights out of San Jose into Chicago in an average week, so prices vary by time and availability. 8,929 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

Merrillville

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Hammond

Benton Harbor

Saint Joseph

Lansing

Portage

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from San Jose to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from San Jose to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from San Jose to Chicago.

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

If you are not ready to book a flight from San Jose to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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Cheap flights from San Jose to Chicago from $98

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 2/18. 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 Jose 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 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 $298. 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 $658.

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 23% 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 October 2025, prices for San Jose to Chicago flights are approximately 43% cheaper when compared to flights at the same time last year.

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

Alaska Airlines, Frontier, and Hawaiian 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: 44% 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 $210.

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 week?

6 flights are operational weekly from San Jose to Chicago as of October 2025. The most popular departure day for this route is Wed, with 50% 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

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is San Jose to Chicago by plane?

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

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

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?

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

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

Best airlines flying from San Jose to Chicago

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

Southwest Flights From San Jose to Chicago

United Airlines Flights From San Jose to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States